U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry RACEMIC
Molecular Formula C21H26ClN3O2
Molecular Weight 387.903
Optical Activity ( + / - )
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of NEMONAPRIDE

SMILES

CNC1=C(Cl)C=C(C(=O)N[C@@H]2CCN(CC3=CC=CC=C3)[C@@H]2C)C(OC)=C1

InChI

InChIKey=KRVOJOCLBAAKSJ-RDTXWAMCSA-N
InChI=1S/C21H26ClN3O2/c1-14-18(9-10-25(14)13-15-7-5-4-6-8-15)24-21(26)16-11-17(22)19(23-2)12-20(16)27-3/h4-8,11-12,14,18,23H,9-10,13H2,1-3H3,(H,24,26)/t14-,18-/m1/s1

HIDE SMILES / InChI

Molecular Formula C21H26ClN3O2
Molecular Weight 387.903
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

Nemonapride, benzamide derivative (YM-09151-2) is essentially a typical antipsychotic drug, similar in structure to sulpiride. This drug was manufactured by Yamanouchi Pharmaceuticals and released in Japan. The mechanism of action of nemonapride is not proven, but its unique antipsychotic effect arises from its selective binding to the dopamine D2 receptor family. Since nemonapride has high affinity for D3 and D4 dopamine receptors, it is conceivable that its effect on negative symptoms might result from blockade of these receptors. Animal studies have suggested that nemonapride has pharmacological features that are different from those of typical neuroleptics. The low extrapyramidal side effect profile of nemonapride treatment appears to coincide with the characteristic features of another benzamide derivative, remoxipride.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Emilace

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Patents

Sample Use Guides

The fixed dose (18 mg/day) of nemonapride was administered to each patient for 3 weeks.
Route of Administration: Oral
In Vitro Use Guide
Curator's Comment: 5-HT1A receptor activation was examined in vitro, by measuring forskolin-stimulated cAMP accumulation in HeLa cells expressing human 5-HT1A receptors. Nemonapride markedly decreased both forskolin-stimulated cAMP accumulation and the extracellular concentration of 5-HT; both effects were antagonized by the 5-HT1A receptor antagonist, N-[2-[4-(2-methoxyphenyl)-1-piperazinyl]ethyl]-N-(2-pyridinyl) cyclohexanecarboxamide (WAY100635).
Unknown
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:55:49 GMT 2023
Edited
by admin
on Fri Dec 15 15:55:49 GMT 2023
Record UNII
Q88T5P3444
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
NEMONAPRIDE
INN   JAN   MART.   MI   WHO-DD  
INN  
Official Name English
NEMONAPRIDE [MI]
Common Name English
nemonapride [INN]
Common Name English
(±)-CIS-N-(1-BENZYL-2-METHYL-3-PYRROLIDINYL)-5-CHLORO-4-(METHYLAMINO)-O-ANISAMIDE
Common Name English
NEMONAPRIDE [JAN]
Common Name English
NEMONAPRIDE [MART.]
Common Name English
BENZAMIDE, 5-CHLORO-2-METHOXY-4-(METHYLAMINO)-N-(2-METHYL-1- (PHENYLMETHYL)-3-PYRROLIDINYL)-, CIS-(±)-
Common Name English
EMONAPRIDE
Common Name English
EMILACE
Brand Name English
Nemonapride [WHO-DD]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C66883
Created by admin on Fri Dec 15 15:55:49 GMT 2023 , Edited by admin on Fri Dec 15 15:55:49 GMT 2023
NCI_THESAURUS C29710
Created by admin on Fri Dec 15 15:55:49 GMT 2023 , Edited by admin on Fri Dec 15 15:55:49 GMT 2023
Code System Code Type Description
EVMPD
SUB09191MIG
Created by admin on Fri Dec 15 15:55:49 GMT 2023 , Edited by admin on Fri Dec 15 15:55:49 GMT 2023
PRIMARY
NCI_THESAURUS
C73036
Created by admin on Fri Dec 15 15:55:49 GMT 2023 , Edited by admin on Fri Dec 15 15:55:49 GMT 2023
PRIMARY
ChEMBL
CHEMBL20734
Created by admin on Fri Dec 15 15:55:49 GMT 2023 , Edited by admin on Fri Dec 15 15:55:49 GMT 2023
PRIMARY
MESH
C030265
Created by admin on Fri Dec 15 15:55:49 GMT 2023 , Edited by admin on Fri Dec 15 15:55:49 GMT 2023
PRIMARY
MERCK INDEX
m7801
Created by admin on Fri Dec 15 15:55:49 GMT 2023 , Edited by admin on Fri Dec 15 15:55:49 GMT 2023
PRIMARY Merck Index
SMS_ID
100000084151
Created by admin on Fri Dec 15 15:55:49 GMT 2023 , Edited by admin on Fri Dec 15 15:55:49 GMT 2023
PRIMARY
INN
6430
Created by admin on Fri Dec 15 15:55:49 GMT 2023 , Edited by admin on Fri Dec 15 15:55:49 GMT 2023
PRIMARY
FDA UNII
Q88T5P3444
Created by admin on Fri Dec 15 15:55:49 GMT 2023 , Edited by admin on Fri Dec 15 15:55:49 GMT 2023
PRIMARY
WIKIPEDIA
NEMONAPRIDE
Created by admin on Fri Dec 15 15:55:49 GMT 2023 , Edited by admin on Fri Dec 15 15:55:49 GMT 2023
PRIMARY
PUBCHEM
156333
Created by admin on Fri Dec 15 15:55:49 GMT 2023 , Edited by admin on Fri Dec 15 15:55:49 GMT 2023
PRIMARY
CAS
93664-94-9
Created by admin on Fri Dec 15 15:55:49 GMT 2023 , Edited by admin on Fri Dec 15 15:55:49 GMT 2023
SUPERSEDED
DRUG CENTRAL
1895
Created by admin on Fri Dec 15 15:55:49 GMT 2023 , Edited by admin on Fri Dec 15 15:55:49 GMT 2023
PRIMARY
CHEBI
31899
Created by admin on Fri Dec 15 15:55:49 GMT 2023 , Edited by admin on Fri Dec 15 15:55:49 GMT 2023
PRIMARY
CAS
75272-39-8
Created by admin on Fri Dec 15 15:55:49 GMT 2023 , Edited by admin on Fri Dec 15 15:55:49 GMT 2023
PRIMARY
Related Record Type Details
ACTIVE MOIETY