VOFOPITANT

Investigational

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C21H23F3N6O
Molecular Weight	432.4421
Optical Activity	UNSPECIFIED
Defined Stereocenters	2 / 2
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

COC1=C(CN[C@H]2CCCN[C@H]2C3=CC=CC=C3)C=C(C=C1)N4N=NN=C4C(F)(F)F

InChI

InChIKey=XILNRORTJVDYRH-HKUYNNGSSA-N

InChI=1S/C21H23F3N6O/c1-31-18-10-9-16(30-20(21(22,23)24)27-28-29-30)12-15(18)13-26-17-8-5-11-25-19(17)14-6-3-2-4-7-14/h2-4,6-7,9-10,12,17,19,25-26H,5,8,11,13H2,1H3/t17-,19-/m0/s1

HIDE SMILES / InChI

Molecular Formula	C21H23F3N6O
Molecular Weight	432.4421
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	2 / 2
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://clinicaltrials.gov/ct2/show/NCT00606697 | https://clinicaltrials.gov/ct2/show/NCT00383786 | https://clinicaltrials.gov/ct2/show/NCT00907985 | https://www.ncbi.nlm.nih.gov/pubmed/10365008 | https://adisinsight.springer.com/drugs/800006383

Vofopitant (previously known as GR205171), a tetrazole-derivative, was developed as a neurokinin1 receptor antagonist. Vofopitant was studied in clinical trials phase II for the treatment of primary insomnia and posttraumatic stress disorder. However, these studies were discontinued due to lack of effectiveness. In addition, vofopitant participated in phase I for patients with bipolar disorder. However, this study was terminated because of the slow recruitment; trial unlikely to reach completion.

Originator

Approval Year

PubMed

Title	Date	PubMed
Increased neurokinin-1 receptor availability in temporal lobe epilepsy: a positron emission tomography study using [(11)C]GR205171.	2011-11	21925840
Differential effects of dexamethasone, ondansetron and a tachykinin NK1 receptor antagonist (GR205171) on cisplatin-induced changes in behaviour, food intake, pica and gastric function in rats.	2007-01-26	17141213
Ionotropic and metabotropic receptors, protein kinase A, protein kinase C, and Src contribute to C-fiber-induced ERK activation and cAMP response element-binding protein phosphorylation in dorsal horn neurons, leading to central sensitization.	2004-09-22	15385614
Stress-induced increase of cortical dopamine metabolism: attenuation by a tachykinin NK1 receptor antagonist.	2004-01-19	14729382
GR205171: a novel antagonist with high affinity for the tachykinin NK1 receptor, and potent broad-spectrum anti-emetic activity.	1996-08-27	8876035

Patents

Sample Use Guides

In Vivo Use Guide

Sleep Initiation and Maintenance Disorders: 10 milligrams; Posttraumatic Stress Disorder: selective neurokinin-1 receptor antagonist, fixed 5 mg dose every day, for 8 weeks.

Route of Administration: Oral

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:28:07 GMT 2025` Edited by `admin` on `Mon Mar 31 18:28:07 GMT 2025`
Record UNII	K08BK043YS
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

GR-205171

Preferred Name

English

VOFOPITANT

Official Name

English

3-PIPERIDINAMINE, N-((2-METHOXY-5-(5-(TRIFLUORO-METHYL)-1H-TETRAZOL-1-YL)PHENYL)METHYL)-2-PHENYL-

Systematic Name

English

Vofopitant [WHO-DD]

Common Name

English

vofopitant [INN]

Common Name

English

GR205171

Code

English

Classification Tree Code System Code

NCI_THESAURUS

C267