Zoniporide HCl
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MedKoo CAT#: 526589

CAS#: 241800-97-5 (HCl)

Description: Zoniporide: a potent and selective inhibitor of the human sodium-hydrogen exchanger isoform 1 (NHE-1). Zoniporide preserves left ventricular compliance during ventricular fibrillation and minimizes postresuscitation myocardial dysfunction through benefits on energy metabolism. Zoniporide produces clinical, electrophysiologic, and microscopic evidence of peripheral sensory axonopathy and establishes the importance of careful preclinical evaluation of neurological function.


Price and Availability

Size
Price

10mg
USD 250
Size
Price

20mg
USD 450
Size
Price

50mg
USD 950

Zoniporide HCl, purity > 98%, is in stock. Current shipping out time is about 2 weeks after order is received. Delivery time: overnight (USA/Canada); 3-5 days (worldwide). Shipping fee: from $30.00 (USA); from $45.00 (Canada); from $70.00 (international).


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 526589
Name: Zoniporide HCl
CAS#: 241800-97-5 (HCl)
Chemical Formula: C17H17ClN6O
Exact Mass:
Molecular Weight: 356.814
Elemental Analysis: C, 57.23; H, 4.80; Cl, 9.94; N, 23.55; O, 4.48


Related CAS #: 241800-97-5 (HCl)   241800-98-6 (HCl hydrate)   249296-45-5 (mesylate)   241800-98-6 (free base)    

Synonym: CP-597396; CP 597396; CP597396; CP-597,396; CP 597,396; CP597,396; Zoniporide HCl.

IUPAC/Chemical Name: N-carbamimidoyl-5-cyclopropyl-1-(quinolin-5-yl)-1H-pyrazole-4-carboxamide hydrochloride

InChi Key: JTEXNYIOROVPIR-UHFFFAOYSA-N

InChi Code: InChI=1S/C17H16N6O.ClH/c18-17(19)22-16(24)12-9-21-23(15(12)10-6-7-10)14-5-1-4-13-11(14)3-2-8-20-13;/h1-5,8-10H,6-7H2,(H4,18,19,22,24);1H

SMILES Code: O=C(C1=C(C2CC2)N(C3=C4C=CC=NC4=CC=C3)N=C1)NC(N)=N.[H]Cl


Technical Data

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).

Harmonized System Code:
293490


References

1: Dalvie D, Xiang C, Kang P, Zhou S. Interspecies variation in the metabolism of zoniporide by aldehyde oxidase. Xenobiotica. 2013 May;43(5):399-408. doi: 10.3109/00498254.2012.727499. Epub 2012 Oct 10. PubMed PMID: 23046389.

2: Watson AJ, Gao L, Sun L, Tsun J, Doyle A, Faddy SC, Jabbour A, Orr Y, Dhital K, Hicks M, Jansz PC, Macdonald PS. Enhanced preservation of pig cardiac allografts by combining erythropoietin with glyceryl trinitrate and zoniporide. Am J Transplant. 2013 Jul;13(7):1676-87. doi: 10.1111/ajt.12249. Epub 2013 May 13. PubMed PMID: 23668842.

3: Spasov AA, Gurova, Timofeeva AS, Sorokin SM. [Experimental study of the antiarrhythmic properties of zoniporide]. Eksp Klin Farmakol. 2014;77(6):13-7. Russian. PubMed PMID: 25102729.

4: Akkoc H, Gurkan A, Kelle I, Hekimoglu AT, Erdinc M. Investigating the effect of the poly(ADP-ribose) polymerase inhibitor 5-aminoisoquinolinone and the Na⁺-H⁺ exchanger inhibitor zoniporide on isolated perfused rat hearts during ischemia-reperfusion injury. Drug Res (Stuttg). 2013 Oct;63(10):521-6. doi: 10.1055/s-0033-1347241. Epub 2013 Jun 11. PubMed PMID: 23756954.

5: Gurova NA, Spasov AA, Timofeeva AS, Zheltova AA, Fedorchuk VIu. [Cardioprotective properties of zoniporide studied on experimental ischemia and reperfusion models in rat myocardium]. Eksp Klin Farmakol. 2013;76(8):17-9. Russian. PubMed PMID: 24228483.

6: Dalvie D, Sun H, Xiang C, Hu Q, Jiang Y, Kang P. Effect of structural variation on aldehyde oxidase-catalyzed oxidation of zoniporide. Drug Metab Dispos. 2012 Aug;40(8):1575-87. doi: 10.1124/dmd.112.045823. Epub 2012 May 15. PubMed PMID: 22587988.

7: Luthra SA, Shalaev EY, Medek A, Hong J, Pikal MJ. Chemical stability of amorphous materials: specific and general media effects in the role of water in the degradation of freeze-dried zoniporide. J Pharm Sci. 2012 Sep;101(9):3110-23. doi: 10.1002/jps.23128. Epub 2012 Mar 27. PubMed PMID: 22461087.

8: Gao L, Tsun J, Sun L, Kwan J, Watson A, Macdonald PS, Hicks M. Critical role of the STAT3 pathway in the cardioprotective efficacy of zoniporide in a model of myocardial preservation - the rat isolated working heart. Br J Pharmacol. 2011 Feb;162(3):633-47. doi: 10.1111/j.1476-5381.2010.01071.x. PubMed PMID: 20942815; PubMed Central PMCID: PMC3041253.

