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MedKoo Cat#: 578290 | Name: Norcisapride

Description:

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

Norcisapride is a metabolite of Cisapride -- a gastroprokinetic agent, serotonin 5-HT4 receptor agonist, and parasympathomimetic that increases motility in the upper gastrointestinal tract. Note: This compound has CAS#83863-69-8, which stereostructure is relative. The absolute stereostructure has CAS#202590-69-0.

Chemical Structure

Norcisapride
Norcisapride
CAS#83863-69-8 (racemic)

Theoretical Analysis

MedKoo Cat#: 578290

Name: Norcisapride

CAS#: 83863-69-8 (racemic)

Chemical Formula: C14H20ClN3O3

Exact Mass: 313.1193

Molecular Weight: 313.78

Elemental Analysis: C, 53.59; H, 6.42; Cl, 11.30; N, 13.39; O, 15.30

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
202590-69-0 (3S4R) 83863-69-8 (racemic)
Synonym
Norcisapride; (±)-Norcisapride;
IUPAC/Chemical Name
cis-4-Amino-5-chloro-2-methoxy-N-(3-methoxy-4-piperidyl)benzamide
InChi Key
OMLDMGPCWMBPAN-YPMHNXCESA-N
InChi Code
InChI=1S/C14H20ClN3O3/c1-20-12-6-10(16)9(15)5-8(12)14(19)18-11-3-4-17-7-13(11)21-2/h5-6,11,13,17H,3-4,7,16H2,1-2H3,(H,18,19)/t11-,13+/m1/s1
SMILES Code
CO[C@H]1CNCC[C@H]1NC(=O)c2cc(Cl)c(N)cc2OC
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
To be determined
Shelf Life
>2 years if stored properly
Drug Formulation
To be determined
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 313.78 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
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A comparison of the pharmacokinetics of two dosing regimens of cisapride and their effects on corrected QT interval in premature infants. Eur J Clin Pharmacol. 2003 May;59(1):17-22. doi: 10.1007/s00228-003-0582-6. Epub 2003 Apr 1. PMID: 12682804. 8: Lowry JA, Kearns GL, Abdel-Rahman SM, Nafziger AN, Khan IS, Kashuba AD, Schuetz EG, Bertino JS Jr, van den Anker JN, Leeder JS. Cisapride: a potential model substrate to assess cytochrome P4503A4 activity in vivo. Clin Pharmacol Ther. 2003 Mar;73(3):209-22. doi: 10.1067/mcp.2003.29. PMID: 12621386. 9: Pearce RE, Gotschall RR, Kearns GL, Leeder JS. Cytochrome P450 Involvement in the biotransformation of cisapride and racemic norcisapride in vitro: differential activity of individual human CYP3A isoforms. Drug Metab Dispos. 2001 Dec;29(12):1548-54. PMID: 11717173. 10: Tréluyer JM, Rey E, Sonnier M, Pons G, Cresteil T. Evidence of impaired cisapride metabolism in neonates. Br J Clin Pharmacol. 2001 Oct;52(4):419-25. doi: 10.1046/j.0306-5251.2001.01470.x. PMID: 11678785; PMCID: PMC2014576. 11: Cools F, Benatar A, Bougatef A, Vandenplas Y. The effect of cisapride on the corrected QT interval and QT dispersion in premature infants. J Pediatr Gastroenterol Nutr. 2001 Aug;33(2):178-81. doi: 10.1097/00005176-200108000-00015. PMID: 11568520. 12: Desta Z, Soukhova N, Morocho AM, Flockhart DA. Stereoselective metabolism of cisapride and enantiomer-enantiomer interaction in human cytochrome P450 enzymes: major role of CYP3A. J Pharmacol Exp Ther. 2001 Aug;298(2):508-20. PMID: 11454912. 13: Offman EM, Freeman DJ, Dresser GK, Munoz C, Bend JR, Bailey DG. Red wine- cisapride interaction: comparison with grapefruit juice. Clin Pharmacol Ther. 2001 Jul;70(1):17-23. doi: 10.1067/mcp.2001.116892. PMID: 11452240. 14: Desta Z, Soukhova N, Mahal SK, Flockhart DA. Interaction of cisapride with the human cytochrome P450 system: metabolism and inhibition studies. Drug Metab Dispos. 2000 Jul;28(7):789-800. PMID: 10859153. 15: Bohets H, Lavrijsen K, Hendrickx J, van Houdt J, van Genechten V, Verboven P, Meuldermans W, Heykants J. Identification of the cytochrome P450 enzymes involved in the metabolism of cisapride: in vitro studies of potential co- medication interactions. Br J Pharmacol. 2000 Apr;129(8):1655-67. doi: 10.1038/sj.bjp.0703246. PMID: 10780971; PMCID: PMC1572003. 16: Gross AS, Goh YD, Addison RS, Shenfield GM. Influence of grapefruit juice on cisapride pharmacokinetics. Clin Pharmacol Ther. 1999 Apr;65(4):395-401. doi: 10.1016/S0009-9236(99)70133-5. PMID: 10223776. 17: Addison RS, Duffy SL, Mathers SR. A simple high-performance liquid chromatography assay for the major cisapride metabolite, norcisapride, in human urine. J Chromatogr Sci. 1999 Mar;37(3):61-4. doi: 10.1093/chromsci/37.3.61. PMID: 10089595. 18: Cisternino S, Schlatter J, Saulnier JL. Determination of cisapride and norcisapride in human plasma using high-performance liquid chromatography with ultraviolet detection. J Chromatogr B Biomed Sci Appl. 1998 Sep 4;714(2):395-8. doi: 10.1016/s0378-4347(98)00213-8. PMID: 9766883. 19: Preechagoon Y, Charles BG. Analysis of cisapride in neonatal plasma using high-performance liquid chromatography with a base-stable column and fluorescence detection. J Chromatogr B Biomed Appl. 1995 Aug 4;670(1):139-43. doi: 10.1016/0378-4347(95)00159-g. PMID: 7493071. 20: Gladziwa U, Bares R, Klotz U, Dakshinamurty KV, Ittel TH, Seiler KU, Sieberth HG. Pharmacokinetics and pharmacodynamics of cisapride in patients undergoing hemodialysis. Clin Pharmacol Ther. 1991 Dec;50(6):673-81. doi: 10.1038/clpt.1991.206. PMID: 1752111.

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