Tretinoin

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, Avita, Biacna, Refissa, Renova, Retin-A, Stieva-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

Similar Structures

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.

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Associated Conditions

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	agonist	Humans
ARetinoic acid receptor beta	agonist	Humans
ARetinoic acid receptor gamma	agonist	Humans
URetinoic acid receptor RXR-alpha	agonist	Humans
ARetinoic acid receptor RXR-beta	agonist	Humans
ARetinoic acid receptor RXR-gamma	agonist	Humans
UCellular retinoic acid-binding protein 1	binder	Humans
URetinoic acid receptor responder protein 1	agonist	Humans
URetinal dehydrogenase 1	substrate	Humans
URetinal dehydrogenase 2	substrate	Humans
URetinoic acid-induced protein 3	regulator	Humans
ULipocalin-1	binder	Humans
UOdorant-binding protein 2a	binder	Humans
URetinol-binding protein 4	binder	Humans
U[Pyruvate dehydrogenase [lipoamide]] kinase isozyme 4, mitochondrial	upregulator	Humans
UCarcinoembryonic antigen	downregulator	Humans

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 C_max 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 C_max varied across different age groups (children, adolescents, and adults). The corresponding ranges for the mean AUC_0-24 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 C_max 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 T_max 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 (V_d) of intravenous tretinoin is dose-dependent and significantly greater at low doses. The V_d 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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Tretinoin

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
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Abametapir	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.
Acemetacin	The risk or severity of elevated intracranial pressure can be increased when Acemetacin is combined with Tretinoin.
Acetyldigitoxin	Acetyldigitoxin may decrease the cardiotoxic activities of Tretinoin.
Acetylsalicylic acid	The risk or severity of elevated intracranial pressure can be increased when Acetylsalicylic acid is combined with Tretinoin.
Adalimumab	The metabolism of Tretinoin can be increased when combined with Adalimumab.
Alclofenac	The risk or severity of elevated intracranial pressure can be increased when Alclofenac is combined with Tretinoin.

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Food Interactions

Take with food. Effect of food on tretinoin absorption is unclear, but food increases the bioavailability of retinoids drug class.

Products

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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
Altreno	Lotion	0.5 mg/1g	Topical	Bausch Health US, LLC	2018-08-24	Not applicable
Altreno	Lotion	0.05 % w/w	Topical	Bausch Health, Canada Inc.	Not applicable	Not applicable
Atralin	Gel	0.05 g/100g	Topical	Bausch Health US, LLC	2007-07-26	Not applicable
Avita	Gel	0.25 mg/1g	Topical	Mylan Pharmaceuticals Inc.	1998-03-18	2023-05-31
Avita	Cream	0.25 mg/1g	Topical	Mylan Pharmaceuticals Inc.	1997-06-01	2023-10-31
Avita	Cream	0.25 mg/1g	Topical	Mylan Bertek Pharmaceuticals	2015-11-01	2015-11-19
Avita	Gel	0.25 mg/1g	Topical	BERTEK PHARMACEUTICALS INC.	2007-04-27	2007-04-27
Rejuva-A	Cream	0.025 %	Topical	Glaxosmithkline Inc	1997-11-04	2014-05-01
Renova	Cream	0.05 %	Topical	Valeant Canada Lp Valeant Canada S.E.C.	1995-12-31	2014-07-30
Renova	Cream	0.2 mg/1g	Topical	Rebel Distributors	2011-10-18	Not applicable

