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Identification
NameTretinoin
Accession NumberDB00755  (NUTR00051, APRD00362)
TypeSmall Molecule
GroupsApproved, Investigational, Nutraceutical
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).

Structure
Thumb
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 (french) (dsl)
AGN 100335
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
Eudyna
Renova
Retin-a
RETINOIC acid
Retionic Acid
Retisol-a
Ro 1-5488
Solage
Stieva-a
trans-Retinoic acid
Tretin m
Tretinoin
Tretinoina
Trétinoïne
Tretinoine (french) (einecs)
Tretinoinum
Vesanoid
Vitamin A acid
Vitinoin
External Identifiers Not Available
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Atralingel.05 g/100gtopicalCoria Laboratories2007-07-262016-04-05Us
Avitacream.25 mg/gtopicalMylan Pharmaceuticals Inc.1997-06-012016-04-23Us
Avitagel.25 mg/gtopicalMylan Pharmaceuticals Inc.1998-03-182016-04-23Us
Obagicream1 mg/gtopicalYS PLUS CORPORATION2014-10-012016-04-05Us
Obagicream.5 mg/gtopicalYS PLUS CORPORATION2014-10-012016-04-05Us
Rejuva-Acream0.025 %topicalGlaxosmithkline Inc1997-11-042014-05-01Canada
Renovacream.2 mg/gtopicalOrtho Mc Neil Janssen Pharmaceuticals, Inc.2011-10-182015-10-31Us
Renovacream.2 mg/gtopicalRebel Distributors Corp2011-10-182016-04-05Us
Renovacream0.05 %topicalValeant Canada Lp Valeant Canada S.E.C.1995-12-312014-07-30Canada
Renovacream.2 mg/gtopicalValeant Pharmaceuticals North America LLC2000-08-312016-04-23Us
Retin-Acream.25 mg/gtopicalOrtho Mc Neil Janssen Pharmaceuticals, Inc.1988-10-302016-04-23Us
Retin-Acream.5 mg/gtopicalPhysicians Total Care, Inc.1996-01-012016-04-05Us
Retin-Acream0.01 %topicalValeant Canada Lp Valeant Canada S.E.C.1991-12-31Not applicableCanada
Retin-Agel0.01 %topicalValeant Canada Lp Valeant Canada S.E.C.1991-12-31Not applicableCanada
Retin-Acream.5 mg/gtopicalA S Medication Solutions Llc1974-07-302016-04-05Us
Retin-Agel0.025 %topicalValeant Canada Lp Valeant Canada S.E.C.1991-12-31Not applicableCanada
Retin-Agel.1 mg/gtopicalValeant Pharmaceuticals North America LLC1979-07-302016-04-23Us
Retin-Acream0.05 %topicalValeant Canada Lp Valeant Canada S.E.C.1991-12-31Not applicableCanada
Retin-Agel.25 mg/gtopicalValeant Pharmaceuticals North America LLC1975-07-302016-04-23Us
Retin-Agel.1 mg/gtopicalOrtho Mc Neil Janssen Pharmaceuticals, Inc.1979-07-302016-04-23Us
Retin-Acream0.1 %topicalValeant Canada Lp Valeant Canada S.E.C.1991-12-31Not applicableCanada
Retin-Acream1 mg/gtopicalValeant Pharmaceuticals North America LLC1973-04-302016-04-23Us
Retin-Agel.25 mg/gtopicalOrtho Mc Neil Janssen Pharmaceuticals, Inc.1975-07-302016-04-23Us
Retin-Acream.5 mg/gtopicalValeant Pharmaceuticals North America LLC1974-07-302016-04-23Us
Retin-Acream1 mg/gtopicalOrtho Mc Neil Janssen Pharmaceuticals, Inc.1973-04-302016-04-23Us
