U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C24H23ClO2
Molecular Weight 378.891
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of OSPEMIFENE

SMILES

OCCOC1=CC=C(C=C1)C(=C(\CCCl)C2=CC=CC=C2)\C3=CC=CC=C3

InChI

InChIKey=LUMKNAVTFCDUIE-VHXPQNKSSA-N
InChI=1S/C24H23ClO2/c25-16-15-23(19-7-3-1-4-8-19)24(20-9-5-2-6-10-20)21-11-13-22(14-12-21)27-18-17-26/h1-14,26H,15-18H2/b24-23-

HIDE SMILES / InChI
Molecular Formula C24H23ClO2
Molecular Weight 378.891
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 1
Optical Activity NONE

Description

Ospemifene (commercial name Osphena produced by Shionogi) is anoral medication indicated for the treatment of dyspareunia – pain during sexual intercourse – encountered by some women, more often in those who are post-menopausal. Ospemifene is a selective estrogen receptor modulator (SERM) that selectively binds to estrogen receptors and either stimulates or blocks estrogen's activity in different tissue types. It has an agonistic effect on the endometrium. It’s building vaginal wall thickness which in turn reduces the pain associated with dyspareunia. Dyspareunia is most commonly caused by "vulval and vaginal atrophy”.

Originator

Approval Year

2013
596
Targets

Targets

Primary TargetPharmacologyConditionPotency
Estrogen receptor
75
Target ID: P03372
Gene ID: 2099.0
Gene Symbol: ESR1
Target Organism: Homo sapiens (Human)
Modulator
828
 827.0 nM [IC50]
Estrogen receptor beta
110
Target ID: Q92731|||O75584
Gene ID: 2100.0
Gene Symbol: ESR2
Target Organism: Homo sapiens (Human)
Modulator
828
 1633.0 nM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
Approved
8429
OSPHENA

Approved Use

Indicated for the treatment of moderate to severe dyspareunia, a symptom of vulvar and vaginal atrophy, due to menopause

Launch Date

2013
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
533 ng/mL
DRUG LABEL
https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/203505s000lbl.pdf
60 mg single, oral
dose: 60 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
OSPEMIFENE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE
food status: FASTED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
4165 ng × h/mL
DRUG LABEL
https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/203505s000lbl.pdf
60 mg single, oral
dose: 60 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
OSPEMIFENE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE
food status: FASTED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
26 h
DRUG LABEL
https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/203505s000lbl.pdf
60 mg single, oral
dose: 60 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
OSPEMIFENE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE
food status: FASTED
Doses

Doses

DosePopulationAdverse events​
200 mg 1 times / day steady, oral
Highest studied dose
Dose: 200 mg, 1 times / day
Route: oral
Route: steady
Dose: 200 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/12443837
healthy, 62 years (range: 55 - 75 years)
n = 8
Health Status: healthy
Age Group: 62 years (range: 55 - 75 years)
Sex: F
Population Size: 8
Sources:
https://pubmed.ncbi.nlm.nih.gov/12443837
Disc. AE: Hot flushes, Dizziness...
AEs leading to
discontinuation/dose reduction:
Hot flushes (1 patient)
Dizziness (1 patient)
Chest pain
Sources:
https://pubmed.ncbi.nlm.nih.gov/12443837
60 mg 1 times / day multiple, oral
Recommended
Dose: 60 mg, 1 times / day
Route: oral
Route: multiple
Dose: 60 mg, 1 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/203505s000lbl.pdf
unhealthy, adult (Postmenopausal)
Health Status: unhealthy
Age Group: adult (Postmenopausal)
Sex: F
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/203505s000lbl.pdf
Other AEs: Thromboembolic stroke, Hemorrhagic stroke...
Other AEs:
Thromboembolic stroke
Hemorrhagic stroke
Deep vein thrombosis
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/203505s000lbl.pdf
60 mg 1 times / day steady, oral
Recommended
Dose: 60 mg, 1 times / day
Route: oral
Route: steady
Dose: 60 mg, 1 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2013/203505Orig1s000MedR.pdf
Page: p. 114
unhealthy, adult (Postmenopausal)
n = 301
Health Status: unhealthy
Condition: Vulvar and Vaginal Atrophy
Age Group: adult (Postmenopausal)
Sex: F
Population Size: 301
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2013/203505Orig1s000MedR.pdf
Page: p. 114
Disc. AE: Nausea, Muscle spasms...
AEs leading to
discontinuation/dose reduction:
Nausea (1%)
Muscle spasms (0.7%)
Headache (1%)
Hyperhidrosis (0.7%)
Rash (0.7%)
Hot flush (2%)
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2013/203505Orig1s000MedR.pdf
Page: p. 114
AEs

