Identification

Name
Tretinoin
Accession Number
DB00755
Description

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
Thumb
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.

Associated Conditions
Contraindications & Blackbox Warnings
Learn about our commercial Contraindications & Blackbox Warnings data.
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Pharmacodynamics

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.

TargetActionsOrganism
ARetinoic acid receptor RXR-beta
agonist
Humans
ARetinoic acid receptor RXR-gamma
agonist
Humans
ARetinoic acid receptor gamma
agonist
Humans
URetinal dehydrogenase 1Not AvailableHumans
URetinoic acid-induced protein 3Not AvailableHumans
URetinal dehydrogenase 2Not AvailableHumans
URetinoic acid receptor responder protein 1
agonist
Humans
URetinoic acid receptor alphaNot AvailableHumans
URetinoic acid receptor betaNot AvailableHumans
ULipocalin-1Not AvailableHumans
UOdorant-binding protein 2aNot AvailableHumans
URetinol-binding protein 4Not AvailableHumans
U[Pyruvate dehydrogenase [lipoamide]] kinase isozyme 4, mitochondrialNot AvailableHumans
URetinoic acid receptor RXR-alphaNot AvailableHumans
UCytochrome P450 26A1Not AvailableHumans
UCytochrome P450 26B1Not AvailableHumans
UCytochrome P450 26C1Not AvailableHumans
UHematopoietic prostaglandin D synthaseNot AvailableHumans
Absorption

1-31% (topical)

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
Learn about our commercial Adverse Effects data.
Learn More
Toxicity
Not Available
Affected organisms
  • Humans and other mammals
Pathways
PathwayCategory
Retinol MetabolismMetabolic
Vitamin A DeficiencyDisease
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.
DrugInteraction
AbametapirThe serum concentration of Tretinoin can be increased when it is combined with Abametapir.
AbataceptThe metabolism of Tretinoin can be increased when combined with Abatacept.
AbirateroneThe metabolism of Tretinoin can be decreased when combined with Abiraterone.
AcalabrutinibThe metabolism of Tretinoin can be decreased when combined with Acalabrutinib.
AcebutololThe risk or severity of adverse effects can be increased when Tretinoin is combined with Acebutolol.
AcenocoumarolThe metabolism of Acenocoumarol can be decreased when combined with Tretinoin.
AcetaminophenThe metabolism of Tretinoin can be decreased when combined with Acetaminophen.
AcetohexamideThe metabolism of Tretinoin can be decreased when combined with Acetohexamide.
Acetyl sulfisoxazoleThe metabolism of Tretinoin can be decreased when combined with Acetyl sulfisoxazole.
AcetyldigitoxinAcetyldigitoxin may decrease the cardiotoxic activities of Tretinoin.
Additional Data Available
  • Extended Description
    Extended Description

    Extended description of the mechanism of action and particular properties of each drug interaction.

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  • Severity
    Severity

    A severity rating for each drug interaction, from minor to major.

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  • Evidence Level
    Evidence Level

    A rating for the strength of the evidence supporting each drug interaction.

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  • Action
    Action

    An effect category for each drug interaction. Know how this interaction affects the subject drug.

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Food Interactions
  • Take with food. Tretinoin absorption may be increased by co-administration with food.

Products

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
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
AltrenoLotion0.5 mg/1gTopicalBausch Health US, LLC2018-08-24Not applicableUS flag
AtralinGel0.05 g/100gTopicalBausch Health US, LLC2007-07-26Not applicableUS flag
AvitaCream0.25 mg/1gTopicalMylan Bertek Pharmaceuticals2015-11-012015-11-19US flag
AvitaGel0.25 mg/1gTopicalMylan Pharmaceuticals Inc.1998-03-18Not applicableUS flag
AvitaCream0.25 mg/1gTopicalMylan Pharmaceuticals Inc.1997-06-01Not applicableUS flag
AvitaGel0.25 mg/1gTopicalBERTEK PHARMACEUTICALS INC.2007-04-272007-04-27US flag
Rejuva-ACreamTopicalGlaxosmithkline Inc1997-11-042014-05-01Canada flag
RenovaCream0.05 g/100gTopicalPhysicians Total Care, Inc.1996-02-012011-05-31US flag
RenovaCream0.2 mg/1gTopicalRebel Distributors2011-10-18Not applicableUS flag
RenovaCream0.2 mg/1gTopicalOrtho Mc Neil Janssen Pharmaceutical2011-10-182015-10-31US flag
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
ObagiCream1 mg/1gTopicalYS PLUS CORPORATION2014-10-012015-12-31US flag
ObagiCream0.5 mg/1gTopicalYS PLUS CORPORATION2014-10-012015-12-31US flag
RefissaCream0.5 mg/1gTopicalSuneva Medical, Inc.2009-06-17Not applicableUS flag
RefissaCream0.5 mg/1gTopicalObagi Medical Products, Inc.2010-02-222016-05-01US flag
RefissaCream0.5 mg/1gTopicalSpear Dermatology Products2009-06-172014-07-31US flag
RefissaCream0.5 mg/1gTopicalCoria Laboratories2011-02-012016-05-01US flag
Refissa Tretinoin (Emollient)Cream0.5 mg/1gTopicalZO Skin Health, Inc.2017-04-03Not applicableUS flag
Tretin-XCream0.25 mg/1gTopicalTriax Pharmaceuticals, LLC2006-04-012015-07-31US flag
Tretin-XCream1 mg/1gTopicalTriax Pharmaceuticals, LLC2010-08-012015-07-31US flag
Tretin-XCream0.25 mg/1gTopicalTriax Pharmaceuticals, LLC2010-08-012015-07-31US flag
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

