CHEBI:6067 - isotretinoin

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ChEBI Name isotretinoin
ChEBI ID CHEBI:6067
Definition A retinoic acid that is all-trans-retinoic acid in which the double bond which is α,β- to the carboxy group is isomerised to Z configuration. A synthetic retinoid, it is used for the treatment of severe cases of acne and other skin diseases.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C20H28O2
Net Charge 0
Average Mass 300.43512
Monoisotopic Mass 300.209
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-
InChIKey SHGAZHPCJJPHSC-XFYACQKRSA-N
SMILES CC(\C=C\C1=C(C)CCCC1(C)C)=C/C=C/C(C)=C\C(O)=O
Roles Classification
Chemical Role(s): Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
Biological Role(s): teratogenic agent
A role played by a chemical compound in biological systems with adverse consequences in embryo developments, leading to birth defects, embryo death or altered development, growth retardation and functional defect.
human metabolite
Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens).
(via retinoic acid )
Application(s): keratolytic drug
A drug that softens, separates, and causes desquamation of the cornified epithelium or horny layer of skin. Keratolytic drugs are used to expose mycelia of infecting fungi or to treat corns, warts, and certain other skin diseases.
antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
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ChEBI Ontology
Outgoing isotretinoin (CHEBI:6067) has role antineoplastic agent (CHEBI:35610)
isotretinoin (CHEBI:6067) has role keratolytic drug (CHEBI:50176)
isotretinoin (CHEBI:6067) has role teratogenic agent (CHEBI:50905)
isotretinoin (CHEBI:6067) is a retinoic acid (CHEBI:26536)
IUPAC Name
(2Z,4E6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenoic acid
INNs Sources
isotretinoin ChemIDplus
isotretinoína WHO MedNet
isotrétinoine WHO MedNet
isotretinoinum ChemIDplus
Synonyms Sources
(7E,9E,11E,13Z)-retinoic acid JCBN
13-cis-retinoic acid JCBN
13-cis-Vitamin A acid ChemIDplus
13-RA ChemIDplus
cis-RA ChEBI
isotretinoino ChemIDplus
Neovitamin A acid ChemIDplus
Brand Names Sources
Accutane DrugBank
Amnesteem DrugBank
Claravis DrugBank
Manual Xrefs Databases
1508 DrugCentral
D00348 KEGG DRUG
DB00982 DrugBank
EP111325 Patent
HMDB0006219 HMDB
Isotretinoin Wikipedia
LMPR01090021 LIPID MAPS
US4556518 Patent
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Registry Numbers Types Sources
1885770 Reaxys Registry Number Reaxys
1885770 Beilstein Registry Number Beilstein
4759-48-2 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
11606947 PubMed citation Europe PMC
11866680 PubMed citation Europe PMC
15304471 PubMed citation Europe PMC
18077132 PubMed citation Europe PMC
18788179 PubMed citation Europe PMC
19568610 PubMed citation Europe PMC
20482692 PubMed citation Europe PMC
23676507 PubMed citation Europe PMC
9807973 PubMed citation Europe PMC
Last Modified
22 February 2017