4890. Idoxifene

Nomenclature

CAS number: 116057-75-1
1-[2-[4-[(1E)-1-(4-Iodophenyl)-2-phenyl-1-butenyl]phenoxy]ethyl]pyrrolidine; 1-[2-[p-[(E)-β-ethyl-α-(p-iodophenyl)styryl]phenoxy]ethyl]pyrrolidine; CB-7432.
C28H30INO; mol wt 523.45.
C 64.25%, H 5.78%, I 24.24%, N 2.68%, O 3.06%.

Description and references

Nonsteroidal estrogen antagonist; structurally analogous to tamoxifen, q.v. Prepn: R. McCague, EP 260066; idem, US 4839155 (1988, 1989 both to Nat. Res. Dev. Corp.); and structural activity: R. McCague et al., J. Med. Chem. 32, 2527 (1989). Stereochemistry: C. M. Nunn, E. J. Parker, Acta Crystallogr. C50, 2043 (1994). Modulating effects on multidrug resistance: J. Kirk et al., Biochem. Pharmacol. 48, 277 (1994); S. Y. Sharp et al., Br. J. Cancer 70, 409 (1994). Clinical evaluation in breast cancer: R. C. Coombes et al., Cancer Res. 55, 1070 (1995).

Chemical structure

Properties

Crystals from light petroleum (pet. ether), mp 108-109° (McCague et al.); also reported as colorless monoclinic prisms from methanol (Nunn).

Therapeutic Category

Antineoplastic.

Keywords

Antineoplastic (Hormonal); Antiestrogens; Selective Estrogen Receptor Modulator (SERM)