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ospemifene

Structure via PubChem · Public domain (PubChem)

EntityQ7107372· pop 11· linked from 601 articles

ospemifene

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Also known as FC-1271, Osphena®, Senshio®, 2-(4-(4-Chloro-1,2-diphenyl-but-1-enyl)phenoxy)ethanol, 2-(p-((Z)-4-Chloro-1,2-diphenyl-1-butenyl)phenoxy)ethanol, Deamino-hydroxytoremifene, FC-1271a, 2-(P-((Z)-4-Chloro-1,2-diphenyl-1-butenyl)phenoxy)ethanol

Ospemifene (brand names Osphena and Senshio produced by Shionogi) is an oral medication indicated for the treatment of dyspareuniapain during sexual intercourseencountered by some women, more often in those who are post-menopausal. Ospemifene is a selective estrogen receptor modulator (SERM) acting similarly to an estrogen on the vaginal epithelium, building vaginal wall thickness which in turn reduces the pain associated with dyspareunia. Dyspareunia is most commonly caused by vulvovaginal atrophy.

Key facts

Drug.image
Ospemifene.svg
Drug.image_class
skin-invert-image
Drug.width
250
Drug.tradename
Osphena, Senshio
Drug.MedlinePlus
a613039
Drug.DailyMedID
Ospemifene
Drug.routes_of_administration
By mouth
Drug.class
Selective estrogen receptor modulator
Drug.ATC_prefix
G03
Drug.ATC_suffix
XC05
Drug.legal_CA
Rx-only
Drug.legal_US
Rx-only
Drug.legal_EU
Rx-only
Drug.CAS_number
128607-22-7
Drug.PubChem
3036505
Drug.DrugBank
DB04938
Drug.ChemSpiderID
2300501
Drug.UNII
B0P231ILBK

via Wikipedia infobox

Chemical data

Formula
C24H23ClO2
Molecular weight
378.9 g/mol
IUPAC name
2-[4-[(Z)-4-chloro-1,2-diphenylbut-1-enyl]phenoxy]ethanol
SMILES
C1=CC=C(C=C1)/C(=C(/C2=CC=CC=C2)\C3=CC=C(C=C3)OCCO)/CCCl
InChIKey
LUMKNAVTFCDUIE-VHXPQNKSSA-N
XLogP
6.5
Polar surface area
29.5 Ų
H-bond donors
1
H-bond acceptors
2
Formal charge
0

via PubChem

Drug data · ChEMBL

Max clinical phase
Approved
Molecule type
Small molecule
First approval
2013
Admin. routes
oral
Indications
reproductive system disease, Atrophy, Dyspareunia, Atrophic Vaginitis

via ChEMBL · EBI

Research

295 papers

via PubMed

Wikidata facts

Subclass of
chemical compound
Mass
378.138658
Has use
medication
Show 6 more facts
chemical formula
C₂₄H₂₃ClO₂
canonical SMILES
C1=CC=C(C=C1)C(=C(C2=CC=CC=C2)C3=CC=C(C=C3)OCCO)CCCl
isomeric SMILES
C1=CC=C(C=C1)/C(=C(/C2=CC=CC=C2)\C3=CC=C(C=C3)OCCO)/CCCl
subject has role
selective estrogen-receptor modulators
Commons category
Ospemifene
legal status (medicine)
boxed warning
Sources (5)

via Wikidata · CC0

~7 min read

Encyclopedic overview

12 sections
Contents
  • Medical uses
  • Contraindications
  • Side effects
  • Pharmacology
  • Pharmacodynamics
  • Pharmacokinetics
  • History
  • Approval process
  • Preclinial and clinical trials
  • Society and culture
  • Economics
  • References

Ospemifene (brand names Osphena and Senshio produced by Shionogi) is an oral medication indicated for the treatment of dyspareuniapain during sexual intercourseencountered by some women, more often in those who are post-menopausal. Ospemifene is a selective estrogen receptor modulator (SERM) acting similarly to an estrogen on the vaginal epithelium, building vaginal wall thickness which in turn reduces the pain associated with dyspareunia. Dyspareunia is most commonly caused by vulvovaginal atrophy.

The medication was approved by the US Food and Drug Administration in February 2013, and by the European Medicines Agency for marketing in the European Union in January 2015.

Excerpted from Wikipedia’s “ospemifene” article, available under the CC BY-SA 4.0 licence.

Available in 10 languages

via Wikidata sitelinks · CC0