WARNING: This product is for research use only, not for human or veterinary use.
MedKoo CAT#: 200650
CAS#: 414910-30-8 (mesylate)
Description: Casopitant mesylate is the mesylate salt of a centrally-acting neurokinin 1 (NK1) receptor antagonist with antidepressant and antiemetic activities. Casopitant competitively binds to and blocks the activity of the NK1 receptor, thereby inhibiting NK1-receptor binding of the endogenous tachykinin neuropeptide substance P (SP), which may result in antiemetic effects. SP is found in neurons of vagal afferent fibers innervating the brain-stem nucleus tractus solitarii and the area postrema, which contains the chemoreceptor trigger zone (CTZ), and may be elevated in response to chemotherapy. The NK1 receptor is a G-protein receptor coupled to the inositol phosphate signal-transduction pathway and is found in both the nucleus tractus solitarii and the area postrema.
MedKoo Cat#: 200650
Name: Casopitant mesylate
CAS#: 414910-30-8 (mesylate)
Chemical Formula: C31H39F7N4O5S
Molecular Weight: 712.72
Elemental Analysis: C, 52.24; H, 5.52; F, 18.66; N, 7.86; O, 11.22; S, 4.50
Related CAS #: 414910-30-8 (mesylate) 414910-27-3 (free base)
Synonym: GW679769; GW 679769; GW-679769; Casopitant mesylate. Trade names: Rezonic (US); Zunrisa (EU).
IUPAC/Chemical Name: (2R,4S)-4-(4-Acetyl-1-piperazinyl)-N-[(1R)-1-[3,5-bis(trifluoromethyl)phenyl]ethyl]-2-(4-fluoro-2-methylphenyl)-N-methyl-1-piperidinecarboxamide
InChi Key: YRFKYVWDPCOSTE-REWBLLDVSA-N
InChi Code: InChI=1S/C30H35F7N4O2.CH4O3S/c1-18-13-24(31)5-6-26(18)27-17-25(40-11-9-39(10-12-40)20(3)42)7-8-41(27)28(43)38(4)19(2)21-14-22(29(32,33)34)16-23(15-21)30(35,36)37;1-5(2,3)4/h5-6,13-16,19,25,27H,7-12,17H2,1-4H3;1H3,(H,2,3,4)/t19-,25+,27-;/m1./s1
SMILES Code: O=C(N1[C@@H](C2=CC=C(F)C=C2C)C[C@@H](N3CCN(C(C)=O)CC3)CC1)N([C@@H](C4=CC(C(F)(F)F)=CC(C(F)(F)F)=C4)C)C.CS(=O)(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, not in water
Shelf Life: >5 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
The following data is based on the product molecular weight 712.72 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.
|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: Kirby LC, Johnson BM, Adams LM, Eberwein DJ, Zhang K, Murray SC, Lates CD, Blum RA, Morris SR. Effect of casopitant, a novel NK-1 receptor antagonist, on the pharmacokinetics and pharmacodynamics of steady-state warfarin. J Clin Pharmacol. 2010 May;50(5):566-75. Epub 2010 Mar 10. PubMed PMID: 20220045.
2: Johnson BM, Adams LM, Zhang K, Gainer SD, Kirby LC, Blum RA, Apseloff G, Morrison RA, Schutz RA, Lebowitz PF. Ketoconazole and Rifampin Significantly Affect the Pharmacokinetics, But Not the Safety or QTc Interval, of Casopitant, a Neurokinin-1 Receptor Antagonist. J Clin Pharmacol. 2010 Feb 2. [Epub ahead of print] PubMed PMID: 20124517.
3: Quartara L, Altamura M, Evangelista S, Maggi CA. Tachykinin receptor antagonists in clinical trials. Expert Opin Investig Drugs. 2009 Dec;18(12):1843-64. Review. PubMed PMID: 19938899.
4: Tomillero A, Moral MA. Gateways to clinical trials. Methods Find Exp Clin Pharmacol. 2009 Sep;31(7):463-93. PubMed PMID: 19907722.
5: Gridelli C, Haiderali AM, Russo MW, Blackburn LM, Lykopoulos K. Casopitant improves the quality of life in patients receiving highly emetogenic chemotherapy. Support Care Cancer. 2009 Oct 31. [Epub ahead of print] PubMed PMID: 19882176.
6: Arpornwirat W, Albert I, Hansen VL, Levin J, Bandekar RR, Grunberg SM. Phase 2 trial results with the novel neurokinin-1 receptor antagonist casopitant in combination with ondansetron and dexamethasone for the prevention of chemotherapy-induced nausea and vomiting in cancer patients receiving moderately emetogenic chemotherapy. Cancer. 2009 Dec 15;115(24):5807-16. PubMed PMID: 19834961.
7: Herrstedt J, Apornwirat W, Shaharyar A, Aziz Z, Roila F, Van Belle S, Russo MW, Levin J, Ranganathan S, Guckert M, Grunberg SM. Phase III trial of casopitant, a novel neurokinin-1 receptor antagonist, for the prevention of nausea and vomiting in patients receiving moderately emetogenic chemotherapy. J Clin Oncol. 2009 Nov 10;27(32):5363-9. Epub 2009 Oct 5. PubMed PMID: 19805683.
8: Tomillero A, Moral MA. Gateways to clinical trials. Methods Find Exp Clin Pharmacol. 2009 May;31(4):263-98. PubMed PMID: 19557204.
9: Roila F, Rolski J, Ramlau R, Dediu M, Russo MW, Bandekar RR, Grunberg SM. Randomized, double-blind, dose-ranging trial of the oral neurokinin-1 receptor antagonist casopitant mesylate for the prevention of cisplatin-induced nausea and vomiting. Ann Oncol. 2009 Nov;20(11):1867-73. Epub 2009 Jun 18. PubMed PMID: 19541792.
10: Ruhlmann C, Herrstedt J. Casopitant: a novel NK(1)-receptor antagonist in the prevention of chemotherapy-induced nausea and vomiting. Ther Clin Risk Manag. 2009 Apr;5(2):375-84. Epub 2009 May 20. PubMed PMID: 19536319; PubMed Central PMCID: PMC2697542.
414910-27-3 (Casopitant free base)
414910-30-8 (Casopitant mesylate).
Casopitant (trade names Rezonic (US), Zunrisa (EU)) is an neurokinin 1 (NK1) receptor antagonist undergoing research for the treatment of chemotherapy-induced nausea and vomiting (CINV). It is currently under development by GlaxoSmithKline (GSK). In July 2008, the company filed a marketing authorisation application with the European Medicines Agency. The application was withdrawn in September 2009 because GSK decided that further safety assessment was necessary. (see: http://en.wikipedia.org/wiki/Casopitant).