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
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
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 |
DescriptionCurator's Comment: description was created based on several sources, including
http://www.ncbi.nlm.nih.gov/pubmed/18457472
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
Sources: http://www.ncbi.nlm.nih.gov/pubmed/?term=21071476
Curator's Comment: Bazedoxifene has not been shown to cross the blood brain barrier
Originator
Sources: http://www.ncbi.nlm.nih.gov/pubmed/18457472
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
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL206 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16203138 |
0.6 nM [IC50] | ||
Target ID: CHEMBL242 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16203138 |
3.8 nM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Palliative | DUAVEE Approved UseDUAVEE 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 Date2013 |
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Preventing | DUAVEE Approved UseDUAVEE 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 Date2013 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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
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: |
healthy, 45 - 70 years Health Status: healthy Age Group: 45 - 70 years Sex: F Sources: |
|
120 mg single, oral Highest studied dose |
healthy, 55.7 yeras (range: 35 - 65 years) Health Status: healthy Age Group: 55.7 yeras (range: 35 - 65 years) Sex: F Sources: |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Page: 5.0 |
no | |||
Page: 5.0 |
no |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Page: 39.0 |
minor | |||
Page: 5.0 |
yes | |||
Page: 39.0 |
yes | |||
Page: 39.0 |
yes |
Tox targets
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Page: 38.0 |
PubMed
Title | Date | PubMed |
---|---|---|
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 |
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New therapies for osteoporosis: zoledronic acid, bazedoxifene, and denosumab. | 2009 Sep |
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Long-term safety and efficacy of raloxifene in the prevention and treatment of postmenopausal osteoporosis: an update. | 2010 Aug 9 |
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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 |
Sample Use Guides
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
Sources: http://www.ncbi.nlm.nih.gov/pubmed/?term=21737572
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
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Record UNII |
Q16TT9C5BK
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Classification Tree | Code System | Code | ||
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LIVERTOX |
NBK548475
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WHO-ATC |
G03CC07
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NDF-RT |
N0000175826
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NCI_THESAURUS |
C1821
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WHO-VATC |
QG03XC02
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WHO-ATC |
G03XC02
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C447119
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8168
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DB06401
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Q16TT9C5BK
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BAZEDOXIFENE
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154257
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C73598
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198481-32-2
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SUB26694
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4334
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CHEMBL46740
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1441386
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Related Record | Type | Details | ||
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BINDER->LIGAND |
BINDING
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METABOLIC ENZYME -> SUBSTRATE | |||
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SALT/SOLVATE -> PARENT | |||
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METABOLIC ENZYME -> SUBSTRATE | |||
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TARGET -> INHIBITOR | |||
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TRANSPORTER -> SUBSTRATE | |||
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METABOLIC ENZYME -> SUBSTRATE |
Related Record | Type | Details | ||
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METABOLITE -> PARENT |
MINOR
FECAL
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METABOLITE -> PARENT |
MINOR
PLASMA
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METABOLITE -> PARENT |
MINOR
PLASMA
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METABOLITE -> PARENT |
MAJOR
PLASMA
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Related Record | Type | Details | ||
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ACTIVE MOIETY |
Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
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Biological Half-life | PHARMACOKINETIC |
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Tmax | PHARMACOKINETIC |
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MULTIPLE DOSE ADMINISTRATION |
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Volume of Distribution | PHARMACOKINETIC |
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