Idoxifene

Idoxifene

Clinical data
Other names	CB-7432, SB-223030; Pyrrolidino-4-iodotamoxifen; 4-Iodopyrrolidinotamoxifen
Routes of administration	Oral
Pharmacokinetic data
Elimination half-life	Acute: 15 hours [1] Chronic: 23 days [1]
Identifiers
IUPAC name 1-[2-[4-[(E)-1-(4-iodophenyl)-2-phenylbut-1-enyl]phenoxy]ethyl]pyrrolidine
CAS Number	116057-75-1
PubChem CID	3034011
ChemSpider	2298565
UNII	456UXE9867
KEGG	D04496
ChEMBL	ChEMBL6318
CompTox Dashboard (EPA)	DTXSID5043926
Chemical and physical data
Formula	C28H30INO
Molar mass	523.458 g·mol−1
3D model (JSmol)	Interactive image
SMILES CC/C(=C(/C1=CC=C(C=C1)OCCN2CCCC2)\C3=CC=C(C=C3)I)/C4=CC=CC=C4
InChI InChI=1S/C28H30INO/c1-2-27(22-8-4-3-5-9-22)28(23-10-14-25(29)15-11-23)24-12-16-26(17-13-24)31-21-20-30-18-6-7-19-30/h3-5,8-17H,2,6-7,18-21H2,1H3/b28-27- Key:JJKOTMDDZAJTGQ-DQSJHHFOSA-N

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 to insufficient effectiveness in both cases. ^[1]

Chemistry

Synthesis

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

References

1. "Idoxifene". AdisInsight. Springer Nature Switzerland AG.
2. Miller WR, Ingle JN (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 (December 1989). "Derivatives of tamoxifen. Dependence of antiestrogenicity on the 4-substituent". Journal of Medicinal Chemistry. 32 (12): 2527–2533. doi:10.1021/jm00132a006. PMID   2585441.
4. McCague R, Potter GA, Jarman M (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.