Retin-Acream.25 mg/gtopicalPhysicians Total Care, Inc.1993-05-282016-04-05Us
Retin-Acream.25 mg/gtopicalValeant Pharmaceuticals North America LLC1988-10-302016-04-23Us
Retin-Agel.25 mg/gtopicalPhysicians Total Care, Inc.1993-05-252016-04-05Us
Retin-Agel.1 mg/gtopicalPhysicians Total Care, Inc.1993-05-252016-04-05Us
Retin-Acream.5 mg/gtopicalOrtho Mc Neil Janssen Pharmaceuticals, Inc.1974-07-302016-04-23Us
Retin-Acream.1 mg/gtopicalPhysicians Total Care, Inc.1996-08-212016-04-05Us
Retin-Acream0.025 %topicalValeant Canada Lp Valeant Canada S.E.C.1991-12-31Not applicableCanada
Retin-A Microgel1 mL/gtopicalPhysicians Total Care, Inc.2008-08-082016-04-05Us
Retin-A Microgel0.04 %topicalValeant Canada Lp Valeant Canada S.E.C.2005-08-30Not applicableCanada
Retin-A Microgel.4 mg/gtopicalValeant Pharmaceuticals North America LLC2002-05-102016-04-23Us
Retin-A Microgel400 mL/gtopicalPhysicians Total Care, Inc.2008-01-242016-04-05Us
Retin-A Microgel.4 mg/gtopicalPhysicians Total Care, Inc.2006-06-212016-04-05Us
Retin-A Microgel.1 mg/gtopicalPhysicians Total Care, Inc.2004-01-232016-04-05Us
Retin-A Microgel.4 mg/gtopicalOrtho Mc Neil Pharmaceuticals2011-05-012016-04-23Us
Retin-A Microgel1 mg/gtopicalValeant Pharmaceuticals North America LLC1997-02-072016-04-23Us
Retin-A Microgel.1 mg/gtopicalOrtho Mc Neil Pharmaceuticals2011-05-012016-04-23Us
Retin-A Microgel0.1 %topicalValeant Canada Lp Valeant Canada S.E.C.2001-08-01Not applicableCanada
Retin-A Microgel.8 mg/gtopicalValeant Pharmaceuticals North America LLC2014-01-282016-04-23Us
Stie Vaa Sol 0.05%liquid.05 %topicalStiefel Canada Ulc1980-12-312005-04-20Canada
Stieva-A Creamcream0.01 %topicalGlaxosmithkline Inc1986-12-31Not applicableCanada
Stieva-A Creamcream0.025 %topicalGlaxosmithkline Inc1983-12-31Not applicableCanada
Stieva-A Creamcream0.05 %topicalGlaxosmithkline Inc1981-12-31Not applicableCanada
Stieva-A Creamcream0.1 %topicalGlaxosmithkline Inc1988-12-31Not applicableCanada
Stieva-A Gelgel0.05 %topicalGlaxosmithkline Inc1985-12-312012-02-21Canada
Stieva-A Gelgel0.025 %topicalGlaxosmithkline Inc1983-12-312012-07-03Canada
Stieva-A Solutionsolution0.025 %topicalGlaxosmithkline Inc1983-12-312011-12-22Canada
Stievaa Gel 0.01%gel.01 %topicalStiefel Canada Ulc1983-12-312007-08-31Canada
Tretinoingel.025 mg/gtopicalSpear Dermatology Products Inc2014-02-062016-04-05Us
Tretinoincream.025 mg/gtopicalPerrigo New York Inc2006-01-052015-12-31Us
Tretinoingel.01 mg/gtopicalSpear Dermatology Products Inc2014-02-062016-04-05Us
Tretinoingel.05 g/100gtopicalValeant Pharmaceuticals North America LLC2009-08-012016-05-31Us
Tretinoincream.1 mg/gtopicalSpear Dermatology Products Inc2014-02-062016-04-05Us
Tretinoincream.25 mg/gtopicalTriax Pharmaceuticals, LLC2009-03-162016-04-05Us
Tretinoingel.05 g/100gtopicalOceanside Pharmaceuticals2007-07-262016-04-05Us
