PF-3274167
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MedKoo CAT#: 522639

CAS#: 900510-03-4

Description: 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

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PF-3274167
CAS# 900510-03-4

Theoretical Analysis

MedKoo Cat#: 522639
Name: PF-3274167
CAS#: 900510-03-4
Chemical Formula: C19H19ClFN5O3
Exact Mass: 419.12
Molecular Weight: 419.841
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
200mg USD 1150
500mg USD 1650
1g USD 2650
2g USD 3950
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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:
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/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 34.0 80.98

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.

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The OXTR protein belongs to the G-protein coupled receptor family, specifically Gq, and acts as a receptor for oxytocin. Its activity is mediated by G proteins that activate several different second messenger systems. Oxytocin receptors are expressed by the myoepithelial cells of the mammary gland, and in both the myometrium and endometrium of the uterus at the end of pregnancy. The oxytocin-oxytocin receptor system plays an important role as an inducer of uterine contractions during parturition and of milk ejection. 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. (https://en.wikipedia.org/wiki/Oxytocin_receptor)