Generic Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
Jamp Tretinoin	Capsule	10 mg	Oral	Jamp Pharma Corporation	2022-08-29	Not applicable
Obagi	Cream	1 mg/1g	Topical	YS PLUS CORPORATION	2014-10-01	2015-12-31
Obagi	Cream	0.5 mg/1g	Topical	YS PLUS CORPORATION	2014-10-01	2015-12-31
Refissa	Cream	0.5 mg/1g	Topical	Obagi Medical Products, Inc.	2010-02-22	2016-05-01
Refissa	Cream	0.5 mg/1g	Topical	Suneva Medical, Inc.	2009-06-17	Not applicable
Refissa	Cream	0.5 mg/1g	Topical	Spear Dermatology Products	2009-06-17	2014-07-31
Refissa	Cream	0.5 mg/1g	Topical	Coria Laboratories	2011-02-01	2016-05-01
Refissa Tretinoin (Emollient)	Cream	0.5 mg/1g	Topical	ZO Skin Health, Inc.	2017-04-03	Not applicable
Tretin-X	Cream	0.25 mg/1g	Topical	Triax Pharmaceuticals, LLC	2010-08-01	2015-07-31
Tretin-X	Cream	0.25 mg/1g	Topical	Triax Pharmaceuticals, LLC	2006-04-01	2015-07-31

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
เรติน - เอ	Cream	0.025 %w/w	Topical	บริษัท โอลิค (ประเทศไทย) จำกัด	1990-10-05	Not applicable

Mixture Products

Name	Ingredients	Dosage	Route	Labeller	Marketing Start	Marketing End
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
Acnatac 10 mg/g + 0,25 mg/g Gel	Tretinoin (0.25 mg/g) + Clindamycin (10 mg/g)	Gel	Topical	Mylan österreich Gmb H	2013-03-26	Not applicable
AKNEMYCIN PLUS SOLUTION	Tretinoin (0.025 g/100g) + Erythromycin (4 g/100g)	Solution	Topical	ZUELLIG PHARMA PTE. LTD.	2000-02-04	Not applicable
ALBAVANCE F	Tretinoin (0.01 %) + Fluocinolone acetonide (4 %) + Hydroquinone (0.05 %)	Cream		Immortal Pharmaceutical Laboratories	2017-09-18	2027-04-19
BALISA VAS	Tretinoin (0.3 mg/g) + Urea (120 mg/g)	Cream	Topical		2006-04-01	Not applicable
BALISA VAS	Tretinoin (0.3 mg/g) + Urea (120 mg/g)	Cream	Topical		2006-04-01	Not applicable
BETARRETIN® H CREMA	Tretinoin (0.05 g) + Hydroquinone (4 g)	Cream	Topical	ALTEA FARMACEUTICA S.A.	2006-11-10	2011-04-12
BETARRETIN® H LOCIÓN	Tretinoin (0.05 g) + Hydroquinone (4 g)	Lotion	Topical	ALTEA FARMACEUTICA S.A.	2006-11-10	Not applicable
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
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

Unapproved/Other Products

Name	Ingredients	Dosage	Route	Labeller	Marketing Start	Marketing End
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
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
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
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
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
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
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
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
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
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

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: 31883
RxNav: 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 …

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Clinical Trials

Clinical Trials

Phase	Status	Purpose	Conditions	Count
4	Active Not Recruiting	Treatment	Photodamaged Skin / Solar Elastosis	1
4	Completed	Other	Acne / Healthy Subjects (HS)	1
4	Completed	Prevention	Acne	1
4	Completed	Treatment	Acne	2
4	Completed	Treatment	Acne Vulgaris	9
4	Completed	Treatment	Acute Promyelocytic Leukemia	1
4	Completed	Treatment	Childhood Acute Promyelocytic Leukemia (M3)	1
4	Completed	Treatment	Hyperpigmentation	1
4	Completed	Treatment	Melasma	2
4	Completed	Treatment	Striae Distensae / Treatments	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
Cream	Cutaneous	0.050 g
Lotion	Topical	50 mg
Solution	Topical	0.05 g
Gel	Topical	0.025 %
Cream	Topical	0.1 %
Capsule	Oral	10.000 mg
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
Capsule	Oral	10.0000 mg
Cream	Topical	0.04 g
Solution	Topical	0.025 g
Lotion	Topical
Lotion	Topical	4 g
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	0.0100 g
Gel	Topical	0.025 % w/w
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
Lotion	Topical	0.05 g
Lotion	Topical	0.025 g
Cream	Topical	0.01 %
Cream	Topical	0.050 g
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
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
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)
US5470567	No	1995-11-28	2010-03-19
US5955109	No	1999-09-21	2016-09-21
US6353029	No	2002-03-05	2020-08-24
US6531141	No	2003-03-11	2020-03-07
US8247395	No	2012-08-21	2022-10-22
US8653053	No	2014-02-18	2022-10-25
US7939516	No	2011-05-10	2025-05-04
US7915243	No	2011-03-29	2026-03-22
US6387383	No	2002-05-14	2020-08-03
US6517847	No	2003-02-11	2020-08-03
US10653656	No	2020-05-19	2038-08-22
US9868103	No	2018-01-16	2028-08-08
US11071878	No	2021-07-27	2030-12-30
US10420743	No	2019-09-24	2038-07-12
US10653899	No	2020-05-19	2030-12-30
US8617580	No	2013-12-31	2028-02-03
US11324710	No	2018-08-22	2038-08-22

