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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 of CLIGOSIBAN

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

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.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
9.5 nM [Ki]
1120.0 nM [Ki]
PubMed

PubMed

TitleDatePubMed
Selective nonpeptidic fluorescent ligands for oxytocin receptor: design, synthesis, and application to time-resolved FRET binding assay.
2015 Mar 12
[(11)C]PF-3274167 as a PET radiotracer of oxytocin receptors: Radiosynthesis and evaluation in rat brain.
2017 Dec
Cligosiban, A Novel Brain-Penetrant, Selective Oxytocin Receptor Antagonist, Inhibits Ejaculatory Physiology in Rodents.
2018 Dec
Pharmacokinetics, Safety, and Tolerability of Single Oral Doses of a Novel Oxytocin Receptor Antagonist-Cligosiban-in Development for Premature Ejaculation: Three Randomized Clinical Trials in Healthy Subjects.
2018 Nov
Pharmacokinetics, Safety, and Tolerability of Multiple Doses of the Novel Oxytocin Receptor Antagonist Cligosiban in Development for Premature Ejaculation: Two Randomized Clinical Trials in Healthy Subjects.
2019 Feb
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
Patents

Sample Use Guides

In Vivo Use Guide
Curator's Comment: Rats data
Single dose - 0.9 mg/kg
Route of Administration: Intravenous
Substance Class Chemical
Created
by admin
on Sat Dec 16 10:03:29 GMT 2023
Edited
by admin
on Sat Dec 16 10:03:29 GMT 2023
Record UNII
D361S17AIF
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CLIGOSIBAN
INN  
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
Created by admin on Sat Dec 16 10:03:29 GMT 2023 , Edited by admin on Sat Dec 16 10:03:29 GMT 2023
PRIMARY
NCI_THESAURUS
C171859
Created by admin on Sat Dec 16 10:03:29 GMT 2023 , Edited by admin on Sat Dec 16 10:03:29 GMT 2023
PRIMARY
FDA UNII
D361S17AIF
Created by admin on Sat Dec 16 10:03:29 GMT 2023 , Edited by admin on Sat Dec 16 10:03:29 GMT 2023
PRIMARY
CAS
900510-03-4
Created by admin on Sat Dec 16 10:03:29 GMT 2023 , Edited by admin on Sat Dec 16 10:03:29 GMT 2023
PRIMARY
SMS_ID
100000181102
Created by admin on Sat Dec 16 10:03:29 GMT 2023 , Edited by admin on Sat Dec 16 10:03:29 GMT 2023
PRIMARY
PUBCHEM
11683187
Created by admin on Sat Dec 16 10:03:29 GMT 2023 , Edited by admin on Sat Dec 16 10:03:29 GMT 2023
PRIMARY
MANUFACTURER PRODUCT INFORMATION
PF-3274167
Created by admin on Sat Dec 16 10:03:29 GMT 2023 , Edited by admin on Sat Dec 16 10:03:29 GMT 2023
PRIMARY Biological Activity of PF-3274167: PF-3274167 is a high-affinity nonpeptide oxytocin receptor (OTR) antagonist, with Ki of 9.5 nM., IC50 value: 9.5 nM (1), Target: oxytocin receptor (OTR)
MANUFACTURER PRODUCT INFORMATION
IX-01
Created by admin on Sat Dec 16 10:03:29 GMT 2023 , Edited by admin on Sat Dec 16 10:03:29 GMT 2023
PRIMARY
Related Record Type Details
TARGET -> INHIBITOR
Related Record Type Details
ACTIVE MOIETY