Tretinoincream.05 mg/gtopicalSpear Dermatology Products Inc2014-02-062016-04-05Us
Tretinoingel.4 mg/gtopicalOceanside Pharmaceuticals2013-03-142016-04-05Us
Tretinoincream.025 mg/gtopicalSpear Dermatology Products Inc2014-02-062016-04-05Us
Tretinoingel.025 mg/gtopicalPerrigo New York Inc2005-12-012015-12-31Us
Tretinoincream.5 mg/gtopicalTriax Pharmaceuticals, LLC2009-03-102016-04-05Us
Tretinoingel.1 mg/gtopicalOceanside Pharmaceuticals2013-03-142016-04-05Us
Tretinoingel.01 mg/gtopicalPerrigo New York Inc2005-12-022015-12-31Us
Tretinoincream1 mg/gtopicalTriax Pharmaceuticals, LLC2009-04-072016-04-05Us
Tretinoincream.05 mg/gtopicalPerrigo New York Inc2006-01-052015-12-31Us
Tretinoincream.25 mg/gtopicalActavis Mid Atlantic LLC1998-05-012016-04-23Us
Tretinoingel.05 g/100gtopicalOMP, INC.2014-06-192016-04-05Us
Tretinoincream.1 mg/gtopicalPerrigo New York Inc2005-12-012015-12-31Us
Tretinoin Creamcream.5 mg/gtopicalOMP, INC.1974-07-192016-04-05Us
Tretinoin Creamcream1 mg/gtopicalOMP, INC.1973-01-262016-04-05Us
Tretinoin Creamcream.25 mg/gtopicalOMP, INC.1988-09-162016-04-05Us
Tretinoin Gel Microspheregel.1 mg/gtopicalSpear Dermatology Products Inc2014-10-012016-04-05Us
Tretinoin Gel Microspheregel.04 mg/gtopicalSpear Dermatology Products Inc2014-10-012016-04-05Us
Vesanoidcapsule10 mgoralCheplapharm Arzneimittel Gmbh Germany1995-12-31Not applicableCanada
Vitamin A Acid 0.01% Creamcream0.01 %topicalSanofi Aventis Canada Inc1989-12-312008-08-04Canada
Vitamin A Acid 0.01% Gelgel0.01 %topicalValeant Canada Lp Valeant Canada S.E.C.1983-12-31Not applicableCanada
Vitamin A Acid 0.025% Creamcream0.025 %topicalSanofi Aventis Canada Inc1989-12-312008-08-04Canada
Vitamin A Acid 0.025% Gelgel0.025 %topicalValeant Canada Lp Valeant Canada S.E.C.1986-12-31Not applicableCanada
Vitamin A Acid 0.05% Creamcream0.05 %topicalSanofi Aventis Canada Inc1980-12-312008-08-04Canada
Vitamin A Acid 0.05% Gelgel0.05 %topicalValeant Canada Lp Valeant Canada S.E.C.1978-12-31Not applicableCanada
Vitamin A Acid 0.1% Creamcream0.1 %topicalSanofi Aventis Canada Inc1989-12-312008-08-04Canada
Vitinoin - Crm 0.025%cream.025 %topicalPenederm Inc.1995-12-312001-08-17Canada
Vitinoin - Crm 0.05%cream.05 %topicalPenederm Inc.1995-12-312001-08-17Canada
Vitinoin - Crm 0.1%cream.1 %topicalPenederm Inc.1995-12-312001-08-17Canada
Vitinoin Gel - 0.025%gel.025 %topicalPenederm Inc.1995-12-312001-08-17Canada
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Refissacream.5 mg/gtopicalSuneva Medical, Inc.2009-06-172016-04-05Us
Refissacream.5 mg/gtopicalObagi Medical Products, Inc.2010-02-222016-05-01Us
Refissacream.5 mg/gtopicalCoria Laboratories, LTD2011-02-012016-05-01Us
Tretin.xcream1 mg/gtopicalOnset Dermatologics LLC2013-04-022016-04-05Us
Tretin.xcream.5 mg/gtopicalOnset Dermatologics LLC2013-04-022016-04-05Us
