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Details

Stereochemistry ABSOLUTE
Molecular Formula C31H35F7N4O2.ClH
Molecular Weight 665.085
Optical Activity UNSPECIFIED
Defined Stereocenters 4 / 4
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ORVEPITANT HYDROCHLORIDE

SMILES

Cl.C[C@@H](N(C)C(=O)N1CC[C@@H](C[C@@H]1C2=CC=C(F)C=C2C)N3CCN4[C@@H](CCC4=O)C3)C5=CC(=CC(=C5)C(F)(F)F)C(F)(F)F

InChI

InChIKey=WKIIEDMRXGVSOO-ISFOHNRCSA-N
InChI=1S/C31H35F7N4O2.ClH/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;1H/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
Molecular Formula ClH
Molecular Weight 36.461
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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.

CNS Activity

Originator

GlaxoSmithKline
197
Curator's Comment: https://www.google.com/patents/EP2297152A1

Approval Year

Unknown
149124
Targets

Targets

Primary TargetPharmacologyConditionPotency
Antagonist
2849
 10.2 null [pKi]
Modulator
846
 2.27 µM [Ki]
Modulator
846
 0.94 µM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Phase II
1147
Unknown

Approved Use

Unknown
Primary
Phase II
1147
Unknown

Approved Use

Unknown
Primary
Phase II
1147
Unknown

Approved Use

Unknown
Primary
Phase II
1147
Unknown

Approved Use

Unknown
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:
https://pubmed.ncbi.nlm.nih.gov/32034016
unhealthy
Health Status: unhealthy
Sex: M+F
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/32034016
Other AEs: Asthenia, Hyperhidrosis...
Other AEs:
Asthenia (mild, 6.3%)
Hyperhidrosis (moderate, 6.3%)
Dry mouth (mild, 6.3%)
Sources:
https://pubmed.ncbi.nlm.nih.gov/32034016
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:
https://pubmed.ncbi.nlm.nih.gov/32034016
unhealthy
Health Status: unhealthy
Sex: M+F
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/32034016
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:
https://pubmed.ncbi.nlm.nih.gov/32034016
unhealthy
Health Status: unhealthy
Sex: M+F
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/32034016
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:
https://pubmed.ncbi.nlm.nih.gov/32034016
unhealthy
Health Status: unhealthy
Sex: M+F
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/32034016
Sourcing

Sourcing

Vendor/AggregatorIDURL
Angene
AGN-PC-0SOQO4
http://www.angenechemical.com/productshow/AGN-PC-0SOQO4.html
Axon MedChem
1618
https://www.axonmedchem.com/product/1618
BOC Sciences
579475-18-6
http://www.bocsci.com/description.asp?cas=579475-18-6
Compound Cloud
44225656
Compound Cloud
9852175
eMolecules
300580143
https://orderbb.emolecules.com/search/#?query=300580143
eMolecules
44848352
https://orderbb.emolecules.com/search/#?query=44848352
eMolecules
50415089
https://orderbb.emolecules.com/search/#?query=50415089
Matrix Scientific
148038
http://www.matrixscientific.com/148038.html
MolPort
MolPort-042-665-725
https://www.molport.com/shop/molecule-link/MolPort-042-665-725
PubMed

PubMed

TitleDatePubMed
Patents

Patents

08309553
3
20050176715
3
20110166150
3
EP2297152 A1
3

Sample Use Guides

In Vivo Use Guide
10 mg/day, 20 mg/day and 30 mg/day
Route of Administration: Oral
In Vitro Use Guide
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 20:09:34 GMT 2025
Edited
by admin
on Mon Mar 31 20:09:34 GMT 2025
Record UNII
7IYQ30782X
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
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-, HYDROCHLORIDE (1:1), (2R,4S)-
Preferred Name English
ORVEPITANT HYDROCHLORIDE
Common Name English
Code System Code Type Description
CAS
579475-21-1
Created by admin on Mon Mar 31 20:09:34 GMT 2025 , Edited by admin on Mon Mar 31 20:09:34 GMT 2025
PRIMARY
FDA UNII
7IYQ30782X
Created by admin on Mon Mar 31 20:09:34 GMT 2025 , Edited by admin on Mon Mar 31 20:09:34 GMT 2025
PRIMARY
PUBCHEM
71587763
Created by admin on Mon Mar 31 20:09:34 GMT 2025 , Edited by admin on Mon Mar 31 20:09:34 GMT 2025
PRIMARY
EPA CompTox
DTXSID20206668
Created by admin on Mon Mar 31 20:09:34 GMT 2025 , Edited by admin on Mon Mar 31 20:09:34 GMT 2025
PRIMARY
Related Record Type Details
Structure of ORVEPITANT
PARENT -> SALT/SOLVATE
NIH
NCATS
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