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
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
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
Title | Date | PubMed |
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Novel neurokinin-1 antagonists as antiemetics for the treatment of chemotherapy-induced emesis. | 2006 Apr 1 |
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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 |
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Synthesis and pharmacological characterization of constrained analogues of Vestipitant as in vitro potent and orally active NK(1) receptor antagonists. | 2010 Jan 15 |
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Application of LC-NMR to the identification of bulk drug impurities in NK1 antagonist GW597599 (vestipitant). | 2010 Jul |
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Application of LC-NMR and HR-NMR to the characterization of biphenyl impurities in the synthetic route development for vestipitant, a novel NK1 antagonist. | 2010 Nov 2 |
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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 |
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Efficacy of vestipitant, a neurokinin-1 receptor antagonist, in primary insomnia. | 2013 Dec 1 |
Sample Use Guides
In Vivo Use Guide
Sources: https://clinicaltrials.gov/ct2/show/NCT01507194
Postoperative Nausea and Vomiting: Single IV dose 6-36 mg.
Route of Administration:
Intravenous
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/18657401
Vestipitant possessed high affinity for human NK(1) receptors (pK(i), 9.4), and potently blocked Substance P-mediated phosphorylation of Extracellular-Regulated-Kinase.
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C267
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ACTIVE MOIETY
SALT/SOLVATE (PARENT)