BAZEDOXIFENE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C30H34N2O3
Molecular Weight	470.6026
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC1=C(N(CC2=CC=C(OCCN3CCCCCC3)C=C2)C4=C1C=C(O)C=C4)C5=CC=C(O)C=C5

InChI

InChIKey=UCJGJABZCDBEDK-UHFFFAOYSA-N

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

HIDE SMILES / InChI

Molecular Formula	C30H34N2O3
Molecular Weight	470.6026
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2015/022247s002lbl.pdf
Curator's Comment: description was created based on several sources, including http://www.ncbi.nlm.nih.gov/pubmed/18457472

Bazedoxifene acetate (WAY-140424; TSE-424) is an oral, nonsteroidal, indole-based selective estrogen-receptor modulator developed by Ligand Pharmaceuticals in collaboration with Wyeth Pharmaceuticals (NJ, USA) (now Pfizer) . It was developed using raloxifene as a template with the benzothiophene core substituted by an indole ring in order to obtain favorable effects on the skeleton and lipid metabolism with the additional improvement of a neutral effect on hot flushes and without stimulating the uterus or the breast. The drug is approved as a monotherapy for the prevention and treatment of osteoporosis and in combination with conjugated estrogens for the treatment of menopausal symptoms and prevention of osteoporosis. Bazedoxifene binds to both ERalpha and ERbeta with high affinity. Bazedoxifene acts as both a receptor agonist and/or antagonist, depending upon the cell and tissue type and target genes. Bazedoxifene decreases bone resorption and reduces biochemical markers of bone turnover to the premenopausal range. These effects on bone remodeling lead to an increase in bone mineral density (BMD), which in turn contributes to a reduction in the risk of fractures. Bazedoxifene functions primarily as an estrogen-receptor antagonist in uterine and breast tissues.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Estrogen receptor alpha 134 Target ID: CHEMBL206 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16203138	Modulator 846		0.6 nM [IC50]
Estrogen receptor beta 113 Target ID: CHEMBL242 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16203138	Inhibitor 8504		3.8 nM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Hot flashes 3 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2015/022247s002lbl.pdf	Palliative		Approved 8583	DUAVEE Approved Use DUAVEE is indicated in women with a uterus for: DUAVEE is a combination of conjugated estrogens with an estrogen agonist/antagonist indicated for treatment of the following conditions in women with a uterus: Treatment of moderate to severe vasomotor symptoms associated with menopause (1.1) Prevention of postmenopausal osteoporosis (1.2) Limitation of Use: DUAVEE should be used for the shortest duration consistent with treatment goals and risks for the individual woman. Launch Date 2013
Postmenopausal osteoporosis 59 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2015/022247s002lbl.pdf	Preventing		Approved 8583	DUAVEE Approved Use DUAVEE is indicated in women with a uterus for: DUAVEE is a combination of conjugated estrogens with an estrogen agonist/antagonist indicated for treatment of the following conditions in women with a uterus: Treatment of moderate to severe vasomotor symptoms associated with menopause (1.1) Prevention of postmenopausal osteoporosis (1.2) Limitation of Use: DUAVEE should be used for the shortest duration consistent with treatment goals and risks for the individual woman. Launch Date 2013

C_max

Value	Dose	Co-administered	Analyte	Population
6.9 ng/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/022247Orig1s001lbl.pdf	20 mg 1 times / day steady-state, oral dose: 20 mg route of administration: Oral experiment type: STEADY-STATE co-administered: ESTROGENS, CONJUGATED	ESTROGENS, CONJUGATED	BAZEDOXIFENE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: UNKNOWN

AUC

Value	Dose	Co-administered	Analyte	Population
71 ng × h/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/022247Orig1s001lbl.pdf	20 mg 1 times / day steady-state, oral dose: 20 mg route of administration: Oral experiment type: STEADY-STATE co-administered: ESTROGENS, CONJUGATED	ESTROGENS, CONJUGATED	BAZEDOXIFENE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: UNKNOWN

T_1/2

Value	Dose	Co-administered	Analyte	Population
30 h DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/022247Orig1s001lbl.pdf	20 mg 1 times / day steady-state, oral dose: 20 mg route of administration: Oral experiment type: STEADY-STATE co-administered: ESTROGENS, CONJUGATED	ESTROGENS, CONJUGATED	BAZEDOXIFENE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: UNKNOWN

