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]
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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: CHEBI:73275
CAS Number: 128607-22-7
DrugBank ID: DB04938
TTD ID: D02CTS
INTEDE ID: DR1208
ACDINA ID: D00496

Combinatorial Drugs (CBD)

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Repurposed Drugs (RPD)

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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]

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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]

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Drug Off-Target (DOT)

DOT Name	DOT ID	UniProt ID	Interaction	REF
Androgen receptor (AR)	OTUBKAZZ	ANDR_HUMAN	Gene/Protein Processing	[5]
Estrogen receptor (ESR1)	OTKLU61J	ESR1_HUMAN	Gene/Protein Processing	[5]
Trefoil factor 1 (TFF1)	OTCYQH4F	TFF1_HUMAN	Gene/Protein Processing	[5]

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Molecular Interaction Atlas (MIA)

MIA Detail

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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)

MEA Detail

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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]	[6]
Troleandomycin	DMUZNIG	Moderate	Decreased metabolism of Ospemifene caused by Troleandomycin mediated inhibition of CYP450 enzyme.	Bacterial infection [1A00-1C4Z]	[6]
Lumacaftor	DMCLWDJ	Moderate	Increased metabolism of Ospemifene caused by Lumacaftor mediated induction of CYP450 enzyme.	Cystic fibrosis [CA25]	[7]
Boceprevir	DMBSHMF	Moderate	Decreased metabolism of Ospemifene caused by Boceprevir mediated inhibition of CYP450 enzyme.	Hepatitis virus infection [1E50-1E51]	[6]
Telaprevir	DMMRV29	Moderate	Decreased metabolism of Ospemifene caused by Telaprevir mediated inhibition of CYP450 enzyme.	Hepatitis virus infection [1E50-1E51]	[6]
Cobicistat	DM6L4H2	Moderate	Decreased metabolism of Ospemifene caused by Cobicistat mediated inhibition of CYP450 enzyme.	Human immunodeficiency virus disease [1C60-1C62]	[6]
Ceritinib	DMB920Z	Moderate	Decreased metabolism of Ospemifene caused by Ceritinib mediated inhibition of CYP450 enzyme.	Lung cancer [2C25]	[6]
Idelalisib	DM602WT	Moderate	Decreased metabolism of Ospemifene caused by Idelalisib mediated inhibition of CYP450 enzyme.	Mature B-cell leukaemia [2A82]	[6]
Carfilzomib	DM48K0X	Major	Additive thrombogenic effects by the combination of Ospemifene and Carfilzomib.	Multiple myeloma [2A83]	[8]
Lonafarnib	DMGM2Z6	Moderate	Decreased metabolism of Ospemifene caused by Lonafarnib mediated inhibition of CYP450 enzyme.	Premature ageing appearance [LD2B]	[6]
Enzalutamide	DMGL19D	Moderate	Increased metabolism of Ospemifene caused by Enzalutamide mediated induction of CYP450 enzyme.	Prostate cancer [2C82]	[6]
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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
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Pharmaceutical Formulation

Formulation Name	Drug Dosage	Dosage Form	Route
Ospemifene 60 mg tablet	60 mg	Oral Tablet	Oral

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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	Effects of ospemifene, a novel selective estrogen-receptor modulator, on human breast tissue ex vivo. Menopause. 2016 Jul;23(7):719-30. doi: 10.1097/GME.0000000000000624.
6	Product Information. Osphena (ospemifene). Shionogi USA Inc, Florham Park, NJ.
7	Patel S, Robinson R, Burk M "Hypertensive crisis associated with St. John's Wort." Am J Med 112 (2002): 507-8. [PMID: 11959071]
8	Cerner Multum, Inc. "Australian Product Information.".