Description
Raloxifene was launched as Evista in the US for the prevention of
postmenopausal osteoporosis. It is noteworthy that this molecule was formerly
under development as keoxifene for breast cancer and prostatic hypertrophy.
Raloxifene can be prepared by acylation of 6-methoxy-2-(4-methoxyphenyl)
benzothiophene followed by simultaneous demethylation of both methoxy
groups. Raloxifen is a selective estrogen receptor modulator, exerting antiestrogenic
action on certain tissues (breast) and also estrogenic action on bone
metabolism or serum lipids. In normal early postmenopausal women, 200 mg
daily produced a trend towards suppression of estrogen effects. Raloxifen
impeded bone loss in osteoporosis. A two-year study in postmenopausal women
with an increased risk for osteoporosis showed that Raloxifen markedly
prevented non-traumatic vertebral fractures. Results of several clinical studies
demonstrated that Raloxifen appreciably reduced the risk of developing breast
cancer. Moreover, it had favourable effect on lipid profiles without having the
potential side-effects of estrogen-based therapies. Several extensions for
different uses of this molecule are planned, for example growth disorder,
obesity, colon tumor and skin atrophy. No serious drug-related events have
been reported in the limited number of clinical trials.
Chemical Properties
Light-Yellow Solid
Uses
amino acid, nutrient
Uses
Labeled Raloxifene, intended for use as an internal standard for the quantification of Raloxifene by GC- or LC-mass spectrometry.
Uses
Raloxifene hydrochloride can be used as a nonsteroidal, selective estrogen receptor modulator (SERM). Antiosteoporotic.
Definition
ChEBI: A hydrochloride salt resulting from the reaction of equimolar amounts of raloxifene and hydrogen chloride.
Brand name
Evista (Lilly).
General Description
Pharmaceutical secondary standards for application in quality control provide pharma laboratories and manufacturers with a convenient and cost-effective alternative to the preparation of in-house working standards
Biochem/physiol Actions
Raloxifene is a selective estrogen receptor modulator (SERM); acts as an anti-estrogen in both breast and uterine tissue while being estrogenic in bone. May have efficacy against estrogen-sensitive cancers.
Clinical Use
Treatment and prevention of osteoporosis in post
menopausal women
Drug interactions
Potentially hazardous interactions with other drugs
Anticoagulants: antagonism of anticoagulant effect of
coumarins.
Colestyramine: reduced absorption of raloxifene -
avoid.
Metabolism
Raloxifene undergoes extensive first pass metabolism
to the glucuronide conjugates: raloxifene-4'-
glucuronide, raloxifene-6-glucuronide, and raloxifene-6,
4′-diglucuronide.
Raloxifene undergoes enterohepatic recycling, and is
excreted almost entirely in the faeces. Less than 6% of
dose is excreted in the urine.
References
[1] obach rs.potent inhibition of human liver aldehyde oxidase by raloxifene.
