Tretinoin
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Identification
- Summary
Tretinoin is a vitamin A derivative used to treat acne vulgaris and certain types of promyelocytic leukemia, as well as various skin conditions in over-the-counter medications.
- Brand Names
- Altreno, Atralin, Biacna, Refissa, Renova, Retin-A, Tri-luma, Twyneo, Veltin, Vesanoid, Ziana
- Generic Name
- Tretinoin
- DrugBank Accession Number
- DB00755
- Background
Tretinoin, also known as all-trans-retinoic acid (ATRA), is a naturally occurring derivative of vitamin A (retinol).1 It is an oxidation product in the physiological pathway of vitamin A metabolism.5 In human circulation, tretinoin is normally found at very low concentrations, approximately 4 to 14 nmol/L.5 Tretinoin exhibits anti-inflammatory, antineoplastic, antioxidant, and free radical-scavenging activities.5 It has been used in dermatology for many years to treat various skin conditions ranging from acne to wrinkles 1,11 and activates nuclear receptors to regulate epithelial cell growth and differentiation.1,2,3 Tretinoin is given orally to treat acute promyelocytic leukemia 13 and topically to treat skin conditions such as acne.15,12,14
- Type
- Small Molecule
- Groups
- Approved, Investigational, Nutraceutical
- Structure
- Weight
- Average: 300.442
Monoisotopic: 300.208930142 - Chemical Formula
- C20H28O2
- Synonyms
- (all-E)-3,7-Dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenoic acid
- 3,7-Dimethyl-9-(2,6,6-trimethyl-1-cyclohexene-1-yl)-2,4,6,8-nonatetraenoic acid (ECL)
- Acide retinoique
- all trans Retinoic acid
- all trans-Retinoic acid
- all-(E)-Retinoic acid
- all-trans-beta-Retinoic acid
- all-trans-Retinoic acid
- all-trans-Tretinoin
- all-trans-Vitamin A acid
- all-trans-Vitamin A1 acid
- ATRA
- beta-Retinoic acid
- Retinoic acid
- Retionic acid
- trans-Retinoic acid
- Tretin M
- Tretinoin
- Tretinoina
- Trétinoïne
- Tretinoinum
- Vitamin A acid
- External IDs
- AGN 100335
- NSC-122758
- Ro 1-5488
Pharmacology
- Indication
Oral tretinoin is indicated for induction of remission in adults and pediatric patients one year of age and older with acute promyelocytic leukemia (APL), characterized by the presence of t(15;17) translocation or presence of PML/RARα gene expression and who are refractory to or who have relapsed from anthracycline chemotherapy or for whom anthracycline-based chemotherapy is contraindicated.13
Topical tretinoin is also indicated alone 15 or in combination with benzoyl peroxide 12 or clindamycin 14 for the treatment of acne vulgaris. It is also used in prescription and over-the-counter for treating various skin conditions such as melasma,16 hyperpigmentation,1 and photoaging 10 alone or in combination with other drugs.
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Associated Conditions
Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Treatment of Acne vulgaris •••••••••••• Used in combination to treat Acne vulgaris Combination Product in combination with: Benzoyl peroxide (DB09096) •••••••••••• ••••• Used in combination to treat Acne vulgaris Combination Product in combination with: Clindamycin (DB01190) •••••••••••• Used in combination to treat Alopecia Combination Product in combination with: Minoxidil (DB00350) •••••••••••• •••••••• Used in combination to treat Cornification and dystrophic skin disorders Combination Product in combination with: Urea (DB03904) •••••••••••• ••••• - Contraindications & Blackbox Warnings
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- Pharmacodynamics
Tretinoin is a vitamin A derivative that promotes cell production, proliferation, and differentiation. When used topically, tretinoin regulates epidermal cell turnover and collagen production. It also prevents collagen loss, reduces inflammation, and blocks the induction of matrix metalloproteinase (MMP), which are enzymes that disrupt collagen and elastic fibres.1,2,3,10 In short-term and long-term studies, topical application of tretinoin at doses ranging from 0.001% to 0.1% was associated with improvements in clinical signs of photoaging and fine wrinkles, increased epidermal thickness, compaction of the stratum corneum, and decreased melanin content.4,10,11,7 It also improved melanocyte differentiation and distribution, promotion of epidermal hyperplasia, and angiogenesis.7
Tretinoin exhibits antineoplastic activities when given orally.13 Tretinoin was shown to induce differentiation in tumour cells.6 It induced cytodifferentiation and decreased acute promyelocytic leukemia (APL) cell proliferation in culture and in vivo. In patients with APL, tretinoin promoted the initial maturation of the primitive promyelocytes derived from the leukemic clone, followed by a repopulation of the bone marrow and peripheral blood by normal, polyclonal hematopoietic cells in patients achieving complete remission.13
- Mechanism of action
The exact mechanism of action of tretinoin in skin conditions and acute promyelocytic leukemia (APL) has not been fully elucidated; however, several proposed mechanisms exist. Tretinoin is believed to exert its pharmacological actions by binding to and activating two types of nuclear receptors - retinoic acid receptors (RARs) alpha, beta, and gamma and retinoid X receptors (RXRs). In the human skin, RARs (especially RAR-alpha) form heterodimers with RXR to act as inducible transcription regulators of genes involved in cell differentiation by binding to retinoic acid response elements.9,11 Tretinoin binds to RXRs to promote epidermal proliferation. It also blocks the actions of inflammatory mediators, enhancing procollagen production and collagen type I and III formations.1,2,3,7 Some animal and human studies suggest that tretinoin induces the expression of transforming growth factor beta (TGF-β), which stimulates the transcription of several types of collagen messenger RNA. Collagen formation curtails further solar UV-induced skin damage and aging processes.7
Acne is associated with abnormal follicular formation from excessive keratinization of epithelial cells. Tretinoin promotes cornified cell detachment and enhances keratinocyte shedding. It also stimulates mitotic activity and loosely-adherent corneocyte turnover to expel comedo contents, reducing microcomedo precursor lesions of acne vulgaris.1,12 Tretinoin may reduce epidermal melanin and pigmentation by increasing keratinocyte turnover and reducing tyrosinase activity.3,10
RAR-alpha and -beta have also been implicated in APL.9 APL is characterized by a t(15;17) chromosomal translocation, which fuses the promyelocytic myeloid leukemia (PML) gene with the RAR-alpha gene.5,6 The resulting PML-RAR-alpha fusion protein plays a role in the pathogenesis of APL by aberrating promyelocyte differentiation. The PML-RAR-alpha fusion protein is found to be predominant in leukemic cells, exerting a dominant negative effect on RAR, RXR and PML function.5 Tretinoin induces terminal differentiation in hemopoietic precursor cell lines and APL cells.6 Tretinoin is believed to promote caspase-mediated cleavage and proteasome-dependent degradation to cause apoptosis and degradation of the PML-RAR-alpha fusion protein.1 It may also convert the fusion protein from a transcription repressor to an activator.1
Target Actions Organism ARetinoic acid receptor alpha agonistHumans ARetinoic acid receptor beta agonistHumans ARetinoic acid receptor gamma agonistHumans ARetinoic acid receptor RXR-beta agonistHumans ARetinoic acid receptor RXR-gamma agonistHumans URetinoic acid receptor RXR-alpha agonistHumans UCellular retinoic acid-binding protein 1 binderHumans URetinoic acid receptor responder protein 1 agonistHumans UAldehyde dehydrogenase 1A1 substrateHumans URetinal dehydrogenase 2 substrateHumans URetinoic acid-induced protein 3 regulatorHumans ULipocalin-1 binderHumans UOdorant-binding protein 2a binderHumans URetinol-binding protein 4 binderHumans U[Pyruvate dehydrogenase (acetyl-transferring)] kinase isozyme 4, mitochondrial upregulatorHumans UCarcinoembryonic antigen downregulatorHumans - Absorption
Tretinoin applied topically is expected to remain on the stratum corneum and undergo minimal systemic absorption.4,7 In one study, the topical application of radiolabelled tretinoin for 28 days was associated with a total percutaneous absorption of 2%.4
The extent of absorption was examined after a once-daily application of 1.9 g of the combination product with benzoyl peroxide for 14 days. On Day 14, at steady-state, the mean Cmax was 0.15-0.19 ng/mL for tretinoin, 0.27-0.34 ng/mL for the metabolite 4-keto 13-cis retinoic acid, and 0.13-0.28 ng/mL for 13-cis retinoic acid, respectively. The Cmax varied across different age groups (children, adolescents, and adults). The corresponding ranges for the mean AUC0-24 were 0.63-2.06, 2.39-2.89, and 0.96-1.99 ng*h/mL.12
Following oral administration, the absolute bioavailability of tretinoin was approximately 50%.13 While the effect of food on tretinoin is unclear, food increases the oral absorption of retinoids, as a class.13,18 When the oral dose of 22.5 mg/m2 tretinoin was administered twice daily, the mean ± SD Cmax was 394 ± 89 ng/mL after the first dose and 138 ± 139 ng/mL after one week of continuous treatment. The area under the curve (AUC) was 537 ± 191 ng·h/mL after the first dose and 249 ± 185 ng·h/mL after one week of continuous treatment. The Tmax was between one and two hours.13
- Volume of distribution
Tretinoin is rapidly and extensively distributed to tissues following oral administration but does not cross the blood-brain barrier. The apparent volume of distribution (Vd) of intravenous tretinoin is dose-dependent and significantly greater at low doses. The Vd was 0.52 ± 0.12 L/kg after 0.0125 mg/kg and 0.21 ± 0.05 L/kg after 0.25 mg/kg.5
- Protein binding
Protein binding of tretinoin is greater than 95%, predominately to albumin.5,13 Plasma protein binding remains constant over the 10 to 500 ng/mL concentration range.13
- Metabolism
Tretinoin is rapidly metabolized to form various oxidized and conjugated metabolites. It forms several metabolites stereoisomerization derivatives (9-cis-retinoic acid or alitretinoin and 13-cis-retinoic acid or isotretinoin), oxidation derivatives (4-hydroxy-retinoic acid, 4-oxo-retinoic acid, 18-hydroxy-retinoic acid, 5,6-epoxy-retinoic acid, 3,4-didehydro-retinoic acid and retinotaurine), stereoisomerization and oxidation derivatives (13-cis-4-oxo-retinoic acid), glucuronidation derivatives (retinoyl beta-glucuronide, 13-cis-retinoyl beta-glucuronide, 4-oxo-retinoyl beta-glucuronide, 5,6-epoxyretinoyl beta-glucuronide and 13-cis-4-oxo-retinoyl beta-glucuronide), nonpolar metabolites of retinoic acid, and retinoic acid esters.5
Tretinoin is metabolized by several CYP enzymes, including CYP3A4, CYP2C8, and CYP2E. It also undergoes glucuronidation by UGT2B7. The metabolites 4-oxo retinoic acid and 4-oxo trans retinoic acid glucuronide have one-third of the pharmacological activity of the parent compound.8,13 When the plasma concentrations decreased to one-third of their day-one concentrations after one week of continuous therapy, tretinoin induced its own metabolism.5,13
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- Route of elimination
Tretinoin metabolites are excreted in bile and urine.18 Following administration of radiolabeled tretinoin at doses of 2.75 mg and 50 mg - which are 0.53 to 9.6 times the approved recommended dosage based on 1.7 m2, respectively - approximately 63% of the radioactivity was recovered in the urine within 72 hours, and 31% appeared in the feces within six days.13
- Half-life
The terminal elimination half-life of tretinoin following initial dosing is 0.5 to 2 hours in patients with APL.13
- Clearance
No information is available.