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

ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

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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Property	Measurement	pH	Temperature (°C)	References
EC 50 (nM)	102	N/A	N/A	A28888 / A28894
EC 50 (nM)	17	N/A	N/A	A28902
EC 50 (nM)	191	N/A	N/A	A28880 / A28883
EC 50 (nM)	21	N/A	N/A	A28885
EC 50 (nM)	220	N/A	N/A	A28900
EC 50 (nM)	23	N/A	N/A	A27668
EC 50 (nM)	240	N/A	N/A	A28897 / A28899
EC 50 (nM)	27	N/A	N/A	A28889
EC 50 (nM)	304	N/A	N/A	A28881
EC 50 (nM)	350	N/A	N/A	A28880 / A28883
EC 50 (nM)	436	N/A	N/A	A28900
EC 50 (nM)	45	N/A	N/A	A28889
EC 50 (nM)	459	N/A	N/A	A28892
EC 50 (nM)	5	N/A	N/A	A28888 / A28894
EC 50 (nM)	563	N/A	N/A	A28881
EC 50 (nM)	6.31	N/A	N/A	A28903
EC 50 (nM)	7	N/A	N/A	A28887
IC 50 (nM)	0.78	N/A	N/A	A28895
IC 50 (nM)	0.89	N/A	N/A	A28896
IC 50 (nM)	15	N/A	N/A	A28880
IC 50 (nM)	7	N/A	N/A	A28880
IC 50 (nM)	9000	N/A	N/A	A28904
Kd (nM)	14	N/A	N/A	A28897 / A28899
Kd (nM)	15	N/A	N/A	A28891 / A28892 / A28893 / A28884 / A28900
Kd (nM)	16	N/A	N/A	A28894
Kd (nM)	2.3	N/A	N/A	A28890
Kd (nM)	90	N/A	N/A	A28885
Kd (nM)	93	N/A	N/A	A28884 / A28900
Ki (nM)	16	N/A	N/A	A27453
Ki (nM)	187	N/A	N/A	A28881
Ki (nM)	22.3	N/A	N/A	A28881
Ki (nM)	3.3	N/A	N/A	A27669

Details1. Retinoic acid receptor alpha

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: 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]

