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
Metabolism	Liver (CYP3A4-mediated oxidation, also isomerised to tretinoin)
Elimination half-life	2–10 hours
Excretion	Urine (64%), faeces (30%)
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 ;
PubChem CID	449171;
IUPHAR/BPS	2645;
DrugBank	DB00523 ;
ChemSpider	395778 ;
UNII	1UA8E65KDZ;
KEGG	D02815;
ChEBI	CHEBI:50648 ;
ChEMBL	ChEMBL705 ;
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+ ; Key:SHGAZHPCJJPHSC-ZVCIMWCZSA-N ;
	(verify)

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.