- Adverse Effects
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- Toxicity
The oral LD50 in rats is 2000 mg/kg. The dermal LD50 in rabbits is >2500 mg/kg.17
Reversible signs of hypervitaminosis A, such as headache, nausea, vomiting, and mucocutaneous symptoms, are expected to appear in tretinoin overdose. Overdosage with other retinoids has been associated with transient headache, facial flushing, cheilosis, abdominal pain, dizziness and ataxia: these symptoms have quickly resolved without apparent residual effects. here is no specific treatment in the case of an overdose and it is advised to treat patients experiencing tretinoin overdose in a special hematological unit.13
- Pathways
Pathway Category Retinol Metabolism Metabolic Vitamin A Deficiency Disease - Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your softwareAbametapir The serum concentration of Tretinoin can be increased when it is combined with Abametapir. Abatacept The metabolism of Tretinoin can be increased when combined with Abatacept. Acalabrutinib The metabolism of Tretinoin can be decreased when combined with Acalabrutinib. Acebutolol Tretinoin may decrease the antihypertensive activities of Acebutolol. Aceclofenac The risk or severity of elevated intracranial pressure can be increased when Aceclofenac is combined with Tretinoin. - Food Interactions
- Take with food. Effect of food on tretinoin absorption is unclear, but food increases the bioavailability of retinoids drug class.
Products
- Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.
- Product Images
- International/Other Brands
- Aberel (Janssen) / Aberela (Janssen) / Airol (Pierre Fabre Dermo) / Dermairol (Roche) / Eudyna (Zydus) / Kétrel (Bailleul) / Sotret (Ranbaxy Laboratories Inc.) / Stieva-A (Stiefel) / Vitinoin
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Altreno Lotion 0.05 % w/w Topical Bausch Health, Canada Inc. Not applicable Not applicable Canada Altreno Lotion 0.5 mg/1g Topical Bausch Health, Canada Inc. 2018-08-24 Not applicable US Atralin Gel 0.05 g/100g Topical Bausch Health, Canada Inc. 2007-07-26 Not applicable US Avita Gel 0.25 mg/1g Topical Mylan Pharmaceuticals Inc. 1998-03-18 2023-05-31 US Avita Cream 0.25 mg/1g Topical Mylan Pharmaceuticals Inc. 1997-06-01 2023-10-31 US - Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Jamp Tretinoin Capsule 10 mg Oral Jamp Pharma Corporation 2022-08-29 Not applicable Canada Obagi Cream 1 mg/1g Topical YS PLUS CORPORATION 2014-10-01 2015-12-31 US Obagi Cream 0.5 mg/1g Topical YS PLUS CORPORATION 2014-10-01 2015-12-31 US Refissa Cream 0.5 mg/1g Topical Suneva Medical, Inc. 2009-06-17 Not applicable US Refissa Cream 0.5 mg/1g Topical Obagi Medical Products, Inc. 2010-02-22 2016-05-01 US - Over the Counter Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image ทีนา - เอ ครีม Cream 0.05 %w/w Topical บริษัท 2 เอ็ม.(เมด-เมเกอร์) จำกัด จำกัด 1990-01-30 Not applicable Thailand เรติน - เอ Cream 0.025 %w/w Topical บริษัท โอลิค (ประเทศไทย) จำกัด 1990-10-05 Not applicable Thailand - Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image ACNATAC Tretinoin (0.025 %) + Clindamycin (1 %) Gel Topical Farmed S.R.L. 2023-12-28 Not applicable Italy Acnatac 10 mg/g + 0,25 mg/g Gel Tretinoin (0.25 mg/g) + Clindamycin (10 mg/g) Gel Topical Mylan S.P.A. 2013-03-26 Not applicable Austria AKNEMYCIN PLUS SOLUTION Tretinoin (0.025 g/100g) + Erythromycin (4 g/100g) Solution Topical ZUELLIG PHARMA SDN. BHD. 2000-02-04 Not applicable Singapore ALBAVANCE F Tretinoin (0.01 %) + Fluocinolone acetonide (4 %) + Hydroquinone (0.05 %) Cream Immortal Pharmaceutical Laboratories 2017-09-18 2027-04-19 Indonesia BALISA VAS Tretinoin (0.3 mg/g) + Urea (120 mg/g) Cream Topical 2006-04-01 Not applicable Germany - Unapproved/Other Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image 011010 Niacinamide 4% / Tretinoin 0.025% Tretinoin (0.025 g/100g) + Nicotinamide (4 g/100g) Gel Topical Sincerus Florida, LLC 2020-07-02 Not applicable US 011013 Niacinamide 4% / Tretinoin 0.025% Tretinoin (0.025 g/100g) + Nicotinamide (4 g/100g) Cream Topical Sincerus Florida, LLC 2020-07-02 Not applicable US 011020 Niacinamide 4% / Tretinoin 0.05% Tretinoin (0.05 g/100g) + Nicotinamide (4 g/100g) Gel Topical Sincerus Florida, LLC 2020-07-02 Not applicable US 011021 Niacinamide 4% / Tretinoin 0.05% Tretinoin (0.05 g/100g) + Nicotinamide (4 g/100g) Cream Topical Sincerus Florida, LLC 2020-07-02 Not applicable US 011218 Niacinamide 2% / Spironolactone 5% / Tretinoin 0.025% Tretinoin (0.025 g/100g) + Nicotinamide (2 g/100g) + Spironolactone (5 g/100g) Gel Topical Sincerus Florida, LLC 2020-07-02 Not applicable US
Categories
- ATC Codes
- L01XF01 — Tretinoin
- L01XF — Retinoids for cancer treatment
- L01X — OTHER ANTINEOPLASTIC AGENTS
- L01 — ANTINEOPLASTIC AGENTS
- L — ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS
- D10AD — Retinoids for topical use in acne
- D10A — ANTI-ACNE PREPARATIONS FOR TOPICAL USE
- D10 — ANTI-ACNE PREPARATIONS
- D — DERMATOLOGICALS
- Drug Categories
- Agents that produce hypertension
- Alkenes
- Anti-Acne Preparations
- Anti-Acne Preparations for Topical Use
- Antineoplastic Agents
- Antineoplastic and Immunomodulating Agents
- Biological Factors
- Cardiotoxic antineoplastic agents
- Carotenoids
- Cell Stimulants and Proliferants
- Cyclohexanes
- Cyclohexenes
- Cycloparaffins
- Cytochrome P-450 CYP2A6 Substrates
- Cytochrome P-450 CYP2B6 Substrates
- Cytochrome P-450 CYP2C18 Substrates
- Cytochrome P-450 CYP2C8 Substrates
- Cytochrome P-450 CYP2C9 Substrates
- Cytochrome P-450 CYP2E1 Substrates
- Cytochrome P-450 CYP3A Substrates
- Cytochrome P-450 CYP3A4 Substrates
- Cytochrome P-450 CYP3A5 Substrates
- Cytochrome P-450 CYP3A7 Substrates
- Cytochrome P-450 Substrates
- Dermatologicals
- Diterpenes
- Hydrocarbons, Acyclic
- Hypotensive Agents
- Immunosuppressive Agents
- Keratolytic Agents
- Pigments, Biological
- Polyenes
- Retinoids
- Retinoids for cancer treatment
- Retinoids for Topical Use in Acne
- Terpenes
- UGT2B7 substrates
- Vitamin A
- Vitamins
- Vitamins (Fat Soluble)
- Classification
- Not classified
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- 5688UTC01R
- CAS number
- 302-79-4
- InChI Key
- SHGAZHPCJJPHSC-YCNIQYBTSA-N
- InChI
- InChI=1S/C20H28O2/c1-15(8-6-9-16(2)14-19(21)22)11-12-18-17(3)10-7-13-20(18,4)5/h6,8-9,11-12,14H,7,10,13H2,1-5H3,(H,21,22)/b9-6+,12-11+,15-8+,16-14+
- IUPAC Name
- (2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenoic acid
- SMILES
- C\C(\C=C\C1=C(C)CCCC1(C)C)=C/C=C/C(/C)=C/C(O)=O
References
- General References
- Yoham AL, Casadesus D: Tretinoin. . [Article]
- Kang S: The mechanism of action of topical retinoids. Cutis. 2005 Feb;75(2 Suppl):10-3; discussion 13. [Article]
- Baldwin HE, Nighland M, Kendall C, Mays DA, Grossman R, Newburger J: 40 years of topical tretinoin use in review. J Drugs Dermatol. 2013 Jun 1;12(6):638-42. [Article]
- Thorne EG: Long-term clinical experience with a topical retinoid. Br J Dermatol. 1992 Sep;127 Suppl 41:31-6. doi: 10.1111/j.1365-2133.1992.tb16985.x. [Article]
- Regazzi MB, Iacona I, Gervasutti C, Lazzarino M, Toma S: Clinical pharmacokinetics of tretinoin. Clin Pharmacokinet. 1997 May;32(5):382-402. doi: 10.2165/00003088-199732050-00004. [Article]
- Gillis JC, Goa KL: Tretinoin. A review of its pharmacodynamic and pharmacokinetic properties and use in the management of acute promyelocytic leukaemia. Drugs. 1995 Nov;50(5):897-923. doi: 10.2165/00003495-199550050-00008. [Article]
- Noble S, Wagstaff AJ: Tretinoin. A review of its pharmacological properties and clinical efficacy in the topical treatment of photodamaged skin. Drugs Aging. 1995 Jun;6(6):479-96. doi: 10.2165/00002512-199506060-00008. [Article]
- Marill J, Cresteil T, Lanotte M, Chabot GG: Identification of human cytochrome P450s involved in the formation of all-trans-retinoic acid principal metabolites. Mol Pharmacol. 2000 Dec;58(6):1341-8. [Article]
- Marill J, Idres N, Capron CC, Nguyen E, Chabot GG: Retinoic acid metabolism and mechanism of action: a review. Curr Drug Metab. 2003 Feb;4(1):1-10. doi: 10.2174/1389200033336900. [Article]
- Sitohang IBS, Makes WI, Sandora N, Suryanegara J: Topical tretinoin for treating photoaging: A systematic review of randomized controlled trials. Int J Womens Dermatol. 2022 Mar 25;8(1):e003. doi: 10.1097/JW9.0000000000000003. eCollection 2022 Mar. [Article]
- Mukherjee S, Date A, Patravale V, Korting HC, Roeder A, Weindl G: Retinoids in the treatment of skin aging: an overview of clinical efficacy and safety. Clin Interv Aging. 2006;1(4):327-48. doi: 10.2147/ciia.2006.1.4.327. [Article]
- DailyMed Label: TWYNEO (tretinoin and benzoyl peroxide) topical cream [Link]
- FDA Approved Drug Products: VESANOID (tretinoin) capsules, for oral use [Link]
- DailyMed Label: CLINDAMYCIN PHOSPHATE and TRETINOIN Gel 1.2% / 0.025%, for topical use only [Link]
- DailyMed Label: Tretinoin Topical Cream or Gel [Link]
- DailyMed Label: TRIDERMA (hydroquinone, tretinoin, fluocinolone acetonide) topical cream [Link]
- Medisca: TRETINOIN, USP (Retinoic Acid) MSDS [Link]
- Cancer Care Ontario Tretinoin Monograph [Link]
- External Links
- Human Metabolome Database
- HMDB0001852
- KEGG Drug
- D00094
- KEGG Compound
- C00777
- PubChem Compound
- 5538
- PubChem Substance
- 46504843
- ChemSpider
- 392618
- BindingDB
- 323588
- 10753
- ChEBI
- 15367
- ChEMBL
- CHEMBL38
- ZINC
- ZINC000012358651
- Therapeutic Targets Database
- DNC000117
- PharmGKB
- PA164746900
- PDBe Ligand
- REA
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Tretinoin
- PDB Entries
- 1cbr / 1cbs / 1fem / 1g5y / 1gx9 / 1n4h / 1rlb / 2acl / 2fr3 / 2g78 … show 12 more
Clinical Trials
- Clinical Trials
Clinical Trial & Rare Diseases Add-on Data Package
Explore 4,000+ rare diseases, orphan drugs & condition pairs, clinical trial why stopped data, & more. Preview package Phase Status Purpose Conditions Count Start Date Why Stopped 100+ additional columns Unlock 175K+ rows when you subscribe.View sample dataNot Available Active Not Recruiting Treatment Acne Vulgaris / Quality of Life (QOL) 1 somestatus stop reason just information to hide Not Available Completed Not Available Acne 1 somestatus stop reason just information to hide Not Available Completed Not Available Immune Thrombocytopenia (ITP) 1 somestatus stop reason just information to hide Not Available Completed Basic Science Melasma 1 somestatus stop reason just information to hide Not Available Completed Prevention Cervical Cancer / Precancerous/Nonmalignant Condition 1 somestatus stop reason just information to hide
Pharmacoeconomics
- Manufacturers
- Hoffmann la roche inc
- Genpharm inc
- Barr laboratories inc
- Ranbaxy pharmaceuticals inc
- Ranbaxy laboratories ltd
- Mylan bertek pharmaceuticals inc
- Ortho dermatologics
- Johnson and johnson consumer companies inc
- Spear pharmaceuticals inc
- Triax pharmaceuticals llc
- Dow pharmaceutical sciences inc
- Mylan pharmaceuticals inc
- Teva pharmaceuticals usa
- Wockhardt eu operations (swiss) ag
- Ranbaxy Pharmaceuticals Inc.
