Identification
- Summary
Tretinoin is a vitamin A derivative used to treat acne vulgaris, certain types of promyelocytic leukemia, and fine wrinkles.
- Brand Names
- Altreno, Atralin, Avita, Biacna, Refissa, Renova, Retin-A, Stieva-A, Tri-luma, 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). Retinoids such as tretinoin are important regulators of cell reproduction, proliferation, and differentiation and are used to treat acne and photodamaged skin and to manage keratinization disorders such as ichthyosis and keratosis follicularis. Tretinoin also represents the class of anticancer drugs called differentiating agents and is used in the treatment of acute promyelocytic leukemia (APL).
- Type
- Small Molecule
- Groups
- Approved, Investigational, Nutraceutical
- Structure
Structure for Tretinoin (DB00755)
- 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
For the the induction of remission in patients with acute promyelocytic leukemia (APL), French-American-British (FAB) classification M3 (including the M3 variant); For the topical treatment of acne vulgaris, flat warts and other skin conditions (psoriasis, ichthyosis congenita, icthyosis vulgaris, lamellar icthyosis, keratosis palmaris et plantaris, epidermolytic hyperkeratosis, senile comedones, senile keratosis, keratosis follicularis (Darier's disease), and basal cell carcinomas.); For palliative therapy to improve fine wrinkling, mottled hyperpigmentation, roughness associated with photodamage.
Tretinoin is also indicated in combination with benzoyl peroxide for the treatment of acne vulgaris in patients aged nine years and older.6
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- Acne Vulgaris
- Alopecia
- Cornification and dystrophic skin disorders
- FAB classification M3 Acute promyelocytic leukemia
- Fine Wrinkles
- Skin hyperpigmentation
- Solar Lentigines
- Keratinization disorders of the feet
- Keratinization disorders of the hand
- Moderate Melasma
- Mottled hyperpigmentation
- Severe Melasma
- Severe, recalcitrant Cystic acne
- Tactile roughness of facial skin
- Contraindications & Blackbox Warnings
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Tretinoin, also known as all-trans-retinoic acid (ATRA), is a naturally occurring derivative of vitamin A (retinol). Retinoids such as tretinoin are important regulators of cell reproduction, proliferation, and differentiation and are used to treat acne and photodamaged skin and to manage keratinization disorders such as ichthyosis and keratosis follicularis. Tretinoin also represents the class of anticancer drugs called differentiating agents and is used in the treatment of acute promyelocytic leukemia (APL).
- Mechanism of action
Tretinoin binds to alpha, beta, and gamma retinoic acid receptors (RARs). RAR-alpha and RAR-beta have been associated with the development of acute promyelocytic leukemia and squamous cell cancers, respectively. RAR-gamma is associated with retinoid effects on mucocutaneous tissues and bone. Although the exact mechanism of action of tretinoin is unknown, current evidence suggests that the effectiveness of tretinoin in acne is due primarily to its ability to modify abnormal follicular keratinization. Comedones form in follicles with an excess of keratinized epithelial cells. Tretinoin promotes detachment of cornified cells and the enhanced shedding of corneocytes from the follicle. By increasing the mitotic activity of follicular epithelia, tretinoin also increases the turnover rate of thin, loosely-adherent corneocytes. Through these actions, the comedo contents are extruded and the formation of the microcomedo, the precursor lesion of acne vulgaris, is reduced. Tretinoin is not a cytolytic agent but instead induces cytodifferentiation and decreased proliferation of APL cells in culture and in vivo. When Tretinoin is given systemically to APL patients, tretinoin treatment produces an 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 (CR). The exact mechanism of action of tretinoin in APL is unknown.
Target Actions Organism ARetinoic acid receptor RXR-beta agonistHumans ARetinoic acid receptor RXR-gamma agonistHumans ARetinoic acid receptor gamma agonistHumans URetinal dehydrogenase 1 Not Available Humans URetinoic acid-induced protein 3 Not Available Humans URetinal dehydrogenase 2 Not Available Humans URetinoic acid receptor responder protein 1 agonistHumans URetinoic acid receptor alpha Not Available Humans URetinoic acid receptor beta Not Available Humans ULipocalin-1 Not Available Humans UOdorant-binding protein 2a Not Available Humans URetinol-binding protein 4 Not Available Humans U[Pyruvate dehydrogenase [lipoamide]] kinase isozyme 4, mitochondrial Not Available Humans URetinoic acid receptor RXR-alpha Not Available Humans UCytochrome P450 26A1 Not Available Humans UCytochrome P450 26B1 Not Available Humans UCytochrome P450 26C1 Not Available Humans UHematopoietic prostaglandin D synthase Not Available Humans - Absorption
Tretinoin applied topically is typically between 1-31% absorbed.
