8098. Raloxifene

Nomenclature

CAS number: 84449-90-1
[6-Hydroxy-2-(4-hydroxyphenyl)benzo[b]thien-3-yl][4-[2-(1-piperidinyl)ethoxy]phenyl]methanone; keoxifene; LY-139481.
C28H27NO4S; mol wt 473.58.
C 71.01%, H 5.75%, N 2.96%, O 13.51%, S 6.77%.

Description and references

Nonsteroidal, selective estrogen receptor modulator (SERM). Prepn: C. D. Jones, EP 62503; idem, US 4418068 (1982, 1983 both to Lilly); idem et al., J. Med. Chem. 27, 1057 (1984). Review of pharmacology and toxicology: J. Buelke-Sam et al., Reprod. Toxicol. 12, 217-221 (1998); of clinical pharmacology and pharmacokinetics: D. Hochner-Celnikier, Eur. J. Obstet. Gynecol. Reprod. Biol. 85, 23-29 (1999); of clinical efficacy in osteoporosis: D. Agnusdei, ibid. 43-46. Clinical effect on risk of breast cancer: S. R. Cummings et al., J. Am. Med. Assoc. 281, 2189 (1999); on reduction of fracture risk: B. Ettinger et al., ibid. 282, 637 (1999).

Chemical structure

Properties

Crystals from acetone, mp 143-147°. uv max (ethanol): 290 nm (ε 34000).

Derivative

Hydrochloride.

Nomenclature

CAS number: 82640-04-8
LY-156758; Evista (Lilly).
C28H27NO4S.HCl; mol wt 510.04.
C 65.94%, H 5.53%, N 2.75%, O 12.55%, S 6.29%, Cl 6.95%.

Properties

Crystals from methanol/water, mp 258°. uv max (ethanol): 286 nm (ε 32800).

Therapeutic Category

Antiosteoporotic.

Keywords

Antiosteoporotic; Selective Estrogen Receptor Modulator (SERM)