- Packagers
- Actavis Group
- Ameri-Pac Inc.
- A-S Medication Solutions LLC
- Barr Pharmaceuticals
- Cardinal Health
- Catalent Pharma Solutions
- Contract Pharm
- Coria Laboratories
- Dispensing Solutions
- Diversified Healthcare Services Inc.
- DPT Laboratories Ltd.
- Draxis Specialty Pharmaceuticals Inc.
- F Hoffmann-La Roche Ltd.
- Galderma Laboratories
- Genesis Pharmaceutical Inc.
- Hill Laboratories Inc.
- Medicis Pharmaceutical Co.
- Medisca Inc.
- Murfreesboro Pharmaceutical Nursing Supply
- Mylan
- Obagi Medical Products Inc.
- Ortho Mcneil Janssen Pharmaceutical Inc.
- Ortho-McNeil-Janssen Pharmaceuticals Inc.
- Perrigo Co.
- Pharmedix
- Physicians Total Care Inc.
- Ranbaxy Laboratories
- Rebel Distributors Corp.
- Rouses Point Pharmaceuticals LLC
- Sandoz
- Spear Dermatology Products Inc.
- Stiefel Labs
- Triax Pharmaceuticals LLC
- Valeant Ltd.
- Wockhardt Ltd.
- Dosage Forms
Form Route Strength Lotion Topical 50 mg Solution Topical 0.05 g Gel Topical 0.025 % Cream Topical 0.04 g Cream Topical 0025 % Capsule Oral 10.000 mg Cream Topical 0.5 MG/G Solution Topical 0.5 MG/ML Solution Topical 4 g/100g Solution Topical Gel Topical 0.05 g Lotion Topical 0.05 % w/w Lotion Topical 0.5 mg/1g Capsule Oral 10.0000 mg Solution Topical 0.025 g Gel Topical 0.025 g Lotion Topical Lotion Topical 0.05 g Kit Topical Cream Topical Cream Topical 0.25 mg/g Cream Topical 1 mg/g Emulsion Topical Cream 0.025 % Cream 0.1 % Cream Cream Cutaneous 0.025 g Cream 0.1 mg/g Cream Topical 0.05 g/100g Cream Topical 0.2 mg/1g Cream Cutaneous 0.050 g Cream Topical 0.05 g Cream Topical 0.025 g Cream Topical 0025 % W/W Cream Topical Gel Topical Lotion Topical Cream Topical 0.1 mg/1g Gel Topical 0.01 % w/w Gel Topical 0.0100 g Gel Topical 0.025 % w/w Gel Topical 0025 % Liquid Topical 0.5 mg/1mL Gel Cutaneous Gel Topical 0.04 % w/w Gel Topical 0.1 % w/w Gel Topical 0.4 mg/1g Gel Topical 0.6 mg/1g Gel Topical 1 mL/1g Gel Topical 400 mL/1g Cream Topical 0025 MG/G Cream Topical 0.02 % Cream Topical 0.050 g Solution Cutaneous 5.000 g Gel Topical 0.1 % Solution Topical 0.1 % Solution Topical Liquid Topical .05 % Cream Topical 0.01 % w/w Cream Topical 0.025 % w/w Cream Topical 0.05 % w/w Cream Topical 0.1 % w/w Solution Topical 0.025 % Gel Topical .01 % Cream Topical 0.1 g Cream 0.05 % Cream Topical 0.375 mg/1g Gel Topical 0.1 mg/1g Gel Topical 0.25 mg/1g Cream Topical 0.75 mg/1g Capsule Oral 10 mg/1 Cream Topical 0.025 mg/1g Cream Topical 0.05 mg/1g Cream Topical 0.25 mg/1g Cream Topical 0.5 mg/1g Cream Topical 1 mg/1g Cream Topical 1.0 mg/1g Gel Topical 0.01 mg/1g Gel Topical 0.025 mg/1g Gel Topical 0.04 mg/1g Gel Topical 0.05 g/100g Gel Topical 0.5 mg/1g Gel Topical 0.8 mg/1g Powder Not applicable 1 g/1g Gel Topical 1 mg/1g Cream Topical 0.5 mg Cream; kit; lotion Topical Kit Topical 0.25 mg/1g Kit Topical 0.5 mg/1g Kit Topical 1 mg/1g Cream Cutaneous Cream Topical 0.1 mg/g Gel Topical Capsule Oral 10 mg Capsule, liquid filled Oral 10 mg/1 Capsule, gelatin coated Oral Capsule Oral Capsule, liquid filled Oral 10 mg Gel Topical 0.25 % Gel Topical 0.5 MG Gel Topical 1 MG Solution Topical 0.05 % Gel Topical 0.01 % Gel Topical 0.025 % Gel Topical 0.05 % Cream Topical 0.01 % Cream Topical 0.025 % Cream Topical 0.05 % Cream Topical 0.1 % Cream Topical .025 % Cream Topical .05 % Cream Topical .1 % Gel Topical .025 % Gel Topical 0.1 %w/w Gel Topical 0.05 %w/w Cream Topical 0.025 %w/w Cream Topical 0.05 %w/w - Prices
Unit description Cost Unit Tretinoin (Emollient) 0.05% Cream 60 gm Tube 200.07USD tube Tri-Luma 0.01-4-0.05% Cream 30 gm Tube 199.99USD tube Solage 2-0.01% Solution 30ml Bottle 168.67USD bottle Tretinoin (Emollient) 0.05% Cream 40 gm Tube 135.99USD tube Tretinoin 0.1% Cream 45 gm Tube 114.16USD tube Tretinoin 0.025% Gel 45 gm Tube 99.64USD tube Tretinoin 0.01% Gel 45 gm Tube 98.85USD tube Tretinoin 0.05% Cream 45 gm Tube 97.94USD tube Tretinoin 0.025% Cream 45 gm Tube 83.97USD tube Tretinoin acid powder 74.21USD g Tretinoin 0.1% Cream 20 gm Tube 60.96USD tube Tretinoin 0.05% Cream 20 gm Tube 52.23USD tube Tretinoin 0.025% Cream 20 gm Tube 44.36USD tube Tretinoin 0.025% Gel 15 gm Tube 42.26USD tube Tretinoin 0.01% Gel 15 gm Tube 35.99USD tube Vesanoid 10 mg capsule 30.32USD capsule Accutane 40 mg capsule 27.62USD capsule Tretinoin 10 mg capsule 27.29USD capsule Accutane 20 mg capsule 23.77USD capsule Amnesteem 40 mg capsule 22.6USD capsule Claravis 40 mg capsule 21.73USD capsule Accutane 10 mg capsule 20.05USD capsule Amnesteem 20 mg capsule 19.45USD capsule Claravis 20 mg capsule 18.7USD capsule Claravis 30 mg capsule 16.78USD capsule Amnesteem 10 mg capsule 16.4USD capsule Claravis 10 mg capsule 15.77USD capsule Sotret 40 mg capsule 10.08USD capsule Sotret 20 mg capsule 8.67USD capsule Sotret 30 mg capsule 8.44USD capsule Sotret 10 mg capsule 7.31USD capsule Tri-luma cream 6.4USD g Retin-a micro 0.04% gel 5.65USD g Retin-a micro 0.1% gel 5.65USD g Solage topical solution 5.59USD ml Retin-a micro pump 0.04% gel 4.74USD g Retin-a micro pump 0.1% gel 4.74USD g Retin-a 0.05% cream 4.64USD g Retin-a 0.1% cream 4.51USD g Renova 0.02% cream 4.46USD g Renova pump 0.02% cream 4.28USD g Retin-a 0.025% cream 4.14USD g Refissa 0.05% cream 3.6USD g Tretinoin 0.05% emollient crm 3.38USD g Avita 0.025% cream 3.19USD g Tretinoin 0.1% cream 2.36USD g Tretinoin 0.025% cream 2.17USD g Tretinoin 0.05% cream 2.02USD g DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
Patent Number Pediatric Extension Approved Expires (estimated) Region US5470567 No 1995-11-28 2010-03-19 US US5955109 No 1999-09-21 2016-09-21 US US6353029 No 2002-03-05 2020-08-24 US US6531141 No 2003-03-11 2020-03-07 US US8247395 No 2012-08-21 2022-10-22 US US8653053 No 2014-02-18 2022-10-25 US US7939516 No 2011-05-10 2025-05-04 US US7915243 No 2011-03-29 2026-03-22 US US6387383 No 2002-05-14 2020-08-03 US US6517847 No 2003-02-11 2020-08-03 US US10653656 No 2020-05-19 2038-08-22 US US9868103 No 2018-01-16 2028-08-08 US US11071878 No 2021-07-27 2030-12-30 US US10420743 No 2019-09-24 2038-07-12 US US10653899 No 2020-05-19 2030-12-30 US US8617580 No 2013-12-31 2028-02-03 US US11324710 No 2018-08-22 2038-08-22 US US12053546 No 2012-06-29 2032-06-29 US
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 178-184 https://www.medisca.com/NDC_SPECS/MUS/0001/MSDS/0001.pdf logP 6.3 https://www.medisca.com/NDC_SPECS/MUS/0001/MSDS/0001.pdf - Predicted Properties
Property Value Source Water Solubility 0.00477 mg/mL ALOGPS logP 5.66 ALOGPS logP 5.01 Chemaxon logS -4.8 ALOGPS pKa (Strongest Acidic) 4.76 Chemaxon Physiological Charge -1 Chemaxon Hydrogen Acceptor Count 2 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 37.3 Å2 Chemaxon Rotatable Bond Count 5 Chemaxon Refractivity 97.79 m3·mol-1 Chemaxon Polarizability 36.85 Å3 Chemaxon Number of Rings 1 Chemaxon Bioavailability 1 Chemaxon Rule of Five No Chemaxon Ghose Filter Yes Chemaxon Veber's Rule Yes Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9925 Blood Brain Barrier + 0.9311 Caco-2 permeable + 0.7603 P-glycoprotein substrate Non-substrate 0.6144 P-glycoprotein inhibitor I Non-inhibitor 0.8912 P-glycoprotein inhibitor II Non-inhibitor 0.8088 Renal organic cation transporter Non-inhibitor 0.8639 CYP450 2C9 substrate Non-substrate 0.8221 CYP450 2D6 substrate Non-substrate 0.9115 CYP450 3A4 substrate Substrate 0.6025 CYP450 1A2 substrate Non-inhibitor 0.9046 CYP450 2C9 inhibitor Non-inhibitor 0.8831 CYP450 2D6 inhibitor Non-inhibitor 0.9231 CYP450 2C19 inhibitor Non-inhibitor 0.9025 CYP450 3A4 inhibitor Non-inhibitor 0.9301 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9252 Ames test Non AMES toxic 0.8944 Carcinogenicity Non-carcinogens 0.7081 Biodegradation Ready biodegradable 0.5554 Rat acute toxicity 2.1455 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9562 hERG inhibition (predictor II) Non-inhibitor 0.9538
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 202.3292981 predictedDarkChem Lite v0.1.0 [M-H]- 204.5572981 predictedDarkChem Lite v0.1.0 [M-H]- 192.63275 predictedDeepCCS 1.0 (2019) [M-H]- 202.3292981 predictedDarkChem Lite v0.1.0 [M-H]- 204.5572981 predictedDarkChem Lite v0.1.0 [M-H]- 202.3292981 predictedDarkChem Lite v0.1.0 [M-H]- 204.5572981 predictedDarkChem Lite v0.1.0 [M-H]- 192.63275 predictedDeepCCS 1.0 (2019) [M-H]- 192.63275 predictedDeepCCS 1.0 (2019) [M+H]+ 194.99077 predictedDeepCCS 1.0 (2019) [M+H]+ 194.99077 predictedDeepCCS 1.0 (2019) [M+H]+ 194.99077 predictedDeepCCS 1.0 (2019) [M+Na]+ 202.33412 predictedDeepCCS 1.0 (2019) [M+Na]+ 202.33412 predictedDeepCCS 1.0 (2019) [M+Na]+ 202.33412 predictedDeepCCS 1.0 (2019)
Targets
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Agonist
- General Function