AEs

AESignificanceDosePopulation
Dizziness 1 patient
Disc. AE
200 mg 1 times / day steady, oral
Highest studied dose
Dose: 200 mg, 1 times / day
Route: oral
Route: steady
Dose: 200 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/12443837
healthy, 62 years (range: 55 - 75 years)
n = 8
Health Status: healthy
Age Group: 62 years (range: 55 - 75 years)
Sex: F
Population Size: 8
Sources:
https://pubmed.ncbi.nlm.nih.gov/12443837
Hot flushes 1 patient
Disc. AE
200 mg 1 times / day steady, oral
Highest studied dose
Dose: 200 mg, 1 times / day
Route: oral
Route: steady
Dose: 200 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/12443837
healthy, 62 years (range: 55 - 75 years)
n = 8
Health Status: healthy
Age Group: 62 years (range: 55 - 75 years)
Sex: F
Population Size: 8
Sources:
https://pubmed.ncbi.nlm.nih.gov/12443837
Chest pain Disc. AE
200 mg 1 times / day steady, oral
Highest studied dose
Dose: 200 mg, 1 times / day
Route: oral
Route: steady
Dose: 200 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/12443837
healthy, 62 years (range: 55 - 75 years)
n = 8
Health Status: healthy
Age Group: 62 years (range: 55 - 75 years)
Sex: F
Population Size: 8
Sources:
https://pubmed.ncbi.nlm.nih.gov/12443837
Deep vein thrombosis
60 mg 1 times / day multiple, oral
Recommended
Dose: 60 mg, 1 times / day
Route: oral
Route: multiple
Dose: 60 mg, 1 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/203505s000lbl.pdf
unhealthy, adult (Postmenopausal)
Health Status: unhealthy
Age Group: adult (Postmenopausal)
Sex: F
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/203505s000lbl.pdf
Hemorrhagic stroke
60 mg 1 times / day multiple, oral
Recommended
Dose: 60 mg, 1 times / day
Route: oral
Route: multiple
Dose: 60 mg, 1 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/203505s000lbl.pdf
unhealthy, adult (Postmenopausal)
Health Status: unhealthy
Age Group: adult (Postmenopausal)
Sex: F
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/203505s000lbl.pdf
Thromboembolic stroke
60 mg 1 times / day multiple, oral
Recommended
Dose: 60 mg, 1 times / day
Route: oral
Route: multiple
Dose: 60 mg, 1 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/203505s000lbl.pdf
unhealthy, adult (Postmenopausal)
Health Status: unhealthy
Age Group: adult (Postmenopausal)
Sex: F
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/203505s000lbl.pdf
Hyperhidrosis 0.7%
Disc. AE
60 mg 1 times / day steady, oral
Recommended
Dose: 60 mg, 1 times / day
Route: oral
Route: steady
Dose: 60 mg, 1 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2013/203505Orig1s000MedR.pdf
Page: p. 114
unhealthy, adult (Postmenopausal)
n = 301
Health Status: unhealthy
Condition: Vulvar and Vaginal Atrophy
Age Group: adult (Postmenopausal)
Sex: F
Population Size: 301
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2013/203505Orig1s000MedR.pdf
Page: p. 114
Muscle spasms 0.7%
Disc. AE
60 mg 1 times / day steady, oral
Recommended
Dose: 60 mg, 1 times / day
Route: oral
Route: steady
Dose: 60 mg, 1 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2013/203505Orig1s000MedR.pdf
Page: p. 114
unhealthy, adult (Postmenopausal)
n = 301
Health Status: unhealthy
Condition: Vulvar and Vaginal Atrophy
Age Group: adult (Postmenopausal)
Sex: F
Population Size: 301
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2013/203505Orig1s000MedR.pdf
Page: p. 114
Rash 0.7%
Disc. AE
60 mg 1 times / day steady, oral
Recommended
Dose: 60 mg, 1 times / day
Route: oral
Route: steady
Dose: 60 mg, 1 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2013/203505Orig1s000MedR.pdf
Page: p. 114
unhealthy, adult (Postmenopausal)
n = 301
Health Status: unhealthy
Condition: Vulvar and Vaginal Atrophy
Age Group: adult (Postmenopausal)
Sex: F
Population Size: 301
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2013/203505Orig1s000MedR.pdf
Page: p. 114
Headache 1%
Disc. AE
60 mg 1 times / day steady, oral
Recommended
Dose: 60 mg, 1 times / day
Route: oral
Route: steady
Dose: 60 mg, 1 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2013/203505Orig1s000MedR.pdf
Page: p. 114
unhealthy, adult (Postmenopausal)
n = 301
Health Status: unhealthy
Condition: Vulvar and Vaginal Atrophy
Age Group: adult (Postmenopausal)
Sex: F
Population Size: 301
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2013/203505Orig1s000MedR.pdf
Page: p. 114
Nausea 1%
Disc. AE
60 mg 1 times / day steady, oral
Recommended
Dose: 60 mg, 1 times / day
Route: oral
Route: steady
Dose: 60 mg, 1 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2013/203505Orig1s000MedR.pdf
Page: p. 114
unhealthy, adult (Postmenopausal)
n = 301
Health Status: unhealthy
Condition: Vulvar and Vaginal Atrophy
Age Group: adult (Postmenopausal)
Sex: F
Population Size: 301
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2013/203505Orig1s000MedR.pdf
Page: p. 114
Hot flush 2%
Disc. AE
60 mg 1 times / day steady, oral
Recommended
Dose: 60 mg, 1 times / day
Route: oral
Route: steady
Dose: 60 mg, 1 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2013/203505Orig1s000MedR.pdf
Page: p. 114
unhealthy, adult (Postmenopausal)
n = 301
Health Status: unhealthy
Condition: Vulvar and Vaginal Atrophy
Age Group: adult (Postmenopausal)
Sex: F
Population Size: 301
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2013/203505Orig1s000MedR.pdf
Page: p. 114
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG
substrate
1737
substrate
1037

