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MedKoo Cat#: 522639 | Name: PF-3274167
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

PF-3274167, also known as PF-03274167 or PF-327,4167, is a potent and selective, high-affinity nonpeptide oxytocin receptor antagonist. Oxytocin receptor, also known as OXTR, is a protein which functions as receptor for the hormone and neurotransmitter oxytocin. Oxytocin receptors are also present in the central nervous system. These receptors modulate a variety of behaviors, including stress and anxiety, social memory and recognition, sexual and aggressive behaviors, bonding (affiliation) and maternal behavior.

Chemical Structure

PF-3274167
PF-3274167
CAS#900510-03-4

Theoretical Analysis

MedKoo Cat#: 522639

Name: PF-3274167

CAS#: 900510-03-4

Chemical Formula: C19H19ClFN5O3

Exact Mass: 419.1160

Molecular Weight: 419.84

Elemental Analysis: C, 54.36; H, 4.56; Cl, 8.44; F, 4.53; N, 16.68; O, 11.43

Price and Availability

Size Price Availability Quantity
100mg USD 850.00 2 Weeks
200mg USD 1,150.00 2 Weeks
500mg USD 1,650.00 2 Weeks
1g USD 2,650.00 2 Weeks
2g USD 3,950.00 2 Weeks
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Related CAS #
No Data
Synonym
PF-03274167; PF 03274167; PF03274167; PF-3274167; PF 3274167; PF3274167; cligosiban;
IUPAC/Chemical Name
5-(3-(3-(2-chloro-4-fluorophenoxy)azetidin-1-yl)-5-(methoxymethyl)-4H-1,2,4-triazol-4-yl)-2-methoxypyridine
InChi Key
HNIFCPBQMKPRCX-UHFFFAOYSA-N
InChi Code
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
SMILES Code
COC1=NC=C(N2C(N3CC(OC4=CC=C(F)C=C4Cl)C3)=NN=C2COC)C=C1
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO, not in water
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Cligosiban (PF-3274167), a high oral bioavailability and good brain-penetrant non-peptide oxytocin receptor antagonist, shows a high-affinity (Ki=9.5 nM) and an excellent selectivity versus the vasopressin receptors with almost no affinity for the V1b and V1a subtypes.
In vitro activity:
Cligosiban is a potent OT receptor antagonist, with a base dissociation constant of 5.7 nmol/L against native human uterine smooth muscle cell OT receptors. Cligosiban displays similar antagonistic potency against human recombinant and rat native OT receptors, including neuronal OT receptors. Cligosiban demonstrates >100-fold selectivity over human V1A, V1B, and V2 vasopressin receptors. Reference: J Sex Med. 2018 Dec;15(12):1698-1706. https://pubmed.ncbi.nlm.nih.gov/30527053/
In vivo activity:
In the electromyography model, cligosiban (0.9 mg/kg, IV bolus) reduced the bulbospongiosum burst pattern and contraction amplitude associated with ejaculation. In the anesthetized CNS neuronal firing model, the same dosing regimen of cligosiban (0.9 mg/kg IV bolus) modulated the OT-mediated response in the nucleus tractus solitarius. After systemic dosing to rats, cligosiban showed good CNS penetration. Reference: J Sex Med. 2018 Dec;15(12):1698-1706. https://pubmed.ncbi.nlm.nih.gov/30527053/
Solvent mg/mL mM comments
Solubility
DMSO 34.0 80.98
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 419.84 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
Wayman C, Russell R, Tang K, Weibly L, Gaboardi S, Fisher L, Allers K, Jackson M, Hawcock T, Robinson N, Wilson L, Gupta J, Casey J, Gibson KR. Cligosiban, A Novel Brain-Penetrant, Selective Oxytocin Receptor Antagonist, Inhibits Ejaculatory Physiology in Rodents. J Sex Med. 2018 Dec;15(12):1698-1706. doi: 10.1016/j.jsxm.2018.10.008. PMID: 30527053.
In vitro protocol:
Wayman C, Russell R, Tang K, Weibly L, Gaboardi S, Fisher L, Allers K, Jackson M, Hawcock T, Robinson N, Wilson L, Gupta J, Casey J, Gibson KR. Cligosiban, A Novel Brain-Penetrant, Selective Oxytocin Receptor Antagonist, Inhibits Ejaculatory Physiology in Rodents. J Sex Med. 2018 Dec;15(12):1698-1706. doi: 10.1016/j.jsxm.2018.10.008. PMID: 30527053.
In vivo protocol:
Wayman C, Russell R, Tang K, Weibly L, Gaboardi S, Fisher L, Allers K, Jackson M, Hawcock T, Robinson N, Wilson L, Gupta J, Casey J, Gibson KR. Cligosiban, A Novel Brain-Penetrant, Selective Oxytocin Receptor Antagonist, Inhibits Ejaculatory Physiology in Rodents. J Sex Med. 2018 Dec;15(12):1698-1706. doi: 10.1016/j.jsxm.2018.10.008. PMID: 30527053.
Hanser F, Marsol C, Valencia C, Villa P, Klymchenko AS, Bonnet D, Karpenko J. Nile Red-Based GPCR Ligands as Ultrasensitive Probes of the Local Lipid Microenvironment of the Receptor. ACS Chem Biol. 2021 Apr 16;16(4):651-660. doi: 10.1021/acschembio.0c00897. Epub 2021 Mar 18. PMID: 33733725. Vidal B, Karpenko IA, Liger F, Fieux S, Bouillot C, Billard T, Hibert M, Zimmer L. [11C]PF-3274167 as a PET radiotracer of oxytocin receptors: Radiosynthesis and evaluation in rat brain. Nucl Med Biol. 2017 Dec;55:1-6. doi: 10.1016/j.nucmedbio.2017.07.008. Epub 2017 Aug 2. PMID: 28917111.