- Receptor for retinoic acid (PubMed:16417524, PubMed:19850744, PubMed:20215566, PubMed:21152046, PubMed:37478846). Retinoic acid receptors bind as heterodimers to their target response elements in response to their ligands, all-trans or 9-cis retinoic acid, and regulate gene expression in various biological processes (PubMed:28167758, PubMed:37478846, PubMed:21152046). The RXR/RAR heterodimers bind to the retinoic acid response elements (RARE) composed of tandem 5'-AGGTCA-3' sites known as DR1-DR5 (PubMed:19398580, PubMed:28167758). In the absence of ligand, the RXR-RAR heterodimers associate with a multiprotein complex containing transcription corepressors that induce histone deacetylation, chromatin condensation and transcriptional suppression (PubMed:16417524). On ligand binding, the corepressors dissociate from the receptors and associate with the coactivators leading to transcriptional activation (PubMed:19850744, PubMed:20215566, PubMed:9267036, PubMed:37478846). Formation of a complex with histone deacetylases might lead to inhibition of RARE DNA element binding and to transcriptional repression (PubMed:28167758). Transcriptional activation and RARE DNA element binding might be supported by the transcription factor KLF2 (PubMed:28167758). RARA plays an essential role in the regulation of retinoic acid-induced germ cell development during spermatogenesis (By similarity). Has a role in the survival of early spermatocytes at the beginning prophase of meiosis (By similarity). In Sertoli cells, may promote the survival and development of early meiotic prophase spermatocytes (By similarity). In concert with RARG, required for skeletal growth, matrix homeostasis and growth plate function (By similarity). Together with RXRA, positively regulates microRNA-10a expression, thereby inhibiting the GATA6/VCAM1 signaling response to pulsatile shear stress in vascular endothelial cells (PubMed:28167758). In association with HDAC3, HDAC5 and HDAC7 corepressors, plays a role in the repression of microRNA-10a and thereby promotes the inflammatory response (PubMed:28167758)
- Specific Function
- alpha-actinin binding
- Gene Name
- RARA
- Uniprot ID
- P10276
- Uniprot Name
- Retinoic acid receptor alpha
- Molecular Weight
- 50770.805 Da
References
- Vollberg TM Sr, Nervi C, George MD, Fujimoto W, Krust A, Jetten AM: Retinoic acid receptors as regulators of human epidermal keratinocyte differentiation. Mol Endocrinol. 1992 May;6(5):667-76. [Article]
- Regazzi MB, Iacona I, Gervasutti C, Lazzarino M, Toma S: Clinical pharmacokinetics of tretinoin. Clin Pharmacokinet. 1997 May;32(5):382-402. doi: 10.2165/00003088-199732050-00004. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Agonist
- General Function
- Receptor for retinoic acid. Retinoic acid receptors bind as heterodimers to their target response elements in response to their ligands, all-trans or 9-cis retinoic acid, and regulate gene expression in various biological processes. The RXR/RAR heterodimers bind to the retinoic acid response elements (RARE) composed of tandem 5'-AGGTCA-3' sites known as DR1-DR5. In the absence or presence of hormone ligand, acts mainly as an activator of gene expression due to weak binding to corepressors (PubMed:12554770). The RXRA/RARB heterodimer can act as a repressor on the DR1 element and as an activator on the DR5 element (PubMed:29021580). In concert with RARG, required for skeletal growth, matrix homeostasis and growth plate function (By similarity)
- Specific Function
- DNA binding
- Gene Name
- RARB
- Uniprot ID
- P10826
- Uniprot Name
- Retinoic acid receptor beta
- Molecular Weight
- 50488.63 Da
References
- Steidl U, Schroeder T, Steidl C, Kobbe G, Graef T, Bork S, Pechtel S, Kliszewski S, Kuendgen A, Rohr UP, Fenk R, Schroeder M, Haase D, Haas R, Kronenwett R: Distinct gene expression pattern of malignant hematopoietic stem and progenitor cells in polycythemia vera. Ann N Y Acad Sci. 2005 Jun;1044:94-108. [Article]
- Regazzi MB, Iacona I, Gervasutti C, Lazzarino M, Toma S: Clinical pharmacokinetics of tretinoin. Clin Pharmacokinet. 1997 May;32(5):382-402. doi: 10.2165/00003088-199732050-00004. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Agonist
- General Function
- Receptor for retinoic acid. Retinoic acid receptors bind as heterodimers to their target response elements in response to their ligands, all-trans or 9-cis retinoic acid, and regulate gene expression in various biological processes. The RAR/RXR heterodimers bind to the retinoic acid response elements (RARE) composed of tandem 5'-AGGTCA-3' sites known as DR1-DR5. In the absence of ligand, acts mainly as an activator of gene expression due to weak binding to corepressors. Required for limb bud development. In concert with RARA or RARB, required for skeletal growth, matrix homeostasis and growth plate function (By similarity)
- Specific Function
- chromatin binding
- Gene Name
- RARG
- Uniprot ID
- P13631
- Uniprot Name
- Retinoic acid receptor gamma
- Molecular Weight
- 50341.405 Da
References
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
- Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
- Reddy AP, Chen JY, Zacharewski T, Gronemeyer H, Voorhees JJ, Fisher GJ: Characterization and purification of human retinoic acid receptor-gamma 1 overexpressed in the baculovirus-insect cell system. Biochem J. 1992 Nov 1;287 ( Pt 3):833-40. [Article]
- Kamei Y, Kawada T, Kazuki R, Sugimoto E: Retinoic acid receptor gamma 2 gene expression is up-regulated by retinoic acid in 3T3-L1 preadipocytes. Biochem J. 1993 Aug 1;293 ( Pt 3):807-12. [Article]
- Borger DR, Mi Y, Geslani G, Zyzak LL, Batova A, Engin TS, Pirisi L, Creek KE: Retinoic acid resistance at late stages of human papillomavirus type 16-mediated transformation of human keratinocytes arises despite intact retinoid signaling and is due to a loss of sensitivity to transforming growth factor-beta. Virology. 2000 May 10;270(2):397-407. [Article]
- Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]
- Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
- Regazzi MB, Iacona I, Gervasutti C, Lazzarino M, Toma S: Clinical pharmacokinetics of tretinoin. Clin Pharmacokinet. 1997 May;32(5):382-402. doi: 10.2165/00003088-199732050-00004. [Article]
- Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Agonist
- General Function
- Receptor for retinoic acid. Retinoic acid receptors bind as heterodimers to their target response elements in response to their ligands, all-trans or 9-cis retinoic acid, and regulate gene expression in various biological processes. The RAR/RXR heterodimers bind to the retinoic acid response elements (RARE)
- Specific Function
- DNA-binding transcription activator activity, RNA polymerase II-specific
- Gene Name
- RXRB
- Uniprot ID
- P28702
- Uniprot Name
- Retinoic acid receptor RXR-beta
- Molecular Weight
- 56921.38 Da
References
- Stafslien DK, Vedvik KL, De Rosier T, Ozers MS: Analysis of ligand-dependent recruitment of coactivator peptides to RXRbeta in a time-resolved fluorescence resonance energy transfer assay. Mol Cell Endocrinol. 2007 Jan 29;264(1-2):82-9. Epub 2006 Dec 20. [Article]
- Redfern CP: Enhancing enhancers: new complexities in the retinoid regulation of gene expression. Biochem J. 2004 Oct 1;383(Pt 1):e1-2. [Article]
- Nagasawa H, Takahashi S, Kobayashi A, Tazawa H, Tashima Y, Sato K: Effect of retinoic acid on murine preosteoblastic MC3T3-E1 cells. J Nutr Sci Vitaminol (Tokyo). 2005 Oct;51(5):311-8. [Article]
- Schrage K, Koopmans G, Joosten EA, Mey J: Macrophages and neurons are targets of retinoic acid signaling after spinal cord contusion injury. Eur J Neurosci. 2006 Jan;23(2):285-95. [Article]
- Hoegberg P, Schmidt CK, Fletcher N, Nilsson CB, Trossvik C, Gerlienke Schuur A, Brouwer A, Nau H, Ghyselinck NB, Chambon P, Hakansson H: Retinoid status and responsiveness to 2,3,7,8-tetrachlorodibenzo-p-dioxin (TCDD) in mice lacking retinoid binding protein or retinoid receptor forms. Chem Biol Interact. 2005 Sep 10;156(1):25-39. [Article]
- Regazzi MB, Iacona I, Gervasutti C, Lazzarino M, Toma S: Clinical pharmacokinetics of tretinoin. Clin Pharmacokinet. 1997 May;32(5):382-402. doi: 10.2165/00003088-199732050-00004. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Agonist
- General Function
- Receptor for retinoic acid. Retinoic acid receptors bind as heterodimers to their target response elements in response to their ligands, all-trans or 9-cis retinoic acid, and regulate gene expression in various biological processes. The RAR/RXR heterodimers bind to the retinoic acid response elements (RARE) composed of tandem 5'-AGGTCA-3' sites known as DR1-DR5. The high affinity ligand for RXRs is 9-cis retinoic acid (By similarity)
- Specific Function
- DNA-binding transcription factor activity, RNA polymerase II-specific
- Gene Name
- RXRG
- Uniprot ID
- P48443
- Uniprot Name
- Retinoic acid receptor RXR-gamma
- Molecular Weight
- 50870.72 Da
References
- Koda T, Imai H, Morita M: Antiestrogenic activity of vitamin A in in vivo uterotrophic assay. Life Sci. 2007 Feb 13;80(10):945-9. Epub 2006 Nov 22. [Article]
- He JC, Lu TC, Fleet M, Sunamoto M, Husain M, Fang W, Neves S, Chen Y, Shankland S, Iyengar R, Klotman PE: Retinoic acid inhibits HIV-1-induced podocyte proliferation through the cAMP pathway. J Am Soc Nephrol. 2007 Jan;18(1):93-102. Epub 2006 Dec 20. [Article]
- Day RM, Lee YH, Park AM, Suzuki YJ: Retinoic acid inhibits airway smooth muscle cell migration. Am J Respir Cell Mol Biol. 2006 Jun;34(6):695-703. Epub 2006 Feb 2. [Article]
- Schrage K, Koopmans G, Joosten EA, Mey J: Macrophages and neurons are targets of retinoic acid signaling after spinal cord contusion injury. Eur J Neurosci. 2006 Jan;23(2):285-95. [Article]
- Wang J, Yen A: A novel retinoic acid-responsive element regulates retinoic acid-induced BLR1 expression. Mol Cell Biol. 2004 Mar;24(6):2423-43. [Article]
- Regazzi MB, Iacona I, Gervasutti C, Lazzarino M, Toma S: Clinical pharmacokinetics of tretinoin. Clin Pharmacokinet. 1997 May;32(5):382-402. doi: 10.2165/00003088-199732050-00004. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Agonist
- Curator comments
- Tretinoin interacts 40-fold less efficiently with RXR-alpha than with RAR-alpha.
