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MedKoo Cat#: 558152 | Name: Cisapride free base
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Description:

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

Cisapride (free base) is a substituted benzamide used for its prokinetic properties. It is used in the management of gastroesophageal reflux disease, functional dyspepsia, and other disorders associated with impaired gastrointestinal motility. Cisapride is a prototype serotonergic agent, evolved from a body of research that defined the key roles of serotonergic receptors in gastrointestinal motor and sensory function. Impressed by its in vitro properties and encouraged by clinical trial data.

Chemical Structure

Cisapride free base
Cisapride free base
CAS#81098-60-4 (free base)

Theoretical Analysis

MedKoo Cat#: 558152

Name: Cisapride free base

CAS#: 81098-60-4 (free base)

Chemical Formula: C23H29ClFN3O4

Exact Mass: 465.1800

Molecular Weight: 465.95

Elemental Analysis: C, 59.29; H, 6.27; Cl, 7.61; F, 4.08; N, 9.02; O, 13.73

Price and Availability

Size Price Availability Quantity
250mg USD 250.00 2 Weeks
500mg USD 400.00 2 Weeks
1g USD 650.00 2 Weeks
2g USD 950.00 2 Weeks
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Related CAS #
260779-88-2 (monohydrate) 81098-60-4 (free base) 189888-25-3 (tartrate)
Synonym
Cisapride (free base); Kaudalit; Kinestase; Prepulsid; Presid; Pridesia; Propulsid;
IUPAC/Chemical Name
Benzamide, 4-amino-5-chloro-N-(1-(3-(4-fluorophenoxy)propyl)-3-methoxy-4-piperidinyl)-2-methoxy-, cis-
InChi Key
DCSUBABJRXZOMT-IRLDBZIGSA-N
InChi Code
InChI=1S/C23H29ClFN3O4/c1-30-21-13-19(26)18(24)12-17(21)23(29)27-20-8-10-28(14-22(20)31-2)9-3-11-32-16-6-4-15(25)5-7-16/h4-7,12-13,20,22H,3,8-11,14,26H2,1-2H3,(H,27,29)/t20-,22+/m1/s1
SMILES Code
O=C(N[C@H]1[C@@H](OC)CN(CCCOC2=CC=C(F)C=C2)CC1)C3=CC(Cl)=C(N)C=C3OC
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
>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).
HS Tariff Code
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 465.95 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
1: Zhou X, Zhang Q, Zhao T, Bai X, Yuan W, Wu Y, Liu D, Li S, Ju J, Chege Gitau S, Chu W, Xu C, Lu Y. Cisapride protects against cardiac hypertrophy via inhibiting the up-regulation of calcineurin and NFATc-3. Eur J Pharmacol. 2014 Jul 15;735:202-10. doi: 10.1016/j.ejphar.2014.04.012. Epub 2014 Apr 21. PubMed PMID: 24769415. 2: Durdagi S, Randall T, Duff HJ, Chamberlin A, Noskov SY. Rehabilitating drug-induced long-QT promoters: in-silico design of hERG-neutral cisapride analogues with retained pharmacological activity. BMC Pharmacol Toxicol. 2014 Mar 8;15:14. doi: 10.1186/2050-6511-15-14. PubMed PMID: 24606761; PubMed Central PMCID: PMC4016140. 3: Mt-Isa S, Tomlin S, Sutcliffe A, Underwood M, Williamson P, Croft NM, Ashby D. Prokinetics prescribing in paediatrics: evidence on cisapride, domperidone, and metoclopramide. J Pediatr Gastroenterol Nutr. 2015 Apr;60(4):508-14. doi: 10.1097/MPG.0000000000000657. PubMed PMID: 25825854. 4: Kempf J, Lewis F, Reusch CE, Kook PH. High-resolution manometric evaluation of the effects of cisapride and metoclopramide hydrochloride administered orally on lower esophageal sphincter pressure in awake dogs. Am J Vet Res. 2014 Apr;75(4):361-6. doi: 10.2460/ajvr.75.4.361. PubMed PMID: 24669921. 