Doses

Dose	Population	Adverse events
80 mg 1 times / day multiple, oral Highest studied dose Dose: 80 mg, 1 times / day Route: oral Route: multiple Dose: 80 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/27128831	healthy, 45 - 70 years Health Status: healthy Age Group: 45 - 70 years Sex: F Sources: https://pubmed.ncbi.nlm.nih.gov/27128831	Sources: https://pubmed.ncbi.nlm.nih.gov/27128831
120 mg single, oral Highest studied dose Dose: 120 mg Route: oral Route: single Dose: 120 mg Sources: https://pubmed.ncbi.nlm.nih.gov/28756067	healthy, 55.7 yeras (range: 35 - 65 years) Health Status: healthy Age Group: 55.7 yeras (range: 35 - 65 years) Sex: F Sources: https://pubmed.ncbi.nlm.nih.gov/28756067	Sources: https://pubmed.ncbi.nlm.nih.gov/28756067

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
			inhibitor 2217

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP 110	CYP 303 UGT 219 UGT1A1 479 UGT1A10 331	CYP 74

Drug as perpetrator

Target	Modality	Activity	Metabolite	Clinical evidence
CYP 150	inducer 1966 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2013/022247Orig1s000ClinPharmR.pdf Page: 5.0	no
CYP 150	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2013/022247Orig1s000ClinPharmR.pdf Page: 5.0	no

Drug as victim

Target	Modality	Activity
CYP 303	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2013/022247Orig1s000PharmR.pdf Page: 39.0	minor
UGT 219	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2013/022247Orig1s000ClinPharmR.pdf Page: 5.0	yes
UGT1A1 479	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2013/022247Orig1s000PharmR.pdf Page: 39.0	yes
UGT1A10 331	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2013/022247Orig1s000PharmR.pdf Page: 39.0	yes

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 2263	inhibitor 2237 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2013/022247Orig1s000PharmR.pdf Page: 38.0

Sourcing

Vendor/Aggregator	ID	URL
001 Chemical	DY428267	https://www.001chemical.com/chem/198481-32-2
AA Blocks	AA002BGW	https://www.aablocks.com/goods/Goods/detail?id=AA002BGW
Achemtek	0102-022126	http://www.achemtek.com/198481-32-2
Acorn PharmaTech	ACN-030060	http://www.acornpharmatech.com/
Adooq BioScience	A15019	https://www.adooq.com/bazedoxifene.html
AK Scientific, Inc. (AKSCI)	3473AH	http://www.aksci.com/item_detail.php?cat=3473AH
AlchemyPharm	AP10432	https://www.alchemypharm.com/pharm/198481-32-2.html
Ambeed	A696565	https://www.ambeed.com/products/198481-32-2.html
Ambinter	Amb22057409	http://www.ambinter.com/reference/22057409
Angene	AGN-PC-0509EJ	http://www.angenechemical.com/productshow/AGN-PC-0509EJ.html
ApexBio Technology	A3232	http://www.apexbt.com/bazedoxifene.html
Ark Pharma Scientific Limited	A-0608	http://www.arkpharmtech.com/product/32559.html
Aurum Pharmatech LLC	W-5320	http://www.Aurumpharmatech.com/Product/ProductDetails/W_5320
BioCrick	BCC1411	http://www.biocrick.com/Bazedoxifene-BCC1411.html
BioSynth	J-012822	https://www.biosynth.com/en/products/all-products/products/J-012822.html
BLD Pharm	BD160016	http://www.bldpharm.com/products/198481-32-2.html
Chem Scene	CS-0932	http://www.chemscene.com/198481-32-2.html
Chemspace	CSSB00020668792	https://chem-space.com/CSSB00020668792
Clearsynth	CS-L-00024	https://www.clearsynth.com/en/CSL00024.html
CSNpharm	CSN12297	https://www.csnpharm.com/products/bazedoxifene.html
DC Chemicals	DC8922	http://www.dcchemicals.com//product_show-Bazedoxifene.html
eNovation Chemicals	D320200	http://www.enovationchem.com/productDetails.asp?productID=D320200
Lab Network	LN01341877	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN01341877
MedChem Express	HY-A0031	https://www.medchemexpress.com/bazedoxifene.html
Molcore	MC428267	https://www.molcore.com/product/198481-32-2
MolPort	MolPort-009-198-833	https://www.molport.com/shop/molecule-link/MolPort-009-198-833
MuseChem	I002519	https://www.musechem.com/product/I002519.html
Parchem	28305	http://www.parchem.com/chemical-supplier-distributor/Bazedoxifene-018305.aspx
Smolecule	S548678	http://www.smolecule.com/products/s548678
Smolecule	S751004	https://www.smolecule.com/products/s751004
Synblock Inc	SB19326	http://www.synblock.com/product/198481-32-2.html
Tenova Pharmaceuticals Inc	T31190	https://www.tenovapharma.com/Bazedoxifene
THE BioTek	bt-288085	https://www.thebiotek.com/product/inhibitors/bt-288085
THE BioTek	bt-302203	https://www.thebiotek.com/product/others/bt-302203

