Idoxifene

Idoxifene (INN, USAN, BAN) (former developmental code names CB-7432, SB-223030), also known as pyrrolidino-4-iodotamoxifen, is a nonsteroidal selective estrogen receptor modulator (SERM) of the triphenylethylene group which was under development for the treatment of breast cancer and postmenopausal osteoporosis but was never marketed.[1][2][3] It reached phase III clinical trials for postmenopausal osteoporosis and phase II clinical trials for breast cancer before development was discontinued in 1999 due insufficient effectiveness in both cases.[1]

Idoxifene
Clinical data
Other namesCB-7432, SB-223030; Pyrrolidino-4-iodotamoxifen; 4-Iodopyrrolidinotamoxifen
Routes of
administration		Oral
Pharmacokinetic data
Elimination half-lifeAcute: 15 hours[1]
Chronic: 23 days[1]
Identifiers
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC28H30INO
Molar mass523.458 g·mol−1
3D model (JSmol)

Chemistry

Synthesis

A large-scale chemical synthesis of idoxifene has been devised.[4]

References
  1. https://adisinsight.springer.com/drugs/800003448%5B%5D
  2. William R. Miller; James N. Ingle (8 March 2002). Endocrine Therapy in Breast Cancer. CRC Press. pp. 58–. ISBN 978-0-203-90983-6.
  3. McCague R, Leclercq G, Legros N, Goodman J, Blackburn GM, Jarman M, Foster AB (1989). "Derivatives of tamoxifen. Dependence of antiestrogenicity on the 4-substituent". J. Med. Chem. 32 (12): 2527–33. doi:10.1021/jm00132a006. PMID 2585441.
  4. McCague, Raymond; Potter, Gerard A.; Jarman, Michael (1994). "AN EFFICIENT, LARGE-SCALE SYNTHESIS OF IDOXIFENE {(E)-1-[4-[2-(N-PYRROLIDINO)ETHOXY]PHENYL]-1-(4-IODOPHENYL)-2-PHENYL-1-BUTENE}". Organic Preparations and Procedures International. 26 (3): 343–346. doi:10.1080/00304949409458432. ISSN 0030-4948.



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