- General Function
- Receptor for retinoic acid that acts as a transcription factor (PubMed:11162439, PubMed:11915042, PubMed:37478846). Forms homo- or heterodimers with retinoic acid receptors (RARs) and binds to target response elements in response to their ligands, all-trans or 9-cis retinoic acid, to regulate gene expression in various biological processes (PubMed:10195690, PubMed:11162439, PubMed:11915042, PubMed:16107141, PubMed:17761950, PubMed:18800767, PubMed:19167885, PubMed:28167758, PubMed:37478846). The RAR/RXR heterodimers bind to the retinoic acid response elements (RARE) composed of tandem 5'-AGGTCA-3' sites known as DR1-DR5 to regulate transcription (PubMed:10195690, PubMed:11162439, PubMed:11915042, PubMed:17761950, PubMed:28167758). The high affinity ligand for retinoid X receptors (RXRs) is 9-cis retinoic acid (PubMed:1310260). In the absence of ligand, the RXR-RAR heterodimers associate with a multiprotein complex containing transcription corepressors that induce histone deacetylation, chromatin condensation and transcriptional suppression (PubMed:20215566). On ligand binding, the corepressors dissociate from the receptors and coactivators are recruited leading to transcriptional activation (PubMed:20215566, PubMed:37478846, PubMed:9267036). Serves as a common heterodimeric partner for a number of nuclear receptors, such as RARA, RARB and PPARA (PubMed:10195690, PubMed:11915042, PubMed:28167758, PubMed:29021580). The RXRA/RARB heterodimer can act as a transcriptional repressor or transcriptional activator, depending on the RARE DNA element context (PubMed:29021580). The RXRA/PPARA heterodimer is required for PPARA transcriptional activity on fatty acid oxidation genes such as ACOX1 and the P450 system genes (PubMed:10195690). Together with RARA, positively regulates microRNA-10a expression, thereby inhibiting the GATA6/VCAM1 signaling response to pulsatile shear stress in vascular endothelial cells (PubMed:28167758). Acts as an enhancer of RARA binding to RARE DNA element (PubMed:28167758). May facilitate the nuclear import of heterodimerization partners such as VDR and NR4A1 (PubMed:12145331, PubMed:15509776). Promotes myelin debris phagocytosis and remyelination by macrophages (PubMed:26463675). Plays a role in the attenuation of the innate immune system in response to viral infections, possibly by negatively regulating the transcription of antiviral genes such as type I IFN genes (PubMed:25417649). Involved in the regulation of calcium signaling by repressing ITPR2 gene expression, thereby controlling cellular senescence (PubMed:30216632)
- Specific Function
- DNA binding domain binding
- Gene Name
- RXRA
- Uniprot ID
- P19793
- Uniprot Name
- Retinoic acid receptor RXR-alpha
- Molecular Weight
- 50810.835 Da
References
- Mizuguchi Y, Wada A, Nakagawa K, Ito M, Okano T: Antitumoral activity of 13-demethyl or 13-substituted analogues of all-trans retinoic acid and 9-cis retinoic acid in the human myeloid leukemia cell line HL-60. Biol Pharm Bull. 2006 Sep;29(9):1803-9. [Article]
- Regazzi MB, Iacona I, Gervasutti C, Lazzarino M, Toma S: Clinical pharmacokinetics of tretinoin. Clin Pharmacokinet. 1997 May;32(5):382-402. doi: 10.2165/00003088-199732050-00004. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Binder
- General Function
- Cytosolic CRABPs may regulate the access of retinoic acid to the nuclear retinoic acid receptors
- Specific Function
- fatty acid binding
- Gene Name
- CRABP1
- Uniprot ID
- P29762
- Uniprot Name
- Cellular retinoic acid-binding protein 1
- Molecular Weight
- 15565.45 Da
References
- Regazzi MB, Iacona I, Gervasutti C, Lazzarino M, Toma S: Clinical pharmacokinetics of tretinoin. Clin Pharmacokinet. 1997 May;32(5):382-402. doi: 10.2165/00003088-199732050-00004. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Agonist
- General Function
- Inhibitor of the cytoplasmic carboxypeptidase AGBL2, may regulate the alpha-tubulin tyrosination cycle
- Specific Function
- metalloendopeptidase inhibitor activity
- Gene Name
- RARRES1
- Uniprot ID
- P49788
- Uniprot Name
- Retinoic acid receptor responder protein 1
- Molecular Weight
- 33284.865 Da
References
- Youssef EM, Chen XQ, Higuchi E, Kondo Y, Garcia-Manero G, Lotan R, Issa JP: Hypermethylation and silencing of the putative tumor suppressor Tazarotene-induced gene 1 in human cancers. Cancer Res. 2004 Apr 1;64(7):2411-7. [Article]
- Zirn B, Samans B, Spangenberg C, Graf N, Eilers M, Gessler M: All-trans retinoic acid treatment of Wilms tumor cells reverses expression of genes associated with high risk and relapse in vivo. Oncogene. 2005 Aug 4;24(33):5246-51. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Cytosolic dehydrogenase that catalyzes the irreversible oxidation of a wide range of aldehydes to their corresponding carboxylic acid (PubMed:12941160, PubMed:15623782, PubMed:17175089, PubMed:19296407, PubMed:25450233, PubMed:26373694). Functions downstream of retinol dehydrogenases and catalyzes the oxidation of retinaldehyde into retinoic acid, the second step in the oxidation of retinol/vitamin A into retinoic acid (By similarity). This pathway is crucial to control the levels of retinol and retinoic acid, two important molecules which excess can be teratogenic and cytotoxic (By similarity). Also oxidizes aldehydes resulting from lipid peroxidation like (E)-4-hydroxynon-2-enal/HNE, malonaldehyde and hexanal that form protein adducts and are highly cytotoxic. By participating for instance to the clearance of (E)-4-hydroxynon-2-enal/HNE in the lens epithelium prevents the formation of HNE-protein adducts and lens opacification (PubMed:12941160, PubMed:15623782, PubMed:19296407). Functions also downstream of fructosamine-3-kinase in the fructosamine degradation pathway by catalyzing the oxidation of 3-deoxyglucosone, the carbohydrate product of fructosamine 3-phosphate decomposition, which is itself a potent glycating agent that may react with lysine and arginine side-chains of proteins (PubMed:17175089). Has also an aminobutyraldehyde dehydrogenase activity and is probably part of an alternative pathway for the biosynthesis of GABA/4-aminobutanoate in midbrain, thereby playing a role in GABAergic synaptic transmission (By similarity)
- Specific Function
- 3-deoxyglucosone dehydrogenase activity
- Gene Name
- ALDH1A1
- Uniprot ID
- P00352
- Uniprot Name
- Aldehyde dehydrogenase 1A1
- Molecular Weight
- 54861.44 Da
References
- Mic FA, Molotkov A, Molotkova N, Duester G: Raldh2 expression in optic vesicle generates a retinoic acid signal needed for invagination of retina during optic cup formation. Dev Dyn. 2004 Oct;231(2):270-7. [Article]
- Everts HB, King LE Jr, Sundberg JP, Ong DE: Hair cycle-specific immunolocalization of retinoic acid synthesizing enzymes Aldh1a2 and Aldh1a3 indicate complex regulation. J Invest Dermatol. 2004 Aug;123(2):258-63. [Article]
- Gidlof AC, Ocaya P, Olofsson PS, Torma H, Sirsjo A: Differences in retinol metabolism and proliferative response between neointimal and medial smooth muscle cells. J Vasc Res. 2006;43(4):392-8. Epub 2006 Jul 6. [Article]
- Matt N, Dupe V, Garnier JM, Dennefeld C, Chambon P, Mark M, Ghyselinck NB: Retinoic acid-dependent eye morphogenesis is orchestrated by neural crest cells. Development. 2005 Nov;132(21):4789-800. Epub 2005 Oct 5. [Article]
- Kim H, Lapointe J, Kaygusuz G, Ong DE, Li C, van de Rijn M, Brooks JD, Pollack JR: The retinoic acid synthesis gene ALDH1a2 is a candidate tumor suppressor in prostate cancer. Cancer Res. 2005 Sep 15;65(18):8118-24. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Catalyzes the NAD-dependent oxidation of aldehyde substrates, such as all-trans-retinal and all-trans-13,14-dihydroretinal, to their corresponding carboxylic acids, all-trans-retinoate and all-trans-13,14-dihydroretinoate, respectively (PubMed:29240402, PubMed:33565183). Retinoate signaling is critical for the transcriptional control of many genes, for instance it is crucial for initiation of meiosis in both male and female (Probable) (PubMed:33565183). Recognizes retinal as substrate, both in its free form and when bound to cellular retinol-binding protein (By similarity). Can metabolize octanal and decanal, but has only very low activity with benzaldehyde, acetaldehyde and propanal (By similarity). Displays complete lack of activity with citral (By similarity)
- Specific Function
- 3-chloroallyl aldehyde dehydrogenase activity
- Gene Name
- ALDH1A2
- Uniprot ID
- O94788
- Uniprot Name
- Retinal dehydrogenase 2
- Molecular Weight
- 56723.495 Da
References
- Mic FA, Sirbu IO, Duester G: Retinoic acid synthesis controlled by Raldh2 is required early for limb bud initiation and then later as a proximodistal signal during apical ectodermal ridge formation. J Biol Chem. 2004 Jun 18;279(25):26698-706. Epub 2004 Apr 6. [Article]
- Bordelon T, Montegudo SK, Pakhomova S, Oldham ML, Newcomer ME: A disorder to order transition accompanies catalysis in retinaldehyde dehydrogenase type II. J Biol Chem. 2004 Oct 8;279(41):43085-91. Epub 2004 Aug 7. [Article]
- Mic FA, Molotkov A, Molotkova N, Duester G: Raldh2 expression in optic vesicle generates a retinoic acid signal needed for invagination of retina during optic cup formation. Dev Dyn. 2004 Oct;231(2):270-7. [Article]
- Doxakis E, Davies AM: Retinoic acid negatively regulates GDNF and neurturin receptor expression and responsiveness in embryonic chicken sympathetic neurons. Mol Cell Neurosci. 2005 Aug;29(4):617-27. [Article]
- Everts HB, Sundberg JP, Ong DE: Immunolocalization of retinoic acid biosynthesis systems in selected sites in rat. Exp Cell Res. 2005 Aug 15;308(2):309-19. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Regulator
- General Function
- Orphan receptor. Could be involved in modulating differentiation and maintaining homeostasis of epithelial cells. This retinoic acid-inducible GPCR provide evidence for a possible interaction between retinoid and G-protein signaling pathways. Functions as a negative modulator of EGFR signaling (By similarity). May act as a lung tumor suppressor (PubMed:18000218)
- Specific Function
- cadherin binding
- Gene Name
- GPRC5A