9: Manevski N, Balavenkatraman KK, Bertschi B, Swart P, Walles M, Camenisch G, Schiller H, Kretz O, Ling B, Wettstein R, Schaefer DJ, Pognan F, Wolf A, Litherland K. Aldehyde oxidase activity in fresh human skin. Drug Metab Dispos. 2014 Dec;42(12):2049-57. doi: 10.1124/dmd.114.060368. Epub 2014 Sep 23. PubMed PMID: 25249692.

10: Quansah H, N'Gouemo P. Amiloride and SN-6 suppress audiogenic seizure susceptibility in genetically epilepsy-prone rats. CNS Neurosci Ther. 2014 Sep;20(9):860-6. doi: 10.1111/cns.12296. Epub 2014 Jun 20. PubMed PMID: 24948133; PubMed Central PMCID: PMC4461064.

11: Dalvie D, Zhang C, Chen W, Smolarek T, Obach RS, Loi CM. Cross-species comparison of the metabolism and excretion of zoniporide: contribution of aldehyde oxidase to interspecies differences. Drug Metab Dispos. 2010 Apr;38(4):641-54. doi: 10.1124/dmd.109.030783. Epub 2009 Dec 29. PubMed PMID: 20040581.

12: Marala RB, Brown JA, Kong JX, Tracey WR, Knight DR, Wester RT, Sun D, Kennedy SP, Hamanaka ES, Ruggeri RB, Hill RJ. Zoniporide: a potent and highly selective inhibitor of human Na(+)/H(+) exchanger-1. Eur J Pharmacol. 2002 Sep 6;451(1):37-41. PubMed PMID: 12223226.

13: Kadar EP, Darrington RT. Initial rate analysis of zoniporide hydrolysis degradants using high-performance liquid chromatography coupled with mass spectrometric detection. Pharm Dev Technol. 2007;12(3):247-57. PubMed PMID: 17613888.

14: Clements-Jewery H, Sutherland FJ, Allen MC, Tracey WR, Avkiran M. Cardioprotective efficacy of zoniporide, a potent and selective inhibitor of Na+/H+ exchanger isoform 1, in an experimental model of cardiopulmonary bypass. Br J Pharmacol. 2004 May;142(1):57-66. Epub 2004 Mar 22. PubMed PMID: 15037516; PubMed Central PMCID: PMC1574931.

15: Tracey WR, Allen MC, Frazier DE, Fossa AA, Johnson CG, Marala RB, Knight DR, Guzman-Perez A. Zoniporide: a potent and selective inhibitor of the human sodium-hydrogen exchanger isoform 1 (NHE-1). Cardiovasc Drug Rev. 2003 Spring;21(1):17-32. Review. PubMed PMID: 12595915.

16: Ayoub IM, Kolarova JD, Kantola RL, Radhakrishnan J, Wang S, Gazmuri RJ. Zoniporide preserves left ventricular compliance during ventricular fibrillation and minimizes postresuscitation myocardial dysfunction through benefits on energy metabolism. Crit Care Med. 2007 Oct;35(10):2329-36. PubMed PMID: 17944021.

17: Knight DR, Smith AH, Flynn DM, MacAndrew JT, Ellery SS, Kong JX, Marala RB, Wester RT, Guzman-Perez A, Hill RJ, Magee WP, Tracey WR. A novel sodium-hydrogen exchanger isoform-1 inhibitor, zoniporide, reduces ischemic myocardial injury in vitro and in vivo. J Pharmacol Exp Ther. 2001 Apr;297(1):254-9. PubMed PMID: 11259552.

18: Fleisher LA, Newman MF, St Aubin LB, Cropp AB, Billing CB, Bonney S, Mackey WC, Poldermans D, Corbalan R, Pereira AH, Coriat P; Perioperative Myocardial Ischemic Injury Investigators. Efficacy of zoniporide, an Na/H exchange ion inhibitor, for reducing perioperative cardiovascular events in vascular surgery patients. J Cardiothorac Vasc Anesth. 2005 Oct;19(5):570-6. PubMed PMID: 16202888.

19: Roginiel AC, Kohut DL, Kaur S, Saleh AM, Weber T, Geibel P, Singh H, Geibel JP. Effect of NSAIDs on Na⁺/H⁺ exchanger activity in rat colonic crypts. Am J Physiol Cell Physiol. 2013 Sep;305(5):C512-8. doi: 10.1152/ajpcell.00303.2012. Epub 2013 Jun 5. PubMed PMID: 23739181.

20: Guzman-Perez A, Wester RT, Allen MC, Brown JA, Buchholz AR, Cook ER, Day WW, Hamanaka ES, Kennedy SP, Knight DR, Kowalczyk PJ, Marala RB, Mularski CJ, Novomisle WA, Ruggeri RB, Tracey WR, Hill RJ. Discovery of zoniporide: a potent and selective sodium-hydrogen exchanger type 1 (NHE-1) inhibitor with high aqueous solubility. Bioorg Med Chem Lett. 2001 Mar 26;11(6):803-7. PubMed PMID: 11277524.