Alitretinoin

Alitretinoin

Clinical data
Trade names	Panretin (gel), Toctino (oral)
AHFS/Drugs.com	Monograph
MedlinePlus	a601012
License data	EU EMA: by INN US DailyMed: Alitretinoin
Routes of administration	Topical, by mouth
ATC code	D11AH04 (WHO) L01XF02 (WHO)
Legal status
Legal status	UK: POM (Prescription only) US: ℞-only EU: Rx-only
Pharmacokinetic data
Protein binding	Highly bound, no exact figure available[1]
Metabolism	Liver (CYP3A4-mediated oxidation, also isomerised to tretinoin)[1]
Elimination half-life	2–10 hours[1]
Excretion	Urine (64%), faeces (30%)[1]
Identifiers
IUPAC name (2E,4E,6Z,8E)-3,7-dimethyl-9-(2,6,6-trimethyl- 1-cyclohexenyl)nona-2,4,6,8-tetraenoic acid
CAS Number	5300-03-8 Y
PubChem CID	449171
IUPHAR/BPS	2645
DrugBank	DB00523 Y
ChemSpider	395778 Y
UNII	1UA8E65KDZ
KEGG	D02815
ChEBI	CHEBI:50648 Y
ChEMBL	ChEMBL705 Y
CompTox Dashboard (EPA)	DTXSID6040404
ECHA InfoCard	100.111.081
Chemical and physical data
Formula	C20H28O2
Molar mass	300.442 g·mol−1
3D model (JSmol)	Interactive image
SMILES O=C(O)\C=C(\C=C\C=C(/C=C/C1=C(/CCCC1(C)C)C)C)C
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+ Y Key:SHGAZHPCJJPHSC-ZVCIMWCZSA-N Y
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Alitretinoin, or 9-cis-retinoic acid, is a form of vitamin A. It is also used in medicine as an antineoplastic (anti-cancer) agent developed by Ligand Pharmaceuticals. It is a first generation retinoid. Ligand gained Food and Drug Administration (FDA) approval for alitretinoin in February 1999.