9-cis retinoic acid

Alitretinoin

Clinical data
Trade names	Panretin (gel), Toctino (oral)
AHFS/Drugs.com	Monograph
MedlinePlus	a601012
License data	EU EMA: by Alitretinoin US FDA: Alitretinoin
Pregnancy category	US: D (Evidence of risk)
Routes of administration	Topical, oral
ATC code	D11AH04 (WHO) L01XX22 (WHO)
Legal status
Legal status	UK: POM (Prescription only) US: ℞-only
Pharmacokinetic data
Protein binding	Highly bound, no exact figure available
Metabolism	Hepatic (CYP3A4-mediated oxidation, also isomerised to tretinoin)
Biological 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 Y
PubChem CID	449171
IUPHAR/BPS	2645
DrugBank	DB00523 Y
ChemSpider	395778 Y
UNII	1UA8E65KDZ
ChEBI	CHEBI:50648 Y
ChEMBL	CHEMBL705 Y
ECHA InfoCard	100.111.081
Chemical and physical data
Formula	C20H28O2
Molar mass	300.435 g/mol
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

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.

In the United States, topical alitretinoin (in the form of a gel; trade name Panretin) is indicated for the treatment of skin lesions in AIDS-related Kaposi's sarcoma. Alitretinoin is not indicated when systemic therapy against Kaposi's sarcoma is required. It has received EMA (11 October 2000) and FDA (2 March 1999) approval for this indication.

Under the trade name Toctino (marketed by GSK, UK) it has been granted prescription rights in the UK (08/09/2008) for oral use in chronic hand eczema. In May 2009 the National Institute for Health and Clinical Excellence (NICE) issued preliminary guidance on the use of Alitretinoin for the treatment of severe chronic hand eczema in adults. The recommendation stated that only patients with severe chronic hand eczema who are unresponsive to potent topical corticosteroids, oral immunosuppressants or phototherapy should receive the drug. Final NICE guidance is expected in August 2009.

Systemic use, when being used to treat chronic hand eczema

Very common (>10% frequency):

Common (1-10% frequency):

Uncommon (0.1-1% frequency):

Rare (<0.1% frequency):

Unknown frequency:

Topical use for Kaposi's sarcoma

Very common (>10% frequency):

Common (1-10% frequency):

Pregnancy is an absolute contraindication as with most other vitamin A products, it should also be avoided when it comes to systemic use in any women that is of childbearing potential and not taking precautions to prevent pregnancy. Toctino (the oral capsule formulation of alitretinoin) contains soya oil and sorbitol. Patients who are allergic to peanut, soya or with rare hereditary fructose intolerance should not take this medicine. It is also contraindicated in nursing mothers. The oral formulation of alitretinoin is contraindicated in patients with: