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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
Structure of CASOPITANT MESYLATE

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

HIDE SMILES / InChI

Description
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.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
10.2 null [pKi]
9.86 µM [IC50]
Conditions

Conditions

PubMed

PubMed

TitleDatePubMed
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

Patents

Sample Use Guides

A single 100 or 150 mg dose schedule of casopitant, orally or intravenously
Route of Administration: Other
Casopitant inhibited CYP3A4 activity in human liver microsomes with an IC50 lower than 10 uM.
Name Type Language
CASOPITANT MESYLATE
DASH   USAN  
USAN  
Official Name English
CASOPITANT MESYLATE [USAN]
Common Name English
1-PIPERIDINECARBOXAMIDE, 4-(4-ACETYL-1-PIPERAZINYL)-N-((1R)-1-(3,5-BIS(TRIFLUOROMETHYL)PHENYL)ETHYL)-2-(4-FLUORO-2-METHYLPHENYL)-N-METHYL-, (2R,4S)-, MONOMETHANESULFONATE
Common Name English
(2R, 4S)-4-(4-ACETYL-PIPERAZIN-1-YL)-2-(4-FLUORO-2-METHYL-PHENYL)-PIPERIDINE-1-CARBOXYLIC ACID ((1R)-1-(3,5-BIS-TRIFLUOROMETHYL-PHENYL)-ETHYL)-METHYLAMIDE METHANESULFONATE
Common Name English
Casopitant mesilate [WHO-DD]
Common Name English
GW-679769B
Code English
CASOPITANT MESILATE
MART.   WHO-DD  
Common Name English
REZONIC
Brand Name English
CASOPITANT MESILATE [MART.]
Common Name English
GW679769B
Code English
(2R,4S)-4-(4-Acetylpiperazin-1-yl)-N-[(1R)-1-[3,5-bis(trifluoromethyl)phenyl]ethyl]-2-(4-fluoro-2-methylphenyl)-N-methylpiperidine-1-carboxamide methanesulfonate
Systematic Name English
Classification Tree Code System Code
NCI_THESAURUS C265
Created by admin on Fri Dec 15 16:30:34 GMT 2023 , Edited by admin on Fri Dec 15 16:30:34 GMT 2023
Code System Code Type Description
EPA CompTox
DTXSID70194384
Created by admin on Fri Dec 15 16:30:34 GMT 2023 , Edited by admin on Fri Dec 15 16:30:34 GMT 2023
PRIMARY
MESH
C531951
Created by admin on Fri Dec 15 16:30:34 GMT 2023 , Edited by admin on Fri Dec 15 16:30:34 GMT 2023
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USAN
RR-52
Created by admin on Fri Dec 15 16:30:34 GMT 2023 , Edited by admin on Fri Dec 15 16:30:34 GMT 2023
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CAS
414910-30-8
Created by admin on Fri Dec 15 16:30:34 GMT 2023 , Edited by admin on Fri Dec 15 16:30:34 GMT 2023
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NCI_THESAURUS
C61086
Created by admin on Fri Dec 15 16:30:34 GMT 2023 , Edited by admin on Fri Dec 15 16:30:34 GMT 2023
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FDA UNII
7VSV9BL497
Created by admin on Fri Dec 15 16:30:34 GMT 2023 , Edited by admin on Fri Dec 15 16:30:34 GMT 2023
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SMS_ID
100000092972
Created by admin on Fri Dec 15 16:30:34 GMT 2023 , Edited by admin on Fri Dec 15 16:30:34 GMT 2023
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ChEMBL
CHEMBL1672054
Created by admin on Fri Dec 15 16:30:34 GMT 2023 , Edited by admin on Fri Dec 15 16:30:34 GMT 2023
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EVMPD
SUB28847
Created by admin on Fri Dec 15 16:30:34 GMT 2023 , Edited by admin on Fri Dec 15 16:30:34 GMT 2023
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PUBCHEM
11686295
Created by admin on Fri Dec 15 16:30:34 GMT 2023 , Edited by admin on Fri Dec 15 16:30:34 GMT 2023
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DRUG BANK
DBSALT002028
Created by admin on Fri Dec 15 16:30:34 GMT 2023 , Edited by admin on Fri Dec 15 16:30:34 GMT 2023
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