    Learn more
  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

    Learn more
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
Biacna Topical GelTretinoin (0.025 %) + Clindamycin phosphate (1.2 %)GelTopicalBausch Health, Canada Inc.2011-05-16Not applicableCanada flag
Clindamycin Phosphate 1.2% and Tretinoin 0.025%Tretinoin (0.25 mg/1g) + Clindamycin phosphate (12 mg/1g)GelTopicalOceanside Pharmaceuticals2020-08-04Not applicableUS flag
Clindamycin Phosphate and TretinionTretinoin (0.25 mg/1g) + Clindamycin phosphate (10 mg/1g)GelTopicalPrasco, Laboratories2018-06-28Not applicableUS flag
Clindamycin Phosphate and TretinoinTretinoin (0.25 mg/1g) + Clindamycin phosphate (12 mg/1g)GelTopicalActavis Pharma, Inc.2016-07-05Not applicableUS flag
Dermawerx Zmt PakTretinoin (0.25 mg/1g) + Levomenthol (0.44 g/100g) + Zinc oxide (20.6 g/100g)KitTopicalPatchwerx Labs2015-09-08Not applicableUS flag
Retisol-ATretinoin (0.025 %) + Avobenzone (2 %) + Octinoxate (7.5 %)CreamTopicalGlaxosmithkline Inc1993-12-312015-07-03Canada flag
Retisol-ATretinoin (0.05 %) + Avobenzone (2 %) + Octinoxate (7.5 %)CreamTopicalGlaxosmithkline Inc1993-12-312015-07-03Canada flag
Retisol-ATretinoin (0.1 %) + Avobenzone (2 %) + Octinoxate (7.5 %)CreamTopicalGlaxosmithkline Inc1993-12-312015-07-03Canada flag
Retisol-ATretinoin (0.01 %) + Avobenzone (2 %) + Octinoxate (7.5 %)CreamTopicalGlaxosmithkline Inc1993-12-312015-07-03Canada flag
SolageTretinoin (0.1 mg/1mL) + Mequinol (20 mg/1mL)SolutionTopicalStiefel Laboratories, Inc.2003-01-012010-11-30US flag
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
011010 Niacinamide 4% / Tretinoin 0.025%Tretinoin (0.025 g/100g) + Nicotinamide (4 g/100g)GelTopicalSincerus Florida, LLC2020-07-02Not applicableUS flag
011013 Niacinamide 4% / Tretinoin 0.025%Tretinoin (0.025 g/100g) + Nicotinamide (4 g/100g)CreamTopicalSincerus Florida, LLC2020-07-02Not applicableUS flag
011020 Niacinamide 4% / Tretinoin 0.05%Tretinoin (0.05 g/100g) + Nicotinamide (4 g/100g)GelTopicalSincerus Florida, LLC2020-07-02Not applicableUS flag
011021 Niacinamide 4% / Tretinoin 0.05%Tretinoin (0.05 g/100g) + Nicotinamide (4 g/100g)CreamTopicalSincerus Florida, LLC2020-07-02Not applicableUS flag
011218 Niacinamide 2% / Spironolactone 5% / Tretinoin 0.025%Tretinoin (0.025 g/100g) + Nicotinamide (2 g/100g) + Spironolactone (5 g/100g)GelTopicalSincerus Florida, LLC2020-07-02Not applicableUS flag
011220 Niacinamide 2% / Spironolactone 5% / Tretinoin 0.05%Tretinoin (0.05 g/100g) + Nicotinamide (2 g/100g) + Spironolactone (5 g/100g)GelTopicalSincerus Florida, LLC2020-07-02Not applicableUS flag
141016 Hydrocortisone 0.5% / Hydroquinone 4% / Tretinoin 0.025%Tretinoin (0.025 g/100g) + Hydrocortisone (0.5 g/100g) + Hydroquinone (4 g/100g)EmulsionTopicalSincerus Florida, LLC2020-07-02Not applicableUS flag
141017 Hydrocortisone 0.5% / Hydroquinone 6% / Tretinoin 0.025%Tretinoin (0.025 g/100g) + Hydrocortisone (0.5 g/100g) + Hydroquinone (6 g/100g)EmulsionTopicalSincerus Florida, LLC2020-07-02Not applicableUS flag
141060 Hydrocortisone 0.5% / Hydroquinone 4% / Tretinoin 0.025%Tretinoin (0.025 g/100g) + Hydrocortisone (0.5 g/100g) + Hydroquinone (4 g/100g)EmulsionTopicalSincerus Florida, LLC2020-07-02Not applicableUS flag
141061 Hydrocortisone 0.5% / Hydroquinone 8% / Tretinoin 0.025%Tretinoin (0.025 g/100g) + Hydrocortisone (0.5 g/100g) + Hydroquinone (8 g/100g)EmulsionTopicalSincerus Florida, LLC2020-07-02Not applicableUS flag

