General Information of the Compound
Compound ID
CP0025100
Compound Name
4-amino-5-chloro-N-[2-(diethylamino)ethyl]-2-methoxy-benzamide;hydrochloride
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Synonyms
(metaclopramide)4-Amino-5-chloro-N-(2-diethylamino-ethyl)-2-methoxy-benzamide
(metoclopramide)4-Amino-5-chloro-N-(2-diethylamino-ethyl)-2-methoxy-benzamide
1,5-Dimethyl-2-phenyl-1,2-dihydro-pyrazol-3-one
2-Methoxy-4-amino-5-chloro-N,N-dimethylaminoethyl)benzamide
2-Methoxy-5-chloroprocainamide
2-methoxy-4-amino-5-chloro-N,N-(dimethylaminoethyl)benzamide
4 Amino-5-chloro-N-(2-(diethylamino)ethyl)-2-methoxybenzamide
4-Amino-5-chloro-2-methoxy-N-(beta-diethylaminoethyl)benzamide
4-Amino-5-chloro-N-(2-(diethylamino)ethyl)-2-methoxybenzamide
4-Amino-5-chloro-N-(2-(diethylamino)ethyl)-o-anisamide
4-Amino-5-chloro-N-(2-diethylamino-ethyl)-2-methoxy-benzamide
4-Amino-5-chloro-N-(2-diethylamino-ethyl)-2-methoxy-benzamide (Mcp)
4-Amino-5-chloro-N-(2-diethylamino-ethyl)-2-methoxy-benzamide (metoclopramide)
4-Amino-5-chloro-N-(2-diethylamino-ethyl)-2-methoxy-benzamide(Metoclopramide)
4-amino-5-chloro-N-(2-diethylaminoethyl)-2-methoxybenzamide
4-amino-5-chloro-N-[2-(diethylamino)ethyl]-2-methoxybenzamide
5-Chloro-2-methoxyprocainamide
Apo-Metoclop
Benzamide, 4-amino-5-chloro-N-(2-(diethylamino)ethyl)-2-methoxy-(9CI)
CLOPRA-YELLOW
Cerucal
Clopra
Clopra-Yellow
Clopromate
DEL 1267
Degan (TN)
Duraclamid
Elieten
Elieten (TN)
Emetid
Emitasol
Emperal
Eucil
Gastrese
Gastro-Timelets
Gastrobid
Gastromax
Gastronerton
Gastrosil
Gastrotablinen
Gastrotem
Imperan
Maxeran
Maxeran (TN)
Maxolon
Maxolon (TN)
Meclopran
Metaclopramide
Metaclopromide
Metamide
Methochlopramide
Methoclopramide
Metochlopramide
Metoclol
Metoclopramida
Metoclopramida [INN-Spanish]
Metoclopramide
Metoclopramide (JP15/INN)
Metoclopramide Monohydrochloride, Monohydrate
Metoclopramide Omega
Metoclopramide [INN:BAN:JAN]
Metoclopramidum
Metoclopramidum [INN-Latin]
Metocobil
Metramid
Moriperan
Mygdalon
N-(Diethylaminoethyl)-2-methoxy-4-amino-5-chlorobenzamide
Neu-Sensamide
Nu-Metoclopramide
O-Anisamide, 4-amino-5-chloro-N-(2-(diethylamino)ethyl)-(8CI)
Octamide
Parmid
Paspertin
Peraprin
Plasil
Plasil (pharmaceutical)
Pms-Metoclopramide
Pramidin
Pramiel
Pramin
Primperan
Primperan (TN)
Pylomid (TN)
Reclomide
Reglan
Reglan (TN)
Reliveran
Terperan
Terperan (TN)
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Structure
Formula
C14H22ClN3O2
Molecular Weight
299.802
Canonical SMILES
CCN(CC)CCNC(=O)c1cc(Cl)c(N)cc1OC
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InChI
InChI=1S/C14H22ClN3O2/c1-4-18(5-2)7-6-17-14(19)10-8-11(15)12(16)9-13(10)20-3/h8-9H,4-7,16H2,1-3H3,(H,17,19)
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InChIKey
TTWJBBZEZQICBI-UHFFFAOYSA-N
CAS
364-62-5
Physicochemical Property
logP
2.0024
Rotatable Bonds
7
Heavy Atom Count
20
Polar Areas
67.59
Hydrogen Bond Donor Count
2
Hydrogen Bond Acceptor Count
4
Complexity
20

"RO5" indicates the cutoff set by lipinski's rule of five:

(1) Molecular weight less than 500 Dalton;

(2) xlogp less than 5;

(3) No more than 5 hbonddonor (Hydrogen Bond Donor Count);

(4) No more than 10 hbondacc (Hydrogen Bond Acceptor Count);

(5) No more than 10 rotbonds (Rotatable Bond Count).

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PubChem ID
CID: 4168
SID: 14873753
ChEMBL ID
CHEMBL86
DrugBank ID
DB01233
Map of Molecular Bioactivity Related to the Compound
Map of Molecular Bioactivity Related to the Compound

Compound
Cell Line
Protein

Bioactivity Value:

<= 0.1 μM
> 0.1 μM and <= 10 μM
> 10 μM
Imprecise Activity
Table of Molecular Bioactivities Related to the Compound
Protein ID: PT00817, Cytochrome P450 2D6
Cell-based Assay
Cell Line ID Cell Line Name Cell Line Organism
CL000023 BTI-Tn-5B1-4 Trichoplusia ni (Cabbage looper)  1
1
IC50 = 800 nM
   TI
   LI
   LO
   TS
Biochemical Assays
1 Ki = 960 nM
Protein ID: PT00943, D(3) dopamine receptor
Cell-based Assay
Cell Line ID Cell Line Name Cell Line Organism
CL000011 CHO Cricetulus griseus (Chinese hamster)  1
1
Ki = 27 nM
   TI
   LI
   LO
   TS
Protein ID: PT03795, Solute carrier family 22 member 1
Cell-based Assay
Cell Line ID Cell Line Name Cell Line Organism
CL000006 HEK293 Homo sapiens (Human)  1
1
IC50 = 94800 nM
   TI
   LI
   LO
   TS
Clinical Information about the Compound
Drug 1 ( Metoclopramide )
Drug Name Metoclopramide
Company Sanofi-Aventis
Indication
Nausea
Approved
Target(s)
Dopamine D2 receptor (D2R)
Antagonist