When formulated with benzoyl peroxide, the extent of absorption was examined after 14 days of once-daily application of 1.9 g of the combination product. On Day 14, at steady-state, the mean Cmax for tretinoin and the metabolites 4-keto 13-cis RA and 13-cis RA were 0.15-0.19, 0.27-0.34, and 0.13-0.28 ng/mL, depending on the patient age group. 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.6
- Volume of distribution
Not Available
- Protein binding
> 95%
- Metabolism
Hepatic
Hover over products below to view reaction partners
- Route of elimination
Not Available
- Half-life
0.5-2 hours
- Clearance
Not Available
- Adverse Effects
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Not Available
- 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. Abiraterone The metabolism of Tretinoin can be decreased when combined with Abiraterone. Acalabrutinib The metabolism of Tretinoin can be decreased when combined with Acalabrutinib. Acebutolol The risk or severity of adverse effects can be increased when Tretinoin is combined with Acebutolol. Acenocoumarol The metabolism of Acenocoumarol can be decreased when combined with Tretinoin. Acetaminophen The metabolism of Tretinoin can be decreased when combined with Acetaminophen. Acetohexamide The metabolism of Tretinoin can be decreased when combined with Acetohexamide. Acetyl sulfisoxazole The metabolism of Tretinoin can be decreased when combined with Acetyl sulfisoxazole. Acetyldigitoxin Acetyldigitoxin may decrease the cardiotoxic activities of Tretinoin. 
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- Take with food. Tretinoin absorption may be increased by co-administration with food.
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 0.5 mg/1g Topical Bausch Health US, LLC 2018-08-24 Not applicable US 
Altreno Lotion 0.05 % w/w Topical Bausch Health, Canada Inc. Not applicable Not applicable Canada 
Atralin Gel 0.05 g/100g Topical Bausch Health US, LLC 2007-07-26 Not applicable US Avita Cream 0.25 mg/1g Topical Mylan Bertek Pharmaceuticals 2015-11-01 2015-11-19 US Avita Gel 0.25 mg/1g Topical BERTEK PHARMACEUTICALS INC. 2007-04-27 2007-04-27 US Avita Gel 0.25 mg/1g Topical Mylan Pharmaceuticals Inc. 1998-03-18 Not applicable US Avita Cream 0.25 mg/1g Topical Mylan Pharmaceuticals Inc. 1997-06-01 Not applicable US Rejuva-A Cream 0.025 % Topical Glaxosmithkline Inc 1997-11-04 2014-05-01 Canada Renova Cream 0.05 g/100g Topical Physicians Total Care, Inc. 1996-02-01 2011-05-31 US Renova Cream 0.05 % Topical Valeant Canada Lp Valeant Canada S.E.C. 1995-12-31 2014-07-30 Canada - Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Jamp Tretinoin Capsule 10 mg Oral Jamp Pharma Corporation Not applicable 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 Coria Laboratories 2011-02-01 2016-05-01 US Refissa Cream 0.5 mg/1g Topical Spear Dermatology Products 2009-06-17 2014-07-31 US Refissa Cream 0.5 mg/1g Topical Obagi Medical Products, Inc. 2010-02-22 2016-05-01 US Refissa Cream 0.5 mg/1g Topical Suneva Medical, Inc. 2009-06-17 Not applicable US Refissa Tretinoin (Emollient) Cream 0.5 mg/1g Topical ZO Skin Health, Inc. 2017-04-03 Not applicable US Tretin-X Cream 1 mg/1g Topical Triax Pharmaceuticals, LLC 2010-08-01 2015-07-31 US Tretin-X Cream 1 mg/1g Topical Triax Pharmaceuticals, LLC 2006-04-01 2015-07-31 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 4D ® CREMA Tretinoin (0.05 g) + Hydroquinone (4 g) + Mometasone furoate (0.1 g) Cream Topical LABORATORIOS LEGRAND S.A. 2010-06-01 Not applicable Colombia 