Categories

ATC Codes
D10AD51 — Tretinoin, combinationsL01XX14 — TretinoinD10AD01 — Tretinoin
Drug Categories
Classification
Not classified

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
  1. 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. [PubMed:3165295]
  2. 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. [PubMed:2224119]
  3. Sanz MA: Treatment of acute promyelocytic leukemia. Hematology Am Soc Hematol Educ Program. 2006:147-55. [PubMed:17124054]
  4. 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. [PubMed:11874821]
  5. 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. [PubMed:17099008]
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
AHFS Codes
  • 10:00.00 — Antineoplastic Agents
  • 84:16.00 — Cell Stimulants and Proliferants
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
PhaseStatusPurposeConditionsCount
4Active Not RecruitingTreatmentAcute Promyelocytic Leukemia (APL)1
4CompletedBasic ScienceAcne Vulgaris1
4CompletedPreventionAcne1
4CompletedTreatmentAcne2
4CompletedTreatmentAcne Vulgaris9
4CompletedTreatmentAcute Promyelocytic Leukemia (APL)1
4CompletedTreatmentHyperpigmentation1
4CompletedTreatmentMelasma2
4CompletedTreatmentStriae Distensae / Treatments1
4Enrolling by InvitationTreatmentChildhood Acute Promyelocytic Leukemia1

