Raloxifene hydrochloride Chemical Properties

Melting point:

250-253°C

storage temp. 

2-8°C

solubility 

DMSO: 28 mg/mL, soluble

form 

solid

color 

light yellow

λmax

286nm(lit.)

Merck 

14,8098

BCS Class

2

InChI

InChI=1S/C28H27NO4S.ClH/c30-21-8-4-20(5-9-21)28-26(24-13-10-22(31)18-25(24)34-28)27(32)19-6-11-23(12-7-19)33-17-16-29-14-2-1-3-15-29;/h4-13,18,30-31H,1-3,14-17H2;1H

InChIKey

BKXVVCILCIUCLG-UHFFFAOYSA-N

SMILES

C1(C(=O)C2C=CC(OCCN3CCCCC3)=CC=2)C2C=CC(O)=CC=2SC=1C1C=CC(O)=CC=1.Cl

CAS DataBase Reference

82640-04-8(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

22-24/25

WGK Germany 

3

RTECS 

PC4956925

HS Code 

2934990002

MSDS

• Language:English Provider:SigmaAldrich

Raloxifene hydrochloride Usage And Synthesis

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

Originator

Lilly (US)

Uses

Raloxifene hydrochloride can be used as a nonsteroidal, selective estrogen receptor modulator (SERM). Antiosteoporotic.

Uses

amino acid, nutrient. A nonsteroidal, selective estrogen receptor modulator (SERM). Antiosteoporotic.Insoluble in water.

Uses

Labeled Raloxifene, intended for use as an internal standard for the quantification of Raloxifene by GC- or LC-mass spectrometry.

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.

storage

+4°C (desiccate)

References

[1] obach rs.potent inhibition of human liver aldehyde oxidase by raloxifene.

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