9550. Toremifene

Nomenclature

CAS number: 89778-26-7
2-[4-[(1Z)-4-Chloro-1,2-diphenyl-1-buten-1-yl]phenoxy]-N,N-dimethylethanamine; (Z)-4-chloro-1,2-diphenyl-1-[4-[2-(N,N-dimethylamino)ethoxy]phenyl]-1-butene.
C26H28ClNO; mol wt 405.96.
C 76.92%, H 6.95%, Cl 8.73%, N 3.45%, O 3.94%.

Description and references

Nonsteroidal antiestrogen structurally similar to tamoxifen, q.v. Prepn: R. J. Toivola et al., EP 95875; eidem, US 4696949 (1983, 1987 both to Farmos). Pharmacology: S. Kallio et al., Cancer Chemother. Pharmacol. 17, 103 (1986). Antitumor effects in vitro and in vivo: L. Kangas et al., ibid. 109. HPLC determn in plasma: W. M. Holleran et al., Anal. Lett. 20, 871 (1987). Clinical evaluation in high-grade prostatic intraepithelial neoplasia: M. S. Steiner, C. R. Pound, Clin. Prostate Cancer 2, 24 (2003). Review of pharmacology and clinical efficacy in advanced breast cancer: L. R. Wiseman, K. L. Goa, Drugs 54, 141-160 (1997); in postmenopausal breast cancer: J. U. Menp, S.-L. Ala-Fossi, Drugs Aging 11, 261-270 (1997).

Chemical structure

Properties

mp 108-110°.

Derivative

Citrate.

Nomenclature

CAS number: 89778-27-8
FC-1157a; Acapodene (GTx); Fareston (GTx).
C26H28ClNO.C6H8O7; mol wt 598.08.
C 64.26%, H 6.07%, Cl 5.93%, N 2.34%, O 21.40%.

Properties

Off-white powder. mp 160-162°. pKa 8.0. Soly at 37° (mg/ml): water 0.63; 0.02N HCl 0.38.

Therapeutic Category

Antineoplastic.

Keywords

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