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
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
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.
CNS Activity
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL2049 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19963374 |
9.5 nM [Ki] | ||
Target ID: CHEMBL1889 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19963374 |
1120.0 nM [Ki] |
PubMed
Title | Date | PubMed |
---|---|---|
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/30527053
Curator's Comment: Rats data
Single dose - 0.9 mg/kg
Route of Administration:
Intravenous
Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Dec 16 10:03:29 GMT 2023
by
admin
on
Sat Dec 16 10:03:29 GMT 2023
|
Record UNII |
D361S17AIF
|
Record Status |
Validated (UNII)
|
Record Version |
|
-
Download
Name | Type | Language | ||
---|---|---|---|---|
|
Official Name | English | ||
|
Common Name | English | ||
|
Code | English | ||
|
Systematic Name | English |
Code System | Code | Type | Description | ||
---|---|---|---|---|---|
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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) | ||
|
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 |