Tretin.xcream.375 mg/gtopicalOnset Dermatologics LLC2013-04-022016-04-05Us
Tretin.xcream.25 mg/gtopicalOnset Dermatologics LLC2013-04-022016-04-05Us
Tretin.xcream.75 mg/gtopicalOnset Dermatologics LLC2013-04-022016-04-05Us
Tretinoincream.25 mg/gtopicalRouses Point Pharm1998-12-242016-04-05Us
Tretinoincream.5 mg/gtopicalRouses Point Pharm1998-12-242016-04-05Us
Tretinoincapsule10 mg/1oralPar Pharmaceutical, Inc.2012-10-242016-04-05Us
Tretinoincream.5 mg/gtopicalOceanside Pharmaceuticals2011-02-012016-04-05Us
Tretinoincapsule10 mg/1oralAmerican Health Packaging2013-07-182016-04-05Us
Tretinoincream1 mg/gtopicalDispensing Solutions, Inc.1998-12-242016-04-05Us
Tretinoincream1 mg/gtopicalRouses Point Pharm1998-12-242016-04-05Us
Tretinoingel.025 mg/gtopicalPhysicians Total Care, Inc.2009-01-052016-04-05Us
Tretinoincream.05 mg/gtopicalRebel Distributors Corp2006-01-052016-04-05Us
Tretinoingel.04 mg/gtopicalSpear Dermatology Products2013-07-312016-04-05Us
Tretinoincream.1 mg/gtopicalPhysicians Total Care, Inc.2008-10-172016-04-05Us
Tretinoincream.1 mg/gtopicalRebel Distributors Corp1998-12-242016-04-05Us
Tretinoincapsule, liquid filled10 mg/1oralBarr Laboratories Inc.2007-06-262016-04-23Us
Tretinoingel.1 mg/gtopicalSpear Dermatology Products2013-07-312016-04-05Us
Tretinoincream.05 mg/gtopicalPhysicians Total Care, Inc.2005-06-162016-04-05Us
Tretinoincream1 mg/gtopicalOMP, INC.2013-10-012017-09-30Us
Tretinoincream.025 mg/gtopicalPhysicians Total Care, Inc.2005-05-092016-04-05Us
Tretinoincream.5 mg/gtopicalRebel Distributors Corp1998-12-242016-04-05Us
Tretinoincream.5 mg/gtopicalPreferred Pharmaceuticals, Inc2012-03-292016-04-05Us
Tretinoincream.5 mg/gtopicalOMP, INC.2013-10-012016-08-31Us
Tretinoingel.25 mg/gtopicalRebel Distributors Corp2000-02-222016-04-05Us
Tretinoingel.1 mg/gtopicalRouses Point Pharm2002-06-112016-04-05Us
Tretinoincream.25 mg/gtopicalRebel Distributors Corp1998-12-242016-04-05Us
Tretinoincream1 mg/gtopicalPreferred Pharmaceuticals, Inc2012-03-292016-04-05Us
Tretinoincream.5 mg/gtopicalClinical Solutions Wholesale1998-12-242016-04-05Us
Tretinoingel.25 mg/gtopicalRouses Point Pharm2000-02-222016-04-05Us
Tretinoincream.1 mg/gtopicalPreferred Pharmaceuticals, Inc.2013-04-222016-04-05Us
Tretinoin Creamcream.25 mg/gtopicalYS PLUS CORPORATION2014-10-012016-04-05Us
Tretinoin Gelgel.05 g/100gtopicalSpear Dermatology Products2015-09-012016-04-05Us
TretinxkitOnset Dermatologics, LLC2013-06-032016-04-05Us
TretinxkittopicalOnset Dermatologics, LLC2013-06-032016-03-01Us
TretinxkittopicalOnset Dermatologics, LLC2013-06-032016-03-01Us
Over the Counter ProductsNot Available
International Brands
NameCompany
AberelJanssen
AberelaJanssen
AirolPierre Fabre Dermo
DermairolRoche
EudynaZydus
KétrelBailleul
Retisol-AStiefel
SotretRanbaxy Laboratories Inc.