inhibitor
1767
inhibitor
1852
inhibitor
1612

OverviewOther

Other InhibitorOther SubstrateOther Inducer
CYP2B6
810

CYP2C19
1478

CYP2C8
911
CYP2C19
991

P-gp
1537
CYP
76
Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
CYP
147
 no
CYP2C9
1819
 yes [IC50 10 uM]
yes (co-administration study)
Comment: ospemifene inhibited CYP2B6, CYP2C9, CYP2C19, CYP2C8 and CYP2D6 with IC50 values in the range of 7.8-49 μM
Page: 5, 66
CYP2C19
1553
 yes [IC50 35 uM]
yes (co-administration study)
Comment: ospemifene inhibited CYP2B6, CYP2C9, CYP2C19, CYP2C8 and CYP2D6 with IC50 values in the range of 7.8-49 μM
Page: 5, 66
CYP2B6
1001
 yes [IC50 7.8 uM]
yes (co-administration study)
Comment: ospemifene inhibited CYP2B6, CYP2C9, CYP2C19, CYP2C8 and CYP2D6 with IC50 values in the range of 7.8-49 μM
Page: 5, 66
CYP2C8
965
 yes
CYP2D6
1891
 yes
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
P-gp
1537
 no
CYP2C19
991
 yes
yes (co-administration study)
Comment: omeprazole increased Cmax 1.2-fold and AUC 1.17-fold, fluconazole increased Cmax 1.7-fold and AUC 2.7-fold; rifampin reduced Cmax by 51% and AUC by 58%
Page: 9, 11, 18
CYP2C9
1037
 yes
yes (co-administration study)
Comment: fluconazole increased Cmax 1.7-fold and AUC 2.7-fold; rifampin reduced Cmax by 51% and AUC by 58%
Page: 9, 11, 18
CYP3A4
1737
 yes
yes (co-administration study)
Comment: ketoconazole increased Cmax 1.5-fold and AUC by 1.4-fold, fluconazole increased Cmax 1.7-fold and AUC 2.7-fold; rifampin reduced Cmax by 51% and AUC by 58%
Page: 9, 10, 11, 18
Tox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
hERG
1647
Sourcing