AKNEMYCIN PLUS SOLUTION Tretinoin (0.025 g/100g) + Erythromycin (4 g/100g) Solution Topical ZUELLIG PHARMA PTE. LTD. 2000-02-04 Not applicable Singapore Biacna Topical Gel Tretinoin (0.025 % w/w) + Clindamycin phosphate (1.2 % w/w) Gel Topical Bausch Health, Canada Inc. 2011-05-16 Not applicable Canada Clindamycin Phosphate 1.2% and Tretinoin 0.025% Tretinoin (0.25 mg/1g) + Clindamycin phosphate (12 mg/1g) Gel Topical Oceanside Pharmaceuticals 2020-08-04 Not applicable US Clindamycin Phosphate and Tretinion Tretinoin (0.25 mg/1g) + Clindamycin phosphate (10 mg/1g) Gel Topical Prasco, Laboratories 2018-06-28 Not applicable US Clindamycin Phosphate and Tretinoin Tretinoin (0.25 mg/1g) + Clindamycin phosphate (12 mg/1g) Gel Topical Actavis Pharma, Inc. 2016-07-05 Not applicable US CLİNDATRE 12 MG/G + 0,25 MG/G JEL, 30 GRAM Tretinoin (0.25 mg/g) + Clindamycin phosphate (12 mg/g) Gel Topical ASSOS İLAÇ KİMYA GIDA ÜRÜNLERİ ÜRETİM VE TİC. A.Ş. 2020-08-14 Not applicable Turkey 
Derma Lightening Tretinoin (0.075 mg/30g) + Hydroquinone (6 mg/30g) Cream Topical Pella Pharmaceuticals Co. ltd 2014-12-24 Not applicable US Dermawerx Zmt Pak Tretinoin (0.25 mg/1g) + Menthol (0.44 g/100g) + Zinc oxide (20.6 g/100g) Kit Topical Patchwerx Labs, Inc. 2015-09-08 Not applicable US ERITRETIN 30 GR JEL Tretinoin (0.025 %) + Erythromycin (4 %) Gel Topical LABORATOIRES BAILLEUL İLAÇ SAN.VE TİC. A.Ş. 2020-08-14 Not applicable Turkey - 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 011220 Niacinamide 2% / Spironolactone 5% / Tretinoin 0.05% Tretinoin (0.05 g/100g) + Nicotinamide (2 g/100g) + Spironolactone (5 g/100g) Gel Topical Sincerus Florida, LLC 2020-07-02 Not applicable US 141016 Hydrocortisone 0.5% / Hydroquinone 4% / Tretinoin 0.025% Tretinoin (0.025 g/100g) + Hydrocortisone (0.5 g/100g) + Hydroquinone (4 g/100g) Emulsion Topical Sincerus Florida, LLC 2020-07-02 Not applicable US 141017 Hydrocortisone 0.5% / Hydroquinone 6% / Tretinoin 0.025% Tretinoin (0.025 g/100g) + Hydrocortisone (0.5 g/100g) + Hydroquinone (6 g/100g) Emulsion Topical Sincerus Florida, LLC 2020-07-02 Not applicable US 141060 Hydrocortisone 0.5% / Hydroquinone 4% / Tretinoin 0.025% Tretinoin (0.025 g/100g) + Hydrocortisone (0.5 g/100g) + Hydroquinone (4 g/100g) Emulsion Topical Sincerus Florida, LLC 2020-07-02 Not applicable US 141061 Hydrocortisone 0.5% / Hydroquinone 8% / Tretinoin 0.025% Tretinoin (0.025 g/100g) + Hydrocortisone (0.5 g/100g) + Hydroquinone (8 g/100g) Emulsion Topical Sincerus Florida, LLC 2020-07-02 Not applicable US
Categories
- ATC Codes
- D10AD51 — Tretinoin, combinations
- D10AD — Retinoids for topical use in acne
- D10A — ANTI-ACNE PREPARATIONS FOR TOPICAL USE
- D10 — ANTI-ACNE PREPARATIONS
- D — DERMATOLOGICALS
- L01XX — Other antineoplastic agents
- L01X — OTHER ANTINEOPLASTIC AGENTS
- L01 — ANTINEOPLASTIC AGENTS
- L — ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS
- Drug Categories
- 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 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 Topical Use in Acne
- Terpenes
- 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
- Huang ME, Ye YC, Chen SR, Chai JR, Lu JX, Zhoa L, Gu LJ, Wang ZY: Use of all-trans retinoic acid in the treatment of acute promyelocytic leukemia. Blood. 1988 Aug;72(2):567-72. [Article]
- Castaigne S, Chomienne C, Daniel MT, Ballerini P, Berger R, Fenaux P, Degos L: All-trans retinoic acid as a differentiation therapy for acute promyelocytic leukemia. I. Clinical results. Blood. 1990 Nov 1;76(9):1704-9. [Article]
