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MedKoo Cat#: 532753 | Name: SM19712 free acid
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Description:

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

SM19712 is a nonpeptide endothelin converting enzyme inhibitor. Pretreatment of NCM460 cells with the ECE-1 inhibitor SM19712 or gene silencing of betaARR1 or betaARR2 inhibits NT-stimulated ERK1/2 and JNK phosphorylation, NF-kappaB p65 nuclear translocation and phosphorylation, and IL-8 secretion.

Chemical Structure

SM19712 free acid
SM19712 free acid
CAS#194542-49-9 (free)

Theoretical Analysis

MedKoo Cat#: 532753

Name: SM19712 free acid

CAS#: 194542-49-9 (free)

Chemical Formula: C18H14ClN5O3S

Exact Mass: 415.0506

Molecular Weight: 415.85

Elemental Analysis: C, 51.99; H, 3.39; Cl, 8.52; N, 16.84; O, 11.54; S, 7.71

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Related CAS #
194542-49-9 (free) 194542-56-8 (sodium)
Synonym
SM19712; SM-19712; SM 19712.
IUPAC/Chemical Name
4-chloro-N-((4-cyano-3-methyl-1-phenyl-1H-pyrazol-5-yl)carbamoyl)benzenesulfonamide
InChi Key
CWLFPWRNPQXWLD-UHFFFAOYSA-N
InChi Code
InChI=1S/C18H14ClN5O3S/c1-12-16(11-20)17(24(22-12)14-5-3-2-4-6-14)21-18(25)23-28(26,27)15-9-7-13(19)8-10-15/h2-10H,1H3,(H2,21,23,25)
SMILES Code
O=S(C1=CC=C(Cl)C=C1)(NC(NC2=C(C#N)C(C)=NN2C3=CC=CC=C3)=O)=O
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
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 415.85 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
1: Chang F, Flavahan S, Flavahan NA. Immature endothelial cells initiate endothelin-mediated constriction of newborn arteries. J Physiol. 2016 Sep 1;594(17):4933-44. doi: 10.1113/JP272176. Epub 2016 Jun 16. PMID: 27062279; PMCID: PMC5009801. 2: McNeish AJ, Roux BT, Aylett SB, Van Den Brink AM, Cottrell GS. Endosomal proteolysis regulates calcitonin gene-related peptide responses in mesenteric arteries. Br J Pharmacol. 2012 Dec;167(8):1679-90. doi: 10.1111/j.1476-5381.2012.02129.x. PMID: 22881710; PMCID: PMC3525870. 3: Law IK, Murphy JE, Bakirtzi K, Bunnett NW, Pothoulakis C. Neurotensin-induced proinflammatory signaling in human colonocytes is regulated by β-arrestins and endothelin-converting enzyme-1-dependent endocytosis and resensitization of neurotensin receptor 1. J Biol Chem. 2012 Apr 27;287(18):15066-75. doi: 10.1074/jbc.M111.327262. Epub 2012 Mar 13. PMID: 22416137; PMCID: PMC3340238. 4: Pelayo JC, Poole DP, Steinhoff M, Cottrell GS, Bunnett NW. Endothelin- converting enzyme-1 regulates trafficking and signalling of the neurokinin 1 receptor in endosomes of myenteric neurones. J Physiol. 2011 Nov 1;589(Pt 21):5213-30. doi: 10.1113/jphysiol.2011.214452. Epub 2011 Aug 30. PMID: 21878523; PMCID: PMC3225675. 5: Tawa M, Fukumoto T, Ohkita M, Yamashita N, Geddawy A, Imamura T, Ayajiki K, Okamura T, Matsumura Y. Contribution of nitric oxide in big endothelin-1-induced cardioprotective effects on ischemia/reperfusion injury in rat hearts. J Cardiovasc Pharmacol. 