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Details

Stereochemistry ABSOLUTE
Molecular Formula C23H24F7N3O.CH4O3S
Molecular Weight 587.551
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of VESTIPITANT MESYLATE

SMILES

CS(O)(=O)=O.C[C@@H](N(C)C(=O)N1CCNC[C@@H]1C2=C(C)C=C(F)C=C2)C3=CC(=CC(=C3)C(F)(F)F)C(F)(F)F

InChI

InChIKey=BHECXGHXWKHZOY-DXPOFMJKSA-N
InChI=1S/C23H24F7N3O.CH4O3S/c1-13-8-18(24)4-5-19(13)20-12-31-6-7-33(20)21(34)32(3)14(2)15-9-16(22(25,26)27)11-17(10-15)23(28,29)30;1-5(2,3)4/h4-5,8-11,14,20,31H,6-7,12H2,1-3H3;1H3,(H,2,3,4)/t14-,20-;/m1./s1

HIDE SMILES / InChI

Molecular Formula CH4O3S
Molecular Weight 96.106
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C23H24F7N3O
Molecular Weight 491.445
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

Vestipitant, also known as GW597599, is a neurokinin1 receptor antagonist that was being developed by GlaxoSmithKline for the treatment of postoperative nausea and vomiting. Vestipitant is one of the most potent and selective NK(1) receptor antagonists ever discovered, showing appropriate pharmacokinetic properties and in vivo activity. Its actions support the utility of NK(1) receptor blockade in the alleviation of anxiety and, possibly, depression. It was under development as a potential antiemetic and anxiolytic drug, and as a treatment for tinnitus and insomnia. Vestipitant was shown to improve sleep maintenance in patients with primary insomnia, with no associated next-day cognitive impairment. The effects on wake after sleep onset and total sleep time were maintained following repeated dosing. Vestipitant has anxiolytic properties and a good safety profile. Vestipitant was investigated for potential effect against chronic tinnitus as a stand-alone treatment and in conjunction with a selective serotonin reuptake inhibitor, paroxetine. Although well-tolerated vestipitant, alone or in combination with paroxetine, was not effective in ameliorating tinnitus in this patient group.

Approval Year

PubMed

PubMed

TitleDatePubMed
Discovery process and pharmacological characterization of 2-(S)-(4-fluoro-2-methylphenyl)piperazine-1-carboxylic acid [1-(R)-(3,5-bis-trifluoromethylphenyl)ethyl]methylamide (vestipitant) as a potent, selective, and orally active NK1 receptor antagonist.
2009 May 28
Efficacy of vestipitant, a neurokinin-1 receptor antagonist, in primary insomnia.
2013 Dec 1
Patents

Sample Use Guides

Postoperative Nausea and Vomiting: Single IV dose 6-36 mg.
Route of Administration: Intravenous
Vestipitant possessed high affinity for human NK(1) receptors (pK(i), 9.4), and potently blocked Substance P-mediated phosphorylation of Extracellular-Regulated-Kinase.
Substance Class Chemical
Created
by admin
on Mon Mar 31 18:49:42 GMT 2025
Edited
by admin
on Mon Mar 31 18:49:42 GMT 2025
Record UNII
OWR424W90Q
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
VESTIPITANT MESYLATE
USAN  
USAN  
Official Name English
VESTIPITANT MESILATE
WHO-DD  
Preferred Name English
Vestipitant mesilate [WHO-DD]
Common Name English
(+)-(2S)-N-((1R)-1-(3,5-BIS(TRIFLUOROMETHYL)PHENYL)ETHYL)-2-(4-FLUORO-2-METHYLPHENYL)-N-METHYLPIPERAZINE-1-CARBOXAMIDE METHANESULFONATE
Systematic Name English
1-PIPERAZINECARBOXAMIDE, N-((1R)-1-(3,5-BIS(TRIFLUOROMETHYL)PHENYL)ETHYL)-2-(4-FLUORO-2-METHYLPHENYL)-N-METHYL, (2S), MONOMETHANESULPHONATE
Common Name English
GW597599B
Code English
GW597588B
Code English
GW-597588B
Code English
(+)-(2S)-N-((1R)-1-(3,5-BIS(TRIFLUOROMETHYL)PHENYL)ETHYL)-2-(4-FLUORO-2-METHYLPHENYL)-N-METHYLPIPERAZINE-1-CARBOXAMIDE METHANESULPHONATE
Systematic Name English
VESTIPITANT MESYLATE [USAN]
Common Name English
1-PIPERAZINECARBOXAMIDE, N-((1R)-1-(3,5-BIS(TRIFLUOROMETHYL)PHENYL)ETHYL)-2-(4-FLUORO-2-METHYLPHENYL)-N-METHYL, (2S), MONOMETHANESULFONATE
Common Name English
GW-597599B
Code English
Classification Tree Code System Code
NCI_THESAURUS C267
Created by admin on Mon Mar 31 18:49:42 GMT 2025 , Edited by admin on Mon Mar 31 18:49:42 GMT 2025
Code System Code Type Description
SMS_ID
300000044504
Created by admin on Mon Mar 31 18:49:42 GMT 2025 , Edited by admin on Mon Mar 31 18:49:42 GMT 2025
PRIMARY
DRUG BANK
DBSALT002111
Created by admin on Mon Mar 31 18:49:42 GMT 2025 , Edited by admin on Mon Mar 31 18:49:42 GMT 2025
PRIMARY
ChEMBL
CHEMBL522987
Created by admin on Mon Mar 31 18:49:42 GMT 2025 , Edited by admin on Mon Mar 31 18:49:42 GMT 2025
PRIMARY
EPA CompTox
DTXSID10187093
Created by admin on Mon Mar 31 18:49:42 GMT 2025 , Edited by admin on Mon Mar 31 18:49:42 GMT 2025
PRIMARY
PUBCHEM
24969622
Created by admin on Mon Mar 31 18:49:42 GMT 2025 , Edited by admin on Mon Mar 31 18:49:42 GMT 2025
PRIMARY
CAS
334476-64-1
Created by admin on Mon Mar 31 18:49:42 GMT 2025 , Edited by admin on Mon Mar 31 18:49:42 GMT 2025
PRIMARY
NCI_THESAURUS
C95195
Created by admin on Mon Mar 31 18:49:42 GMT 2025 , Edited by admin on Mon Mar 31 18:49:42 GMT 2025
PRIMARY
USAN
PP-65
Created by admin on Mon Mar 31 18:49:42 GMT 2025 , Edited by admin on Mon Mar 31 18:49:42 GMT 2025
PRIMARY
FDA UNII
OWR424W90Q
Created by admin on Mon Mar 31 18:49:42 GMT 2025 , Edited by admin on Mon Mar 31 18:49:42 GMT 2025
PRIMARY
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PARENT -> SALT/SOLVATE
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ACTIVE MOIETY