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Details

Stereochemistry ACHIRAL
Molecular Formula C24H23ClO2
Molecular Weight 378.891
Optical Activity UNSPECIFIED
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
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

Targets

Targets

Primary TargetPharmacologyConditionPotency
1633.0 nM [IC50]
827.0 nM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
OSPHENA
PubMed

PubMed

TitleDatePubMed
In vitro and in vivo biologic effects of Ospemifene (FC-1271a) in breast cancer.
2001 Jun
Ospemifene inhibits the growth of dimethylbenzanthracene-induced mammary tumors in Sencar mice.
2005 Nov
Effects of ospemifene and raloxifene on biochemical markers of bone turnover in postmenopausal women.
2006
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

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 Mon Oct 21 22:06:38 UTC 2019
Edited
by admin
on Mon Oct 21 22:06:38 UTC 2019
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 [MI]
Common Name English
OSPEMIFENE [WHO-DD]
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 Mon Oct 21 22:06:38 UTC 2019 , Edited by admin on Mon Oct 21 22:06:38 UTC 2019
WHO-ATC G03XC05
Created by admin on Mon Oct 21 22:06:38 UTC 2019 , Edited by admin on Mon Oct 21 22:06:38 UTC 2019
NDF-RT N0000175826
Created by admin on Mon Oct 21 22:06:38 UTC 2019 , Edited by admin on Mon Oct 21 22:06:38 UTC 2019
EMA ASSESSMENT REPORTS SENSHIO (AUTHORIZED: POSTMENOPAUSE)
Created by admin on Mon Oct 21 22:06:38 UTC 2019 , Edited by admin on Mon Oct 21 22:06:38 UTC 2019
NCI_THESAURUS C1821
Created by admin on Mon Oct 21 22:06:38 UTC 2019 , Edited by admin on Mon Oct 21 22:06:38 UTC 2019
Code System Code Type Description
PUBCHEM
3036505
Created by admin on Mon Oct 21 22:06:38 UTC 2019 , Edited by admin on Mon Oct 21 22:06:38 UTC 2019
PRIMARY
NCI_THESAURUS
C76958
Created by admin on Mon Oct 21 22:06:38 UTC 2019 , Edited by admin on Mon Oct 21 22:06:38 UTC 2019
PRIMARY
DRUG BANK
DB04938
Created by admin on Mon Oct 21 22:06:38 UTC 2019 , Edited by admin on Mon Oct 21 22:06:38 UTC 2019
PRIMARY
WIKIPEDIA
Ospemifene
Created by admin on Mon Oct 21 22:06:38 UTC 2019 , Edited by admin on Mon Oct 21 22:06:38 UTC 2019
PRIMARY
MESH
C119141
Created by admin on Mon Oct 21 22:06:38 UTC 2019 , Edited by admin on Mon Oct 21 22:06:38 UTC 2019
PRIMARY
RXCUI
1370971
Created by admin on Mon Oct 21 22:06:38 UTC 2019 , Edited by admin on Mon Oct 21 22:06:38 UTC 2019
PRIMARY RxNorm
ChEMBL
CHEMBL2105395
Created by admin on Mon Oct 21 22:06:38 UTC 2019 , Edited by admin on Mon Oct 21 22:06:38 UTC 2019
PRIMARY
IUPHAR
7349
Created by admin on Mon Oct 21 22:06:38 UTC 2019 , Edited by admin on Mon Oct 21 22:06:38 UTC 2019
PRIMARY
MERCK INDEX
M8261
Created by admin on Mon Oct 21 22:06:38 UTC 2019 , Edited by admin on Mon Oct 21 22:06:38 UTC 2019
PRIMARY Merck Index
CAS
128607-22-7
Created by admin on Mon Oct 21 22:06:38 UTC 2019 , Edited by admin on Mon Oct 21 22:06:38 UTC 2019
PRIMARY
EVMPD
SUB33020
Created by admin on Mon Oct 21 22:06:38 UTC 2019 , Edited by admin on Mon Oct 21 22:06:38 UTC 2019
PRIMARY
INN
7859
Created by admin on Mon Oct 21 22:06:38 UTC 2019 , Edited by admin on Mon Oct 21 22:06:38 UTC 2019
PRIMARY
Related Record Type Details
METABOLIC ENZYME -> INHIBITOR
IC50
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
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
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
METABOLIC ENZYME -> INHIBITOR
IC50
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
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.
BINDER->LIGAND
BINDING
METABOLIC ENZYME -> INHIBITOR
IC50
TARGET -> INHIBITOR
Related Record Type Details
PARENT -> METABOLITE ACTIVE
MAJOR
Related Record Type Details
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Biological Half-life PHARMACOKINETIC
Tmax PHARMACOKINETIC SINGLE DOSE

Volume of Distribution PHARMACOKINETIC