- Uniprot ID
- Q8NFJ5
- Uniprot Name
- Retinoic acid-induced protein 3
- Molecular Weight
- 40250.69 Da
References
- Xu J, Tian J, Shapiro SD: Normal lung development in RAIG1-deficient mice despite unique lung epithelium-specific expression. Am J Respir Cell Mol Biol. 2005 May;32(5):381-7. Epub 2005 Jan 27. [Article]
- Inoue S, Nambu T, Shimomura T: The RAIG family member, GPRC5D, is associated with hard-keratinized structures. J Invest Dermatol. 2004 Mar;122(3):565-73. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Binder
- General Function
- Could play a role in taste reception. Could be necessary for the concentration and delivery of sapid molecules in the gustatory system. Can bind various ligands, with chemical structures ranging from lipids and retinoids to the macrocyclic antibiotic rifampicin and even to microbial siderophores. Exhibits an extremely wide ligand pocket
- Specific Function
- chloride ion binding
- Gene Name
- LCN1
- Uniprot ID
- P31025
- Uniprot Name
- Lipocalin-1
- Molecular Weight
- 19249.845 Da
References
- Breustedt DA, Schonfeld DL, Skerra A: Comparative ligand-binding analysis of ten human lipocalins. Biochim Biophys Acta. 2006 Feb;1764(2):161-73. Epub 2006 Jan 6. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Binder
- General Function
- Binds and transports small hydrophobic volatile molecules with a higher affinity for aldehydes and large fatty acids, including undecanal, palmitic acid, efficient aldehydes, benzenic aldehydes, heterocyclic aldehydes and aliphatic acids
- Specific Function
- odorant binding
- Gene Name
- OBP2A
- Uniprot ID
- Q9NY56
- Uniprot Name
- Odorant-binding protein 2a
- Molecular Weight
- 19318.245 Da
References
- Breustedt DA, Schonfeld DL, Skerra A: Comparative ligand-binding analysis of ten human lipocalins. Biochim Biophys Acta. 2006 Feb;1764(2):161-73. Epub 2006 Jan 6. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Binder
- General Function
- Retinol-binding protein that mediates retinol transport in blood plasma (PubMed:5541771). Delivers retinol from the liver stores to the peripheral tissues (Probable). Transfers the bound all-trans retinol to STRA6, that then facilitates retinol transport across the cell membrane (PubMed:22665496)
- Specific Function
- retinal binding
- Gene Name
- RBP4
- Uniprot ID
- P02753
- Uniprot Name
- Retinol-binding protein 4
- Molecular Weight
- 23009.8 Da
References
- Breustedt DA, Schonfeld DL, Skerra A: Comparative ligand-binding analysis of ten human lipocalins. Biochim Biophys Acta. 2006 Feb;1764(2):161-73. Epub 2006 Jan 6. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Upregulator
- General Function
- Kinase that plays a key role in regulation of glucose and fatty acid metabolism and homeostasis via phosphorylation of the pyruvate dehydrogenase subunits PDHA1 and PDHA2. This inhibits pyruvate dehydrogenase activity, and thereby regulates metabolite flux through the tricarboxylic acid cycle, down-regulates aerobic respiration and inhibits the formation of acetyl-coenzyme A from pyruvate. Inhibition of pyruvate dehydrogenase decreases glucose utilization and increases fat metabolism in response to prolonged fasting and starvation. Plays an important role in maintaining normal blood glucose levels under starvation, and is involved in the insulin signaling cascade. Via its regulation of pyruvate dehydrogenase activity, plays an important role in maintaining normal blood pH and in preventing the accumulation of ketone bodies under starvation. In the fed state, mediates cellular responses to glucose levels and to a high-fat diet. Regulates both fatty acid oxidation and de novo fatty acid biosynthesis. Plays a role in the generation of reactive oxygen species. Protects detached epithelial cells against anoikis. Plays a role in cell proliferation via its role in regulating carbohydrate and fatty acid metabolism
- Specific Function
- ATP binding
- Gene Name
- PDK4
- Uniprot ID
- Q16654
- Uniprot Name
- [Pyruvate dehydrogenase (acetyl-transferring)] kinase isozyme 4, mitochondrial
- Molecular Weight
- 46468.79 Da
References
- Kwon HS, Huang B, Ho Jeoung N, Wu P, Steussy CN, Harris RA: Retinoic acids and trichostatin A (TSA), a histone deacetylase inhibitor, induce human pyruvate dehydrogenase kinase 4 (PDK4) gene expression. Biochim Biophys Acta. 2006 Mar-Apr;1759(3-4):141-51. Epub 2006 Apr 27. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Downregulator
- General Function
- Not Available
- Specific Function
- Not Available
- Gene Name
- Not Available
- Uniprot ID
- Q14081
- Uniprot Name
- Carcinoembryonic antigen
- Molecular Weight
- 4903.595 Da
References
- Friedman J, Seger M, Levinsky H, Allalouf D: Modulation of carcinoembryonic antigen release by HT-29 colon carcinoma line in the presence of different agents. Experientia. 1987 Oct 15;43(10):1121-2. doi: 10.1007/BF01956058. [Article]
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- A cytochrome P450 monooxygenase involved in the metabolism of sterols, steroid hormones, retinoids and fatty acids (PubMed:10681376, PubMed:11093772, PubMed:11555828, PubMed:12865317, PubMed:14559847, PubMed:15373842, PubMed:15764715, PubMed:19965576, PubMed:20702771, PubMed:21490593, PubMed:21576599). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase). Catalyzes the hydroxylation of carbon-hydrogen bonds (PubMed:12865317, PubMed:14559847, PubMed:15373842, PubMed:15764715, PubMed:21490593, PubMed:21576599, PubMed:2732228). Exhibits high catalytic activity for the formation of hydroxyestrogens from estrone (E1) and 17beta-estradiol (E2), namely 2-hydroxy E1 and E2, as well as D-ring hydroxylated E1 and E2 at the C-16 position (PubMed:11555828, PubMed:12865317, PubMed:14559847). Plays a role in the metabolism of androgens, particularly in oxidative deactivation of testosterone (PubMed:15373842, PubMed:15764715, PubMed:22773874, PubMed:2732228). Metabolizes testosterone to less biologically active 2beta- and 6beta-hydroxytestosterones (PubMed:15373842, PubMed:15764715, PubMed:2732228). Contributes to the formation of hydroxycholesterols (oxysterols), particularly A-ring hydroxylated cholesterol at the C-4beta position, and side chain hydroxylated cholesterol at the C-25 position, likely contributing to cholesterol degradation and bile acid biosynthesis (PubMed:21576599). Catalyzes bisallylic hydroxylation of polyunsaturated fatty acids (PUFA) (PubMed:9435160). Catalyzes the epoxidation of double bonds of PUFA with a preference for the last double bond (PubMed:19965576). Metabolizes endocannabinoid arachidonoylethanolamide (anandamide) to 8,9-, 11,12-, and 14,15-epoxyeicosatrienoic acid ethanolamides (EpETrE-EAs), potentially modulating endocannabinoid system signaling (PubMed:20702771). Plays a role in the metabolism of retinoids. Displays high catalytic activity for oxidation of all-trans-retinol to all-trans-retinal, a rate-limiting step for the biosynthesis of all-trans-retinoic acid (atRA) (PubMed:10681376). Further metabolizes atRA toward 4-hydroxyretinoate and may play a role in hepatic atRA clearance (PubMed:11093772). Responsible for oxidative metabolism of xenobiotics. Acts as a 2-exo-monooxygenase for plant lipid 1,8-cineole (eucalyptol) (PubMed:11159812). Metabolizes the majority of the administered drugs. Catalyzes sulfoxidation of the anthelmintics albendazole and fenbendazole (PubMed:10759686). Hydroxylates antimalarial drug quinine (PubMed:8968357). Acts as a 1,4-cineole 2-exo-monooxygenase (PubMed:11695850). Also involved in vitamin D catabolism and calcium homeostasis. Catalyzes the inactivation of the active hormone calcitriol (1-alpha,25-dihydroxyvitamin D(3)) (PubMed:29461981)
- Specific Function
- 1,8-cineole 2-exo-monooxygenase activity
- Gene Name
- CYP3A4
- Uniprot ID
- P08684
- Uniprot Name
- Cytochrome P450 3A4
- Molecular Weight
- 57342.67 Da
References
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- Substrate
- General Function
- A cytochrome P450 monooxygenase involved in the metabolism of steroid hormones and vitamins (PubMed:10681376, PubMed:11093772, PubMed:12865317, PubMed:2732228). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase). Catalyzes the hydroxylation of carbon-hydrogen bonds (PubMed:10681376, PubMed:11093772, PubMed:12865317, PubMed:2732228). Exhibits high catalytic activity for the formation of catechol estrogens from 17beta-estradiol (E2) and estrone (E1), namely 2-hydroxy E1 and E2 (PubMed:12865317). Catalyzes 6beta-hydroxylation of the steroid hormones testosterone, progesterone, and androstenedione (PubMed:2732228). Catalyzes the oxidative conversion of all-trans-retinol to all-trans-retinal, a rate-limiting step for the biosynthesis of all-trans-retinoic acid (atRA) (PubMed:10681376). Further metabolizes all trans-retinoic acid (atRA) to 4-hydroxyretinoate and may play a role in hepatic atRA clearance (PubMed:11093772). Also involved in the oxidative metabolism of xenobiotics, including calcium channel blocking drug nifedipine and immunosuppressive drug cyclosporine (PubMed:2732228)
- Specific Function
- aromatase activity
- Gene Name
- CYP3A5
- Uniprot ID
- P20815
- Uniprot Name
- Cytochrome P450 3A5
- Molecular Weight
- 57108.065 Da
References
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- A cytochrome P450 monooxygenase involved in the metabolism of steroid hormones and vitamins during embryogenesis (PubMed:11093772, PubMed:12865317, PubMed:14559847, PubMed:17178770, PubMed:9555064). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase) (PubMed:11093772, PubMed:12865317, PubMed:14559847, PubMed:17178770, PubMed:9555064). Catalyzes the hydroxylation of carbon-hydrogen bonds. Metabolizes 3beta-hydroxyandrost-5-en-17-one (dehydroepiandrosterone, DHEA), a precursor in the biosynthesis of androgen and estrogen steroid hormones (PubMed:17178770, PubMed:9555064). Exhibits high catalytic activity for the formation of hydroxyestrogens from estrone (E1), particularly D-ring hydroxylated estrone at the C16-alpha position (PubMed:12865317, PubMed:14559847). Mainly hydroxylates all trans-retinoic acid (atRA) to 4-hydroxyretinoate and may play a role in atRA clearance during fetal development (PubMed:11093772). Also involved in the oxidative metabolism of xenobiotics including anticonvulsants (PubMed:9555064)