Property	Measurement	pH	Temperature (°C)	References
EC 50 (nM)	1	N/A	N/A	A28887
EC 50 (nM)	1.5	N/A	N/A	A28888 / A28894
EC 50 (nM)	105	N/A	N/A	A28881
EC 50 (nM)	12	N/A	N/A	A28889 / A28902
EC 50 (nM)	22	N/A	N/A	A28889
EC 50 (nM)	25.12	N/A	N/A	A28903
EC 50 (nM)	29	N/A	N/A	A28900
EC 50 (nM)	3	N/A	N/A	A28885
EC 50 (nM)	3.3	N/A	N/A	A28888 / A28894
EC 50 (nM)	38	N/A	N/A	A28897 / A28899
EC 50 (nM)	50	N/A	N/A	A28880 / A28883
EC 50 (nM)	52	N/A	N/A	A28881
EC 50 (nM)	6.31	N/A	N/A	A28903
EC 50 (nM)	78	N/A	N/A	A28900
EC 50 (nM)	80	N/A	N/A	A28880 / A28883
EC 50 (nM)	87	N/A	N/A	A28892
IC 50 (nM)	0.9	N/A	N/A	A28895
IC 50 (nM)	0.94	N/A	N/A	A28896
IC 50 (nM)	13	N/A	N/A	A28880
IC 50 (nM)	3000	N/A	N/A	A28904
IC 50 (nM)	7	N/A	N/A	A28880
Kd (nM)	0.4	N/A	N/A	A28890
Kd (nM)	100	N/A	N/A	A28885
Kd (nM)	11	N/A	N/A	A28897 / A28899
Kd (nM)	12	N/A	N/A	A28887
Kd (nM)	13	N/A	N/A	A28891 / A28892 / A28893 / A28884
Kd (nM)	17	N/A	N/A	A28900
Kd (nM)	7	N/A	N/A	A28894
Kd (nM)	97	N/A	N/A	A28884 / A28900
Ki (nM)	10.9	N/A	N/A	A28881
Ki (nM)	17.4	N/A	N/A	A28881
Ki (nM)	4.1	N/A	N/A	A27669
Ki (nM)	7	N/A	N/A	A27453

Details2. Retinoic acid receptor beta

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: 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]

Property	Measurement	pH	Temperature (°C)	References
EC 50 (nM)	0.2	N/A	N/A	A28902
EC 50 (nM)	0.5	N/A	N/A	A28888 / A28894
EC 50 (nM)	0.7	N/A	N/A	A28887
EC 50 (nM)	10	N/A	N/A	A28880 / A28883
EC 50 (nM)	12	N/A	N/A	A28889
EC 50 (nM)	19	N/A	N/A	A28900
EC 50 (nM)	20	N/A	N/A	A28892
EC 50 (nM)	33	N/A	N/A	A28881
EC 50 (nM)	4	N/A	N/A	A28885
EC 50 (nM)	45	N/A	N/A	A28880 / A28883
EC 50 (nM)	50	N/A	N/A	A28900
EC 50 (nM)	50.12	N/A	N/A	A28903
EC 50 (nM)	6	N/A	N/A	A28888 / A28894 / A28897 / A28899
EC 50 (nM)	74	N/A	N/A	A28881
EC 50 (nM)	8	N/A	N/A	A28889
IC 50 (nM)	0.5	N/A	N/A	A28895
IC 50 (nM)	0.62	N/A	N/A	A28896
IC 50 (nM)	17	N/A	N/A	A28880
IC 50 (nM)	18	N/A	N/A	A28880
Kd (nM)	0.2	N/A	N/A	A28901
Kd (nM)	0.3	N/A	N/A	A28890
Kd (nM)	0.8	N/A	N/A	A28901
Kd (nM)	148	N/A	N/A	A28884 / A28900
Kd (nM)	150	N/A	N/A	A28885
Kd (nM)	16	N/A	N/A	A28897 / A28899
Kd (nM)	17	N/A	N/A	A28900
Kd (nM)	18	N/A	N/A	A28891 / A28892 / A28893 / A28884
Kd (nM)	19	N/A	N/A	A28887
Kd (nM)	3	N/A	N/A	A28894
Ki (nM)	0.04	N/A	N/A	A27669
Ki (nM)	0.7	N/A	N/A	A28898
Ki (nM)	1	N/A	N/A	A27669
Ki (nM)	18.5	N/A	N/A	A28881
Ki (nM)	20	N/A	N/A	A28881
Ki (nM)	3	N/A	N/A	A27453

Details3. Retinoic acid receptor gamma

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]
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]

