MedKoo Cat#: 412955 | Name: Cisapride tartrate

Description:

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

Cisapride tartrate is chemically related to metoclopramide, but unlike metoclopramide, it does not cross the blood-brain barrier or have antidopaminergic effects. Cisapride is a serotonin-4 (5-HT4) receptor agonist. Cisapride was indicated for the symptomatic treatment of adult patients with nocturnal heartburn due to gastroesophageal reflux disease. The Food and Drug Administration (FDA) in America stopped the marketing of cisapride as of 14th July 2000. They had received at least 341 reports of heart rhythm abnormalities and these led to 80 deaths. Other reported adverse effects are: headache, diarrhea, abdominal pain, nausea, constipation. Cisapride for animals has been found helpful in some cases of megaesophagus and is a common treatment for feline megacolon. Clarithromycin, erythromycin, and troleandomycin markedly inhibit the metabolism of cisapride. Concurrent administration of certain anticholinergic compounds, such as belladonna alkaloids and dicyclomine, would be expected to compromise the beneficial effects of cisapride.

Chemical Structure

Cisapride tartrate
Cisapride tartrate
CAS#189888-25-3 (tartrate)

Theoretical Analysis

MedKoo Cat#: 412955

Name: Cisapride tartrate

CAS#: 189888-25-3 (tartrate)

Chemical Formula: C27H35ClFN3O10

Exact Mass: 615.1995

Molecular Weight: 616.04

Elemental Analysis: C, 52.64; H, 5.73; Cl, 5.75; F, 3.08; N, 6.82; O, 25.97

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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Synonym
Cisapride tartrate; UNII-Z4XXZ45H2O
IUPAC/Chemical Name
Benzamide, 4-amino-5-chloro-N-(1-(3-(4-fluorophenoxy)propyl)-3-methoxy-4-piperidinyl)-2-methoxy-, cis-, (R-(R*,R*))-2,3-dihydroxybutanedioate (1:1)
InChi Key
QFMZVCBZQAEZSJ-NXTHFSGHSA-N
InChi Code
InChI=1S/C23H29ClFN3O4.C4H6O6/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;5-1(3(7)8)2(6)4(9)10/h4-7,12-13,20,22H,3,8-11,14,26H2,1-2H3,(H,27,29);1-2,5-6H,(H,7,8)(H,9,10)/t20-,22-;1-,2?/m11/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.O=C(O)[C@H](O)C(O)C(O)=O
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 616.04 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: Park KR, Yun HM. RANKL-induced osteoclastogenesis in bone marrow-derived macrophages is suppressed by cisapride. Toxicology. 2019 Jun 15;422:95-101. doi: 10.1016/j.tox.2019.05.010. Epub 2019 May 28. PMID: 31150804. 2: García-Garayoa E, Monge A, Roca J, Del Río J, Lasheras B. VB20B7, a novel 5-HT-ergic agent with gastrokinetic activity. II. Evaluation of the gastroprokinetic activity in rats and dogs. J Pharm Pharmacol. 1997 Jan;49(1):66-73. doi: 10.1111/j.2042-7158.1997.tb06754.x. PMID: 9120773.