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Details

Stereochemistry ABSOLUTE
Molecular Formula C31H35F7N4O2.C4H4O4
Molecular Weight 744.6962
Optical Activity UNSPECIFIED
Defined Stereocenters 4 / 4
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of ORVEPITANT MALEATE

SMILES

OC(=O)\C=C/C(O)=O.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=IPACOHTZCSBGBV-WUXDIRCFSA-N
InChI=1S/C31H35F7N4O2.C4H4O4/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;5-3(6)1-2-4(7)8/h4,6,12-15,19,24-25,27H,5,7-11,16-17H2,1-3H3;1-2H,(H,5,6)(H,7,8)/b;2-1-/t19-,24+,25+,27-;/m1./s1

HIDE SMILES / InChI

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

Molecular Formula C4H4O4
Molecular Weight 116.0722
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry
Defined Stereocenters 0 / 0
E/Z Centers 1
Optical Activity NONE

Description

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

Approval Year

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

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 Tue Oct 22 01:40:39 UTC 2019
Edited
by admin
on Tue Oct 22 01:40:39 UTC 2019
Record UNII
HAX0H28B6W
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ORVEPITANT MALEATE
USAN  
USAN  
Official 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)-, (2Z)-2-BUTENEDIOATE (1:1)
Common Name English
GW823296B
Code English
GW-823296B
Code English
(2R,4S)-N-((1R)-1-(3,5-BIS(TRIFLUOROMETHYL)PHENYL)ETHYL)-2-(4-FLUORO-2-METHYLPHENYL)-N-METHYL-4-((8AS)-6-OXOHEXAHYDROPYRROLO(1,2-A)PYRAZIN-2(1H)-YL)PIPERIDINE-1-CARBOXAMIDE HYDROGEN MONO((2Z)-BUT-2-ENEDIOATE)
Common Name English
ORVEPITANT MALEATE [USAN]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C265
Created by admin on Tue Oct 22 01:40:40 UTC 2019 , Edited by admin on Tue Oct 22 01:40:40 UTC 2019
NCI_THESAURUS C28197
Created by admin on Tue Oct 22 01:40:40 UTC 2019 , Edited by admin on Tue Oct 22 01:40:40 UTC 2019
Code System Code Type Description
PUBCHEM
44225656
Created by admin on Tue Oct 22 01:40:40 UTC 2019 , Edited by admin on Tue Oct 22 01:40:40 UTC 2019
PRIMARY
ChEMBL
CHEMBL2105667
Created by admin on Tue Oct 22 01:40:40 UTC 2019 , Edited by admin on Tue Oct 22 01:40:40 UTC 2019
PRIMARY
NCI_THESAURUS
C90614
Created by admin on Tue Oct 22 01:40:40 UTC 2019 , Edited by admin on Tue Oct 22 01:40:40 UTC 2019
PRIMARY
CAS
579475-24-4
Created by admin on Tue Oct 22 01:40:40 UTC 2019 , Edited by admin on Tue Oct 22 01:40:40 UTC 2019
PRIMARY
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ACTIVE MOIETY