- Specific Function
- all-trans retinoic acid 18-hydroxylase activity
- Gene Name
- CYP3A7
- Uniprot ID
- P24462
- Uniprot Name
- Cytochrome P450 3A7
- Molecular Weight
- 57469.95 Da
References
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- A cytochrome P450 monooxygenase involved in the metabolism of endocannabinoids and steroids (PubMed:12865317, PubMed:21289075). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase). Catalyzes the epoxidation of double bonds of arachidonoylethanolamide (anandamide) to 8,9-, 11,12-, and 14,15-epoxyeicosatrienoic acid ethanolamides (EpETrE-EAs), potentially modulating endocannabinoid system signaling (PubMed:21289075). Hydroxylates steroid hormones, including testosterone at C-16 and estrogens at C-2 (PubMed:12865317, PubMed:21289075). Plays a role in the oxidative metabolism of xenobiotics, including plant lipids and drugs (PubMed:11695850, PubMed:22909231). Acts as a 1,4-cineole 2-exo-monooxygenase (PubMed:11695850)
- Specific Function
- anandamide 11,12 epoxidase activity
- Gene Name
- CYP2B6
- Uniprot ID
- P20813
- Uniprot Name
- Cytochrome P450 2B6
- Molecular Weight
- 56277.81 Da
References
- Marill J, Cresteil T, Lanotte M, Chabot GG: Identification of human cytochrome P450s involved in the formation of all-trans-retinoic acid principal metabolites. Mol Pharmacol. 2000 Dec;58(6):1341-8. [Article]
- Rendic S: Summary of information on human CYP enzymes: human P450 metabolism data. Drug Metab Rev. 2002 Feb-May;34(1-2):83-448. [Article]
- FDA Approved Drug Products: VESANOID (tretinoin) capsules, for oral use [Link]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- A cytochrome P450 monooxygenase involved in the metabolism of various endogenous substrates, including fatty acids, steroid hormones and vitamins (PubMed:11093772, PubMed:14559847, PubMed:15766564, PubMed:19965576, PubMed:7574697). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase) (PubMed:11093772, PubMed:14559847, PubMed:15766564, PubMed:19965576, PubMed:7574697). Primarily catalyzes the epoxidation of double bonds of polyunsaturated fatty acids (PUFA) with a preference for the last double bond (PubMed:15766564, PubMed:19965576, PubMed:7574697). Catalyzes the hydroxylation of carbon-hydrogen bonds. Metabolizes all trans-retinoic acid toward its 4-hydroxylated form (PubMed:11093772). Displays 16-alpha hydroxylase activity toward estrogen steroid hormones, 17beta-estradiol (E2) and estrone (E1) (PubMed:14559847). Plays a role in the oxidative metabolism of xenobiotics. It is the principal enzyme responsible for the metabolism of the anti-cancer drug paclitaxel (taxol) (PubMed:26427316)
- Specific Function
- arachidonic acid epoxygenase activity
- Gene Name
- CYP2C8
- Uniprot ID
- P10632
- Uniprot Name
- Cytochrome P450 2C8
- Molecular Weight
- 55824.275 Da
References
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- A cytochrome P450 monooxygenase involved in the metabolism of various endogenous substrates, including fatty acids and steroids (PubMed:12865317, PubMed:15766564, PubMed:19965576, PubMed:21576599, PubMed:7574697, PubMed:9435160, PubMed:9866708). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase) (PubMed:12865317, PubMed:15766564, PubMed:19965576, PubMed:21576599, PubMed:7574697, PubMed:9435160, PubMed:9866708). Catalyzes the epoxidation of double bonds of polyunsaturated fatty acids (PUFA) (PubMed:15766564, PubMed:19965576, PubMed:7574697, PubMed:9866708). Catalyzes the hydroxylation of carbon-hydrogen bonds. Metabolizes cholesterol toward 25-hydroxycholesterol, a physiological regulator of cellular cholesterol homeostasis (PubMed:21576599). Exhibits low catalytic activity for the formation of catechol estrogens from 17beta-estradiol (E2) and estrone (E1), namely 2-hydroxy E1 and E2 (PubMed:12865317). Catalyzes bisallylic hydroxylation and hydroxylation with double-bond migration of polyunsaturated fatty acids (PUFA) (PubMed:9435160, PubMed:9866708). Also metabolizes plant monoterpenes such as limonene. Oxygenates (R)- and (S)-limonene to produce carveol and perillyl alcohol (PubMed:11950794). Contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenytoin, tolbutamide and losartan (PubMed:25994031)
- Specific Function
- (R)-limonene 6-monooxygenase activity
- Gene Name
- CYP2C9
- Uniprot ID
- P11712
- Uniprot Name
- Cytochrome P450 2C9
- Molecular Weight
- 55627.365 Da
References
- Marill J, Cresteil T, Lanotte M, Chabot GG: Identification of human cytochrome P450s involved in the formation of all-trans-retinoic acid principal metabolites. Mol Pharmacol. 2000 Dec;58(6):1341-8. [Article]
- Rendic S: Summary of information on human CYP enzymes: human P450 metabolism data. Drug Metab Rev. 2002 Feb-May;34(1-2):83-448. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Exhibits a high coumarin 7-hydroxylase activity. Can act in the hydroxylation of the anti-cancer drugs cyclophosphamide and ifosphamide. Competent in the metabolic activation of aflatoxin B1. Constitutes the major nicotine C-oxidase. Acts as a 1,4-cineole 2-exo-monooxygenase. Possesses low phenacetin O-deethylation activity
- Specific Function
- arachidonic acid epoxygenase activity
- Gene Name
- CYP2A6
- Uniprot ID
- P11509
- Uniprot Name
- Cytochrome P450 2A6
- Molecular Weight
- 56517.005 Da
References
- Marill J, Cresteil T, Lanotte M, Chabot GG: Identification of human cytochrome P450s involved in the formation of all-trans-retinoic acid principal metabolites. Mol Pharmacol. 2000 Dec;58(6):1341-8. [Article]
- Rendic S: Summary of information on human CYP enzymes: human P450 metabolism data. Drug Metab Rev. 2002 Feb-May;34(1-2):83-448. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- A cytochrome P450 monooxygenase involved in retinoid metabolism. Hydroxylates all trans-retinoic acid (atRA) to 4-hydroxyretinoate and may modulate atRA signaling and clearance. Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (CPR; NADPH-ferrihemoprotein reductase)
- Specific Function
- arachidonic acid epoxygenase activity
- Gene Name
- CYP2C18
- Uniprot ID
- P33260
- Uniprot Name
- Cytochrome P450 2C18
- Molecular Weight
- 55710.075 Da
References
- Marill J, Cresteil T, Lanotte M, Chabot GG: Identification of human cytochrome P450s involved in the formation of all-trans-retinoic acid principal metabolites. Mol Pharmacol. 2000 Dec;58(6):1341-8. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- A cytochrome P450 monooxygenase involved in the metabolism of various endogenous substrates, including fatty acids, steroid hormones and vitamins (PubMed:10681376, PubMed:11555828, PubMed:12865317, PubMed:14559847, PubMed:15041462, PubMed:15805301, PubMed:18577768, PubMed:19965576, PubMed:20972997). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase) (PubMed:10681376, PubMed:11555828, PubMed:12865317, PubMed:14559847, PubMed:15041462, PubMed:15805301, PubMed:18577768, PubMed:19965576, PubMed:20972997). Catalyzes the hydroxylation of carbon-hydrogen bonds. Exhibits high catalytic activity for the formation of hydroxyestrogens from estrone (E1) and 17beta-estradiol (E2), namely 2-hydroxy E1 and E2, as well as D-ring hydroxylated E1 and E2 at the C15-alpha and C16-alpha positions (PubMed:11555828, PubMed:12865317, PubMed:14559847, PubMed:15805301). Displays different regioselectivities for polyunsaturated fatty acids (PUFA) hydroxylation (PubMed:15041462, PubMed:18577768). Catalyzes the epoxidation of double bonds of certain PUFA (PubMed:15041462, PubMed:19965576, PubMed:20972997). Converts arachidonic acid toward epoxyeicosatrienoic acid (EET) regioisomers, 8,9-, 11,12-, and 14,15-EET, that function as lipid mediators in the vascular system (PubMed:20972997). Displays an absolute stereoselectivity in the epoxidation of eicosapentaenoic acid (EPA) producing the 17(R),18(S) enantiomer (PubMed:15041462). May play an important role in all-trans retinoic acid biosynthesis in extrahepatic tissues. Catalyzes two successive oxidative transformation of all-trans retinol to all-trans retinal and then to the active form all-trans retinoic acid (PubMed:10681376). May also participate in eicosanoids metabolism by converting hydroperoxide species into oxo metabolites (lipoxygenase-like reaction, NADPH-independent) (PubMed:21068195)
- Specific Function
- arachidonic acid monooxygenase activity
- Gene Name
- CYP1A1
- Uniprot ID
- P04798
- Uniprot Name
- Cytochrome P450 1A1
- Molecular Weight
- 58164.815 Da
References
- Marill J, Cresteil T, Lanotte M, Chabot GG: Identification of human cytochrome P450s involved in the formation of all-trans-retinoic acid principal metabolites. Mol Pharmacol. 2000 Dec;58(6):1341-8. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- A cytochrome P450 monooxygenase involved in the metabolism of fatty acids and their oxygenated derivatives (oxylipins) (PubMed:10553002, PubMed:10660572, PubMed:15611369, PubMed:1739747, PubMed:7679927, PubMed:8914854). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (CPR; NADPH-ferrihemoprotein reductase) (PubMed:10553002, PubMed:10660572, PubMed:15611369, PubMed:1739747, PubMed:7679927, PubMed:8914854). Catalyzes predominantly the oxidation of the terminal carbon (omega-oxidation) of saturated and unsaturated fatty acids, the catalytic efficiency decreasing in the following order: dodecanoic > tetradecanoic > (9Z)-octadecenoic > (9Z,12Z)-octadecadienoic > hexadecanoic acid (PubMed:10553002, PubMed:10660572). Acts as a major omega-hydroxylase for dodecanoic (lauric) acid in liver (PubMed:15611369, PubMed:1739747, PubMed:7679927, PubMed:8914854). Participates in omega-hydroxylation of (5Z,8Z,11Z,14Z)-eicosatetraenoic acid (arachidonate) to 20-hydroxyeicosatetraenoic acid (20-HETE), a signaling molecule acting both as vasoconstrictive and natriuretic with overall effect on arterial blood pressure (PubMed:10620324, PubMed:10660572, PubMed:15611369). Can also catalyze the oxidation of the penultimate carbon (omega-1 oxidation) of fatty acids with lower efficiency (PubMed:7679927). May contribute to the degradation of saturated very long-chain fatty acids (VLCFAs) such as docosanoic acid, by catalyzing successive omega-oxidations to the corresponding dicarboxylic acid, thereby initiating chain shortening (PubMed:18182499). Omega-hydroxylates (9R,10S)-epoxy-octadecanoate stereoisomer (PubMed:15145985). Plays a minor role in omega-oxidation of long-chain 3-hydroxy fatty acids (PubMed:18065749). Has little activity toward prostaglandins A1 and E1 (PubMed:7679927)