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
FormRouteStrength
SolutionTopical0.05 g
Cream0.025 %
CreamTopical0.1 %
CreamTopical0.04 g
Cream0.05 %
Solution0.05 %
SolutionTopical0.5 mg/mL
GelTopical0.05 g
LotionTopical0.5 mg/1g
CreamTopical
GelTopical0.025 g
LotionTopical0.05 g
KitTopical
Gel12 mg/g
CreamTopical0.5 mg/g
CreamTopical
Gel0.025 %
SolutionTopical100 mg
SolutionTopical5 g
EmulsionTopical
CreamTopical0.05 g/100g
CreamTopical0.05 %
CreamTopical0.2 mg/1g
CreamTopical0.05 g
CreamTopical0.025 g
CreamTopical0.01 %
CreamTopical0.025 %
CreamTopical0.1 mg/1g
GelTopical0.01 %
GelTopical0.025 %
LiquidTopical0.5 mg/1mL
GelTopical0.04 %
GelTopical0.1 %
GelTopical0.4 mg/1g
GelTopical0.6 mg/1g
GelTopical1 mL/1g
GelTopical400 mL/1g
LotionTopical0.025 g
SolutionTopical
LiquidTopical
SolutionTopical
Cream
CreamTopical0.375 mg/1g
GelTopical0.1 mg/1g
GelTopical0.25 mg/1g
CreamTopical0.75 mg/1g
CapsuleOral10 mg/1
CreamTopical0.025 mg/1g
CreamTopical0.05 mg/1g
CreamTopical0.25 mg/1g
CreamTopical0.5 mg/1g
CreamTopical1 mg/1g
CreamTopical1.0 mg/1g
GelTopical0.01 mg/1g
GelTopical0.025 mg/1g
GelTopical0.04 mg/1g
GelTopical0.05 g/100g
GelTopical0.5 mg/1g
GelTopical0.8 mg/1g
PowderNot applicable1 g/1g
GelTopical1 mg/1g
KitTopical0.25 mg/1g
KitTopical0.5 mg/1g
KitTopical1 mg/1g
CreamTopical0.01 g
CreamTopical120 mg/g
GelTopical
CapsuleOral10 MG
Capsule, liquid filledOral10 mg/1
Capsule, gelatin coatedOral10 mg
GelTopical
CreamTopical12 %
Prices
Unit descriptionCostUnit
Tretinoin (Emollient) 0.05% Cream 60 gm Tube200.07USD tube
Tri-Luma 0.01-4-0.05% Cream 30 gm Tube199.99USD tube
Solage 2-0.01% Solution 30ml Bottle168.67USD bottle
Tretinoin (Emollient) 0.05% Cream 40 gm Tube135.99USD tube
Tretinoin 0.1% Cream 45 gm Tube114.16USD tube
Tretinoin 0.025% Gel 45 gm Tube99.64USD tube
Tretinoin 0.01% Gel 45 gm Tube98.85USD tube
Tretinoin 0.05% Cream 45 gm Tube97.94USD tube
Tretinoin 0.025% Cream 45 gm Tube83.97USD tube
Tretinoin acid powder74.21USD g
Tretinoin 0.1% Cream 20 gm Tube60.96USD tube
Tretinoin 0.05% Cream 20 gm Tube52.23USD tube
Tretinoin 0.025% Cream 20 gm Tube44.36USD tube
Tretinoin 0.025% Gel 15 gm Tube42.26USD tube
Tretinoin 0.01% Gel 15 gm Tube35.99USD tube
Vesanoid 10 mg capsule30.32USD capsule
Accutane 40 mg capsule27.62USD capsule
Tretinoin 10 mg capsule27.29USD capsule
Accutane 20 mg capsule23.77USD capsule
Amnesteem 40 mg capsule22.6USD capsule
Claravis 40 mg capsule21.73USD capsule
Accutane 10 mg capsule20.05USD capsule
Amnesteem 20 mg capsule19.45USD capsule
Claravis 20 mg capsule18.7USD capsule
Claravis 30 mg capsule16.78USD capsule
Amnesteem 10 mg capsule16.4USD capsule
Claravis 10 mg capsule15.77USD capsule
Sotret 40 mg capsule10.08USD capsule
Sotret 20 mg capsule8.67USD capsule
Sotret 30 mg capsule8.44USD capsule
Sotret 10 mg capsule7.31USD capsule
Tri-luma cream6.4USD g
Retin-a micro 0.04% gel5.65USD g
Retin-a micro 0.1% gel5.65USD g
Solage topical solution5.59USD ml
Retin-a micro pump 0.04% gel4.74USD g
Retin-a micro pump 0.1% gel4.74USD g
Retin-a 0.05% cream4.64USD g
Retin-a 0.1% cream4.51USD g
Renova 0.02% cream4.46USD g
Renova pump 0.02% cream4.28USD g
Retin-a 0.025% cream4.14USD g
Refissa 0.05% cream3.6USD g
Tretinoin 0.05% emollient crm3.38USD g
Avita 0.025% cream3.19USD g
Tretinoin 0.1% cream2.36USD g
Tretinoin 0.025% cream2.17USD g
Tretinoin 0.05% cream2.02USD g
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)Region
US5470567No1995-11-282010-03-19US flag
US5955109No1999-09-212016-09-21US flag
US6353029No2002-03-052020-08-24US flag
US6531141No2003-03-112020-03-07US flag
US8247395No2012-08-212022-10-22US flag
US8653053No2014-02-182022-10-25US flag
US7939516No2011-05-102025-05-04US flag
US7915243No2011-03-292026-03-22US flag
US6387383No2002-05-142020-08-03US flag
US6517847No2003-02-112020-08-03US flag
US10653656No2018-08-222038-08-22US flag
Additional Data Available
  • Filed On
    Filed On

    The date on which a patent was filed with the relevant government.

