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CHEBI:6067 - isotretinoin

ChEBI IDCHEBI:6067
ChEBI Nameisotretinoin
Stars
DefinitionA 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.
Last Modified22 February 2017
DownloadsMolfile
FormulaC20H28O2
Net Charge0
Average Mass300.442
Monoisotopic Mass300.20893
SMILESCC1=C(/C=C/C(C)=C/C=C/C(C)=C\C(=O)O)C(C)(C)CCC1
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-XFYACQKRSA-N
Wikipedia
Roles Classification
Chemical Roles:
Bronsted acid  A molecular entity capable of donating a hydron to an acceptor (Brønsted base).
Bronsted acid  A molecular entity capable of donating a hydron to an acceptor (Brønsted base).
Biological Roles:
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).
Applications:
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.
ChEBI Ontology
Outgoing Relation(s)
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)
isotretinoin (CHEBI:6067) is conjugate acid of 13-cis-retinoate (CHEBI:169952)
Incoming Relation(s)
13-cis-retinoate (CHEBI:169952) is conjugate base of isotretinoin (CHEBI:6067)
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  Source
isotretinoinChemIDplus
isotrétinoineWHO MedNet
isotretinoinumChemIDplus
isotretinoínaWHO MedNet
Synonyms  Source
isotretinoinoChemIDplus
13-cis-retinoic acidJCBN
(7E,9E,11E,13Z)-retinoic acidJCBN
13-RAChemIDplus
13-cis-Vitamin A acidChemIDplus
Neovitamin A acidChemIDplus
Brand Names  Source
AccutaneDrugBank
AmnesteemDrugBank
ClaravisDrugBank
Manual XrefsDatabases
D00348KEGG DRUG
EP111325Patent
US4556518Patent
DB00982DrugBank
LMPR01090021LIPID MAPS
IsotretinoinWikipedia
HMDB0006219HMDB
1508DrugCentral
Registry NumbersSources
Reaxys:1885770Reaxys
CAS:4759-48-2ChemIDplus
Citations