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
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL249 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24106886 |
10.2 null [pKi] | ||
Target ID: CHEMBL340 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21149541 |
9.86 µM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Palliative | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
---|---|---|
Disposition and metabolism of radiolabeled casopitant in humans. | 2009 Aug |
|
Casopitant: a new warrior in the antiemetic crusade. | 2009 Jun |
|
Antiemetic control: toward a new standard of care for emetogenic chemotherapy. | 2009 Mar |
|
Impact of casopitant, a novel NK-1 antagonist, on the pharmacokinetics of ondansetron and dexamethasone. | 2009 Sep |
|
Neurokinin-1 receptor antagonists: a comprehensive patent survey. | 2010 Aug |
|
Casopitant improves the quality of life in patients receiving highly emetogenic chemotherapy. | 2010 Nov |
|
Management of chemotherapy-induced nausea and vomiting. | 2010 Sep-Oct |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/19445564
A single 100 or 150 mg dose schedule of casopitant, orally or intravenously
Route of Administration:
Other
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/21149541
Casopitant inhibited CYP3A4 activity in human liver microsomes with an IC50 lower than 10 uM.
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C265
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ACTIVE MOIETY
SUBSTANCE RECORD