Bazedoxifene

Bazedoxifene
Names
Pronunciationba" ze dox' i feen[1]
Trade namesConbriza, Viviant, others
Other namesBazedoxifene acetate, TSE-424; WAY-140424; WAY-TSE-424
IUPAC name
  • 1-[4-[2-(azepan-1-yl)ethoxy]benzyl]-2-(4-hydroxyphenyl)-3-methyl-1H-indol-5-ol
Clinical data
Drug classSelective estrogen receptor modulator (SERM)[2]
Main usesOsteoporosis after menopause[2]
Side effectsHot flushes, muscle spasms, swelling of the legs[2]
WHO AWaReUnlinkedWikibase error: ⧼unlinkedwikibase-error-statements-entity-not-set⧽
Routes of
use		By mouth
Typical dose20 mg OD[2]
External links
AHFS/Drugs.comMonograph
Legal
License data
Legal status
  • In general: ℞ (Prescription only)
Chemical and physical data
FormulaC30H34N2O3
Molar mass470.613 g·mol−1
3D model (JSmol)
SMILES
  • Oc1ccc(cc1)c3c(c2cc(O)ccc2n3Cc5ccc(OCCN4CCCCCC4)cc5)C
InChI
  • 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 checkY
  • Key:UCJGJABZCDBEDK-UHFFFAOYSA-N checkY

Bazedoxifene, sold under the brand name Conbriza is a medication used to treat osteoporosis after menopause.[2] It reduces the risk of spinal fractures but not hip fractures.[2] It is taken by mouth.[2]

Common side effects include hot flushes, muscle spasms, and swelling of the legs.[2] Other side effects may include blood clots.[2] It should not be used in pregnancy.[2] It is a selective estrogen receptor modulator (SERM).[2]

Bazedoxifene was approved for medical use in Europe in 2009.[2] In the United States it is only available in combination as bazedoxifene/conjugated estrogens.[1]

Medical uses

Bazedoxifene is used in the treatment of postmenopausal osteoporosis.[2]

Dosage

It is taken as 20 mg once per day.[2]

Bazedoxifene is marketed both alone and in combination with conjugated estrogens (bazedoxifene/conjugated estrogens).[3]

Pharmacology

Pharmacodynamics

Bazedoxifene is a selective estrogen receptor modulator (SERM), or a mixed agonist and antagonist of the estrogen receptor (ER) in different tissues.

Tissue-specific estrogenic and antiestrogenic activity of SERMs
MedicationBreastBoneLiverUterusVaginaBrain
LipidsCoagulationSHBGIGF-1Hot flashesGonadotropins
Estradiol++++++++++
"Ideal SERM"–++±±±–++±
Bazedoxifene–++++ ?–±– ?
Clomifene–++ ?++– ?–±
Lasofoxifene–+++ ? ?±±– ?
Ospemifene–+++++±±–±
Raloxifene–+++++±––±
Tamoxifen–++++++––±
Toremifene–++++++––±
Effect: + = Estrogenic / agonistic. ± = Mixed or neutral. – = Antiestrogenic / antagonistic. Note: SERMs generally increase gonadotropin levels in hypogonadal and eugonadal men as well as premenopausal women (antiestrogenic) but decrease gonadotropin levels in postmenopausal women (estrogenic). Sources: See template.

Chemistry

The drug is a member of the 2-phenylindole group of SERMs, along with zindoxifene and pipendoxifene.[4]

History

Development

Bazedoxifene was developed by Pfizer following the completion of their takeover of Wyeth Pharmaceuticals. It is the result of a research collaboration between Wyeth Pharmaceuticals and Ligand Pharmaceuticals.

Approval

The drug was approved in the European Union by the European Medicines Agency on April 27, 2009.[5]

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 menopausal hormone therapy product that contains a SERM (bazedoxifene) and an estrogen.

Society and culture

Brand names

Bazedoxifene is marketed alone under the brand names Conbriza and Viviant and in combination with conjugated estrogens under the brand names Duavee and Duavive.[3]

References

  1. 1 2 "Selective Estrogen Receptor Modulators". LiverTox: Clinical and Research Information on Drug-Induced Liver Injury. National Institute of Diabetes and Digestive and Kidney Diseases. 2012. Archived from the original on 11 January 2022. Retrieved 8 January 2022.
  2. 1 2 3 4 5 6 7 8 9 10 11 12 13 14 "Conbriza". Archived from the original on 6 January 2021. Retrieved 8 January 2022.
  3. 1 2 "Bazedoxifene". drugs.com. Archived from the original on 2019-08-24. Retrieved 2021-03-11.
  4. ↑ Gordon W. Gribble (9 October 2010). Heterocyclic Scaffolds II:: Reactions and Applications of Indoles. Springer Science & Business Media. pp. 14–. ISBN 978-3-642-15732-5. Archived from the original on 12 April 2017. Retrieved 11 March 2021.
  5. ↑ "EPARs for authorised medicinal products for human use - Conbriza". European Medicines Agency. 26 May 2009. Archived from the original on 11 June 2009. Retrieved 2009-07-08.
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