Sourcing

Vendor/AggregatorIDURL
ChEBI
CHEBI:73275
https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:73275
ChemicalBook
CB01335273
https://www.chemicalbook.com/ChemicalProductProperty_EN_CB01335273
MolPort
MolPort-006-170-032
https://www.molport.com/shop/molecule-link/MolPort-006-170-032
ZINC
ZINC000001550766
http://zinc15.docking.org/substances/ZINC000001550766
PubMed

PubMed

TitleDatePubMed
In vitro and in vivo biologic effects of Ospemifene (FC-1271a) in breast cancer.
2001 Jun
Effects of ospemifene (FC-1271a) on uterine endometrium, vaginal maturation index, and hormonal status in healthy postmenopausal women.
2002 Nov 20
Effects of ospemifene, a novel SERM, on vascular markers and function in healthy, postmenopausal women.
2003 Sep-Oct
Effects of ospemifene, a novel SERM, on hormones, genital tract, climacteric symptoms, and quality of life in postmenopausal women: a double-blind, randomized trial.
2003 Sep-Oct
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 Jan 1
Pharmacologic evaluation of ospemifene.
2010 Jun
Liver X receptors as regulators of macrophage inflammatory and metabolic pathways.
2011 Aug
Ospemifene metabolism in humans in vitro and in vivo: metabolite identification, quantitation, and CYP assignment of major hydroxylations.
2013
Patents

