CLIGOSIBAN

Details

Stereochemistry	ACHIRAL
Molecular Formula	C19H19ClFN5O3
Molecular Weight	419.837
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

COCC1=NN=C(N2CC(C2)OC3=C(Cl)C=C(F)C=C3)N1C4=CN=C(OC)C=C4

InChI

InChIKey=HNIFCPBQMKPRCX-UHFFFAOYSA-N

InChI=1S/C19H19ClFN5O3/c1-27-11-17-23-24-19(26(17)13-4-6-18(28-2)22-8-13)25-9-14(10-25)29-16-5-3-12(21)7-15(16)20/h3-8,14H,9-11H2,1-2H3

HIDE SMILES / InChI

Molecular Formula	C19H19ClFN5O3
Molecular Weight	419.837
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/28917111 | https://www.ncbi.nlm.nih.gov/pubmed/30527053 | https://adisinsight.springer.com/drugs/800025596

PF-3274167 (Cligosiban) is a potent, selective, brain penetrant oxytocin receptor antagonist. Cligosiban interrupts the expulsion phase of ejaculation by reducing the normal bulbospongiosum burst pattern and reducing the expulsions that accompany bursts. Cligosiban represents a promising compound to test the clinical hypothesis that antagonism of central oxytocin receptors may be of therapeutic benefit in the treatment of premature ejaculation. [11C]PF-3274167 is not a suitable tracer for imaging of OTR in rat brain, probably because of a too low affinity for this receptor in addition to a poor brain penetration. PF-3274167 had been in phase I clinical trial for the treatment of sexual function disorders and urinary incontinence. However, this research has been discontinued.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Oxytocin receptor 19 Target ID: CHEMBL2049 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19963374	Antagonist 2778		9.5 nM [Ki]
Vasopressin V1a receptor 17 Target ID: CHEMBL1889 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19963374	Antagonist 2778		1120.0 nM [Ki]

PubMed

Title	Date	PubMed
Pharmacokinetics, bioavailability and metabolism of cligosiban, an antagonist of oxytocin receptor, in rat by liquid chromatography hyphenated with electrospray ionization tandem mass spectrometry.	2019 Feb 5	30472591

Patents

Sample Use Guides

In Vivo Use Guide

Single dose - 0.9 mg/kg

Route of Administration: Intravenous

Substance Class	Chemical Created by `admin` on `Sat Dec 16 10:03:29 UTC 2023` Edited by `admin` on `Sat Dec 16 10:03:29 UTC 2023`
Record UNII	D361S17AIF
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

CLIGOSIBAN

Official Name

English

cligosiban [INN]

Common Name

English

PF 3274167

Code

English

PYRIDINE, 5-(3-(3-(2-CHLORO-4-FLUOROPHENOXY)-1-AZETIDINYL)-5-(METHOXYMETHYL)-4H-1,2,4-TRIAZOL-4-YL)-2-METHOXY-

Systematic Name

English

Code System Code Type Description

INN

10778