2011 May;57(5):575-8. doi: 10.1097/FJC.0b013e31821325ad. PMID: 21326108. 6: Tawa M, Fukumoto T, Ohkita M, Yamashita N, Geddawy A, Imamura T, Ayajiki K, Okamura T, Matsumura Y. Effects of exogenous big endothelin-1 on postischemic cardiac dysfunction and norepinephrine overflow in rat hearts. Hypertens Res. 2011 Feb;34(2):218-24. doi: 10.1038/hr.2010.213. Epub 2010 Nov 4. PMID: 21048781. 7: Goel A, Su B, Flavahan S, Lowenstein CJ, Berkowitz DE, Flavahan NA. Increased endothelial exocytosis and generation of endothelin-1 contributes to constriction of aged arteries. Circ Res. 2010 Jul 23;107(2):242-51. doi: 10.1161/CIRCRESAHA.109.210229. Epub 2010 Jun 3. PMID: 20522806; PMCID: PMC2909353. 8: Cattaruzza F, Cottrell GS, Vaksman N, Bunnett NW. Endothelin-converting enzyme 1 promotes re-sensitization of neurokinin 1 receptor-dependent neurogenic inflammation. Br J Pharmacol. 2009 Mar;156(5):730-9. doi: 10.1111/j.1476-5381.2008.00039.x. Epub 2009 Feb 6. PMID: 19222484; PMCID: PMC2697762. 9: Lee S, Carter PR, Watts MN, Bao JR, Harris NR. Effects of the endothelin- converting enzyme inhibitor SM-19712 in a mouse model of dextran sodium sulfate- induced colitis. Inflamm Bowel Dis. 2009 Jul;15(7):1007-13. doi: 10.1002/ibd.20877. PMID: 19202571; PMCID: PMC2697258. 10: Sen U, Tyagi N, Patibandla PK, Dean WL, Tyagi SC, Roberts AM, Lominadze D. Fibrinogen-induced endothelin-1 production from endothelial cells. Am J Physiol Cell Physiol. 2009 Apr;296(4):C840-7. doi: 10.1152/ajpcell.00515.2008. Epub 2009 Feb 4. PMID: 19193866; PMCID: PMC2670653. 11: Tawa M, Fukumoto T, Ohkita M, Matsumura Y. Role of endogenous endothelin-1 in post-ischemic cardiac dysfunction and norepinephrine overflow in rat hearts. Eur J Pharmacol. 2008 Sep 4;591(1-3):182-8. doi: 10.1016/j.ejphar.2008.06.039. Epub 2008 Jun 14. PMID: 18586023. 12: Roosterman D, Kempkes C, Cottrell GS, Padilla BE, Bunnett NW, Turck CW, Steinhoff M. Endothelin-converting enzyme-1 degrades internalized somatostatin-14. Endocrinology. 2008 May;149(5):2200-7. doi: 10.1210/en.2007-1628. Epub 2008 Feb 14. PMID: 18276747; PMCID: PMC2329273. 13: Doggrell SA. The endothelin system and its role in acute myocardial infarction. Expert Opin Ther Targets. 2004 Jun;8(3):191-201. doi: 10.1517/14728222.8.3.191. PMID: 15161426. 14: Matsumura Y, Kuro T, Kobayashi Y, Umekawa K, Ohashi N, Takaoka M. Protective effect of SM-19712, a novel and potent endothelin converting enzyme inhibitor, on ischemic acute renal failure in rats. Jpn J Pharmacol. 2000 Sep;84(1):16-24. doi: 10.1254/jjp.84.16. PMID: 11043448. 15: Umekawa K, Hasegawa H, Tsutsumi Y, Sato K, Matsumura Y, Ohashi N. Pharmacological characterization of a novel sulfonylureid-pyrazole derivative, SM-19712, a potent nonpeptidic inhibitor of endothelin converting enzyme. Jpn J Pharmacol. 2000 Sep;84(1):7-15. doi: 10.1254/jjp.84.7. PMID: 11043447.

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