Details of the Drug

General Information of Drug (ID: DMC4GEI)

Drug Name
Ospemifene
Synonyms
Ospemifene; 128607-22-7; Osphena; FC-1271a; Deamino-hydroxytoremifene; Fc-1271; 2-(4-(4-chloro-1,2-diphenyl-but-1-enyl)phenoxy)ethanol; UNII-B0P231ILBK; CCRIS 9205; B0P231ILBK; CHEBI:73275; 2-(p-((Z)-4-Chloro-1,2-diphenyl-1-butenyl)phenoxy)ethanol; senshio; Ethanol, 2-[4-[(1Z)-4-chloro-1,2-diphenyl-1-butenyl]phenoxy]-; 2-{4-[(1Z)-4-chloro-1,2-diphenylbut-1-en-1-yl]phenoxy}ethanol; Ophena; Ospemifene [USAN:INN:BAN]; Deaminotoremifene; Osphena (TN); Deaminohydroxytoremifene; AC1MI19T; C24H23ClO2
Indication
Disease Entry ICD 11 Status REF
Dyspareunia GA12 Approved [1]
Postmenopausal vaginal atrophy GA30.2 Phase 3 [1]
Affected Organisms
Humans and other mammals
ATC Code
G03XC05: Ospemifene
G03XC: Selective estrogen receptor modulators
G03X: OTHER SEX HORMONES AND MODULATORS OF THE GENITAL SYSTEM
G03: SEX HORMONES AND MODULATORS OF THE GENITAL SYSTEM
G: GENITO URINARY SYSTEM AND SEX HORMONES
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 1 Molecular Weight (mw) 378.9
Logarithm of the Partition Coefficient (xlogp) 6.5
Rotatable Bond Count (rotbonds) 8
Hydrogen Bond Donor Count (hbonddonor) 1
Hydrogen Bond Acceptor Count (hbondacc) 2
ADMET Property
Clearance
The total body clearance of drug is 9.16 L/h []
Half-life
The concentration or amount of drug in body reduced by one-half in 26 hours [2]
Metabolism
The drug is metabolized via the hepatic []
Vd
The volume of distribution (Vd) of drug is 448 L []
Chemical Identifiers
Formula
C24H23ClO2
IUPAC Name
2-[4-[(Z)-4-chloro-1,2-diphenylbut-1-enyl]phenoxy]ethanol
Canonical SMILES
C1=CC=C(C=C1)/C(=C(/C2=CC=CC=C2)\\C3=CC=C(C=C3)OCCO)/CCCl
InChI
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-
InChIKey
LUMKNAVTFCDUIE-VHXPQNKSSA-N
Cross-matching ID
PubChem CID
3036505
ChEBI ID
CHEMBL73275
CAS Number
128607-22-7
UNII
B0P231ILBK
DrugBank ID
DB04938
TTD ID
D02CTS
INTEDE ID
DR1208
ACDINA ID
D00496
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Drug ADMET Endpoint Profile (DAE)NEW Click to Jump to the Detailed DAE Information of This Drug
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Repurposed Drugs (RPD) Click to Jump to the Detailed RPD Information of This Drug

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Estrogen receptor (ESR) TTZAYWL ESR1_HUMAN Modulator [3]

Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
Cytochrome P450 3A4 (CYP3A4)
Main DME 		DE4LYSA CP3A4_HUMAN Substrate [4]
Cytochrome P450 2C9 (CYP2C9)
Main DME 		DE5IED8 CP2C9_HUMAN Substrate [4]
Mephenytoin 4-hydroxylase (CYP2C19)
Main DME 		DEGTFWK CP2CJ_HUMAN Substrate [4]
Cytochrome P450 2B6 (CYP2B6)
Main DME 		DEPKLMQ CP2B6_HUMAN Substrate [4]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Molecular Expression Atlas of This Drug

The Studied Disease Dyspareunia
ICD Disease Classification GA12
Molecule Name Molecule Type Gene Name p-value Fold-Change Z-score
Cytochrome P450 2B6 (CYP2B6) DME CYP2B6 3.97E-02 -1.72E-01 -9.29E-01
Mephenytoin 4-hydroxylase (CYP2C19) DME CYP2C19 3.44E-01 -1.85E-01 -5.25E-01
Cytochrome P450 2C9 (CYP2C9) DME CYP2C9 9.09E-01 -9.26E-02 -3.68E-01
Cytochrome P450 3A4 (CYP3A4) DME CYP3A4 9.85E-01 2.24E-02 7.33E-02
Molecular Expression Atlas (MEA) Jump to Detail Molecular Expression Atlas of This Drug