Patents

05750576
1
05912273
1
06037379
1

Sample Use Guides

In Vivo Use Guide
One tablet (60 mg ) taken orally once daily with food
Route of Administration: Oral
In Vitro Use Guide
The growth inhibitory effects of FC-1271a and its main metabolite are investigated in MCF-7 and MDA-MB-231 human breast cancer cells at doses ranging from 0.1 to 10 uM.
Substance Class Chemical
Created
by admin
on Sat Dec 16 17:15:15 GMT 2023
Edited
by admin
on Sat Dec 16 17:15:15 GMT 2023
Record UNII
B0P231ILBK
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
OSPEMIFENE
DASH   INN   MART.   MI   ORANGE BOOK   USAN   VANDF   WHO-DD  
USAN   INN  
Official Name English
(DEAMINOHYDROXY) TOREMIFENE
Common Name English
SENSHIO
Brand Name English
TORE III
Common Name English
OSPEMIFENE [MART.]
Common Name English
OSPEMIFENE [ORANGE BOOK]
Common Name English
ospemifene [INN]
Common Name English
FC-1271
Code English
Ospemifene [WHO-DD]
Common Name English
OSPEMIFENE [MI]
Common Name English
ETHANOL, 2-(4-((1Z)-4-CHLORO-1,2-DIPHENYL-1-BUTENYL)PHENOXY)-
Systematic Name English
OSPEMIFENE [USAN]
Common Name English
OSPHENA
Brand Name English
OSPEMIFENE [VANDF]
Common Name English
FC-1271A
Code English
2-(P-((Z)-4-CHLORO-1,2-DIPHENYL-1-BUTENYL)PHENOXY)ETHANOL
Common Name English
Classification Tree Code System Code
WHO-VATC QG03XC05
Created by admin on Sat Dec 16 17:15:17 GMT 2023 , Edited by admin on Sat Dec 16 17:15:17 GMT 2023
WHO-ATC G03XC05
Created by admin on Sat Dec 16 17:15:17 GMT 2023 , Edited by admin on Sat Dec 16 17:15:17 GMT 2023
NDF-RT N0000175826
Created by admin on Sat Dec 16 17:15:17 GMT 2023 , Edited by admin on Sat Dec 16 17:15:17 GMT 2023
EMA ASSESSMENT REPORTS SENSHIO (AUTHORIZED: POSTMENOPAUSE)
Created by admin on Sat Dec 16 17:15:17 GMT 2023 , Edited by admin on Sat Dec 16 17:15:17 GMT 2023
NCI_THESAURUS C1821
Created by admin on Sat Dec 16 17:15:17 GMT 2023 , Edited by admin on Sat Dec 16 17:15:17 GMT 2023
Code System Code Type Description
CHEBI
73275
Created by admin on Sat Dec 16 17:15:17 GMT 2023 , Edited by admin on Sat Dec 16 17:15:17 GMT 2023
PRIMARY
PUBCHEM
3036505
Created by admin on Sat Dec 16 17:15:17 GMT 2023 , Edited by admin on Sat Dec 16 17:15:17 GMT 2023
PRIMARY
NCI_THESAURUS
C76958
Created by admin on Sat Dec 16 17:15:17 GMT 2023 , Edited by admin on Sat Dec 16 17:15:17 GMT 2023
PRIMARY
DRUG BANK
DB04938
Created by admin on Sat Dec 16 17:15:17 GMT 2023 , Edited by admin on Sat Dec 16 17:15:17 GMT 2023
PRIMARY
SMS_ID
100000126074
Created by admin on Sat Dec 16 17:15:17 GMT 2023 , Edited by admin on Sat Dec 16 17:15:17 GMT 2023
PRIMARY
DAILYMED
B0P231ILBK
Created by admin on Sat Dec 16 17:15:17 GMT 2023 , Edited by admin on Sat Dec 16 17:15:17 GMT 2023
PRIMARY
WIKIPEDIA
Ospemifene
Created by admin on Sat Dec 16 17:15:17 GMT 2023 , Edited by admin on Sat Dec 16 17:15:17 GMT 2023
PRIMARY
MESH
C119141
Created by admin on Sat Dec 16 17:15:17 GMT 2023 , Edited by admin on Sat Dec 16 17:15:17 GMT 2023
PRIMARY
RXCUI
1370971
Created by admin on Sat Dec 16 17:15:17 GMT 2023 , Edited by admin on Sat Dec 16 17:15:17 GMT 2023
PRIMARY RxNorm
ChEMBL
CHEMBL2105395
Created by admin on Sat Dec 16 17:15:17 GMT 2023 , Edited by admin on Sat Dec 16 17:15:17 GMT 2023
PRIMARY
IUPHAR
7349
Created by admin on Sat Dec 16 17:15:17 GMT 2023 , Edited by admin on Sat Dec 16 17:15:17 GMT 2023
PRIMARY
EPA CompTox
DTXSID101025426
Created by admin on Sat Dec 16 17:15:17 GMT 2023 , Edited by admin on Sat Dec 16 17:15:17 GMT 2023
