Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C30H35F7N4O2.CH4O3S |
| Molecular Weight | 712.719 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 3 / 3 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CS(O)(=O)=O.C[C@@H](N(C)C(=O)N1CC[C@@H](C[C@@H]1C2=C(C)C=C(F)C=C2)N3CCN(CC3)C(C)=O)C4=CC(=CC(=C4)C(F)(F)F)C(F)(F)F
InChI
InChIKey=YRFKYVWDPCOSTE-REWBLLDVSA-N
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
DescriptionCurator's Comment: Description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/19445564 |
http://adisinsight.springer.com/drugs/800018590
Curator's Comment: Description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/19445564 |
http://adisinsight.springer.com/drugs/800018590
Casopitant (GW679769) is a novel substituted piperidine derivative that competitively binds with NK1 receptors. The full occupancy of the receptor by their piperidine compound
inhibits its binding with tachykinin neurotransmitters, including SP. Casopitant, in a series of in vitro and in vivo experimentations, has exhibited a potent NK1 receptor antagonism. On 29 May 2008, GlaxoSmithKline announced the submission of a new drug application to the FDA for intravenous and oral formulations of casopitant mesylate. This drug was proposed for the prevention of chemotherapy-induced nausea and vomiting as an add-on therapy to the standard dual therapy of 5-HT3 receptor antagonists + dexamethasone. The submission also included a proposed indication for postoperative nausea and vomiting prevention. Rezonic™ is the proposed trade name for casopitant mesylate in the United States; Zunrisa™ is the proposed trade name for casopitant mesylate for GlaxoSmithKline’s global group of companies. In September 2009, GlaxoSmithKline decided to discontinue all regulatory filings for casopitant based on an estimate of the amount of additional safety data.
Originator
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Novel neurokinin-1 antagonists as antiemetics for the treatment of chemotherapy-induced emesis. | 2006 Apr 1 |
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| (S)-1-[3,5-Bis-(trifluoro-meth-yl)phen-yl]-N-methylethyl-amine-(R)-2-hydroxy-butane-dioic acid (1/1). | 2008 Dec 24 |
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| Casopitant, a neurokinin-1 receptor antagonist with anti-emetic and anti-nausea activities. | 2008 Jul |
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| Chemotherapy-induced nausea and vomiting. | 2008 Mar-Apr |
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| Pharmacokinetics and brain penetration of casopitant, a potent and selective neurokinin-1 receptor antagonist, in the ferret. | 2008 Sep |
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| Pharmacological management of chemotherapy-induced nausea and vomiting: focus on recent developments. | 2009 |
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| Casopitant: a novel NK(1)-receptor antagonist in the prevention of chemotherapy-induced nausea and vomiting. | 2009 Apr |
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| Disposition and metabolism of radiolabeled casopitant in humans. | 2009 Aug |
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| Tachykinin receptor antagonists in clinical trials. | 2009 Dec |
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| 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. | 2009 Dec 15 |
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| Management of postoperative nausea and vomiting: focus on palonosetron. | 2009 Feb |
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| Casopitant: a new warrior in the antiemetic crusade. | 2009 Jun |
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| Efficacy and safety of casopitant mesylate, a neurokinin 1 (NK1)-receptor antagonist, in prevention of chemotherapy-induced nausea and vomiting in patients receiving cisplatin-based highly emetogenic chemotherapy: a randomised, double-blind, placebo-controlled trial. | 2009 Jun |
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| Antiemetic control: toward a new standard of care for emetogenic chemotherapy. | 2009 Mar |
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| Randomized, double-blind, dose-ranging trial of the oral neurokinin-1 receptor antagonist casopitant mesylate for the prevention of cisplatin-induced nausea and vomiting. | 2009 Nov |
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| Phase III trial of casopitant, a novel neurokinin-1 receptor antagonist, for the prevention of nausea and vomiting in patients receiving moderately emetogenic chemotherapy. | 2009 Nov 10 |
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| Impact of casopitant, a novel NK-1 antagonist, on the pharmacokinetics of ondansetron and dexamethasone. | 2009 Sep |
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| Effect of casopitant, a novel NK-1 antagonist, on the pharmacokinetics of dolasetron and granisetron. | 2009 Sep |
|
| Neurokinin-1 receptor antagonists: a comprehensive patent survey. | 2010 Aug |
|
| Ketoconazole and rifampin significantly affect the pharmacokinetics, but not the safety or QTc interval, of casopitant, a neurokinin-1 receptor antagonist. | 2010 Aug |
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| The evaluation of drug rechallenge: the casopitant Phase III program. | 2010 Dec |
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| Phase II study to evaluate the safety and efficacy of the oral neurokinin-1 receptor antagonist casopitant (GW679769) administered with ondansetron for the prevention of postoperative and postdischarge nausea and vomiting in high-risk patients. | 2010 Jul |
|
| Winning a won game: caffeine panacea for obesity syndemic. | 2010 Jun |
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| Effect of casopitant, a novel NK-1 receptor antagonist, on the pharmacokinetics and pharmacodynamics of steady-state warfarin. | 2010 May |
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| Casopitant improves the quality of life in patients receiving highly emetogenic chemotherapy. | 2010 Nov |
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| Determination of casopitant and its three major metabolites in dog and rat plasma by positive ion liquid chromatography/tandem mass spectrometry. | 2010 Nov 1 |
|
| Effect of single and repeat doses of casopitant on the pharmacokinetics of CYP450 3A4 substrates midazolam and nifedipine. | 2010 Oct |
|
| Metabolic disposition of casopitant, a potent neurokinin-1 receptor antagonist, in mice, rats, and dogs. | 2010 Oct |
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| Quantitation of a de-fluorinated analogue of casopitant mesylate by normal-phase liquid chromatography/mass spectrometry. | 2010 Sep 15 |
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| Management of chemotherapy-induced nausea and vomiting. | 2010 Sep-Oct |
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| A novel and integrated approach for the identification and characterization of drug-induced cardiac toxicity in the dog. | 2011 Feb |
|
| Discovery and biological characterization of (2R,4S)-1'-acetyl-N-{(1R)-1-[3,5-bis(trifluoromethyl)phenyl]ethyl}-2-(4-fluoro-2-methylphenyl)-N-methyl-4,4'-bipiperidine-1-carboxamide as a new potent and selective neurokinin 1 (NK1) receptor antagonist clinical candidate. | 2011 Feb 24 |
|
| Why receptor reserve matters for neurokinin1 (NK1) receptor antagonists. | 2013 Dec |
Patents
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NCI_THESAURUS |
C265
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DTXSID70194384
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C531951
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RR-52
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414910-30-8
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C61086
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7VSV9BL497
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100000092972
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CHEMBL1672054
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SUB28847
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11686295
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DBSALT002028
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ACTIVE MOIETY
SUBSTANCE RECORD
