Chemical Component Summary

NameRETINOIC ACID
Identifiers(2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,4,6,8-tetraenoic acid
FormulaC20 H28 O2
Molecular Weight300.435
TypeNON-POLYMER
Isomeric SMILESCC1=C(C(CCC1)(C)C)/C=C/C(=C/C=C/C(=C/C(=O)O)/C)/C
InChIInChI=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+
InChIKeySHGAZHPCJJPHSC-YCNIQYBTSA-N

Chemical Details

Formal Charge0
Atom Count50
Chiral Atom Count0
Bond Count50
Aromatic Bond Count0

Drug Info: DrugBank

DrugBank IDDB00755 
NameTretinoin
Groups
  • approved
  • investigational
  • nutraceutical
DescriptionTretinoin, also known as all-trans-retinoic acid (ATRA), is a naturally occurring derivative of [vitamin A] (retinol).[A257474] It is an oxidation product in the physiological pathway of vitamin A metabolism.[A257689] In human circulation, tretinoin is normally found at very low concentrations, approximately 4 to 14 nmol/L.[A257689] Tretinoin exhibits anti-inflammatory, antineoplastic, antioxidant, and free radical-scavenging activities.[A257689] It has been used in dermatology for many years to treat various skin conditions ranging from acne to wrinkles [A257474,A258185] and activates nuclear receptors to regulate epithelial cell growth and differentiation.[A257474,A257629,A257609] Tretinoin is given orally to treat acute promyelocytic leukemia [L45349] and topically to treat skin conditions such as acne.[L45389,L34869,L45384]
Synonyms
  • Vitamin A acid
  • all-trans-Tretinoin
  • beta-Retinoic acid
  • Trétinoïne
  • trans-Retinoic acid
Brand Names
  • TRETIN-X Gel 0.01%
  • TRETIN-X Cream 0.1%
  • Vitamin A Acid 0.1% Cream
  • Dr. Throwers Pbc No. 1
  • Ziana
IndicationOral tretinoin is indicated for induction of remission in adults and pediatric patients one year of age and older with acute promyelocytic leukemia (APL), characterized by the presence of t(15;17) translocation or presence of PML/RARα gene expression and who are refractory to or who have relapsed from anthracycline chemotherapy or for whom anthracycline-based chemotherapy is contraindicated.[L45349] Topical tretinoin is also indicated alone [L45389] or in combination with [benzoyl peroxide] [L34869] or [clindamycin] [L45384] for the treatment of acne vulgaris. It is also used in prescription and over-the-counter for treating various skin conditions such as melasma,[L45394] hyperpigmentation,[A257474] and photoaging [A258180] alone or in combination with other drugs.
Categories
  • Agents that produce hypertension
  • Alkenes
  • Anti-Acne Preparations
  • Anti-Acne Preparations for Topical Use
  • Antineoplastic Agents
ATC-Code
  • L01XF01
  • D10AD51
  • D10AD01
CAS number302-79-4

Drug Targets

NameTarget SequencePharmacological ActionActions
Retinoic acid receptor alphaMASNSSSCPTPGGGHLNGYPVPPYAFFFPPMLGGLSPPGALTTLQHQLPV...unknownagonist
Retinoic acid receptor betaMTTSGHACPVPAVNGHMTHYPATPYPLLFPPVIGGLSLPPLHGLHGHPPP...unknownagonist
Retinoic acid receptor gammaMATNKERLFAAGALGPGSGYPGAGFPFAFPGALRGSPPFEMLSPSFRGLG...unknownagonist
Retinoic acid receptor RXR-alphaMDTKHFLPLDFSTQVNSSLTSPTGRGSMAAPSLHPSLGPGIGSPGQLHSP...unknownagonist
Retinoic acid receptor RXR-betaMSWAARPPFLPQRHAAGQCGPVGVRKEMHCGVASRWRRRRPWLDPAAAAA...unknownagonist
View More
Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682

Related Resource References

Resource NameReference
Pharos CHEMBL38
PubChem 444795
ChEMBL CHEMBL38
ChEBI CHEBI:15367
CCDC/CSD VITAAC01, VITAAC10, VITAAC11