Alitretinoin

Title: Alitretinoin
CAS Registry Number: 5300-03-8
CAS Name: 9-cis-Retinoic acid
Additional Names: 6-cis-retinoic acid
Manufacturers' Codes: ALRT-1057; LGD-1057
Trademarks: Panretin (Ligand)
Molecular Formula: C20H28O2
Molecular Weight: 300.44
Percent Composition: C 79.95%, H 9.39%, O 10.65%
Literature References: Naturally occurring derivative of vitamin A, q.v. Morphogenic agent that modulates cell growth and differentiation; activates both retinoic acid (RAR) and retinoid X (RXR) receptors. Prepn: C. D. Robeson et al., J. Am. Chem. Soc. 77, 4111 (1955); M. Matsui et al., J. Vitaminol. 4, 178 (1958); M. F. Boehm et al., J. Med. Chem. 37, 408 (1994). Identification as physiological ligand of RXR: R. A. Heyman et al., Cell 68, 397 (1992); A. A. Levin et al., Nature 355, 359 (1992). Role in morphogenesis: C. Thaller et al., Development 118, 957 (1993). Biosynthesis from all-trans-retinoic acid: J. Urbach, R. R. Rando, Biochem. J. 299, 459 (1994). HPLC determn in plasma: A. M. Dzerk et al., J. Pharm. Biomed. Anal. 16, 1013 (1998). Clinical pharmacokinetics: C. Weber, E. Dumont, J. Clin. Pharmacol. 37, 566 (1997). Clinical evaluation in acute promyelocytic leukemia: S. L. Soignet et al., Leukemia 12, 1518 (1998); in advanced cancers: N. A. Rizvi et al., Clin. Cancer Res. 4, 1437 (1998). Review of role as hormone: B. F. Tate et al., Trends Endocrinol. Metab. 5, 189-194 (1994); of clinical development: J. Cell. Biochem. Suppl. 26, 158-167 (1996).
Properties: Yellow fine needles from ethanol, mp 190-191°. uv max (methanol): 343 nm (e 39000).
Melting point: mp 190-191°
Absorption maximum: uv max (methanol): 343 nm (e 39000)
Therap-Cat: Antineoplastic.
Keywords: Antineoplastic; Retinoids and Analogs.
Alizapride Alizarin Alizarin Cyanine Green F Alizarine Blue Alizarine Orange

Alitretinoin
Alitretinoin2DACS.svg
Alitretinoin3Dan.gif
Systematic (IUPAC) name
(2E,4E,6Z,8E)-3,7-dimethyl-9-(2,6,6-trimethyl-
1-cyclohexenyl)nona-2,4,6,8-tetraenoic acid
Clinical data
Trade names Panretin (gel), Toctino (oral)
AHFS/Drugs.com monograph
MedlinePlus a601012
Licence data EMA:Link, US FDA:link
Pregnancy cat. D (US)
Legal status POM (UK) -only (US)
Routes Topical, oral
Pharmacokinetic data
Protein binding Highly bound, no exact figure available[1]
Metabolism Hepatic (CYP3A4-mediated oxidation, also isomerised to tretinoin)[1]
Half-life 2-10 hours[1]
Excretion Urine (64%), faeces (30%)[1]
Identifiers
CAS number 5300-03-8 YesY
ATC code D11AH04 L01XX22
PubChem CID 449171
IUPHAR ligand 2645
DrugBank DB00523
ChemSpider 395778 YesY
UNII 1UA8E65KDZ YesY
ChEBI CHEBI:50648 YesY
ChEMBL CHEMBL705 YesY
Chemical data
Formula C20H28O2 
Mol. mass 300.435 g/mol
 YesY (what is this?)  (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.