PRIMARY
USAN
SS-11
Created by admin on Sat Dec 16 17:15:17 GMT 2023 , Edited by admin on Sat Dec 16 17:15:17 GMT 2023
PRIMARY
MERCK INDEX
m8261
Created by admin on Sat Dec 16 17:15:17 GMT 2023 , Edited by admin on Sat Dec 16 17:15:17 GMT 2023
PRIMARY Merck Index
CAS
128607-22-7
Created by admin on Sat Dec 16 17:15:17 GMT 2023 , Edited by admin on Sat Dec 16 17:15:17 GMT 2023
PRIMARY
EVMPD
SUB33020
Created by admin on Sat Dec 16 17:15:17 GMT 2023 , Edited by admin on Sat Dec 16 17:15:17 GMT 2023
PRIMARY
DRUG CENTRAL
4749
Created by admin on Sat Dec 16 17:15:17 GMT 2023 , Edited by admin on Sat Dec 16 17:15:17 GMT 2023
PRIMARY
INN
7859
Created by admin on Sat Dec 16 17:15:17 GMT 2023 , Edited by admin on Sat Dec 16 17:15:17 GMT 2023
PRIMARY
FDA UNII
B0P231ILBK
Created by admin on Sat Dec 16 17:15:17 GMT 2023 , Edited by admin on Sat Dec 16 17:15:17 GMT 2023
PRIMARY
Related Record Type Details
CYTOCHROME P450 2C9
METABOLIC ENZYME -> INHIBITOR
IC50
CYTOCHROME P450 3A4
METABOLIC ENZYME -> SUBSTRATE
Ospemifene is primarily metabolized by CYP3A4, 2C9, and 2C19 responsible for approximately 40 to 50%, ~25%, and ~25%, respectively, of its clearance.
MAJOR
CYTOCHROME P450 2C9
METABOLIC ENZYME -> SUBSTRATE
Ospemifene is primarily metabolized by CYP3A4, 2C9, and 2C19 responsible for approximately 40 to 50%, ~25%, and ~25%, respectively, of its clearance.
MAJOR
CYTOCHROME P450 2C19
METABOLIC ENZYME -> SUBSTRATE
Ospemifene is primarily metabolized by CYP3A4, 2C9, and 2C19 responsible for approximately 40 to 50%, ~25%, and ~25%, respectively, of its clearance.
MAJOR
CYTOCHROME P450 2B6
METABOLIC ENZYME -> INHIBITOR
IC50
Structure of OSPEMIFENE
EXCRETED UNCHANGED
Following an oral administration of ospemifene, approximately 75% and 7% of the dose was excreted in feces and urine, respectively. Less than 0.2% of the ospemifene dose was excreted unchanged in urine.
URINE
MULTIDRUG RESISTANCE PROTEIN 1
TRANSPORTER -> SUBSTRATE
The sponsor evaluated ospemifene as a potential substrate for transporters in a P-gp in vitro study. No in vivo transporter studies were conducted.
PLASMA PROTEIN FRACTION (HUMAN)
BINDER->LIGAND
BINDING
CYTOCHROME P450 2C19
METABOLIC ENZYME -> INHIBITOR
IC50
ESTROGEN RECEPTOR
TARGET -> INHIBITOR
Related Record Type Details
Structure of TOREMIFENE
PARENT -> METABOLITE ACTIVE
MAJOR
Structure of ACETIC ACID, (4-(4-CHLORO-1-(4-HYDROXYPHENYL)-2-PHENYL-1-BUTENYL)PHENOXY)-, (Z)-
METABOLITE -> PARENT
Structure of (Z)-4-(1-(2-CHLOROETHYL)-2-(4-(2-HYDROXYETHOXY)PHENYL)-2-PHENYLVINYL)PHENOL
METABOLITE -> PARENT
4-hydroxyospemifene (M1) is the major metabolite with a serum concentration of approximately 25% of ospemifene.
MAJOR
Structure of ACETIC ACID, (4-((1Z)-4-CHLORO-1,2-DIPHENYL-1-BUTENYL)PHENOXY)-
METABOLITE -> PARENT
Structure of 4'-HYDROXYOSPEMIFENE
METABOLITE -> PARENT
4’-hydroxyospemifene (M2) is the major metabolite with a serum concentration of approximately 7% of ospemifene.
MAJOR
Related Record Type Details
Structure of OSPEMIFENE E-ISOMER
IMPURITY -> PARENT
Related Record Type Details
Structure of OSPEMIFENE
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Biological Half-life PHARMACOKINETIC
Tmax PHARMACOKINETIC SINGLE DOSE

Volume of Distribution PHARMACOKINETIC
NIH
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National Center for Advancing Translational Sciences (NCATS),
6701 Democracy Boulevard, Bethesda MD 20892-4874 • 301-594-8966