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Details

Stereochemistry ABSOLUTE
Molecular Formula C23H24F7N3O
Molecular Weight 491.445
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of VESTIPITANT

SMILES

C[C@@H](N(C)C(=O)N1CCNC[C@@H]1C2=CC=C(F)C=C2C)C3=CC(=CC(=C3)C(F)(F)F)C(F)(F)F

InChI

InChIKey=SBBYBXSFWOLDDG-JLTOFOAXSA-N
InChI=1S/C23H24F7N3O/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/h4-5,8-11,14,20,31H,6-7,12H2,1-3H3/t14-,20-/m1/s1

HIDE SMILES / InChI

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
Novel neurokinin-1 antagonists as antiemetics for the treatment of chemotherapy-induced emesis.
2006 Apr 1
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
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 Fri Dec 15 16:11:14 GMT 2023
Edited
by admin
on Fri Dec 15 16:11:14 GMT 2023
Record UNII
S052TOI9BI
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
VESTIPITANT
INN   WHO-DD  
INN  
Official Name English
GW-597599
Code English
vestipitant [INN]
Common Name English
1-PIPERAZINECARBOXAMIDE, N-(1-(3,5-BIS(TRIFLUOROMETHYL)PHENYL)ETHYL)-2-(4-FLUORO-2-METHYLPHENYL)-N-METHYL-
Systematic Name English
N-(1-(3,5-BIS(TRIFLUOROMETHYL)PHENYL)ETHYL)-2-(4-FLUORO-2-METHYLPHENYL)-N-METHYLPIPERAZINE-1-CARBOXAMIDE
Systematic Name English
GW597599
Common Name English
Vestipitant [WHO-DD]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C267
Created by admin on Fri Dec 15 16:11:14 GMT 2023 , Edited by admin on Fri Dec 15 16:11:14 GMT 2023
Code System Code Type Description
SMS_ID
100000092720
Created by admin on Fri Dec 15 16:11:14 GMT 2023 , Edited by admin on Fri Dec 15 16:11:14 GMT 2023
PRIMARY
CAS
334476-46-9
Created by admin on Fri Dec 15 16:11:14 GMT 2023 , Edited by admin on Fri Dec 15 16:11:14 GMT 2023
PRIMARY
EVMPD
SUB29227
Created by admin on Fri Dec 15 16:11:14 GMT 2023 , Edited by admin on Fri Dec 15 16:11:14 GMT 2023
PRIMARY
DRUG BANK
DB11949
Created by admin on Fri Dec 15 16:11:14 GMT 2023 , Edited by admin on Fri Dec 15 16:11:14 GMT 2023
PRIMARY
WIKIPEDIA
VESTIPITANT
Created by admin on Fri Dec 15 16:11:14 GMT 2023 , Edited by admin on Fri Dec 15 16:11:14 GMT 2023
PRIMARY
MESH
C534550
Created by admin on Fri Dec 15 16:11:14 GMT 2023 , Edited by admin on Fri Dec 15 16:11:14 GMT 2023
PRIMARY
PUBCHEM
9832383
Created by admin on Fri Dec 15 16:11:14 GMT 2023 , Edited by admin on Fri Dec 15 16:11:14 GMT 2023
PRIMARY
FDA UNII
S052TOI9BI
Created by admin on Fri Dec 15 16:11:14 GMT 2023 , Edited by admin on Fri Dec 15 16:11:14 GMT 2023
PRIMARY
ChEMBL
CHEMBL522987
Created by admin on Fri Dec 15 16:11:14 GMT 2023 , Edited by admin on Fri Dec 15 16:11:14 GMT 2023
PRIMARY
NCI_THESAURUS
C95194
Created by admin on Fri Dec 15 16:11:14 GMT 2023 , Edited by admin on Fri Dec 15 16:11:14 GMT 2023
PRIMARY
EPA CompTox
DTXSID50187092
Created by admin on Fri Dec 15 16:11:14 GMT 2023 , Edited by admin on Fri Dec 15 16:11:14 GMT 2023
PRIMARY
INN
8522
Created by admin on Fri Dec 15 16:11:14 GMT 2023 , Edited by admin on Fri Dec 15 16:11:14 GMT 2023
PRIMARY
Related Record Type Details
TARGET -> INHIBITOR
SALT/SOLVATE -> PARENT
Related Record Type Details
ACTIVE MOIETY