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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 of VOFOPITANT

SMILES

COC1=CC=C(C=C1CN[C@H]2CCCN[C@H]2C3=CC=CC=C3)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

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.

Approval Year

PubMed

PubMed

TitleDatePubMed
GR205171: a novel antagonist with high affinity for the tachykinin NK1 receptor, and potent broad-spectrum anti-emetic activity.
1996 Aug 27
Stress-induced increase of cortical dopamine metabolism: attenuation by a tachykinin NK1 receptor antagonist.
2004 Jan 19
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 Sep 22
Patents

Patents

Sample Use Guides

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 Fri Dec 15 16:26:38 GMT 2023
Edited
by admin
on Fri Dec 15 16:26:38 GMT 2023
Record UNII
K08BK043YS
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
VOFOPITANT
INN   WHO-DD  
INN  
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
GR-205171
Code English
GR205171
Code English
Classification Tree Code System Code
NCI_THESAURUS C267
Created by admin on Fri Dec 15 16:26:38 GMT 2023 , Edited by admin on Fri Dec 15 16:26:38 GMT 2023
Code System Code Type Description
DRUG BANK
DB12436
Created by admin on Fri Dec 15 16:26:38 GMT 2023 , Edited by admin on Fri Dec 15 16:26:38 GMT 2023
PRIMARY
FDA UNII
K08BK043YS
Created by admin on Fri Dec 15 16:26:38 GMT 2023 , Edited by admin on Fri Dec 15 16:26:38 GMT 2023
PRIMARY
CAS
168266-90-8
Created by admin on Fri Dec 15 16:26:38 GMT 2023 , Edited by admin on Fri Dec 15 16:26:38 GMT 2023
PRIMARY
ChEMBL
CHEMBL522302
Created by admin on Fri Dec 15 16:26:38 GMT 2023 , Edited by admin on Fri Dec 15 16:26:38 GMT 2023
PRIMARY
PUBCHEM
6918331
Created by admin on Fri Dec 15 16:26:38 GMT 2023 , Edited by admin on Fri Dec 15 16:26:38 GMT 2023
PRIMARY
NCI_THESAURUS
C72949
Created by admin on Fri Dec 15 16:26:38 GMT 2023 , Edited by admin on Fri Dec 15 16:26:38 GMT 2023
PRIMARY
EVMPD
SUB05124MIG
Created by admin on Fri Dec 15 16:26:38 GMT 2023 , Edited by admin on Fri Dec 15 16:26:38 GMT 2023
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WIKIPEDIA
Vofopitant
Created by admin on Fri Dec 15 16:26:38 GMT 2023 , Edited by admin on Fri Dec 15 16:26:38 GMT 2023
PRIMARY
SMS_ID
100000087885
Created by admin on Fri Dec 15 16:26:38 GMT 2023 , Edited by admin on Fri Dec 15 16:26:38 GMT 2023
PRIMARY
EPA CompTox
DTXSID10870099
Created by admin on Fri Dec 15 16:26:38 GMT 2023 , Edited by admin on Fri Dec 15 16:26:38 GMT 2023
PRIMARY
INN
7942
Created by admin on Fri Dec 15 16:26:38 GMT 2023 , Edited by admin on Fri Dec 15 16:26:38 GMT 2023
PRIMARY
Related Record Type Details
TARGET -> INHIBITOR
SALT/SOLVATE -> PARENT
LABELED -> NON-LABELED
Related Record Type Details
ACTIVE MOIETY