    Learn more

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)181 °CPhysProp
water solubility<0.1 g/100 mLNot Available
logP6.30HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility0.00477 mg/mLALOGPS
logP5.66ALOGPS
logP5.01ChemAxon
logS-4.8ALOGPS
pKa (Strongest Acidic)4.76ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity97.79 m3·mol-1ChemAxon
Polarizability36.85 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9925
Blood Brain Barrier+0.9311
Caco-2 permeable+0.7603
P-glycoprotein substrateNon-substrate0.6144
P-glycoprotein inhibitor INon-inhibitor0.8912
P-glycoprotein inhibitor IINon-inhibitor0.8088
Renal organic cation transporterNon-inhibitor0.8639
CYP450 2C9 substrateNon-substrate0.8221
CYP450 2D6 substrateNon-substrate0.9115
CYP450 3A4 substrateSubstrate0.6025
CYP450 1A2 substrateNon-inhibitor0.9046
CYP450 2C9 inhibitorNon-inhibitor0.8831
CYP450 2D6 inhibitorNon-inhibitor0.9231
CYP450 2C19 inhibitorNon-inhibitor0.9025
CYP450 3A4 inhibitorNon-inhibitor0.9301
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9252
Ames testNon AMES toxic0.8944
CarcinogenicityNon-carcinogens0.7081
BiodegradationReady biodegradable0.5554
Rat acute toxicity2.1455 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9562
hERG inhibition (predictor II)Non-inhibitor0.9538
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Targets

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
  1. 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. [PubMed:17184907]
  2. Redfern CP: Enhancing enhancers: new complexities in the retinoid regulation of gene expression. Biochem J. 2004 Oct 1;383(Pt 1):e1-2. [PubMed:15379735]
  3. 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. [PubMed:16392701]
  4. 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. [PubMed:16420438]
  5. 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. [PubMed:16109390]
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
  1. 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. [PubMed:17161848]
  2. 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. [PubMed:17182884]
  3. 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. [PubMed:16456186]
  4. 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. [PubMed:16420438]
  5. 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. [PubMed:14993281]
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
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. 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. [PubMed:17016423]
  3. 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. [PubMed:1332684]
  4. 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. [PubMed:8394693]
  5. 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. [PubMed:10792999]
  6. 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. [PubMed:10592235]
  7. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
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
  1. 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. [PubMed:15366004]
  2. 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. [PubMed:15245423]
  3. 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. [PubMed:16837774]
  4. 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. [PubMed:16207763]
  5. 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. [PubMed:16166285]
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
  1. 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. [PubMed:15677768]
  2. 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. [PubMed:15086536]
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
  1. 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. [PubMed:15069081]
  2. 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. [PubMed:15299009]
  3. 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. [PubMed:15366004]
  4. 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. [PubMed:15950488]
  5. 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. [PubMed:15950969]
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
  1. 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. [PubMed:15059893]
  2. 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. [PubMed:15897880]
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
  1. 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. [PubMed:1318502]
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
  1. 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. [PubMed:15958702]
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
  1. 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. [PubMed:16461020]
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
  1. 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. [PubMed:16461020]
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
  1. 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. [PubMed:16461020]
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
  1. 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. [PubMed:16757381]
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
  1. 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. [PubMed:16946489]
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
  1. 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. [PubMed:21906690]
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
  1. 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. [PubMed:21906690]
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
  1. 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. [PubMed:21906690]
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
  1. 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. [PubMed:22043816]

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
  1. 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. [PubMed:11093772]
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
  1. 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. [PubMed:11093772]
  2. Rendic S: Summary of information on human CYP enzymes: human P450 metabolism data. Drug Metab Rev. 2002 Feb-May;34(1-2):83-448. [PubMed:11996015]
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
  1. 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. [PubMed:11093772]
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
  1. 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. [PubMed:11093772]
  2. Rendic S: Summary of information on human CYP enzymes: human P450 metabolism data. Drug Metab Rev. 2002 Feb-May;34(1-2):83-448. [PubMed:11996015]
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
  1. 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. [PubMed:11093772]
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
  1. 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. [PubMed:11093772]
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
  1. 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. [PubMed:11093772]
  2. Rendic S: Summary of information on human CYP enzymes: human P450 metabolism data. Drug Metab Rev. 2002 Feb-May;34(1-2):83-448. [PubMed:11996015]
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
  1. 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. [PubMed:11093772]
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
  1. 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. [PubMed:11093772]
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
  1. 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. [PubMed:11093772]

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
  1. 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. [PubMed:16569428]
  2. 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. [PubMed:17184834]
  3. 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. [PubMed:17217919]

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
  1. 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. [PubMed:16109390]
  2. 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. [PubMed:20552429]
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
  1. 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. [PubMed:16109390]
  2. 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. [PubMed:17929112]
  3. 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. [PubMed:20552429]

Drug created on June 13, 2005 07:24 / Updated on September 27, 2020 08:17

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