Bexarotene

Title: Bexarotene
CAS Registry Number: 153559-49-0
CAS Name: 4-[1-(5,6,7,8-Tetrahydro-3,5,5,8,8-pentamethyl-2-naphthalenyl)ethenyl]benzoic acid
Manufacturers' Codes: SR-11247; LGD-1069
Trademarks: Targretin (Ligand)
Molecular Formula: C24H28O2
Molecular Weight: 348.48
Percent Composition: C 82.72%, H 8.10%, O 9.18%
Literature References: Selective retinoid X receptor (RXR) agonist. Prepn: M. F. Boehm et al., WO 9321146 (1993 to Ligand Pharm.); M. L. Dawson et al., US 5466861 (1995 to SRI Int.; La Jolla Cancer Res. Found.); and structure-activity study: M. F. Boehm et al., J. Med. Chem. 37, 2930 (1994); M. I. Dawson et al., ibid. 38, 3368 (1995). Chemopreventive effect in rat mammary carcinoma: M. M. Gottardis et al., Cancer Res. 56, 5566 (1996). Effect on glucose homeostasis in exptl diabetes: R. Mukherjee et al., Nature 386, 407 (1997). Clinical pharmacokinetics and evaluation in advanced cancers: V. A. Miller et al., J. Clin. Oncol. 15, 790 (1997). Clinical evaluation in cutaneous T-cell lymphoma: D. Breneman et al., Arch. Dermatol. 138, 325 (2002).
Properties: White solid from methylene chloride, mp 230-231° (Dawson, 1995); also reported as white crystals, mp 234° (Boehm, 1994). uv max (methanol): 264 nm (e 16400).
Melting point: mp 230-231° (Dawson, 1995); mp 234° (Boehm, 1994)
Absorption maximum: uv max (methanol): 264 nm (e 16400)
Therap-Cat: Antineoplastic.
Keywords: Antineoplastic; Retinoids and Analogs.
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Bexarotene
Bexarotene2DACS.svg
Bexarotene3Dan.gif
Systematic (IUPAC) name
4-[1-(3,5,5,8,8-pentamethyltetralin-2-yl)ethenyl]benzoic acid
Clinical data
Trade names Targretin
AHFS/Drugs.com monograph
MedlinePlus a608006
Licence data EMA:Link, US FDA:link
Pregnancy cat. X (US)
Legal status POM (UK) -only (US)
Routes Oral and topical
Pharmacokinetic data
Protein binding >99%
Metabolism Hepatic (CYP3A4-mediated)
Half-life 7 hours
Excretion Parent drug and metabolites are eliminated primarily through the hepatobiliary system. Less than 1% is excreted in the urine unchanged.
Identifiers
CAS number 153559-49-0 YesY
ATC code L01XX25
PubChem CID 82146
IUPHAR ligand 2807
DrugBank DB00307
ChemSpider 74139 YesY
UNII A61RXM4375 YesY
ChEBI CHEBI:50859 YesY
ChEMBL CHEMBL1023 YesY
Chemical data
Formula C24H28O2 
Mol. mass 348.478 g/mol
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Bexarotene (brand name: Targretin) is an antineoplastic (anti-cancer) agent indicated by the U.S.Food and Drug Administration (FDA) (in late 1999) and the European Medicines Agency (EMA) (early 2001) for use as a treatment for cutaneous T cell lymphoma (CTCL).[1]