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Details

Stereochemistry ABSOLUTE
Molecular Formula C31H35F7N4O2
Molecular Weight 628.624
Optical Activity UNSPECIFIED
Defined Stereocenters 4 / 4
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ORVEPITANT

SMILES

C[C@@H](N(C)C(=O)N1CC[C@@H](C[C@@H]1C2=C(C)C=C(F)C=C2)N3CCN4[C@@H](CCC4=O)C3)C5=CC(=CC(=C5)C(F)(F)F)C(F)(F)F

InChI

InChIKey=XWNBGDJPEXZSQM-VZOBGQTKSA-N
InChI=1S/C31H35F7N4O2/c1-18-12-23(32)4-6-26(18)27-16-24(40-10-11-41-25(17-40)5-7-28(41)43)8-9-42(27)29(44)39(3)19(2)20-13-21(30(33,34)35)15-22(14-20)31(36,37)38/h4,6,12-15,19,24-25,27H,5,7-11,16-17H2,1-3H3/t19-,24+,25+,27-/m1/s1

HIDE SMILES / InChI

Molecular Formula C31H35F7N4O2
Molecular Weight 628.624
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 4 / 4
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment: description was created based on several sources, including: https://www.ncbi.nlm.nih.gov/pubmed/23539641 | https://en.wikipedia.org/wiki/Orvepitant | http://adisinsight.springer.com/drugs/800020168 | https://www.ncbi.nlm.nih.gov/pubmed/24075145

Orvepitant is a novel generation brain penetrant, selective and potent, small molecule NK-1 receptor antagonist. Orvepitant’s (GW823296) mode of action and developability characteristics made it a suitable development candidate for the treatment of common anxiety disorders, posttraumatic stress disorder and major depressive disorder. It’s in phase II clinical trials as an effective inhibitor of itch-associated response.

Originator

Curator's Comment: https://www.google.com/patents/EP2297152A1

Approval Year

TargetsConditions
Doses

Doses

DosePopulationAdverse events​
30 mg 1 times / day multiple, oral
Highest studied dose,Studied dose
Dose: 30 mg, 1 times / day
Route: oral
Route: multiple
Dose: 30 mg, 1 times / day
Sources:
unhealthy
Health Status: unhealthy
Sex: M+F
Food Status: UNKNOWN
Sources:
Other AEs: Asthenia, Hyperhidrosis...
Other AEs:
Asthenia (mild, 6.3%)
Hyperhidrosis (moderate, 6.3%)
Dry mouth (mild, 6.3%)
Sources:
AEs

AEs

AESignificanceDosePopulation
Asthenia mild, 6.3%
30 mg 1 times / day multiple, oral
Highest studied dose,Studied dose
Dose: 30 mg, 1 times / day
Route: oral
Route: multiple
Dose: 30 mg, 1 times / day
Sources:
unhealthy
Health Status: unhealthy
Sex: M+F
Food Status: UNKNOWN
Sources:
Dry mouth mild, 6.3%
30 mg 1 times / day multiple, oral
Highest studied dose,Studied dose
Dose: 30 mg, 1 times / day
Route: oral
Route: multiple
Dose: 30 mg, 1 times / day
Sources:
unhealthy
Health Status: unhealthy
Sex: M+F
Food Status: UNKNOWN
Sources:
Hyperhidrosis moderate, 6.3%
30 mg 1 times / day multiple, oral
Highest studied dose,Studied dose
Dose: 30 mg, 1 times / day
Route: oral
Route: multiple
Dose: 30 mg, 1 times / day
Sources:
unhealthy
Health Status: unhealthy
Sex: M+F
Food Status: UNKNOWN
Sources:
PubMed

PubMed

TitleDatePubMed
Full central neurokinin-1 receptor blockade is required for efficacy in depression: evidence from orvepitant clinical studies.
2013 May
Identification, biological characterization and pharmacophoric analysis of a new potent and selective NK1 receptor antagonist clinical candidate.
2013 Nov 1
Neurokinin-1 receptor antagonist orvepitant is an effective inhibitor of itch-associated response in a Mongolian gerbil model of scratching behaviour.
2014 Nov
Patents

