Bazedoxifene free base
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    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 120203

CAS#: 198481-32-2 (free base)

Description: Bazedoxifene is a third generation selective estrogen receptor modulator (SERM), developed by Pfizer following the completion of their takeover of Wyeth Pharmaceuticals. In late 2013, Pfizer received approval for bazedoxifene as part of the combination drug DUAVEE in the prevention (not treatment) of postmenopausal osteoporosis. Bazedoxifene is an indole-based ER ligand that binds to both ERα (IC50 = 26 nM) and ERβ (IC50 = 99 nM).


Price and Availability

Size
Price

5mg
USD 350
Size
Price

10mg
USD 650
Size
Price

Bazedoxifene free base, purity > 98%, is in stock. Current shipping out time is about 2 weeks after order is received. CoA, QC data and MSDS documents are available in one week after order is received.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 120203
Name: Bazedoxifene free base
CAS#: 198481-32-2 (free base)
Chemical Formula: C30H34N2O3
Exact Mass: 470.25694
Molecular Weight: 470.6
Elemental Analysis: C, 76.57; H, 7.28; N, 5.95; O, 10.20


Related CAS #: 198481-32-2 (free base)   198480-56-7 (HCl)   198481-33-3 (acetate)  

Synonym: Bazedoxifene free base, WAY-140424; WAY140424; WAY 140424; TSE 424; TSE424; TSE-424; Viviant.

IUPAC/Chemical Name: 1-(4-(2-(azepan-1-yl)ethoxy)benzyl)-2-(4-hydroxyphenyl)-3-methyl-1H-indol-5-ol

InChi Key: UCJGJABZCDBEDK-UHFFFAOYSA-N

InChi Code: InChI=1S/C30H34N2O3/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/h6-15,20,33-34H,2-5,16-19,21H2,1H3

SMILES Code: OC1=CC2=C(N(CC3=CC=C(OCCN4CCCCCC4)C=C3)C(C5=CC=C(O)C=C5)=C2C)C=C1


Technical Data

Appearance:
Solid powder

Purity:
>98% (or refer to the Certificate of Analysis)

Shipping Condition:
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition:
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility:
Soluble in DMSO, not in water

Shelf Life:
>2 years if stored properly

Drug Formulation:
This drug may be formulated in DMSO

Stock Solution Storage:
0 - 4 C for short term (days to weeks), or -20 C for long term (months).

Harmonized System Code:
293490


Additional Information

 As of December 2011, the FDA have not given approval for the use of bazedoxifene in the US.
The drug was approved in the European Union by the European Medicines Agency on April 27, 2009.
On October 3, 2013 the FDA approved the combination product of bazedoxifene 20 mg with 0.45 mg Premarin (conjugated estrogens) for the treatment of menopausal osteoporosis and the treatment of moderate to severe hot flushes. This is the first approved hormone replacement therapy product that contains a SERM (bazedoxifene) and an estrogen.
 


References

1: Rzemieniec J, Litwa E, Wnuk A, Lason W, Kajta M. Bazedoxifene and raloxifene protect neocortical neurons undergoing hypoxia via targeting ERα and PPAR-γ. Mol Cell Endocrinol. 2017 Aug 30. pii: S0303-7207(17)30450-1. doi: 10.1016/j.mce.2017.08.014. [Epub ahead of print] PubMed PMID: 28859903.

2: Bueno JAH, Arias L, Yu CR, Williams R, Komm BS. Efficacy and safety of bazedoxifene in postmenopausal Latino women with osteoporosis. Menopause. 2017 Sep;24(9):1033-1039. doi: 10.1097/GME.0000000000000889. PubMed PMID: 28837504.

3: Conjugated oestrogens/bazedoxifene. Aust Prescr. 2017 Jun;40(3):114-115. doi: 10.18773/austprescr.2017.039. Epub 2017 May 10. Review. PubMed PMID: 28798519; PubMed Central PMCID: PMC5478405.

4: McKeand W. Pharmacokinetics, Dose Proportionality, and Bioavailability of Bazedoxifene in Healthy Postmenopausal Women. Clin Ther. 2017 Sep;39(9):1769-1779. doi: 10.1016/j.clinthera.2017.07.012. Epub 2017 Jul 26. PubMed PMID: 28756067.

5: Xiao H, Bid HK, Chen X, Wu X, Wei J, Bian Y, Zhao C, Li H, Li C, Lin J. Repositioning Bazedoxifene as a novel IL-6/GP130 signaling antagonist for human rhabdomyosarcoma therapy. PLoS One. 2017 Jul 3;12(7):e0180297. doi: 10.1371/journal.pone.0180297. eCollection 2017. PubMed PMID: 28672024; PubMed Central PMCID: PMC5495564.

6: Pinkerton JV, Bushmakin AG, Bobula J, Lavenberg J, Komm BS, Abraham L. Hot flush frequency and severity at baseline as predictors of time to transient and stable treatment success: pooled analysis of two CE/BZA studies. Menopause. 2017 Jun 26. doi: 10.1097/GME.0000000000000918. [Epub ahead of print] PubMed PMID: 28654628.