- Sanz MA: Treatment of acute promyelocytic leukemia. Hematology Am Soc Hematol Educ Program. 2006:147-55. [Article]
- Mao JT, Goldin JG, Dermand J, Ibrahim G, Brown MS, Emerick A, McNitt-Gray MF, Gjertson DW, Estrada F, Tashkin DP, Roth MD: A pilot study of all-trans-retinoic acid for the treatment of human emphysema. Am J Respir Crit Care Med. 2002 Mar 1;165(5):718-23. [Article]
- Roth MD, Connett JE, D'Armiento JM, Foronjy RF, Friedman PJ, Goldin JG, Louis TA, Mao JT, Muindi JR, O'Connor GT, Ramsdell JW, Ries AL, Scharf SM, Schluger NW, Sciurba FC, Skeans MA, Walter RE, Wendt CH, Wise RA: Feasibility of retinoids for the treatment of emphysema study. Chest. 2006 Nov;130(5):1334-45. [Article]
- FDA Approved Drug Products: TWYNEO (tretinoin and benzoyl peroxide) topical cream [Link]
- External Links
- Human Metabolome Database
- HMDB0001852
- KEGG Drug
- D00094
- KEGG Compound
- C00777
- PubChem Compound
- 5538
- PubChem Substance
- 46504843
- ChemSpider
- 392618
- BindingDB
- 31883
- 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 11 more
- FDA label
- Download (42.8 KB)
- MSDS
- Download (29.1 KB)
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 4 Active Not Recruiting Treatment Acute Promyelocytic Leukemia (APL) 1 4 Active Not Recruiting Treatment Photodamaged Skin / Solar Elastosis 1 4 Completed Prevention Acne 1 4 Completed Treatment Acne 2 4 Completed Treatment Acne Vulgaris 9 4 Completed Treatment Acute Promyelocytic Leukemia (APL) 1 4 Completed Treatment Hyperpigmentation 1 4 Completed Treatment Melasma 2 4 Completed Treatment Striae Distensae / Treatments 1 4 Enrolling by Invitation Treatment Childhood Acute Promyelocytic Leukemia 1
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 0.1 % Cream Topical 0.5 MG/G Solution Topical 0.5 MG/ML Solution Topical 4 g/100g Lotion Topical 0.05 % w/w Lotion Topical 0.5 mg/1g Solution Topical 0.025 g Lotion Topical Kit Topical Cream Topical Solution Topical 100 mg Emulsion Topical Cream Cream Topical 0.05 g/100g Cream Topical 0.2 mg/1g Cream Topical 0.05 g Cream Topical 0.025 g Gel Topical 0.025 g Gel Topical 0.05 g Lotion Topical Cream Topical 0.1 mg/1g Gel Topical 0.01 % w/w Gel Topical 0.025 % w/w Liquid Topical 0.5 mg/1mL 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 Lotion Topical 0.05 g Lotion Topical 0.025 g Cream Topical 0.01 % Gel Topical 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 Topical 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 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, liquid filled Oral 10 mg/1 Capsule, gelatin coated Oral Capsule Oral Capsule Oral 10 mg Capsule, liquid filled Oral 10 mg Cream Topical 0.025 % Cream Topical 0.05 % Gel Topical 0.025 % Solution Topical Gel Topical 0.01 % Gel Topical 0.05 % 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 2010-12-30 2030-12-30 US US10420743 No 2018-07-12 2038-07-12 US US10653899 No 2010-12-30 2030-12-30 US US8617580 No 2008-02-03 2028-02-03 US
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 181 °C PhysProp water solubility <0.1 g/100 mL Not Available logP 6.30 HANSCH,C ET AL. (1995) - 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
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available
Targets
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Agonist
- General Function
- Zinc ion binding
- Specific 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 expressi...
