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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=CC=C(F)C=C2C)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

Description

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.

CNS Activity

Originator

Approval Year

PubMed

Sample Use Guides

In Vivo Use Guide
Postoperative Nausea and Vomiting: Single IV dose 6-36 mg.
Route of Administration: Intravenous
In Vitro Use Guide
Vestipitant possessed high affinity for human NK(1) receptors (pK(i), 9.4), and potently blocked Substance P-mediated phosphorylation of Extracellular-Regulated-Kinase.