UR-PI376 | CAS#1192559-94-6 | Histamine H4 Receptor Agonist

MedKoo Cat#: 522691 | Name: UR-PI376

Description:

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

UR-PI376 is a histamine H4 receptor agonist ( hH4R agonist) (pEC50 = 7.47, alpha = 0.93) showing negligible hH1R and hH2R activities and significant selectivity over the hH3R (pKB = 6.00, alpha = -0.28), as determined in steady-state GTPase assays using membrane preparations of hH(x)R-expressing Sf9 cells. Modeling of the binding mode of UR-PI376 suggests that the cyanoguanidine moiety forms charge-assisted hydrogen bonds not only with the conserved Asp-94 but also with the hH4R-specific Arg-341 residue.

Chemical Structure

UR-PI376

CAS#1192559-94-6

Theoretical Analysis

MedKoo Cat#: 522691

Name: UR-PI376

CAS#: 1192559-94-6

Chemical Formula: C17H22N6S

Exact Mass: 342.1627

Molecular Weight: 342.47

Elemental Analysis: C, 59.62; H, 6.48; N, 24.54; S, 9.36

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.

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Related CAS #

No Data

Synonym

UR-PI376, UR-PI-376, UR-PI 376, URPI376, URPI-376, URPI 376

IUPAC/Chemical Name

1-cyano-2-[4-(1H-imidazol-5-yl)butyl]-3-(2-phenylsulfanylethyl)guanidine

InChi Key

DHHDEHNHEBYRPQ-UHFFFAOYSA-N

InChi Code

InChI=1S/C17H22N6S/c18-13-22-17(20-9-5-4-6-15-12-19-14-23-15)21-10-11-24-16-7-2-1-3-8-16/h1-3,7-8,12,14H,4-6,9-11H2,(H,19,23)(H2,20,21,22)

SMILES Code

N#CN/C(NCCSC1=CC=CC=C1)=N\CCCCC2=CN=CN2

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

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 342.47 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.

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

1: Geyer R, Nordemann U, Strasser A, Wittmann HJ, Buschauer A. Conformational Restriction and Enantioseparation Increase Potency and Selectivity of Cyanoguanidine-Type Histamine H(4) Receptor Agonists. J Med Chem. 2016 Apr 5. [Epub ahead of print] PubMed PMID: 27007611. 2: Wifling D, Bernhardt G, Dove S, Buschauer A. The extracellular loop 2 (ECL2) of the human histamine H4 receptor substantially contributes to ligand binding and constitutive activity. PLoS One. 2015 Jan 28;10(1):e0117185. doi: 10.1371/journal.pone.0117185. eCollection 2015. Erratum in: PLoS One. 2015;10(3):e0122162. PubMed PMID: 25629160; PubMed Central PMCID: PMC4309601. 3: Werner K, Neumann D, Buschauer A, Seifert R. No evidence for histamine H4 receptor in human monocytes. J Pharmacol Exp Ther. 2014 Dec;351(3):519-26. doi: 10.1124/jpet.114.218107. Epub 2014 Oct 1. PubMed PMID: 25273276. 4: Gschwandtner M, Koether B, Werfel T, Stark H, Gutzmer R. Profiling of histamine H4 receptor agonists in native human monocytes. Br J Pharmacol. 2013 Sep;170(1):136-43. doi: 10.1111/bph.12237. PubMed PMID: 23638754; PubMed Central PMCID: PMC3764855. 5: Reher TM, Neumann D, Buschauer A, Seifert R. Incomplete activation of human eosinophils via the histamine H4-receptor: evidence for ligand-specific receptor conformations. Biochem Pharmacol. 2012 Jul 15;84(2):192-203. doi: 10.1016/j.bcp.2012.04.004. Epub 2012 Apr 11. PubMed PMID: 22516788. 6: Geyer R, Buschauer A. Synthesis and histamine H(3) and H(4) receptor activity of conformationally restricted cyanoguanidines related to UR-PI376. Arch Pharm (Weinheim). 2011 Dec;344(12):775-85. doi: 10.1002/ardp.201100144. Epub 2011 Oct 11. PubMed PMID: 21987304. 7: Igel P, Geyer R, Strasser A, Dove S, Seifert R, Buschauer A. Synthesis and structure-activity relationships of cyanoguanidine-type and structurally related histamine H4 receptor agonists. J Med Chem. 2009 Oct 22;52(20):6297-313. doi: 10.1021/jm900526h. PubMed PMID: 19791743.