- 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]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Agonist
- General Function
- Zinc ion binding
- Specific 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 expressi...
- 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]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Agonist
- General Function
- Zinc ion binding
- Specific 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 expressi...
- 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]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Retinal dehydrogenase activity
- Specific Function
- Binds free retinal and cellular retinol-binding protein-bound retinal. Can convert/oxidize retinaldehyde to retinoic acid (By similarity).
- Gene Name
- ALDH1A1
- Uniprot ID
- P00352
- Uniprot Name
- Retinal dehydrogenase 1
- 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
- General Function
- G-protein coupled receptor activity
- Specific 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 betwe...
- 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
- General Function
- Retinal dehydrogenase activity
- Specific Function
- Recognizes as substrates free retinal and cellular retinol-binding protein-bound retinal. Does metabolize octanal and decanal but does not metabolize citral, benzaldehyde, acetaldehyde and propanal...
- 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
- Agonist
- General Function
- Not Available
- Specific Function
- Inhibitor of the cytoplasmic carboxypeptidase AGBL2, may regulate the alpha-tubulin tyrosination cycle.
- 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
- General Function
- Zinc ion binding
- Specific 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 expressi...
- 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]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Zinc ion binding
- Specific 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 expressi...
- 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]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Cysteine-type endopeptidase inhibitor activity
- Specific 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 fr...
- 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
- General Function
- Odorant binding
- Specific Function
- Probably binds and transports small hydrophobic volatile molecules with a higher affinity for aldehydes and large fatty acids.
- 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
- General Function
- Retinol transporter activity
- Specific Function
- Delivers retinol from the liver stores to the peripheral tissues. In plasma, the RBP-retinol complex interacts with transthyretin, this prevents its loss by filtration through the kidney glomeruli.
- 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
- General Function
- Pyruvate dehydrogenase (acetyl-transferring) kinase activity
- Specific 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 de...
- 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
- General Function
- Zinc ion binding
- Specific 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 expressi...
- 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]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Retinoic acid binding
- Specific Function
- Plays a key role in retinoic acid metabolism. Acts on retinoids, including all-trans-retinoic acid (RA) and its stereoisomer 9-cis-RA. Capable of both 4-hydroxylation and 18-hydroxylation. Responsi...
- Gene Name
- CYP26A1
- Uniprot ID
- O43174
- Uniprot Name
- Cytochrome P450 26A1
- Molecular Weight
- 56198.11 Da
References
- Helvig C, Taimi M, Cameron D, Jones G, Petkovich M: Functional properties and substrate characterization of human CYP26A1, CYP26B1, and CYP26C1 expressed by recombinant baculovirus in insect cells. J Pharmacol Toxicol Methods. 2011 Nov-Dec;64(3):258-63. doi: 10.1016/j.vascn.2011.08.005. Epub 2011 Aug 31. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Involved in the metabolism of retinoic acid (RA), rendering this classical morphogen inactive through oxidation. Involved in the specific inactivation of all-trans-retinoic acid (all-trans-RA), with a preference for the following substrates: all-trans-RA > 9-cis-RA > 13-cis-RA. Generates several hydroxylated forms of RA, including 4-OH-RA, 4-oxo-RA, and 18-OH-RA. Essential for postnatal survival. Plays a central role in germ cell development: acts by degrading RA in the developing testis, preventing STRA8 expression, thereby leading to delay of meiosis. Required for the maintenance of the undifferentiated state of male germ cells during embryonic development in Sertoli cells, inducing arrest in G0 phase of the cell cycle and preventing meiotic entry. Plays a role in skeletal development, both at the level of patterning and in the ossification of bone and the establishment of some synovial joints.