7: Leignadier J, Dalenc F, Poirot M, Silvente-Poirot S. Improving the efficacy of hormone therapy in breast cancer: The role of cholesterol metabolism in SERM-mediated autophagy, cell differentiation and death. Biochem Pharmacol. 2017 Jun 19. pii: S0006-2952(17)30444-6. doi: 10.1016/j.bcp.2017.06.120. [Epub ahead of print] Review. PubMed PMID: 28642035.

8: Pinkerton JV, Bushmakin AG, Bobula J, Lavenberg J, Komm BS, Abraham L. Time to first occurrence of breast pain and vaginal bleeding in phase 3 trials of CE/BZA. Menopause. 2017 Jun 12. doi: 10.1097/GME.0000000000000935. [Epub ahead of print] PubMed PMID: 28609389.

9: Nordqvist J, Bernardi A, Islander U, Carlsten H. Effects of a tissue-selective estrogen complex on B lymphopoiesis and B cell function. Immunobiology. 2017 Aug;222(8-9):918-923. doi: 10.1016/j.imbio.2017.05.013. Epub 2017 May 16. PubMed PMID: 28551078.

10: Pinkerton JV, Bushmakin AG, Komm BS, Abraham L. Relationship between changes in vulvar-vaginal atrophy and changes in sexual functioning. Maturitas. 2017 Jun;100:57-63. doi: 10.1016/j.maturitas.2017.03.315. Epub 2017 Mar 22. PubMed PMID: 28539177.

11: Jover-Mengual T, Castelló-Ruiz M, Burguete MC, Jorques M, López-Morales MA, Aliena-Valero A, Jurado-Rodríguez A, Pérez S, Centeno JM, Miranda FJ, Alborch E, Torregrosa G, Salom JB. Molecular mechanisms mediating the neuroprotective role of the selective estrogen receptor modulator, bazedoxifene, in acute ischemic stroke: A comparative study with 17β-estradiol. J Steroid Biochem Mol Biol. 2017 Jul;171:296-304. doi: 10.1016/j.jsbmb.2017.05.001. Epub 2017 May 4. PubMed PMID: 28479229.

12: Pinkerton JV, Bushmakin AG, Abraham L, Komm BS, Bobula J. Time to transient and stable reductions in hot flush frequency in postmenopausal women using conjugated estrogens/bazedoxifene. Menopause. 2017 Sep;24(9):1011-1016. doi: 10.1097/GME.0000000000000888. PubMed PMID: 28463874.

13: Saito M, Marumo K. [Calcium and bone metabolism across women's life stages. Bone quality and treatment of osteoporosis by SERM.]. Clin Calcium. 2017;27(5):723-732. doi: CliCa1705723732. Japanese. PubMed PMID: 28439061.

14: Bazedoxifene for HRT? Drug Ther Bull. 2017 Apr;55(4):42-44. doi: 10.1136/dtb.2017.4.0466. Review. PubMed PMID: 28408389.

15: Xu B, Lovre D, Mauvais-Jarvis F. The effect of selective estrogen receptor modulators on type 2 diabetes onset in women: Basic and clinical insights. J Diabetes Complications. 2017 Apr;31(4):773-779. doi: 10.1016/j.jdiacomp.2016.12.010. Epub 2017 Jan 20. Review. PubMed PMID: 28185712; PubMed Central PMCID: PMC5350049.

16: Parish SJ, Gillespie JA. The evolving role of oral hormonal therapies and review of conjugated estrogens/bazedoxifene for the management of menopausal symptoms. Postgrad Med. 2017 Apr;129(3):340-351. doi: 10.1080/00325481.2017.1281083. Epub 2017 Jan 30. Review. PubMed PMID: 28132583.

17: Franks LN, Ford BM, Prather PL. Selective Estrogen Receptor Modulators: Cannabinoid Receptor Inverse Agonists with Differential CB1 and CB2 Selectivity. Front Pharmacol. 2016 Dec 22;7:503. doi: 10.3389/fphar.2016.00503. eCollection 2016. PubMed PMID: 28066250; PubMed Central PMCID: PMC5177629.

18: Sato Y, Tando T, Morita M, Miyamoto K, Kobayashi T, Watanabe R, Oike T, Matsumoto M, Nakamura M, Miyamoto T. Selective estrogen receptor modulators and the vitamin D analogue eldecalcitol block bone loss in male osteoporosis. Biochem Biophys Res Commun. 2017 Jan 22;482(4):1430-1436. doi: 10.1016/j.bbrc.2016.12.053. Epub 2016 Dec 11. PubMed PMID: 27974229.

19: Palacios S, Coronado PJ. New options for menopausal symptoms after 15 years of WHI Study. Minerva Ginecol. 2017 Apr;69(2):160-170. doi: 10.23736/S0026-4784.16.04007-7. Epub 2016 Dec 14. Review. PubMed PMID: 27973466.

20: Hill DA, Crider M, Hill SR. Hormone Therapy and Other Treatments for Symptoms of Menopause. Am Fam Physician. 2016 Dec 1;94(11):884-889. Review. PubMed PMID: 27929271.