Zacopride

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MedKoo CAT#: 461128

CAS#: 90182-92-6

Description: Zacopride is a selective inward rectifier potassium current (I K1) channel agonist, suppressing ventricular arrhythmias without affecting atrial arrhythmias.


Price and Availability

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Pricing updated 2020-10-30. Prices are subject to change without notice.

Zacopride is not in stock, may be available through custom synthesis. For cost-effective reason, minimum 1 gram order is requested. The product will be characterized by NMR, HPLC and MS analysis. Purity (HPLC) is usually >98%. CoA, QC data, MSDS will be provided when product is successfully made. The estimated lead time is 2-3 months. Please send email to sales@medkoo.com to inquire quote.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 461128
Name: Zacopride
CAS#: 90182-92-6
Chemical Formula: C15H20ClN3O2
Exact Mass: 309.1244
Molecular Weight: 309.79
Elemental Analysis: C, 58.16; H, 6.51; Cl, 11.44; N, 13.56; O, 10.33


Synonym: Zacopride; Racemic zacopride;

IUPAC/Chemical Name: 4-amino-5-chloro-2-methoxy-N-(quinuclidin-3-yl)benzamide

InChi Key: FEROPKNOYKURCJ-UHFFFAOYSA-N

InChi Code: 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)

SMILES Code: COc1c(C(NC2CN3CCC2CC3)=O)cc(Cl)c(N)c1


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

Shelf Life:
>3 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:
2934.99.03.00


References

1: Liu CF, Liu QH, Liu EL, Zhai XW, Zhang L, Luo TE, Zhang WF, Feng QL, Cui XL, Zhao ZQ, Cao JM, Wu BW. Activation of IK1 channel by zacopride attenuates left ventricular remodeling in rats with myocardial infarction. J Cardiovasc Pharmacol. 2014 Oct;64(4):345-56. doi: 10.1097/FJC.0000000000000127. Retraction in: J Cardiovasc Pharmacol. 2015 Mar;65(3):296. PubMed PMID: 25286360.

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.

7: Wu B, Long C, Hei F, Wang S. The protective effect of St. Thomas cardioplegia enriched with zacopride on the isolated rat heart. Artif Organs. 2013 Jan;37(1):E44-50. doi: 10.1111/j.1525-1594.2012.01547.x. Epub 2012 Oct 16. PubMed PMID: 23067559.

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.

9: Ge J, Barnes JM, Towers P, Barnes NM. Distribution of S(-)-zacopride-insensitive [125I]R(+)-zacopride binding sites in the rat brain and peripheral tissues. Eur J Pharmacol. 1997 Aug 13;332(3):307-12. PubMed PMID: 9300265.

10: Laporte AM, Koscielniak T, Ponchant M, Vergé D, Hamon M, Gozlan H. Quantitative autoradiographic mapping of 5-HT3 receptors in the rat CNS using [125I]iodo-zacopride and [3H]zacopride as radioligands. Synapse. 1992 Apr;10(4):271-81. PubMed PMID: 1585260.

11: Sancilio LF, Pinkus LM, Jackson CB, Munson HR Jr. Studies on the emetic and antiemetic properties of zacopride and its enantiomers. Eur J Pharmacol. 1991 Jan 17;192(3):365-9. PubMed PMID: 2055236.

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.

13: Smith WL, Alphin RS, Jackson CB, Sancilio LF. The antiemetic profile of zacopride. J Pharm Pharmacol. 1989 Feb;41(2):101-5. PubMed PMID: 2568416.

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.

19: Barnes JM, Barnes NM, Champaneria S, Costall B, Naylor RJ. Characterisation and autoradiographic localisation of 5-HT3 receptor recognition sites identified with [3H]-(S)-zacopride in the forebrain of the rat. Neuropharmacology. 1990 Nov;29(11):1037-45. PubMed PMID: 2087255.

20: Wade PR, Mawe GM, Branchek TA, Gershon MD. Use of stereoisomers of zacopride to analyze actions of 5-hydroxytryptamine on enteric neurons. Am J Physiol. 1991 Jan;260(1 Pt 1):G80-90. PubMed PMID: 1987811.