- Specific Function
- Heme binding
- Gene Name
- CYP26B1
- Uniprot ID
- Q9NR63
- Uniprot Name
- Cytochrome P450 26B1
- Molecular Weight
- 57512.075 Da
References
- Helvig C, Taimi M, Cameron D, Jones G, Petkovich M: Functional properties and substrate characterization of human CYP26A1, CYP26B1, and CYP26C1 expressed by recombinant baculovirus in insect cells. J Pharmacol Toxicol Methods. 2011 Nov-Dec;64(3):258-63. doi: 10.1016/j.vascn.2011.08.005. Epub 2011 Aug 31. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Plays a role in retinoic acid metabolism. Acts on retinoids, including all-trans-retinoic acid (RA) and its stereoisomer 9-cis-RA (preferred substrate).
- Specific Function
- Heme binding
- Gene Name
- CYP26C1
- Uniprot ID
- Q6V0L0
- Uniprot Name
- Cytochrome P450 26C1
- Molecular Weight
- 57110.385 Da
References
- Helvig C, Taimi M, Cameron D, Jones G, Petkovich M: Functional properties and substrate characterization of human CYP26A1, CYP26B1, and CYP26C1 expressed by recombinant baculovirus in insect cells. J Pharmacol Toxicol Methods. 2011 Nov-Dec;64(3):258-63. doi: 10.1016/j.vascn.2011.08.005. Epub 2011 Aug 31. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Protein homodimerization activity
- Specific Function
- Bifunctional enzyme which catalyzes both the conversion of PGH2 to PGD2, a prostaglandin involved in smooth muscle contraction/relaxation and a potent inhibitor of platelet aggregation, and the con...
- Gene Name
- HPGDS
- Uniprot ID
- O60760
- Uniprot Name
- Hematopoietic prostaglandin D synthase
- Molecular Weight
- 23343.65 Da
References
- Fujimori K, Fukuhara A, Inui T, Allhorn M: Prevention of paraquat-induced apoptosis in human neuronal SH-SY5Y cells by lipocalin-type prostaglandin D synthase. J Neurochem. 2012 Jan;120(2):279-91. doi: 10.1111/j.1471-4159.2011.07570.x. Epub 2011 Nov 24. [Article]
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Oxygen binding
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
- Gene Name
- CYP3A7
- Uniprot ID
- P24462
- Uniprot Name
- Cytochrome P450 3A7
- Molecular Weight
- 57525.03 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
- Steroid hydroxylase activity
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
- 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]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Steroid hydroxylase activity
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
- Gene Name
- CYP2C8
- Uniprot ID
- P10632
- Uniprot Name
- Cytochrome P450 2C8
- Molecular Weight
- 55824.275 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
- Steroid hydroxylase activity
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
- 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
- Vitamin d3 25-hydroxylase activity
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
- Gene Name
- CYP3A4
- Uniprot ID
- P08684
- Uniprot Name
- Cytochrome P450 3A4
- Molecular Weight
- 57342.67 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
- No
- Actions
- Substrate
- General Function
- Oxygen binding
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
- Gene Name
- CYP3A5
- Uniprot ID
- P20815
- Uniprot Name
- Cytochrome P450 3A5
- Molecular Weight
- 57108.065 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
- Steroid hydroxylase activity
- Specific 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. Const...
- Gene Name
- CYP2A6
- Uniprot ID
- P11509
- Uniprot Name
- Cytochrome P450 2A6
- Molecular Weight
- 56501.005 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
- Steroid hydroxylase activity
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
- 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
- Vitamin d 24-hydroxylase activity
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
- 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
- Leukotriene-b4 20-monooxygenase activity
- Specific Function
- Catalyzes the omega- and (omega-1)-hydroxylation of various fatty acids such as laurate, myristate and palmitate. Has little activity toward prostaglandins A1 and E1. Oxidizes arachidonic acid to 2...
- 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]
Carriers
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Toxic substance binding
- Specific Function
- Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloid...
- Gene Name
- ALB
- Uniprot ID
- P02768
- Uniprot Name
- Serum 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]
Transporters
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Transporter activity
- Specific Function
- Cytosolic CRABPs may regulate the access of retinoic acid to the nuclear retinoic acid receptors.
- 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]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Transporter activity
- Specific Function
- Transports retinoic acid to the nucleus. Regulates the access of retinoic acid to the nuclear retinoic acid receptors.
- 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]
Drug created at June 13, 2005 13:24 / Updated at January 16, 2022 18:54