5: Aboumarzouk OM, Agarwal T, Antakia R, Shariff U, Nelson RL. Cisapride for intestinal constipation. Cochrane Database Syst Rev. 2011 Jan 19;(1):CD007780. doi: 10.1002/14651858.CD007780.pub2. Review. PubMed PMID: 21249695. 6: Quigley EM. Cisapride: what can we learn from the rise and fall of a prokinetic? J Dig Dis. 2011 Jun;12(3):147-56. doi: 10.1111/j.1751-2980.2011.00491.x. Review. PubMed PMID: 21615867. 7: Ullal TV, Kass PH, Conklin JL, Belafsky PC, Marks SL. High-resolution manometric evaluation of the effects of cisapride on the esophagus during administration of solid and liquid boluses in awake healthy dogs. Am J Vet Res. 2016 Aug;77(8):818-27. doi: 10.2460/ajvr.77.8.818. PubMed PMID: 27463544. 8: Al Okab RA. Cisapride a green analytical reagent for rapid and sensitive determination of bromate in drinking water, bread and flour additives by oxidative coupling spectrophotometric methods. Spectrochim Acta A Mol Biomol Spectrosc. 2013 Feb 15;103:333-7. doi: 10.1016/j.saa.2012.10.071. Epub 2012 Nov 23. PubMed PMID: 23261631. 9: Cameron JC, Vaillancourt R, Major-Cook N, Boland M, Zucker M, Lariviere D. Clinical recovery of chronic intestinal pseudo-obstruction with cisapride in a complex pediatric patient. Am J Hosp Palliat Care. 2013 Jun;30(4):403-5. doi: 10.1177/1049909112457238. Epub 2012 Sep 9. PubMed PMID: 22964344. 10: Michalets EL, Williams CR. Drug interactions with cisapride: clinical implications. Clin Pharmacokinet. 2000 Jul;39(1):49-75. Review. PubMed PMID: 10926350. 11: Maclennan S, Augood C, Cash-Gibson L, Logan S, Gilbert RE. Cisapride treatment for gastro-oesophageal reflux in children. Cochrane Database Syst Rev. 2010 Apr 14;(4):CD002300. doi: 10.1002/14651858.CD002300.pub2. Review. PubMed PMID: 20393933. 12: Louis H. [Management of gastroparesis and functional dyspepsia after cisapride withdrawal]. Rev Med Brux. 2012 Sep;33(4):425-9. Review. French. PubMed PMID: 23091951. 13: Kirch W, Janisch HD, Ohnhaus EE, van Peer A. Cisapride-cimetidine interaction: enhanced cisapride bioavailability and accelerated cimetidine absorption. Ther Drug Monit. 1989;11(4):411-4. PubMed PMID: 2741189. 14: Gales MA, Harms DW. Is rectally administered cisapride an effective prokinetic agent? Ann Pharmacother. 1999 Nov;33(11):1217-20. Review. PubMed PMID: 10573323. 15: van Haarst AD, van 't Klooster GA, van Gerven JM, Schoemaker RC, van Oene JC, Burggraaf J, Coene MC, Cohen AF. The influence of cisapride and clarithromycin on QT intervals in healthy volunteers. Clin Pharmacol Ther. 1998 Nov;64(5):542-6. PubMed PMID: 9834046. 16: Hegar B, Alatas S, Advani N, Firmansyah A, Vandenplas Y. Domperidone versus cisapride in the treatment of infant regurgitation and increased acid gastro-oesophageal reflux: a pilot study. Acta Paediatr. 2009 Apr;98(4):750-5. doi: 10.1111/j.1651-2227.2008.01158.x. Epub 2008 Dec 10. PubMed PMID: 19076984. 17: 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. PubMed PMID: 11452240. 18: 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. PubMed PMID: 12621386. 19: Ward RM, Lemons JA, Molteni RA. Cisapride: a survey of the frequency of use and adverse events in premature newborns. Pediatrics. 1999 Feb;103(2):469-72. PubMed PMID: 9925843. 20: Premji SS, Paes B. Cisapride: the problem of the heart. Neonatal Netw. 1999 Oct;18(7):21-5. Review. PubMed PMID: 10808885.