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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 of BAZEDOXIFENE

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
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

Curator's Comment: Bazedoxifene has not been shown to cross the blood brain barrier

Originator

Curator's Comment: Bazedoxifene was developed by Ligand Pharmaceuticals in collaboration with Wyeth.Wyeth and Ligand entered into a discovery research collaboration for bazedoxifene in September 1994.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
0.6 nM [IC50]
3.8 nM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
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
Preventing
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
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
6.9 ng/mL
20 mg 1 times / day steady-state, oral
dose: 20 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered: ESTROGENS, CONJUGATED
BAZEDOXIFENE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
71 ng × h/mL
20 mg 1 times / day steady-state, oral
dose: 20 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered: ESTROGENS, CONJUGATED
BAZEDOXIFENE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
30 h
20 mg 1 times / day steady-state, oral
dose: 20 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered: ESTROGENS, CONJUGATED
BAZEDOXIFENE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse 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:
healthy, 45 - 70 years
Health Status: healthy
Age Group: 45 - 70 years
Sex: F
Sources:
120 mg single, oral
Highest studied dose
Dose: 120 mg
Route: oral
Route: single
Dose: 120 mg
Sources:
healthy, 55.7 yeras (range: 35 - 65 years)
Health Status: healthy
Age Group: 55.7 yeras (range: 35 - 65 years)
Sex: F
Sources:
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer






Drug as perpetrator​Drug as victimTox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
The future of the new selective estrogen receptor modulators.
2007 Mar
Clinical issues regarding cardiovascular disease and selective estrogen receptor modulators in postmenopausal women.
2009
New therapies for osteoporosis: zoledronic acid, bazedoxifene, and denosumab.
2009 Sep
Long-term safety and efficacy of raloxifene in the prevention and treatment of postmenopausal osteoporosis: an update.
2010 Aug 9
Management of osteoporosis in patients hospitalized for hip fractures.
2010 Dec
What is the best balance of benefits and risks among anti-resorptive therapies for postmenopausal osteoporosis?
2010 Nov
Tissue-selective agents: selective estrogen receptor modulators and the tissue-selective estrogen complex.
2010 Sep
Patents

Sample Use Guides

The recommended dosage is one tablet (containing conjugated estrogens 0.45 mg and bazedoxifene 20 mg) daily.
Route of Administration: Oral
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
  • Download
Name Type Language
BAZEDOXIFENE
DASH   EMA EPAR   INN   MI   VANDF   WHO-DD  
INN  
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
Created by admin on Mon Mar 31 18:17:31 GMT 2025 , Edited by admin on Mon Mar 31 18:17:31 GMT 2025
WHO-ATC G03CC07
Created by admin on Mon Mar 31 18:17:31 GMT 2025 , Edited by admin on Mon Mar 31 18:17:31 GMT 2025
NDF-RT N0000175826
Created by admin on Mon Mar 31 18:17:31 GMT 2025 , Edited by admin on Mon Mar 31 18:17:31 GMT 2025
NCI_THESAURUS C1821
Created by admin on Mon Mar 31 18:17:31 GMT 2025 , Edited by admin on Mon Mar 31 18:17:31 GMT 2025
WHO-VATC QG03XC02
Created by admin on Mon Mar 31 18:17:31 GMT 2025 , Edited by admin on Mon Mar 31 18:17:31 GMT 2025
WHO-ATC G03XC02
Created by admin on Mon Mar 31 18:17:31 GMT 2025 , Edited by admin on Mon Mar 31 18:17:31 GMT 2025
Code System Code Type Description
EPA CompTox
DTXSID70173593
Created by admin on Mon Mar 31 18:17:31 GMT 2025 , Edited by admin on Mon Mar 31 18:17:31 GMT 2025
PRIMARY
MESH
C447119
Created by admin on Mon Mar 31 18:17:31 GMT 2025 , Edited by admin on Mon Mar 31 18:17:31 GMT 2025
PRIMARY
INN
8168
Created by admin on Mon Mar 31 18:17:31 GMT 2025 , Edited by admin on Mon Mar 31 18:17:31 GMT 2025
PRIMARY
DRUG BANK
DB06401
Created by admin on Mon Mar 31 18:17:31 GMT 2025 , Edited by admin on Mon Mar 31 18:17:31 GMT 2025
PRIMARY
DAILYMED
Q16TT9C5BK
Created by admin on Mon Mar 31 18:17:31 GMT 2025 , Edited by admin on Mon Mar 31 18:17:31 GMT 2025
PRIMARY
WIKIPEDIA
BAZEDOXIFENE
Created by admin on Mon Mar 31 18:17:31 GMT 2025 , Edited by admin on Mon Mar 31 18:17:31 GMT 2025
PRIMARY
PUBCHEM
154257
Created by admin on Mon Mar 31 18:17:31 GMT 2025 , Edited by admin on Mon Mar 31 18:17:31 GMT 2025
PRIMARY
SMS_ID
100000089657
Created by admin on Mon Mar 31 18:17:31 GMT 2025 , Edited by admin on Mon Mar 31 18:17:31 GMT 2025
PRIMARY
FDA UNII
Q16TT9C5BK
Created by admin on Mon Mar 31 18:17:31 GMT 2025 , Edited by admin on Mon Mar 31 18:17:31 GMT 2025
PRIMARY
NCI_THESAURUS
C73598
Created by admin on Mon Mar 31 18:17:31 GMT 2025 , Edited by admin on Mon Mar 31 18:17:31 GMT 2025
PRIMARY
CAS
198481-32-2
Created by admin on Mon Mar 31 18:17:31 GMT 2025 , Edited by admin on Mon Mar 31 18:17:31 GMT 2025
PRIMARY
EVMPD
SUB26694
Created by admin on Mon Mar 31 18:17:31 GMT 2025 , Edited by admin on Mon Mar 31 18:17:31 GMT 2025
PRIMARY
DRUG CENTRAL
4334
Created by admin on Mon Mar 31 18:17:31 GMT 2025 , Edited by admin on Mon Mar 31 18:17:31 GMT 2025
PRIMARY
ChEMBL
CHEMBL46740
Created by admin on Mon Mar 31 18:17:31 GMT 2025 , Edited by admin on Mon Mar 31 18:17:31 GMT 2025
PRIMARY
RXCUI
1441386
Created by admin on Mon Mar 31 18:17:31 GMT 2025 , Edited by admin on Mon Mar 31 18:17:31 GMT 2025
PRIMARY
Related Record Type Details
BINDER->LIGAND
BINDING
METABOLIC ENZYME -> SUBSTRATE
SALT/SOLVATE -> PARENT
METABOLIC ENZYME -> SUBSTRATE
TARGET -> INHIBITOR
TRANSPORTER -> SUBSTRATE
METABOLIC ENZYME -> SUBSTRATE
Related Record Type Details
METABOLITE -> PARENT
MINOR
FECAL
METABOLITE -> PARENT
MINOR
PLASMA
METABOLITE -> PARENT
MINOR
PLASMA
METABOLITE -> PARENT
MAJOR
PLASMA
Related Record Type Details
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Biological Half-life PHARMACOKINETIC
Tmax PHARMACOKINETIC MULTIPLE DOSE ADMINISTRATION

Volume of Distribution PHARMACOKINETIC