AC-264613
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MedKoo CAT#: 551012

CAS#: 1051487-82-1

Description: AC-264613 is the first agonist of the G-protein-coupled receptor (GPCR) protease activated receptor 2 (PAR2). AC-264613 suppresses interferon regulatory factor 5 and decreases interleukin-12p40 production by lipopolysaccharide-stimulated macrophages. AC-264613 activated PAR2 signaling in cellular proliferation assays, phosphatidylinositol hydrolysis assays, and Ca(2+) mobilization assays, with potencies ranging from 30 to 100 nM.


Chemical Structure

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AC-264613
CAS# 1051487-82-1

Theoretical Analysis

MedKoo Cat#: 551012
Name: AC-264613
CAS#: 1051487-82-1
Chemical Formula: C19H18BrN3O2
Exact Mass: 399.0582
Molecular Weight: 400.276
Elemental Analysis: C, 57.01; H, 4.53; Br, 19.96; N, 10.50; O, 7.99

Price and Availability

Size Price Availability Quantity
10.0mg USD 260.0 2 Weeks
25.0mg USD 520.0 2 Weeks
50.0g USD 840.0 2 Weeks
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Synonym: AC-264613; AC 264613; AC264613

IUPAC/Chemical Name: (3R,​4S)​-​rel-2-​Oxo-​4-​phenyl-​3-​pyrrolidinecarboxyli​c acid 2-​[1-​(3-​bromophenyl)​ethylidene]​hydrazide

InChi Key: RQKXQCSEZPQBNZ-CBCLUANDSA-N

InChi Code: InChI=1S/C19H18BrN3O2/c1-12(14-8-5-9-15(20)10-14)22-23-19(25)17-16(11-21-18(17)24)13-6-3-2-4-7-13/h2-10,16-17H,11H2,1H3,(H,21,24)(H,23,25)/b22-12+/t16-,17-/m1/s1

SMILES Code: O=C([C@H]1C(NC[C@@H]1C2=CC=CC=C2)=O)N/N=C(C3=CC=CC(Br)=C3)\C

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

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

Preparing Stock Solutions

The following data is based on the product molecular weight 400.276 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

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1: Cosimi E, Saadi J, Wennemers H. Stereoselective Synthesis of α-Fluoro-γ-nitro Thioesters under Organocatalytic Conditions. Org Lett. 2016 Dec 2;18(23):6014-6017. Epub 2016 Nov 11. PubMed PMID: 27934387.

2: Yamaguchi R, Yamamoto T, Sakamoto A, Ishimaru Y, Narahara S, Sugiuchi H, Yamaguchi Y. A protease-activated receptor 2 agonist (AC-264613) suppresses interferon regulatory factor 5 and decreases interleukin-12p40 production by lipopolysaccharide-stimulated macrophages: Role of p53. Cell Biol Int. 2016 Jun;40(6):629-41. doi: 10.1002/cbin.10589. Epub 2016 Mar 3. PubMed PMID: 26833899.

3: Ma JN, Burstein ES. The protease activated receptor 2 (PAR2) polymorphic variant F240S constitutively activates PAR2 receptors and potentiates responses to small-molecule PAR2 agonists. J Pharmacol Exp Ther. 2013 Dec;347(3):697-704. doi: 10.1124/jpet.113.208744. Epub 2013 Sep 27. PubMed PMID: 24078870.

4: Gardell LR, Ma JN, Seitzberg JG, Knapp AE, Schiffer HH, Tabatabaei A, Davis CN, Owens M, Clemons B, Wong KK, Lund B, Nash NR, Gao Y, Lameh J, Schmelzer K, Olsson R, Burstein ES. Identification and characterization of novel small-molecule protease-activated receptor 2 agonists. J Pharmacol Exp Ther. 2008 Dec;327(3):799-808. doi: 10.1124/jpet.108.142570. Epub 2008 Sep 3. PubMed PMID: 18768780.