Sample Use Guides

10 mg/day, 20 mg/day and 30 mg/day
Route of Administration: Oral
Orvepitant (0.3–10 nM) pre-incubated for 1 h at 37 C before adding the agonist substance P produced a non-surmountable antagonism of agonist CRC with apparent pKB values of 10.30 ± 0.30 (n = 4).
Substance Class Chemical
Created
by admin
on Mon Mar 31 18:38:28 GMT 2025
Edited
by admin
on Mon Mar 31 18:38:28 GMT 2025
Record UNII
IIU6V0W3JD
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ORVEPITANT
INN   USAN  
INN   USAN  
Official Name English
GW-823296X
Preferred Name English
orvepitant [INN]
Common Name English
ORVEPITANT [USAN]
Common Name English
GW-823296
Common Name English
(2R,4S)-N-{(1R)-1-[3,5-Bis(trifluoromethyl)phenyl]ethyl}-2-(4-fluoro-2-methylphenyl)-N-methyl-4-[(8aS)-6-oxohexahydro-1H-pyrrolo[1,2-a]pyrazin-2-yl]piperidine-1-carboxamide
Common Name English
1-PIPERIDINECARBOXAMIDE, N-((1R)-1-(3,5-BIS(TRIFLUOROMETHYL)PHENYL)ETHYL)-2-(4-FLUORO-2-METHYLPHENYL)-4-((8AS)-HEXAHYDRO-6-OXOPYRROLO(1,2-A)PYRAZIN-2(1H)-YL)-N-METHYL-, (2R,4S)-
Common Name English
GW823296X
Code English
Classification Tree Code System Code
NCI_THESAURUS C28197
Created by admin on Mon Mar 31 18:38:28 GMT 2025 , Edited by admin on Mon Mar 31 18:38:28 GMT 2025
NCI_THESAURUS C265
Created by admin on Mon Mar 31 18:38:28 GMT 2025 , Edited by admin on Mon Mar 31 18:38:28 GMT 2025
Code System Code Type Description
DRUG BANK
DB12427
Created by admin on Mon Mar 31 18:38:28 GMT 2025 , Edited by admin on Mon Mar 31 18:38:28 GMT 2025
PRIMARY
USAN
WW-127
Created by admin on Mon Mar 31 18:38:28 GMT 2025 , Edited by admin on Mon Mar 31 18:38:28 GMT 2025
PRIMARY
NCI_THESAURUS
C90613
Created by admin on Mon Mar 31 18:38:28 GMT 2025 , Edited by admin on Mon Mar 31 18:38:28 GMT 2025
PRIMARY
PUBCHEM
9852175
Created by admin on Mon Mar 31 18:38:28 GMT 2025 , Edited by admin on Mon Mar 31 18:38:28 GMT 2025
PRIMARY
INN
8684
Created by admin on Mon Mar 31 18:38:28 GMT 2025 , Edited by admin on Mon Mar 31 18:38:28 GMT 2025
PRIMARY
FDA UNII
IIU6V0W3JD
Created by admin on Mon Mar 31 18:38:28 GMT 2025 , Edited by admin on Mon Mar 31 18:38:28 GMT 2025
PRIMARY
SMS_ID
100000175883
Created by admin on Mon Mar 31 18:38:28 GMT 2025 , Edited by admin on Mon Mar 31 18:38:28 GMT 2025
PRIMARY
CAS
579475-18-6
Created by admin on Mon Mar 31 18:38:28 GMT 2025 , Edited by admin on Mon Mar 31 18:38:28 GMT 2025
PRIMARY
WIKIPEDIA
Orvepitant
Created by admin on Mon Mar 31 18:38:28 GMT 2025 , Edited by admin on Mon Mar 31 18:38:28 GMT 2025
PRIMARY
EPA CompTox
DTXSID40973522
Created by admin on Mon Mar 31 18:38:28 GMT 2025 , Edited by admin on Mon Mar 31 18:38:28 GMT 2025
PRIMARY
ChEMBL
CHEMBL2105667
Created by admin on Mon Mar 31 18:38:28 GMT 2025 , Edited by admin on Mon Mar 31 18:38:28 GMT 2025
PRIMARY
Related Record Type Details
TARGET -> INHIBITOR
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
Related Record Type Details
ACTIVE MOIETY