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Ospemifene

drug
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Also known as (deaminohydroxy) toremifeneFC-1271FC-1271AOspemifenoOsphenaSenshioTore iii

Summary

Ospemifene (CHEMBL2105395) is an approved small-molecule estrogen receptor modulator (ATC G03XC05) targeting ESR1 and ESR2; indicated across 6 conditions including psychologic dyspareunia and postmenopausal atrophic vaginitis.

At a glance

  • Status: Approved (max clinical phase 4)
  • Modality: Small molecule
  • ATC class: G03XC05
  • Targets: 2 (ESR1, ESR2)
  • Indications: 6 conditions
  • Clinical trials: 8
  • Chemistry: 378.9 Da · C24H23ClO2

Identifiers

Drug identity and classification

FieldValue
ChEMBL IDCHEMBL2105395
NameOspemifene
TypeSmall molecule
Max phase4
FDA approvedyes
PubChem CID3036505
ChEBICHEBI:73275
ATCG03XC05
Molecular formulaC24H23ClO2
Molecular weight378.9
InChIKeyLUMKNAVTFCDUIE-VHXPQNKSSA-N

SMILES: C1=CC=C(C=C1)/C(=C(/C2=CC=CC=C2)\C3=CC=C(C=C3)OCCO)/CCCl

IUPAC name: 2-[4-[(Z)-4-chloro-1,2-diphenylbut-1-enyl]phenoxy]ethanol

ChEBI definition: An organochlorine compound that is a selective estrogen receptor modulator; used for treatment of dyspareunia.

Pharmacological roles (ChEBI): estrogen receptor modulator, antineoplastic agent, anti-inflammatory agent.

Also known as: (deaminohydroxy) toremifene, FC-1271, FC-1271A, Ospemifene, Ospemifeno, Osphena, Senshio, Tore iii, OSPEMIFENE

Patent coverage: 353 distinct patent families (829 SureChEMBL compound mentions), from 1 matched compound structure(s). Mentions count patents naming the compound (not distinct inventions), so promiscuous / reference molecules inflate the mention figure — families are the dedup metric.

Targets

Targets

Primary targets (GtoPdb curated mechanism): the Cancer dependency column is the DepMap CRISPR fitness signal (% of screened cell lines dependent on the target).

GeneTargetActionpAffinityCancer dependencyUniProt
ESR1Estrogen receptor-αAntagonist6.421.7%P03372
ESR2Estrogen receptor-βAntagonist6.390.2%Q92731

Bioactivity

No ChEMBL bioactivity rows at pChembl ≥ 5 (expected for biologics / antibodies).

Target pathways

Aggregated over 2 target gene(s): ESR1, ESR2.

Top Reactome pathways

17 total, by targets touching each:

PathwayTargetsGenes
PIP3 activates AKT signaling2ESR1, ESR2
Constitutive Signaling by Aberrant PI3K in Cancer2ESR1, ESR2
Nuclear Receptor transcription pathway2ESR1, ESR2
PI5P, PP2A and IER3 Regulate PI3K/AKT Signaling2ESR1, ESR2
ESR-mediated signaling2ESR1, ESR2
Extra-nuclear estrogen signaling2ESR1, ESR2
Nuclear signaling by ERBB41ESR1
SUMOylation of intracellular receptors1ESR1
Ovarian tumor domain proteases1ESR1
TFAP2 (AP-2) family regulates transcription of growth factors and their receptors1ESR1
RUNX1 regulates estrogen receptor mediated transcription1ESR1
RUNX1 regulates transcription of genes involved in WNT signaling1ESR1
Regulation of RUNX2 expression and activity1ESR1
Estrogen-dependent gene expression1ESR1
Mitochondrial unfolded protein response (UPRmt)1ESR1
Developmental Lineage of Mammary Gland Luminal Epithelial Cells1ESR1
Developmental Lineage of Mammary Gland Alveolar Cells1ESR1

Dominant GO biological processes

GO termTargets
negative regulation of transcription by RNA polymerase II2
regulation of DNA-templated transcription2
regulation of transcription by RNA polymerase II2
signal transduction2
estrogen receptor signaling pathway2
positive regulation of DNA-templated transcription2
positive regulation of transcription by RNA polymerase II2
obsolete positive regulation of DNA-binding transcription factor activity2
cellular response to estradiol stimulus2
cellular response to oxygen-containing compound2
antral ovarian follicle growth1
epithelial cell development1
chromatin remodeling1
phospholipase C-activating G protein-coupled receptor signaling pathway1
positive regulation of cytosolic calcium ion concentration1

Indications & clinical

Indications

6 indications (5 at ChEMBL trial phase 4). Phase below is the highest clinical-trial phase recorded for this drug against each disease — not the molecule’s overall approval status (that is in the Summary).

