Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C17H16N6O.ClH.H2O |
| Molecular Weight | 374.825 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
O.Cl.NC(=N)NC(=O)C1=C(C2CC2)N(N=C1)C3=CC=CC4=NC=CC=C34
InChI
InChIKey=UCIJUEGJEFJRMP-UHFFFAOYSA-N
InChI=1S/C17H16N6O.ClH.H2O/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;1H2
| Molecular Formula | ClH |
| Molecular Weight | 36.461 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
| Molecular Formula | H2O |
| Molecular Weight | 18.0153 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
| Molecular Formula | C17H16N6O |
| Molecular Weight | 320.3485 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
DescriptionCurator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/11259552
http://www.abcam.com/zoniporide-hydrochloride-ab142012.html
Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/11259552
http://www.abcam.com/zoniporide-hydrochloride-ab142012.html
Zoniporide hydrochloride is a novel, potent and selective NHE-1 inhibitor (IC50 = 14 nM). Reduces infarct size in the isolated heart (EC50 = 0.25 nM). Attenuates post-ischemic cardiac contractile dysfunction and ischemia-reperfusion-induced ventricular fibrillation in vivo. Zoniporide hydrochloride represents a novel class of potent and selective human NHE-1 inhibitors with potential utility for providing cardioprotection in a clinical setting.
Originator
Approval Year
AUC
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
0.07 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11277524 |
1 mg/kg single, intravenous dose: 1 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered: |
ZONIPORIDE plasma | Rattus norvegicus population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
T1/2
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
0.5 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11277524 |
1 mg/kg single, intravenous dose: 1 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered: |
ZONIPORIDE plasma | Rattus norvegicus population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
Funbound
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
46% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11277524 |
1 mg/kg single, intravenous dose: 1 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered: |
ZONIPORIDE plasma | Rattus norvegicus population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
Doses
| Dose | Population | Adverse events |
|---|---|---|
12 mg/kg 1 times / day multiple, intravenous Highest studied dose Dose: 12 mg/kg, 1 times / day Route: intravenous Route: multiple Dose: 12 mg/kg, 1 times / day Sources: Page: p.573 |
unhealthy, ADULT n = 266 Health Status: unhealthy Condition: peripheral vascular disease Age Group: ADULT Sex: M+F Food Status: UNKNOWN Population Size: 266 Sources: Page: p.573 |
Disc. AE: Hepatic failure, Bilirubin elevated... Other AEs: Headache, Atrial fibrillation... AEs leading to discontinuation/dose reduction: Hepatic failure (0.8%) Other AEs:Bilirubin elevated Vomiting (25.6%) Headache (6.4%) Sources: Page: p.573Atrial fibrillation (6.4%) Tachycardia (10.9%) Jaundice (2.3%) Nausea (41.7%) Elevated liver enzyme levels |
AEs
| AE | Significance | Dose | Population |
|---|---|---|---|
| Elevated liver enzyme levels | 12 mg/kg 1 times / day multiple, intravenous Highest studied dose Dose: 12 mg/kg, 1 times / day Route: intravenous Route: multiple Dose: 12 mg/kg, 1 times / day Sources: Page: p.573 |
unhealthy, ADULT n = 266 Health Status: unhealthy Condition: peripheral vascular disease Age Group: ADULT Sex: M+F Food Status: UNKNOWN Population Size: 266 Sources: Page: p.573 |
|
| Hepatic failure | 0.8% Disc. AE |
12 mg/kg 1 times / day multiple, intravenous Highest studied dose Dose: 12 mg/kg, 1 times / day Route: intravenous Route: multiple Dose: 12 mg/kg, 1 times / day Sources: Page: p.573 |
unhealthy, ADULT n = 266 Health Status: unhealthy Condition: peripheral vascular disease Age Group: ADULT Sex: M+F Food Status: UNKNOWN Population Size: 266 Sources: Page: p.573 |
| Tachycardia | 10.9% | 12 mg/kg 1 times / day multiple, intravenous Highest studied dose Dose: 12 mg/kg, 1 times / day Route: intravenous Route: multiple Dose: 12 mg/kg, 1 times / day Sources: Page: p.573 |
unhealthy, ADULT n = 266 Health Status: unhealthy Condition: peripheral vascular disease Age Group: ADULT Sex: M+F Food Status: UNKNOWN Population Size: 266 Sources: Page: p.573 |
| Jaundice | 2.3% | 12 mg/kg 1 times / day multiple, intravenous Highest studied dose Dose: 12 mg/kg, 1 times / day Route: intravenous Route: multiple Dose: 12 mg/kg, 1 times / day Sources: Page: p.573 |
unhealthy, ADULT n = 266 Health Status: unhealthy Condition: peripheral vascular disease Age Group: ADULT Sex: M+F Food Status: UNKNOWN Population Size: 266 Sources: Page: p.573 |
| Vomiting | 25.6% Disc. AE |
12 mg/kg 1 times / day multiple, intravenous Highest studied dose Dose: 12 mg/kg, 1 times / day Route: intravenous Route: multiple Dose: 12 mg/kg, 1 times / day Sources: Page: p.573 |
unhealthy, ADULT n = 266 Health Status: unhealthy Condition: peripheral vascular disease Age Group: ADULT Sex: M+F Food Status: UNKNOWN Population Size: 266 Sources: Page: p.573 |
