Basic information Safety Supplier Related

BAZEDOXIFENE ACETATE

Basic information Safety Supplier Related

BAZEDOXIFENE ACETATE Basic information

Product Name:
BAZEDOXIFENE ACETATE
Synonyms:
  • BAZEDOXIFENE ACETATE
  • 1-(p-(2-(Hexahydro-1H-azepin-1-yl)ethoxy)benzyl)-2-(p-hydroxyphenyl)-3-methylindol-5-ol monoacetate (salt)
  • 1H-Indol-5-ol, 1-((4-(2-(hexahydro-1H-azepin-1-yl)ethoxy)phenyl)methyl)-2-(4-hydroxyphenyl)-3-methyl-, monoacetate (salt)
  • Bazedoxifene acetate [usan]
  • Unii-J70472ud3d
  • Viviant
  • Way-140424
  • 1-((4-(2-(Hexahydro-1H-azepin-1-yl)ethoxy)phenyl)methyl)-2-(4-hydroxyphenyl)-3-methyl-1H-indol-5-ol monoacetate
CAS:
198481-33-3
MF:
C32H38N2O5
MW:
530.67
EINECS:
638-804-4
Product Categories:
  • Bazedoxifene Acetate
  • Inhibitors
  • 198481-33-3
Mol File:
198481-33-3.mol
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BAZEDOXIFENE ACETATE Chemical Properties

Melting point:
174-178°
storage temp. 
-20°C
solubility 
DMSO: soluble15mg/mL, clear
form 
powder
color 
white to beige
InChI
InChI=1S/C30H34N2O3.C2H4O2/c1-22-28-20-26(34)12-15-29(28)32(30(22)24-8-10-25(33)11-9-24)21-23-6-13-27(14-7-23)35-19-18-31-16-4-2-3-5-17-31;1-2(3)4/h6-15,20,33-34H,2-5,16-19,21H2,1H3;1H3,(H,3,4)
InChIKey
DGEPGJZKMFNSDD-UHFFFAOYSA-N
SMILES
C(=O)(O)C.C(C1C=CC(OCCN2CCCCCC2)=CC=1)N1C2C=CC(O)=CC=2C(C)=C1C1C=CC(O)=CC=1
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Safety Information

WGK Germany 
3
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BAZEDOXIFENE ACETATE Usage And Synthesis

Chemical Properties

Pale Beige Solid

Uses

Bazedoxifene acetate has been used to study its efficacy in inhibiting the interleukin-6 (IL-6)/IL-6R/glycoprotein 130 pathway and its effects on medulloblastoma cells.

Uses

Bazedoxifene Acetate is a nonsteroidal selective estrogen receptor modulator (SERM). Bazedoxifene Acetate is used as an antiosteoporotic.

Biological Activity

bazedoxifene, a novel selective estrogen receptor modulator (serm), has been developed to have favorable effects on bone and the lipid profile while minimizing stimulation of uterine or breast tissues. two large phase iii

Biochem/physiol Actions

Bazedoxifene is a third generation nonsteroidal selective estrogen receptor modulator (SERM), used clinically to treat postmenopausal osteoporosis. Bazedoxifene binds to estrogen receptor-α with IC50 = 26 nM, similar to that of raloxifene, but lower affinity than 17-β estradiol. Bazedoxifene did not stimulate proliferation of MCF-7 cells, instead inhibited 17β -estradiol-induced proliferation with IC50 = 0.19 nM, exhibiting a desirable profile of agonist/antagonist activity.

Clinical Use

The selective estrogen receptor modulator bazedoxifene acetate was approved in Spain for the treatment of osteoporosis in postmenopausal women. The drug was discovered by Wyeth (now Pfizer) and licensed to Almirall. Clinical trials with bazedoxifene along with conjugated estrogens demonstrated significant improvement in bone mineral density and prevented bone loss in postmenopausal women without osteoporosis. It also reduces fracture risks among women with postmenopausal osteroporosis.

Synthesis

Among many syntheses reported for this drug, the most recent process scale synthesis (multi-kg scale) is highlighted and involves the union of azepane ether 9 and indole 12. 4-Hydroxybenzyl alcohol (6) was converted in two steps to chloride 9 (the Scheme). The reaction of 6 with 2-chloroethyl azepane hydrochloride (7) in a biphasic mixture of sodium hydroxide and toluene in the presence of tetrabutylammonium bromide (TBAB) gave the desired intermediate alcohol 8 in 61% yield. Treatment of 8 with thionyl chloride (SOCl2) gave the requisite chloride 9 in 61% yield. The reaction of 2-bromopropiophenone (10) with an excess of 4-benzyloxy aniline hydrochloride (11) in the presence of triethylamine (TEA) in N,N-dimethylformamide (DMF) at elevated temperatures resulted in indole 12 in 65% yield. Alkylation of 12 with benzylchloride 9 in the presence of sodium hydride (NaH) afforded N-alkylated compound 13. The benzyl ether functionalities from compound 13 were removed via hydrogenolysis and subsequently subjected to acidic conditions, providing diol 14 as the hydrochloride salt in 91% yield. The hydrochloride was then exchanged for the acetate via free base preparation with 5% sodium bicarbonate or triethylamine, followed by treatment with acetic acid giving bazedoxifene acetate (II) in 73¨C85% yield.

BAZEDOXIFENE ACETATESupplier

EnliPharma Technology Co., Ltd Gold
Tel
0551-66399836 18955197623
Email
sales@enlipharma.com
Nanjing Sunlida Biological Technology Co., Ltd. Gold
Tel
025-57798810
Email
sales@sunlidabio.com
NANJING ZENJI PHARMACEUTICALS Gold
Tel
025-58231105-8151
Email
marketing@zenjipharma.com
Nanjing Becas pharmatech Ltd. Gold
Tel
13912903754
Email
info@becaspharma.com
Shanghai Haoyuan Chemexpress Co., Ltd. Gold
Tel
021-58950125
Email
info@chemexpress.com