Property	Measurement	pH	Temperature (°C)	References
EC 50 (nM)	>0.001	N/A	N/A	A28888
EC 50 (nM)	1.5	N/A	N/A	A28885
EC 50 (nM)	100	N/A	N/A	A28880 / A28883
EC 50 (nM)	1015	N/A	N/A	A28900
EC 50 (nM)	1084	N/A	N/A	A28881
EC 50 (nM)	13	N/A	N/A	A28888 / A28889 / A28894
EC 50 (nM)	195	N/A	N/A	A28900
EC 50 (nM)	316	N/A	N/A	A28881
EC 50 (nM)	430	N/A	N/A	A28889
EC 50 (nM)	530	N/A	N/A	A27668
EC 50 (nM)	54	N/A	N/A	A27668
EC 50 (nM)	6	N/A	N/A	A27668
EC 50 (nM)	900	N/A	N/A	A28880 / A28883
IC 50 (nM)	>1000	N/A	N/A	A28880
IC 50 (nM)	29	N/A	N/A	A28907
IC 50 (nM)	32	N/A	N/A	A28880
Kd (nM)	>0.001	N/A	N/A	A28884
Kd (nM)	>200	N/A	N/A	A28905 / A28906
Kd (nM)	1.5	N/A	N/A	A28901
Kd (nM)	13	N/A	N/A	A28885
Kd (nM)	13	7.4	4	A27673
Kd (nM)	240	N/A	N/A	A28908
Kd (nM)	3	N/A	N/A	A28906
Kd (nM)	30	7.4	4	A27673
Kd (nM)	40	7.4	4	A27673
Kd (nM)	50	N/A	N/A	A27674
Kd (nM)	53	N/A	N/A	A28900
Kd (nM)	8	N/A	N/A	A28884 / A28900
Kd (nM)	9	N/A	N/A	A28887
Ki (nM)	0.4	N/A	N/A	A28886
Ki (nM)	12	N/A	N/A	A27669
Ki (nM)	330	N/A	N/A	A27669
Ki (nM)	350	N/A	N/A	A28881
Ki (nM)	8	N/A	N/A	A28882
Ki (nM)	8.4	N/A	N/A	A28881

Details4. Retinoic acid receptor RXR-alpha

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: 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]
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]

Property	Measurement	pH	Temperature (°C)	References
EC 50 (nM)	1394	N/A	N/A	A28881
EC 50 (nM)	1400	N/A	N/A	A28880 / A28883
EC 50 (nM)	2.6	N/A	N/A	A27668
EC 50 (nM)	200	N/A	N/A	A28880 / A28881 / A28883
EC 50 (nM)	29	N/A	N/A	A28885
EC 50 (nM)	4.5	N/A	N/A	A27668
IC 50 (nM)	>1000	N/A	N/A	A28880
IC 50 (nM)	12	N/A	N/A	A28880
Kd (nM)	>0.001	N/A	N/A	A28884
Kd (nM)	15	N/A	N/A	A28884
Kd (nM)	35	N/A	N/A	A28885
Ki (nM)	0.5	N/A	N/A	A28886
Ki (nM)	3.8	N/A	N/A	A27669
Ki (nM)	54	N/A	N/A	A27669
Ki (nM)	7.4	N/A	N/A	A28881
Ki (nM)	881	N/A	N/A	A28881
Ki (nM)	9	N/A	N/A	A28882

Details5. Retinoic acid receptor RXR-beta

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]
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]

