Zacopride

For research use only. Not for therapeutic Use.

  • CAT Number: I038653
  • CAS Number: 90182-92-6
  • Molecular Formula: C15H20ClN3O2
  • Molecular Weight: 309.79
  • Purity: 98%
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Zacopride (Cat No.:I038653), also known as Racemic zacopride, is a selective inwardly rectifying potassium current channel agonist that inhibits ventricular arrhythmias without affecting atrial arrhythmias.


Catalog Number I038653
CAS Number 90182-92-6
Synonyms

Zacopride; Racemic zacopride;

Molecular Formula C15H20ClN3O2
Purity 98%
Solubility Soluble in DMSO
Appearance Solid powder
Storage Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
IUPAC Name 4-amino-5-chloro-2-methoxy-N-(quinuclidin-3-yl)benzamide
InChI InChI=1S/C15H20ClN3O2/c1-21-14-7-12(17)11(16)6-10(14)15(20)18-13-8-19-4-2-9(13)3-5-19/h6-7,9,13H,2-5,8,17H2,1H3,(H,18,20)
InChIKey FEROPKNOYKURCJ-UHFFFAOYSA-N
SMILES COc1c(C(NC2CN3CCC2CC3)=O)cc(Cl)c(N)c1
Reference

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2: Zhang L, Liu Q, Liu C, Zhai X, Feng Q, Xu R, Cui X, Zhao Z, Cao J, Wu B. Zacopride selectively activates the Kir2.1 channel via a PKA signaling pathway in rat cardiomyocytes. Sci China Life Sci. 2013 Sep;56(9):788-96. doi: 10.1007/s11427-013-4531-z. Epub 2013 Aug 8. PubMed PMID: 23929001.
3: Bourdin CM, Lebreton J, Mathé-Allainmat M, Thany SH. Pharmacological profile of zacopride and new quaternarized fluorobenzamide analogues on mammalian α7 nicotinic acetylcholine receptor. Bioorg Med Chem Lett. 2015 Aug 15;25(16):3184-8. doi: 10.1016/j.bmcl.2015.05.094. Epub 2015 Jun 4. PubMed PMID: 26087938.
4: Curtis MJ. Activation of IK1 by zacopride: amelioration of left ventricular remodeling, but at what risk? J Cardiovasc Pharmacol. 2014 Oct;64(4):343-4. doi: 10.1097/FJC.0000000000000140. PubMed PMID: 25000479.
5: Activation of I(K1) channel by zacopride attenuates left ventricular remodeling in rats with myocardial infarction: Retraction. J Cardiovasc Pharmacol. 2015 Mar;65(3):296. doi: 10.1097/01.fjc.0000462727.05737.2c. PubMed PMID: 25748699.
6: Wu BW, Cao JM. On the risk concerns of zacopride, a moderate IK1 channel agonist with cardiac protective action. J Cardiovasc Pharmacol. 2014 Oct;64(4):357-9. doi: 10.1097/FJC.0000000000000148. PubMed PMID: 25072868.
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8: Liu QH, Li XL, Xu YW, Lin YY, Cao JM, Wu BW. A novel discovery of IK1 channel agonist: zacopride selectively enhances IK1 current and suppresses triggered arrhythmias in the rat. J Cardiovasc Pharmacol. 2012 Jan;59(1):37-48. doi: 10.1097/FJC.0b013e3182350bcc. PubMed PMID: 21921806.
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12: Lefebvre H, Contesse V, Delarue C, Soubrane C, Legrand A, Kuhn JM, Wolf LM, Vaudry H. Effect of the serotonin-4 receptor agonist zacopride on aldosterone secretion from the human adrenal cortex: in vivo and in vitro studies. J Clin Endocrinol Metab. 1993 Dec;77(6):1662-6. PubMed PMID: 8263156.
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14: Barnes JM, Barnes NM, Costall B, Domeney AM, Johnson DN, Kelly ME, Munson HR, Naylor RJ, Young R. The differential activities of R (+)- and S(-)-zacopride as 5-HT3 receptor antagonists. Pharmacol Biochem Behav. 1990 Dec;37(4):717-27. PubMed PMID: 2128757.
15: Gordon JC, Barefoot DS, Sarbin NS, Pinkus LM. [3H]zacopride binding to 5-hydroxytryptamine3 sites on partially purified rabbit enteric neuronal membranes. J Pharmacol Exp Ther. 1989 Dec;251(3):962-8. PubMed PMID: 2600824.
16: Mele PC, McDonough JR, McLean DB, O’Halloran KP. Cisplatin-induced conditioned taste aversion: attenuation by dexamethasone but not zacopride or GR38032F. Eur J Pharmacol. 1992 Aug 6;218(2-3):229-36. PubMed PMID: 1330594.
17: Fontana DJ, Daniels SE, Eglen RM, Wong EH. Stereoselective effects of (R)- and (S)-zacopride on cognitive performance in a spatial navigation task in rats. Neuropharmacology. 1996 Mar;35(3):321-7. PubMed PMID: 8783207.
18: Bill DJ, Coleman J, Hallett I, Middlefell VC, Rhodes KF, Fletcher A. The enantiomers of zacopride: an intra-species comparison of their potencies in functional and anxiolytic models. Br J Pharmacol. 1995 Jul;115(5):775-80. PubMed PMID: 8548176; PubMed Central PMCID: PMC1908521.
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