Stieva-AStiefel
VitinoinNot Available
Brand mixtures
NameLabellerIngredients
Biacna Topical GelValeant Canada Lp Valeant Canada S.E.C.
Dr. Throwers HydrotetDr. Thrower's Skincare, Inc.
Dr. Throwers Pbc No. 1Dr. Thrower's Skincare, Inc.
Retisol-AGlaxosmithkline Inc
SolagéGlaxosmithkline Inc
Stievamycin ForteGlaxosmithkline Inc
Stievamycin MildGlaxosmithkline Inc
Stievamycin RegularGlaxosmithkline Inc
Tri-lumaGalderma Laboratories, L.P.
VeltinStiefel Laboratories Inc
ZianaMedicis Pharmaceutical Corp
SaltsNot Available
Categories
UNII5688UTC01R
CAS number302-79-4
WeightAverage: 300.4351
Monoisotopic: 300.20893014
Chemical FormulaC20H28O2
InChI KeyInChIKey=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
3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenoic acid
SMILES
CC(C=CC1=C(C)CCCC1(C)C)=CC=CC(C)=CC(O)=O
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as retinoids. These are oxygenated derivatives of 3,7-dimethyl-1-(2,6,6-trimethylcyclohex-1-enyl)nona-1,3,5,7-tetraene and derivatives thereof.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassRetinoids
Direct ParentRetinoids
Alternative Parents
Substituents
  • Retinoid skeleton
  • Diterpenoid
  • Carbocyclic fatty acid
  • Medium-chain fatty acid
  • Methyl-branched fatty acid
  • Branched fatty acid
  • Fatty acyl
  • Fatty acid
  • Unsaturated fatty acid
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External Descriptors
Pharmacology
IndicationFor 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.
PharmacodynamicsTretinoin, 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 actionTretinoin 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.
Related Articles
Absorption1-31% (topical)
Volume of distributionNot Available
Protein binding> 95%
Metabolism

Hepatic

SubstrateEnzymesProduct
Tretinoin
4-Hydroxyretinoic acidDetails
Tretinoin
18-Hydroxyretinoic acidDetails
Tretinoin
5,6-Epoxyretinoic acidDetails
Tretinoin
4-Oxoretinoic acidDetails
Tretinoin
Not Available
Retinoyl b-glucuronideDetails
Tretinoin
Not Available
Retinyl beta-glucuronideDetails
Route of eliminationNot Available
Half life0.5-2 hours
ClearanceNot Available
ToxicityNot Available
Affected organisms
  • Humans and other mammals
Pathways
PathwayCategorySMPDB ID
Retinol MetabolismMetabolicSMP00074
Vitamin A DeficiencyDiseaseSMP00336
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
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 )
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
Dosage forms
FormRouteStrength
Creamtopical.2 mg/g
Creamtopical.25 mg/g
Creamtopical.5 mg/g
Creamtopical0.01 %
Creamtopical0.025 %
Creamtopical0.05 %
Creamtopical0.1 %
Creamtopical1 mg/g
Geltopical.25 mg/g
Geltopical0.025 %
Geltopical.1 mg/g
Geltopical.4 mg/g
Geltopical.8 mg/g
Geltopical0.04 %
Geltopical0.1 %
Geltopical1 mL/g
Geltopical1 mg/g
Geltopical400 mL/g
Solutiontopical
Liquidtopical.05 %
Solutiontopical0.025 %
Geltopical.01 %
Creamtopical.375 mg/g
Creamtopical.75 mg/g
Capsuleoral10 mg/1
Capsule, liquid filledoral10 mg/1
Creamtopical.025 mg/g
Creamtopical.05 mg/g
Creamtopical.1 mg/g
Geltopical.01 mg/g
Geltopical.025 mg/g
Geltopical.04 mg/g
Geltopical.05 g/100g
Kit
Kittopical
Creamtopical
Geltopical
Capsuleoral10 mg
Geltopical0.01 %
Geltopical0.05 %
Creamtopical.025 %
Creamtopical.05 %
Creamtopical.1 %
Geltopical.025 %
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