- Specific Function
- alkane 1-monooxygenase activity
- Gene Name
- CYP4A11
- Uniprot ID
- Q02928
- Uniprot Name
- Cytochrome P450 4A11
- Molecular Weight
- 59347.31 Da
References
- Marill J, Cresteil T, Lanotte M, Chabot GG: Identification of human cytochrome P450s involved in the formation of all-trans-retinoic acid principal metabolites. Mol Pharmacol. 2000 Dec;58(6):1341-8. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- UDP-glucuronosyltransferase (UGT) that catalyzes phase II biotransformation reactions in which lipophilic substrates are conjugated with glucuronic acid to increase the metabolite's water solubility, thereby facilitating excretion into either the urine or bile (PubMed:10702251, PubMed:15470161, PubMed:15472229, PubMed:17442341, PubMed:18674515, PubMed:18719240, PubMed:19022937, PubMed:23288867, PubMed:23756265, PubMed:26220143). Essential for the elimination and detoxification of drugs, xenobiotics and endogenous compounds (PubMed:15470161, PubMed:18674515, PubMed:23756265). Catalyzes the glucuronidation of endogenous steroid hormones such as androgens (epitestosterone, androsterone) and estrogens (estradiol, epiestradiol, estriol, catechol estrogens) (PubMed:15472229, PubMed:17442341, PubMed:18719240, PubMed:19022937, PubMed:2159463, PubMed:23288867, PubMed:26220143). Also regulates the levels of retinoic acid, a major metabolite of vitamin A involved in apoptosis, cellular growth and differentiation, and embryonic development (PubMed:10702251). Contributes to bile acid (BA) detoxification by catalyzing the glucuronidation of BA substrates, which are natural detergents for dietary lipids absorption (PubMed:23756265). Involved in the glucuronidation of the AGTR1 angiotensin receptor antagonist losartan, caderastan and zolarsatan, drugs which can inhibit the effect of angiotensin II (PubMed:18674515). Also metabolizes mycophenolate, an immunosuppressive agent (PubMed:15470161)
- Specific Function
- glucuronosyltransferase activity
- Gene Name
- UGT2B7
- Uniprot ID
- P16662
- Uniprot Name
- UDP-glucuronosyltransferase 2B7
- Molecular Weight
- 60720.15 Da
References
- FDA Approved Drug Products: VESANOID (tretinoin) capsules, for oral use [Link]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- A cytochrome P450 monooxygenase involved in the metabolism of fatty acids (PubMed:10553002, PubMed:18577768). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase) (PubMed:10553002, PubMed:18577768). Catalyzes the hydroxylation of carbon-hydrogen bonds. Hydroxylates fatty acids specifically at the omega-1 position displaying the highest catalytic activity for saturated fatty acids (PubMed:10553002, PubMed:18577768). May be involved in the oxidative metabolism of xenobiotics (Probable)
- Specific Function
- 4-nitrophenol 2-monooxygenase activity
- Gene Name
- CYP2E1
- Uniprot ID
- P05181
- Uniprot Name
- Cytochrome P450 2E1
- Molecular Weight
- 56848.42 Da
References
- FDA Approved Drug Products: VESANOID (tretinoin) capsules, for oral use [Link]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- A cytochrome P450 monooxygenase involved in the metabolism of retinoates (RAs), the active metabolites of vitamin A, and critical signaling molecules in animals (PubMed:22020119, PubMed:9228017, PubMed:9716180). RAs exist as at least four different isomers: all-trans-RA (atRA), 9-cis-RA, 13-cis-RA, and 9,13-dicis-RA, where atRA is considered to be the biologically active isomer, although 9-cis-RA and 13-cis-RA also have activity (Probable). Catalyzes the hydroxylation of atRA primarily at C-4 and C-18, thereby contributing to the regulation of atRA homeostasis and signaling (PubMed:22020119, PubMed:9228017, PubMed:9716180). Hydroxylation of atRA limits its biological activity and initiates a degradative process leading to its eventual elimination (Probable). Involved in the convertion of atRA to all-trans-4-oxo-RA. Able to metabolize other RAs such as 9-cis, 13-cis and 9,13-di-cis RA (By similarity) (PubMed:9228017). Can oxidize all-trans-13,14-dihydroretinoate (DRA) to metabolites which could include all-trans-4-oxo-DRA, all-trans-4-hydroxy-DRA, all-trans-5,8-epoxy-DRA, and all-trans-18-hydroxy-DRA (By similarity). May play a role in the oxidative metabolism of xenobiotics such as tazarotenic acid (PubMed:26937021)
- Specific Function
- all-trans retinoic acid 18-hydroxylase activity
- Gene Name
- CYP26A1
- Uniprot ID
- O43174
- Uniprot Name
- Cytochrome P450 26A1
- Molecular Weight
- 56198.11 Da
References
- Heise R, Mey J, Neis MM, Marquardt Y, Joussen S, Ott H, Wiederholt T, Kurschat P, Megahed M, Bickers DR, Merk HF, Baron JM: Skin retinoid concentrations are modulated by CYP26AI expression restricted to basal keratinocytes in normal human skin and differentiated 3D skin models. J Invest Dermatol. 2006 Nov;126(11):2473-80. doi: 10.1038/sj.jid.5700432. Epub 2006 Jun 15. [Article]
- Lee SJ, Perera L, Coulter SJ, Mohrenweiser HW, Jetten A, Goldstein JA: The discovery of new coding alleles of human CYP26A1 that are potentially defective in the metabolism of all-trans retinoic acid and their assessment in a recombinant cDNA expression system. Pharmacogenet Genomics. 2007 Mar;17(3):169-80. doi: 10.1097/FPC.0b013e32801152d6. [Article]
Carriers
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Binder
- General Function
- Binds water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs (Probable). Its main function is the regulation of the colloidal osmotic pressure of blood (Probable). Major zinc transporter in plasma, typically binds about 80% of all plasma zinc (PubMed:19021548). Major calcium and magnesium transporter in plasma, binds approximately 45% of circulating calcium and magnesium in plasma (By similarity). Potentially has more than two calcium-binding sites and might additionally bind calcium in a non-specific manner (By similarity). The shared binding site between zinc and calcium at residue Asp-273 suggests a crosstalk between zinc and calcium transport in the blood (By similarity). The rank order of affinity is zinc > calcium > magnesium (By similarity). Binds to the bacterial siderophore enterobactin and inhibits enterobactin-mediated iron uptake of E.coli from ferric transferrin, and may thereby limit the utilization of iron and growth of enteric bacteria such as E.coli (PubMed:6234017). Does not prevent iron uptake by the bacterial siderophore aerobactin (PubMed:6234017)
- Specific Function
- antioxidant activity
- Gene Name
- ALB
- Uniprot ID
- P02768
- Uniprot Name
- Albumin
- Molecular Weight
- 69365.94 Da
References
- Maiti TK, Ghosh KS, Debnath J, Dasgupta S: Binding of all-trans retinoic acid to human serum albumin: fluorescence, FT-IR and circular dichroism studies. Int J Biol Macromol. 2006 May 30;38(3-5):197-202. Epub 2006 Mar 6. [Article]
- N'soukpoe-Kossi CN, Sedaghat-Herati R, Ragi C, Hotchandani S, Tajmir-Riahi HA: Retinol and retinoic acid bind human serum albumin: stability and structural features. Int J Biol Macromol. 2007 Apr 10;40(5):484-90. Epub 2006 Nov 24. [Article]
- Karnaukhova E: Interactions of human serum albumin with retinoic acid, retinal and retinyl acetate. Biochem Pharmacol. 2007 Mar 15;73(6):901-10. Epub 2006 Dec 2. [Article]
- Regazzi MB, Iacona I, Gervasutti C, Lazzarino M, Toma S: Clinical pharmacokinetics of tretinoin. Clin Pharmacokinet. 1997 May;32(5):382-402. doi: 10.2165/00003088-199732050-00004. [Article]
- FDA Approved Drug Products: VESANOID (tretinoin) capsules, for oral use [Link]
Transporters
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Cytosolic CRABPs may regulate the access of retinoic acid to the nuclear retinoic acid receptors
- Specific Function
- fatty acid binding
- Gene Name
- CRABP1
- Uniprot ID
- P29762
- Uniprot Name
- Cellular retinoic acid-binding protein 1
- Molecular Weight
- 15565.45 Da
References
- Hoegberg P, Schmidt CK, Fletcher N, Nilsson CB, Trossvik C, Gerlienke Schuur A, Brouwer A, Nau H, Ghyselinck NB, Chambon P, Hakansson H: Retinoid status and responsiveness to 2,3,7,8-tetrachlorodibenzo-p-dioxin (TCDD) in mice lacking retinoid binding protein or retinoid receptor forms. Chem Biol Interact. 2005 Sep 10;156(1):25-39. [Article]
- Donato LJ, Noy N: Fluorescence-based technique for analyzing retinoic acid. Methods Mol Biol. 2010;652:177-87. doi: 10.1007/978-1-60327-325-1_10. [Article]
- Napoli JL: Functions of Intracellular Retinoid Binding-Proteins. Subcell Biochem. 2016;81:21-76. doi: 10.1007/978-94-024-0945-1_2. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Transports retinoic acid to the nucleus. Regulates the access of retinoic acid to the nuclear retinoic acid receptors
- Specific Function
- cyclin binding
- Gene Name
- CRABP2
- Uniprot ID
- P29373
- Uniprot Name
- Cellular retinoic acid-binding protein 2
- Molecular Weight
- 15692.925 Da
References
- Hoegberg P, Schmidt CK, Fletcher N, Nilsson CB, Trossvik C, Gerlienke Schuur A, Brouwer A, Nau H, Ghyselinck NB, Chambon P, Hakansson H: Retinoid status and responsiveness to 2,3,7,8-tetrachlorodibenzo-p-dioxin (TCDD) in mice lacking retinoid binding protein or retinoid receptor forms. Chem Biol Interact. 2005 Sep 10;156(1):25-39. [Article]
- Ohnishi K: PML-RARalpha inhibitors (ATRA, tamibaroten, arsenic troxide) for acute promyelocytic leukemia. Int J Clin Oncol. 2007 Oct;12(5):313-7. Epub 2007 Oct 22. [Article]
- Donato LJ, Noy N: Fluorescence-based technique for analyzing retinoic acid. Methods Mol Biol. 2010;652:177-87. doi: 10.1007/978-1-60327-325-1_10. [Article]
- Napoli JL: Functions of Intracellular Retinoid Binding-Proteins. Subcell Biochem. 2016;81:21-76. doi: 10.1007/978-94-024-0945-1_2. [Article]
Drug created at June 13, 2005 13:24 / Updated at October 29, 2024 18:04