| Nausea | 41.7% | 12 mg/kg 1 times / day multiple, intravenous Highest studied dose Dose: 12 mg/kg, 1 times / day Route: intravenous Route: multiple Dose: 12 mg/kg, 1 times / day Sources: Page: p.573 |
unhealthy, ADULT n = 266 Health Status: unhealthy Condition: peripheral vascular disease Age Group: ADULT Sex: M+F Food Status: UNKNOWN Population Size: 266 Sources: Page: p.573 |
| Atrial fibrillation | 6.4% | 12 mg/kg 1 times / day multiple, intravenous Highest studied dose Dose: 12 mg/kg, 1 times / day Route: intravenous Route: multiple Dose: 12 mg/kg, 1 times / day Sources: Page: p.573 |
unhealthy, ADULT n = 266 Health Status: unhealthy Condition: peripheral vascular disease Age Group: ADULT Sex: M+F Food Status: UNKNOWN Population Size: 266 Sources: Page: p.573 |
| Headache | 6.4% | 12 mg/kg 1 times / day multiple, intravenous Highest studied dose Dose: 12 mg/kg, 1 times / day Route: intravenous Route: multiple Dose: 12 mg/kg, 1 times / day Sources: Page: p.573 |
unhealthy, ADULT n = 266 Health Status: unhealthy Condition: peripheral vascular disease Age Group: ADULT Sex: M+F Food Status: UNKNOWN Population Size: 266 Sources: Page: p.573 |
| Bilirubin elevated | Disc. AE | 12 mg/kg 1 times / day multiple, intravenous Highest studied dose Dose: 12 mg/kg, 1 times / day Route: intravenous Route: multiple Dose: 12 mg/kg, 1 times / day Sources: Page: p.573 |
unhealthy, ADULT n = 266 Health Status: unhealthy Condition: peripheral vascular disease Age Group: ADULT Sex: M+F Food Status: UNKNOWN Population Size: 266 Sources: Page: p.573 |
PubMed
| Title | Date | PubMed |
|---|---|---|
| A novel sodium-hydrogen exchanger isoform-1 inhibitor, zoniporide, reduces ischemic myocardial injury in vitro and in vivo. | 2001 Apr |
|
| Discovery of zoniporide: a potent and selective sodium-hydrogen exchanger type 1 (NHE-1) inhibitor with high aqueous solubility. | 2001 Mar 26 |
|
| Zoniporide: a potent and highly selective inhibitor of human Na(+)/H(+) exchanger-1. | 2002 Sep 6 |
|
| Apelin, the novel endogenous ligand of the orphan receptor APJ, regulates cardiac contractility. | 2002 Sep 6 |
|
| An overview of inhibitors of Na(+)/H(+) exchanger. | 2003 Jun |
|
| Zoniporide: a potent and selective inhibitor of the human sodium-hydrogen exchanger isoform 1 (NHE-1). | 2003 Spring |
|
| Basolateral Na+-H+ exchanger-1 in rat taste receptor cells is involved in neural adaptation to acidic stimuli. | 2004 Apr 1 |
|
| Cardioprotective efficacy of zoniporide, a potent and selective inhibitor of Na+/H+ exchanger isoform 1, in an experimental model of cardiopulmonary bypass. | 2004 May |
|
| Efficacy of zoniporide, an Na/H exchange ion inhibitor, for reducing perioperative cardiovascular events in vascular surgery patients. | 2005 Oct |
|
| Initial rate analysis of zoniporide hydrolysis degradants using high-performance liquid chromatography coupled with mass spectrometric detection. | 2007 |
|
| Solute diffusion through stripped mouse duodenum. | 2007 Dec |
|
| Zoniporide preserves left ventricular compliance during ventricular fibrillation and minimizes postresuscitation myocardial dysfunction through benefits on energy metabolism. | 2007 Oct |
|
| The rise of [Na(+)] (i) during ischemia and reperfusion in the rat heart-underlying mechanisms. | 2007 Sep |
|
| Does the use of a volatile anesthetic regimen attenuate the incidence of cardiac events after vascular surgery? | 2008 |
|
| Targeting Na+/H+ exchanger regulation for cardiac protection: a RSKy approach? | 2008 Apr |
|
| Neurotoxic effects of zoniporide: a selective inhibitor of the NA+/H+ exchanger isoform 1. | 2008 Jun |
|
| Na+/H+ exchanger-1 inhibitors reduce neuronal excitability and alter na+ channel inactivation properties in rat primary sensory neurons. | 2008 Jun |
|
| Paradoxical resistance to myocardial ischemia and age-related cardiomyopathy in NHE1 transgenic mice: a role for ER stress? | 2009 Feb |
|
| Effects of KR-33028, a novel Na+/H+ exchanger-1 inhibitor, on glutamate-induced neuronal cell death and ischemia-induced cerebral infarct. | 2009 Jan 12 |
|
| Cross-species comparison of the metabolism and excretion of zoniporide: contribution of aldehyde oxidase to interspecies differences. | 2010 Apr |
|
| In vitro-in vivo correlation for intrinsic clearance for drugs metabolized by human aldehyde oxidase. | 2010 Aug |
|
| Role of the spinal Na+/H+ exchanger in formalin-induced nociception. | 2011 Aug 21 |
|
| Critical role of the STAT3 pathway in the cardioprotective efficacy of zoniporide in a model of myocardial preservation - the rat isolated working heart. | 2011 Feb |
| Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Dec 16 00:02:13 GMT 2023
by
admin
on
Sat Dec 16 00:02:13 GMT 2023
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| Record UNII |
70297XU9ZO
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| Record Status |
Validated (UNII)
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| Record Version |
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ANHYDROUS->SOLVATE |