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Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US5470567 No1993-03-192010-03-19Us
US5955109 No1996-09-212016-09-21Us
US6353029 No2000-08-242020-08-24Us
US6387383 No2000-08-032020-08-03Us
US6531141 No2000-03-072020-03-07Us
US7915243 No2006-03-222026-03-22Us
US7939516 No2005-05-042025-05-04Us
US8247395 No2002-10-222022-10-22Us
US8653053 No2002-10-252022-10-25Us
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point181 °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)5ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity97.79 m3·mol-1ChemAxon
Polarizability36.62 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
References
Synthesis ReferenceNot Available
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 ]
External Links
ATC CodesD10AD01D10AD51L01XX14
AHFS Codes
  • 84:16.00
  • 92:00.00
PDB Entries
FDA labelDownload (42.8 KB)
MSDSDownload (29.1 KB)
Interactions
Drug Interactions
Drug
AbirateroneThe serum concentration of Tretinoin can be increased when it is combined with Abiraterone.
Aminocaproic AcidTretinoin may increase the thrombogenic activities of Aminocaproic Acid.
ChlorotrianiseneThe therapeutic efficacy of Chlorotrianisene can be decreased when used in combination with Tretinoin.
DabrafenibThe serum concentration of Tretinoin can be decreased when it is combined with Dabrafenib.
DeferasiroxThe serum concentration of Tretinoin can be increased when it is combined with Deferasirox.
DenosumabThe risk or severity of adverse effects can be increased when Denosumab is combined with Tretinoin.
LeflunomideThe risk or severity of adverse effects can be increased when Tretinoin is combined with Leflunomide.
LumacaftorThe serum concentration of Tretinoin can be increased when it is combined with Lumacaftor.
MenadioneTretinoin may increase the thrombogenic activities of Menadione.
MifepristoneThe serum concentration of Tretinoin can be increased when it is combined with Mifepristone.
NatalizumabThe risk or severity of adverse effects can be increased when Tretinoin is combined with Natalizumab.
NorethisteroneThe therapeutic efficacy of Norethindrone can be decreased when used in combination with Tretinoin.
OxytetracyclineThe risk or severity of adverse effects can be increased when Oxytetracycline is combined with Tretinoin.
PhenytoinThe metabolism of Tretinoin can be increased when combined with Phenytoin.
PhylloquinoneTretinoin may increase the thrombogenic activities of Phylloquinone.
PimecrolimusThe risk or severity of adverse effects can be increased when Pimecrolimus is combined with Tretinoin.
PorfimerTretinoin may increase the photosensitizing activities of Porfimer.
RitonavirThe metabolism of Tretinoin can be decreased when combined with Ritonavir.
RoflumilastRoflumilast may increase the immunosuppressive activities of Tretinoin.
RosiglitazoneThe metabolism of Tretinoin can be decreased when combined with Rosiglitazone.
Sipuleucel-TThe therapeutic efficacy of Sipuleucel-T can be decreased when used in combination with Tretinoin.
TacrolimusThe risk or severity of adverse effects can be increased when Tacrolimus is combined with Tretinoin.
TofacitinibTretinoin may increase the immunosuppressive activities of Tofacitinib.
Tranexamic AcidTretinoin may increase the thrombogenic activities of Tranexamic Acid.
TrastuzumabTrastuzumab may increase the neutropenic activities of Tretinoin.
TrimethoprimThe metabolism of Tretinoin can be decreased when combined with Trimethoprim.
