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=CC=C(F)C=C3Cl)N1C4=CC=C(OC)N=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
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
PubMed
| Title | Date | PubMed |
|---|---|---|
| Pharmacokinetics of cligosiban in dog plasma after oral administration by liquid chromatography electrospray ionization tandem mass spectrometry. | 2019-10 |
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| Pharmacokinetics, bioavailability and metabolism of cligosiban, an antagonist of oxytocin receptor, in rat by liquid chromatography hyphenated with electrospray ionization tandem mass spectrometry. | 2019-02-05 |
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| 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. | 2019-02 |
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| Cligosiban, A Novel Brain-Penetrant, Selective Oxytocin Receptor Antagonist, Inhibits Ejaculatory Physiology in Rodents. | 2018-12 |
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| 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. | 2018-11 |
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| [11C]PF-3274167 as a PET radiotracer of oxytocin receptors: Radiosynthesis and evaluation in rat brain. | 2017-12 |
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| Selective nonpeptidic fluorescent ligands for oxytocin receptor: design, synthesis, and application to time-resolved FRET binding assay. | 2015-03-12 |
Patents
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10778
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C171859
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PF-3274167
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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) | ||
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IX-01
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ACTIVE MOIETY
