84449-90-1 Usage
Description
Raloxifene, also known as Evista, is a benzothiophene derivative and a member of the class of 1-benzothiophenes. It is a nonsteroidal, selective estrogen receptor modulator (SERM) with a unique structure that includes a carbonyl "hinge" connecting the modified phenolic side chain to the benzothiophene ring system. This hinge is the key structural element that leads to the differing actions at the estrogen receptors (ERs). Raloxifene exhibits antagonist properties on the endometrium and breast tissue and agonist properties on bone and the cardiovascular system. It is a light-yellow solid and is approved for the prevention and treatment of osteoporosis in postmenopausal women. Additionally, it has been investigated for preventing breast cancer in comparison with tamoxifen, showing similar effectiveness but with a preferable side effect profile.
Uses
Used in Pharmaceutical Industry:
Raloxifene is used as an antiosteoporotic agent for the prevention and treatment of osteoporosis in postmenopausal women. Its agonist properties on bone help to increase bone mineral density and reduce the risk of fractures.
Used in Oncology:
Raloxifene is used as a breast cancer prevention agent, particularly in postmenopausal women at high risk of developing the disease. It has been compared with tamoxifen and has shown similar effectiveness in preventing breast cancer, but with a more favorable side effect profile.
Used in Research:
Raloxifene is used in research for studying the effects of selective estrogen receptor modulators on various tissues and diseases. Its unique structure and properties allow for a better understanding of the mechanisms of action of SERMs and their potential applications in the treatment and prevention of various conditions, including cardiovascular diseases and osteoporosis.
Application in Particular Diseases
In Osteoporosis:
Raloxifene is an estrogen agonist on bone but an antagonist on the breast and uterus. It is approved for prevention and treatment of postmenopausal osteoporosis. Other estrogen agonists/antagonists may be approved soon (e.g., bazedoxifene, lasofoxifene).
Raloxifene decreases vertebral fractures and increases spine and hip BMD, but to a lesser extent than bisphosphonates. After discontinuation, the beneficial effect is lost and bone loss returns to age- or disease-related rates.
Raloxifene (like tamoxifen) is associated with decreased breast cancer risk. Raloxifene is associated with decreases in total and low-density lipoprotein cholesterol, neutral effects on high-density lipoprotein cholesterol, but slight increases in triglycerides; no beneficial cardiovascular effects have yet been demonstrated.
Raloxifene is well tolerated overall. Hot flushes occur more frequently in women recently finishing menopause or discontinuing estrogen therapy (ET). Endometrial bleeding occurs rarely. Raloxifene is contraindicated in women with an active or past history of venous thromboembolism. Therapy should be stopped if a patient anticipates extended immobility.
Indications
Raloxifene (Evista) is a new SERM approved for
use in the treatment and prevention of osteoporosis because
it has estrogenic activity in bone. Raloxifene is an
estrogen antagonist in both breast and endometrial tissues.
The estrogenlike properties of raloxifene result in
the maintenance of a favorable serum lipid profile (decreased
low-density lipoprotein levels with no change
in either high-density lipoproteins or triglycerides).
Raloxifene is 95% bound to plasma proteins. Absorption
of raloxifene is impaired by cholestyramine.
Biological Activity
Selective estrogen receptor modulator (SERM) that binds to ER α and ER β , and tissue-dependently activates or blocks estrogen-induced transcription. Acts as an antiestrogen in breast and uterine tissue, but displays estrogen agonist activity in bone. In D12 rat hypothalamic cells, inhibits progesterone receptor induction by estrogen with an IC 50 of 1 nM.
Clinical Use
Raloxifene, the first SERM
approved for the prevention of osteoporosis in postmenopausal women, acts as an estrogen agonist on
receptors in osteoblasts and osteoclasts but as an antagonist at breast and uterine estrogen receptors.
Check Digit Verification of cas no
The CAS Registry Mumber 84449-90-1 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 8,4,4,4 and 9 respectively; the second part has 2 digits, 9 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 84449-90:
(7*8)+(6*4)+(5*4)+(4*4)+(3*9)+(2*9)+(1*0)=161
161 % 10 = 1
So 84449-90-1 is a valid CAS Registry Number.
InChI:InChI=1/C28H27NO4S/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
84449-90-1Relevant articles and documents
Efficient synthesis of 3-benzoyl Benzo[b]thiophenes and raloxifene via Mercury(II)-Catalyzed cyclization of 2-alkynylphenyl alkyl sulfoxides
Wen, Shi-Ming,Lin, Cheng-Han,Chen, Chin-Chau,Wu, Ming-Jung
, p. 2493 - 2499 (2018/04/16)
The unique selective estrogen receptor modulator, Raloxifene (1), and antitubulin agent 2 were synthesized through the key intermediate, 4-methoxybenzyl 2-bromo-4-methoxyphenyl sulfoxide (6), respectively. It was found that compared with the o-sulfanyl aryl bromides, the sulfinyl group at ortho position accelerated the Sonogashira coupling reaction of aryl bromides. Thus, compound 6 was coupled with 3,4,5-trimethoxyphenyl acetylene, followed by mercury-catalyzed cyclization reaction afford compound 2 in 79% overall yield. Raloxifene (1) was prepared from compound 6 in four steps and 33% overall yield via coupling reaction with 1-trimethylsily-2-(4-tert-butyldimethylsiloxy)phenylethyne, mercury-catalyzed cyclization reaction, alkylation and demethylation.
Methods for Determining the Oncogenic Condition of Cell, Uses Thereof, and Methods for Treating Cancer
-
, (2017/07/14)
The invention relates to methods for detecting the oncogenic condition of cells, including step where the amount of the OCDO compound in said cells is measured, and to the uses thereof. The invention further relates to OCDO inhibitors for use in methods for treating cancer.
Piperidine nucleophilic substitution without solvent: An efficient synthesis of raloxifene
Yang, Yewei,Zhang, Tao,Huang, Wenhai,Shen, Zhenrong
, p. 3271 - 3276 (2015/10/06)
Mild and high-yielding synthesis is described for raloxifene via piperdine nucleophilic substitution of a new raloxifene intermediate 3-aroyl-2-aryl-substituted benzo[b]thiophenes, which is obtained by acylation of para-substituted benzoyl chlorides and 2-arylbenzo[b]thiophenes. The key step is solvent free and offers valuable advantages, such as low cost, and is suitable for industrial production.