VerteporfinTretinoin may increase the photosensitizing activities of Verteporfin.
Vitamin AThe risk or severity of adverse effects can be increased when Vitamin A is combined with Tretinoin.
Food InteractionsNot Available

Targets

Kind
Protein
Organism
Human
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 expression in various biological processes. The RAR/RXR heterodimers bind to the retinoic acid response elements (RARE) composed of tandem 5'-AGGTCA-3' sites known as DR1-DR5 (By similarity). Specifically bin...
Gene Name:
RXRB
Uniprot ID:
P28702
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
Human
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 expression in various biological processes. The RAR/RXR heterodimers bind to the retinoic acid response elements (RARE) composed of tandem 5'-AGGTCA-3' sites known as DR1-DR5. The high affinity ligand for RXR...
Gene Name:
RXRG
Uniprot ID:
P48443
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
Human
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 expression in various biological processes. The RAR/RXR heterodimers bind to the retinoic acid response elements (RARE) composed of tandem 5'-AGGTCA-3' sites known as DR1-DR5. In the absence of ligand, acts m...
Gene Name:
RARG
Uniprot ID:
P13631
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
Human
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
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
Human
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 between retinoid and G-protein signaling pathways. Functions as a negative modulator of EGFR signaling (By similarity). May act as a lung tumor suppressor (PubMed:18000218).
Gene Name:
GPRC5A
Uniprot ID:
Q8NFJ5
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
Human
Pharmacological action
unknown
General Function:
Transcription factor binding
Specific Function:
Orphan nuclear receptor. Component of a cascade required for the development of the hypothalamic-pituitary-adrenal-gonadal axis. Acts as a coregulatory protein that inhibits the transcriptional activity of other nuclear receptors through heterodimeric interactions. May also have a role in the development of the embryo and in the maintenance of embryonic stem cell pluripotency (By similarity).
Gene Name:
NR0B1
Uniprot ID:
P51843
Molecular Weight:
51717.185 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 ]
Kind
Protein
Organism
Human
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 efficiently (By similarity).
Gene Name:
ALDH1A2
Uniprot ID:
O94788
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
Human
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
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 ]

Enzymes

Kind
Protein
Organism
Human
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 unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:
CYP3A7
Uniprot ID:
P24462
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
Human
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 unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,4-cineole 2-exo-monooxygenase.
Gene Name:
CYP2B6
Uniprot ID:
P20813
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 ]
Kind
Protein
Organism
Human
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 unrelated compounds, including steroids, fatty acids, and xenobiotics. In the epoxidation of arachidonic acid it generates only 14,15- and 11,12-cis-epoxyeicosatrienoic acids. It is the principal enzyme...
Gene Name:
CYP2C8
Uniprot ID:
P10632
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
Human
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 unrelated compounds, including steroids, fatty acids, and xenobiotics. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenyto...
Gene Name:
CYP2C9
Uniprot ID:
P11712
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 ]
Kind
Protein
Organism
Human
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 reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiot...
Gene Name:
CYP3A4
Uniprot ID:
P08684
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
Human
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 unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:
CYP3A5
Uniprot ID:
P20815
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
Human
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. Constitutes the major nicotine C-oxidase. Acts as a 1,4-cineole 2-exo-monooxygenase. Possesses low phenacetin O-deethylation activity.
Gene Name:
CYP2A6
Uniprot ID:
P11509
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 ]
Kind
Protein
Organism
Human
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 unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:
CYP2C18
Uniprot ID:
P33260
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
Human
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 unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:
CYP1A1
Uniprot ID:
P04798
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
Human
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 20-hydroxyeicosatetraenoic acid (20-HETE).
Gene Name:
CYP4A11
Uniprot ID:
Q02928
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 ]

Transporters

Kind
Protein
Organism
Human
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
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
Human
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
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 ]
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Drug created on June 13, 2005 07:24 / Updated on April 29, 2016 02:29