PubMed

Title	Date	PubMed
Bazedoxifene when paired with conjugated estrogens is a new paradigm for treatment of postmenopausal women.	2010-12	21073353
Management of osteoporosis in patients hospitalized for hip fractures.	2010-12	21058000
The utility and limitations of FRAX: A US perspective.	2010-12	20811963
What is the best balance of benefits and risks among anti-resorptive therapies for postmenopausal osteoporosis?	2010-11	20309524
Evidence-based guidelines for the pharmacological treatment of postmenopausal osteoporosis: a consensus document by the Belgian Bone Club.	2010-10	20480148
Tissue-selective agents: selective estrogen receptor modulators and the tissue-selective estrogen complex.	2010-09	20956688
New selective estrogen receptor modulators (SERMs) in development.	2010-09	20603714
Assessment of individual fracture risk: FRAX and beyond.	2010-09	20563901
In vitro metabolism, permeability, and efflux of bazedoxifene in humans.	2010-09	20516255
Treating postmenopausal osteoporosis in women at increased risk of fracture - critical appraisal of bazedoxifene: a review.	2010-08-09	21072279
Long-term safety and efficacy of raloxifene in the prevention and treatment of postmenopausal osteoporosis: an update.	2010-08-09	21072271
Disposition of bazedoxifene in rats.	2010-08	20528166
FRAX and its applications in health economics--cost-effectiveness and intervention thresholds using bazedoxifene in a Swedish setting as an example.	2010-08	20493983
Efficacy and safety of bazedoxifene, a novel selective estrogen receptor modulator for the prevention and treatment of postmenopausal osteoporosis.	2010-07	20429824
Safety of bazedoxifene in a randomized, double-blind, placebo- and active-controlled Phase 3 study of postmenopausal women with osteoporosis.	2010-06-22	20569451
Lasofoxifene: Evidence of its therapeutic value in osteoporosis.	2010-06-15	20694069
Bazedoxifene: a novel selective estrogen receptor modulator for postmenopausal osteoporosis.	2010-06	20184423
Aprela, a single tablet formulation of bazedoxifene and conjugated equine estrogens (Premarin) for the potential treatment of menopausal symptoms.	2010-04	20336595
Effects of bazedoxifene/conjugated estrogens on quality of life in postmenopausal women with symptoms of vulvar/vaginal atrophy.	2010-04	19863455
New treatment modalities in osteoporosis.	2010-03-31	20350910
SERMs in the prevention and treatment of postmenopausal osteoporosis: an update.	2010-03	20485909
Selective estrogen receptor modulator (SERM) for the treatment of osteoporosis in postmenopausal women: focus on lasofoxifene.	2010-02-02	20169039
Endometrial safety: a key hurdle for selective estrogen receptor modulators in development.	2010-01-29	20107426
Acute administration of non-classical estrogen receptor agonists attenuates ischemia-induced hippocampal neuron loss in middle-aged female rats.	2010-01-08	20062809
Selective estrogen receptor modulators decrease the production of interleukin-6 and interferon-gamma-inducible protein-10 by astrocytes exposed to inflammatory challenge in vitro.	2010-01-01	19533603
Gene expression profiling studies of three SERMs and their conjugated estrogen combinations in human breast cancer cells: insights into the unique antagonistic effects of bazedoxifene on conjugated estrogens.	2010-01	19914376
Modulators of androgen and estrogen receptor activity.	2010	21395502
Cross-geographic region differences in quality of life in women with and without vertebral fracture.	2009-10	19238305
New therapies for osteoporosis: zoledronic acid, bazedoxifene, and denosumab.	2009-09	19723467
Bazedoxifene acetate: a novel selective estrogen receptor modulator for the prevention and treatment of postmenopausal osteoporosis.	2009-07	19834628
Advances in the treatment of menopausal symptoms.	2009-07	19586429
Bazedoxifene effects on the reproductive tract in postmenopausal women at risk for osteoporosis.	2009-06-24	19546825
Bazedoxifene, a selective estrogen receptor modulator: effects on the endometrium, ovaries, and breast from a randomized controlled trial in osteoporotic postmenopausal women.	2009-06-23	19543129
The effects of bazedoxifene on mammographic breast density in postmenopausal women with osteoporosis.	2009-06-09	19503006
Bazedoxifene: a new selective estrogen receptor modulator for the treatment of postmenopausal osteoporosis.	2009-06	19445558
Metabolic disposition of [14C]bazedoxifene in healthy postmenopausal women.	2009-06	19273530
Bazedoxifene reduces vertebral and clinical fractures in postmenopausal women at high risk assessed with FRAX.	2009-06	19254788
Vitamin D status, parathyroid function, bone turnover, and BMD in postmenopausal women with osteoporosis: global perspective.	2009-04	19049341
Effects of various selective estrogen receptor modulators with or without conjugated estrogens on mouse mammary gland.	2009-04	19022889
Emerging drugs for postmenopausal osteoporosis.	2009-03	19249985
Designing the ideal selective estrogen receptor modulator--an achievable goal?	2009-02-03	19182697
Differential biochemical and cellular actions of Premarin estrogens: distinct pharmacology of bazedoxifene-conjugated estrogens combination.	2009-01	19036900
Lasofoxifene for the prevention and treatment of postmenopausal osteoporosis.	2009	19898646
Progress in osteoporosis and fracture prevention: focus on postmenopausal women.	2009	19849819
Clinical issues regarding cardiovascular disease and selective estrogen receptor modulators in postmenopausal women.	2009	19811253
Bazedoxifene for the prevention of postmenopausal osteoporosis.	2008-12	19337430
The pairing of a selective estrogen receptor modulator, bazedoxifene, with conjugated estrogens as a new paradigm for the treatment of menopausal symptoms and osteoporosis prevention.	2008-12	18703623
Efficacy of bazedoxifene in reducing new vertebral fracture risk in postmenopausal women with osteoporosis: results from a 3-year, randomized, placebo-, and active-controlled clinical trial.	2008-12	18665787
[Newly developed drugs for osteoporosis in overseas and their future roles for the therapy].	2008-10	18830046
Bazedoxifene: a selective estrogen-receptor modulator.	2008-07	19072496