IndicationTrial phaseMONDOEFO
psychologic dyspareunia4MONDO:0001196HP:0030016
postmenopausal atrophic vaginitis4MONDO:0001410EFO:1001271
reproductive system disorder3MONDO:0005039EFO:0000512

3 further indication records had no mapped disease name (EFO/MeSH-only) or were duplicates, and are omitted.

Clinical trials

Total trials: 8.

Phase distribution

PhaseTrials
PHASE34
PHASE43
PHASE21

Top trials by phase / activity

NCTPhaseStatusTitle
NCT02784613PHASE4COMPLETEDVulvoscopy Changes of the Vulva, Vestibule and Vagina With Daily Ospemifene in Women With Dyspareunia From VVA
NCT03018106PHASE4TERMINATEDOspemifene vs. Conjugated Estrogens in the Treatment of Postmenopausal Sexual Dysfunction
NCT04677491PHASE4COMPLETEDEffects of Ospemifene on Brain Activation Patterns in Women With Sexual Interest-arousal Disorders
NCT00276094PHASE3COMPLETEDA Clinical Study to Evaluate Ospemifene in the Treatment of Vulvar and Vaginal Atrophy in Postmenopausal Women
NCT00566982PHASE3COMPLETEDA Clinical Study to Evaluate the Safety of Ospemifene
NCT00729469PHASE3COMPLETEDEfficacy and Safety of Ospemifene in the Treatment of Moderate to Severe Vaginal Dryness and Vaginal Pain Associated With Sexual Activity
NCT02638337PHASE3COMPLETEDStudy to Evaluate Ospemifene in Patients With Moderate to Severe Vaginal Dryness Due to Menopause
NCT00630539PHASE2COMPLETEDA Clinical Study to Evaluate the Efficacy and Safety of Ospemifene in the Treatment of Vulvar and Vaginal Atrophy (VVA) in Postmenopausal Women

Clinical evidence (CIViC)

No CIViC predictive evidence (expected for non-precision-medicine drugs).

Pharmacology

Pharmacogenomics

No CPIC/DPWG dosing guideline or drug-level clinical/variant annotations in PharmGKB for this molecule.

Molecules sharing ≥1 of this drug’s curated primary targets, merged from two biobtree sources and ranked by shared-target count, then clinical phase: ChEMBL clinical-stage candidates (development phase ≥2) and PubChem drug-class bioactivity (approved / known drugs acting on the target). Deduplicated by drug name; the drug’s own salt forms are excluded. Note: for a drug with few primary targets a shared-target match can reflect off-target / promiscuous binding rather than the same therapeutic mechanism — the phase ordering surfaces bona-fide therapeutics first.

179 molecules share ≥1 primary target. Top 60 by shared-target count:

MoleculeSourceStatusShared targets
FULVESTRANTChEMBL + PubChemPhase 4 (approved)ESR1, ESR2
BAZEDOXIFENEChEMBLPhase 4 (approved)ESR1, ESR2
BITHIONOLChEMBLPhase 4 (approved)ESR1, ESR2
CISPLATINChEMBLPhase 4 (approved)ESR1, ESR2
DIETHYLSTILBESTROLChEMBLPhase 4 (approved)ESR1, ESR2
ELACESTRANTChEMBLPhase 4 (approved)ESR1, ESR2
ESTETROLChEMBLPhase 4 (approved)ESR1, ESR2
ESTRADIOLChEMBLPhase 4 (approved)ESR1, ESR2
ESTRIOLChEMBLPhase 4 (approved)ESR1, ESR2
ESTRONEChEMBLPhase 4 (approved)ESR1, ESR2
ETHINYL ESTRADIOLChEMBLPhase 4 (approved)ESR1, ESR2
HEXACHLOROPHENEChEMBLPhase 4 (approved)ESR1, ESR2
LASOFOXIFENEChEMBLPhase 4 (approved)ESR1, ESR2
MEDROXYPROGESTERONEChEMBLPhase 4 (approved)ESR1, ESR2
MIFEPRISTONEChEMBLPhase 4 (approved)ESR1, ESR2
PHENOLPHTHALEINChEMBLPhase 4 (approved)ESR1, ESR2
RALOXIFENEChEMBLPhase 4 (approved)ESR1, ESR2
SPIRONOLACTONEChEMBLPhase 4 (approved)ESR1, ESR2
TAMOXIFENChEMBLPhase 4 (approved)ESR1, ESR2
ACOLBIFENEChEMBLPhase 3ESR1, ESR2
AFIMOXIFENEChEMBLPhase 3ESR1, ESR2
AMCENESTRANTChEMBLPhase 3ESR1, ESR2
ARZOXIFENEChEMBLPhase 3ESR1, ESR2
BENSERAZIDEChEMBLPhase 3ESR1, ESR2
ALFATRADIOLChEMBLPhase 2ESR1, ESR2
AUS-131ChEMBLPhase 2ESR1, ESR2
BRILANESTRANTChEMBLPhase 2ESR1, ESR2
DAIDZEINChEMBLPhase 2ESR1, ESR2
ERTEBERELChEMBLPhase 2ESR1, ESR2
GENISTEINChEMBLPhase 2ESR1, ESR2
GTX-758ChEMBLPhase 2ESR1, ESR2
IDOXIFENEChEMBLPhase 2ESR1, ESR2
LEVORMELOXIFENEChEMBLPhase 2ESR1, ESR2
MOXESTROLChEMBLPhase 2ESR1, ESR2
PIPENDOXIFENEChEMBLPhase 2ESR1, ESR2
PRINABERELChEMBLPhase 2ESR1, ESR2
STALLIMYCINChEMBLPhase 2ESR1, ESR2
BosentanPubChemApprovedESR1, ESR2
DihydroergotaminePubChemApprovedESR1, ESR2
FidaxomicinPubChemApprovedESR1, ESR2
PropoxyphenePubChemApprovedESR1, ESR2
PyrazinamidePubChemApprovedESR1, ESR2
ACETOPHENAZINEChEMBLPhase 4 (approved)ESR1
ALECTINIBChEMBLPhase 4 (approved)ESR1
APOMORPHINEChEMBLPhase 4 (approved)ESR1
ARIPIPRAZOLEChEMBLPhase 4 (approved)ESR1
ASPIRINChEMBLPhase 4 (approved)ESR1
AZTREONAMChEMBLPhase 4 (approved)ESR1
BELINOSTATChEMBLPhase 4 (approved)ESR1
BENZBROMARONEChEMBLPhase 4 (approved)ESR1
BEXAROTENEChEMBLPhase 4 (approved)ESR1
BISACODYLChEMBLPhase 4 (approved)ESR1
BROMOCRIPTINEChEMBLPhase 4 (approved)ESR1
BUTOCONAZOLEChEMBLPhase 4 (approved)ESR1
CANDESARTAN CILEXETILChEMBLPhase 4 (approved)ESR1
CASPOFUNGINChEMBLPhase 4 (approved)ESR1
CEFADROXILChEMBLPhase 4 (approved)ESR1
CEFEPIMEChEMBLPhase 4 (approved)ESR1
CEFTAZIDIMEChEMBLPhase 4 (approved)ESR1
CERIVASTATINChEMBLPhase 4 (approved)ESR1

About this page

Generated deterministically by Sugi Atlas from primary biomedical databases via BioBTree. Every record on this page traces to a primary source.

Generated
Atlas version
v1.1.2
BioBTree
v2.0.2

Sources 30

This page pulls from 30 datasets indexed by BioBTree:

chebichembl_activitychembl_moleculechembl_targetcivic_evidenceclingen_dosageclinical_trialsdepmapefoensemblentrezgogoparentgtopdbgtopdb_interactiongtopdb_ligandhgncmeshmondomsigdbpatent_compoundpharmgkbpharmgkb_guidelinepubchempubchem_activityreactomereactomeparentrefseqtranscriptuniprot