Property	Measurement	pH	Temperature (°C)	References
EC 50 (nM)	1100	N/A	N/A	A28880 / A28883
EC 50 (nM)	1225	N/A	N/A	A28881
EC 50 (nM)	140	N/A	N/A	A28880 / A28883
EC 50 (nM)	2	N/A	N/A	A27668
EC 50 (nM)	219	N/A	N/A	A28881
EC 50 (nM)	4.3	N/A	N/A	A27668
EC 50 (nM)	4.5	N/A	N/A	A28885
IC 50 (nM)	350	N/A	N/A	A28880
IC 50 (nM)	4	N/A	N/A	A28880
Kd (nM)	>0.001	N/A	N/A	A28884
Kd (nM)	14	N/A	N/A	A28884 / A28900
Kd (nM)	30	N/A	N/A	A28885
Kd (nM)	306	N/A	N/A	A28900
Ki (nM)	1.4	N/A	N/A	A28886
Ki (nM)	11	N/A	N/A	A27669
Ki (nM)	120	N/A	N/A	A27669
Ki (nM)	13	N/A	N/A	A28881
Ki (nM)	14	N/A	N/A	A28882
Ki (nM)	288	N/A	N/A	A28881

Details6. Retinoic acid receptor RXR-gamma

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]
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]

Details7. Cellular retinoic acid-binding protein 1

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Binder

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

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]

Details8. Retinoic acid receptor responder protein 1

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]

Details9. Retinal dehydrogenase 1

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Substrate

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]

Details10. Retinal dehydrogenase 2

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Substrate

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]

Details11. Retinoic acid-induced protein 3

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Regulator

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]

Details12. Lipocalin-1

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Binder

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]

Details13. Odorant-binding protein 2a

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Binder

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]

Details14. Retinol-binding protein 4

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Binder

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]

Details15. [Pyruvate dehydrogenase [lipoamide]] kinase isozyme 4, mitochondrial

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Upregulator

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]

Details16. Carcinoembryonic antigen

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

Details1. Cytochrome P450 3A4

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]
FDA Approved Drug Products: VESANOID (tretinoin) capsules, for oral use [Link]

Details2. Cytochrome P450 3A5

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]
FDA Approved Drug Products: VESANOID (tretinoin) capsules, for oral use [Link]

Details3. Cytochrome P450 3A7

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]
FDA Approved Drug Products: VESANOID (tretinoin) capsules, for oral use [Link]

Details4. Cytochrome P450 2B6

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]
FDA Approved Drug Products: VESANOID (tretinoin) capsules, for oral use [Link]

Details5. Cytochrome P450 2C8

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]
FDA Approved Drug Products: VESANOID (tretinoin) capsules, for oral use [Link]

Details6. Cytochrome P450 2C9

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]

Details7. Cytochrome P450 2A6

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]

Details8. Cytochrome P450 2C18

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]

Details9. Cytochrome P450 1A1

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]

Details10. Cytochrome P450 4A11

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]

Details11. UDP-glucuronosyltransferase 2B7

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Substrate

General Function: Glucuronosyltransferase activity
Specific Function: UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds.Its unique specificity for 3,4-catechol estrogens and estriol su...
Gene Name: UGT2B7
Uniprot ID: P16662
Uniprot Name: UDP-glucuronosyltransferase 2B7
Molecular Weight: 60694.12 Da

References

FDA Approved Drug Products: VESANOID (tretinoin) capsules, for oral use [Link]

Details12. Cytochrome P450 2E1

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Substrate

General Function: Steroid hydroxylase activity
Specific Function: Metabolizes several precarcinogens, drugs, and solvents to reactive metabolites. Inactivates a number of drugs and xenobiotics and also bioactivates many xenobiotic substrates to their hepatotoxic ...
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]

Details13. Cytochrome P450 26A1

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Substrate

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

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

Details1. Serum albumin

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Binder

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]
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

Details1. Cellular retinoic acid-binding protein 1

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]
Napoli JL: Functions of Intracellular Retinoid Binding-Proteins. Subcell Biochem. 2016;81:21-76. doi: 10.1007/978-94-024-0945-1_2. [Article]

Details2. Cellular retinoic acid-binding protein 2

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]
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 September 21, 2023 08:43

Tretinoin

Identification

Structure for Tretinoin (DB00755)

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Pharmacoeconomics

Properties

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Enzymes

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Carriers

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Transporters

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