Drug-Drug Interaction (DDI) Information of This Drug

Coadministration of a Drug Treating the Disease Different from Ospemifene (Comorbidity)
DDI Drug Name DDI Drug ID Severity Mechanism Comorbidity REF
Arn-509 DMT81LZ Moderate Increased metabolism of Ospemifene caused by Arn-509 mediated induction of CYP450 enzyme. Acute myeloid leukaemia [2A60] [5]
Troleandomycin DMUZNIG Moderate Decreased metabolism of Ospemifene caused by Troleandomycin mediated inhibition of CYP450 enzyme. Bacterial infection [1A00-1C4Z] [5]
Lumacaftor DMCLWDJ Moderate Increased metabolism of Ospemifene caused by Lumacaftor mediated induction of CYP450 enzyme. Cystic fibrosis [CA25] [6]
Boceprevir DMBSHMF Moderate Decreased metabolism of Ospemifene caused by Boceprevir mediated inhibition of CYP450 enzyme. Hepatitis virus infection [1E50-1E51] [5]
Telaprevir DMMRV29 Moderate Decreased metabolism of Ospemifene caused by Telaprevir mediated inhibition of CYP450 enzyme. Hepatitis virus infection [1E50-1E51] [5]
Cobicistat DM6L4H2 Moderate Decreased metabolism of Ospemifene caused by Cobicistat mediated inhibition of CYP450 enzyme. Human immunodeficiency virus disease [1C60-1C62] [5]
Ceritinib DMB920Z Moderate Decreased metabolism of Ospemifene caused by Ceritinib mediated inhibition of CYP450 enzyme. Lung cancer [2C25] [5]
Idelalisib DM602WT Moderate Decreased metabolism of Ospemifene caused by Idelalisib mediated inhibition of CYP450 enzyme. Mature B-cell leukaemia [2A82] [5]
Carfilzomib DM48K0X Major Additive thrombogenic effects by the combination of Ospemifene and Carfilzomib. Multiple myeloma [2A83] [7]
Lonafarnib DMGM2Z6 Moderate Decreased metabolism of Ospemifene caused by Lonafarnib mediated inhibition of CYP450 enzyme. Premature ageing appearance [LD2B] [5]
Enzalutamide DMGL19D Moderate Increased metabolism of Ospemifene caused by Enzalutamide mediated induction of CYP450 enzyme. Prostate cancer [2C82] [5]
⏷ Show the Full List of 11 DDI Information of This Drug

Drug Inactive Ingredient(s) (DIG) and Formulation(s) of This Drug

DIG
DIG Name DIG ID PubChem CID Functional Classification
Mannitol E00103 6251 Diluent; Flavoring agent; Lyophilization aid; Plasticizing agent; Tonicity agent
Lactose monohydrate E00393 104938 Binding agent; Diluent; Dry powder inhaler carrier; Lyophilization aid
Magnesium stearate E00208 11177 lubricant
Silicon dioxide E00670 Not Available Anticaking agent; Opacifying agent; Viscosity-controlling agent
Titanium dioxide E00322 26042 Coating agent; Colorant; Opacifying agent
Triacetin E00080 5541 Humectant; Plasticizing agent; Solvent
⏷ Show the Full List of 6 Pharmaceutical Excipients of This Drug
Pharmaceutical Formulation
Formulation Name Drug Dosage Dosage Form Route
Ospemifene 60 mg tablet 60 mg Oral Tablet Oral
Jump to Detail Pharmaceutical Formulation Page of This Drug

References

1 URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 7349).
2 Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds
3 Clinical pipeline report, company report or official report of Shionogi (2011).
4 Ospemifene metabolism in humans in vitro and in vivo: metabolite identification, quantitation, and CYP assignment of major hydroxylations. Drug Metabol Drug Interact. 2013;28(3):153-61.
5 Product Information. Osphena (ospemifene). Shionogi USA Inc, Florham Park, NJ.
6 Patel S, Robinson R, Burk M "Hypertensive crisis associated with St. John's Wort." Am J Med 112 (2002): 507-8. [PMID: 11959071]
7 Cerner Multum, Inc. "Australian Product Information.".