Patents

Sample Use Guides

In Vivo Use Guide

The recommended dosage is one tablet (containing conjugated estrogens 0.45 mg and bazedoxifene 20 mg) daily.

Route of Administration: Oral

In Vitro Use Guide

The inhibitory effects of BZA (Bazedoxifene acetate) on MCF-7, T47D, MCF-7:5C, and MCF-7:2A cells were determined. MCF-7 and T47D cells were grown in fully estrogenized media, and MCF-7:5C and MCF-7:2A cells were grown in estrogen-free media and then treated with 10^(−12) to 10^(−6) M BZA for 7 days, and cellular DNA was measured as an index of growth.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:17:31 GMT 2025` Edited by `admin` on `Mon Mar 31 18:17:31 GMT 2025`
Record UNII	Q16TT9C5BK
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

BAZEDOXIFENE

Official Name

English

1-(P-(2-(HEXAHYDRO-1H-AZEPIN-1-YL)ETHOXY)BENZYL)-2-(P-HYDROXYPHENYL)-3-METHYLINDOL-5-OL

Preferred Name

English

BAZEDOXIFENE [MI]

Common Name

English

AK-R215 COMPONENT BAZEDOXIFENE

Common Name

English

AK R215 COMPONENT BAZEDOXIFENE

Common Name

English

1H-INDOL-5-OL, 1-((4-(2-(HEXAHYDRO-1H-AZEPIN-1-YL)ETHOXY)PHENYL)METHYL)-2-(4-HYDROXYPHENYL)-3-METHYL-

Systematic Name

English

BAZEDOXIFENE [VANDF]

Common Name

English

Bazedoxifene [WHO-DD]

Common Name

English

bazedoxifene [INN]

Common Name

English

BZA

Common Name

English

BAZEDOXIFENE [EMA EPAR]

Common Name

English

Classification Tree Code System Code

LIVERTOX

NBK548475