UCSF

ZINC01530716

Substance Information

In ZINC since Heavy atoms Benign functionality
October 6th, 2004 20 Yes

Other Names:

"Metoclopramide hydrochloride, 99%"

(metaclopramide)4-Amino-5-chloro-N-(2-diethylamino-ethyl)-2-methoxy-benzamide

(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; 4-Amino-5-chloro-N-(2-diethylamino-ethyl)-2-meth

(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-4-amino-5-chloro-N,N-(dimethylaminoethyl)benzamide; 2-methoxy-5-chloroprocainamide; 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-(diethylamin

2-Methoxy-4-amino-5-chloro-N,N-dimethylaminoethyl)benzamide

2-methoxy-4-amino-5-chloro-N-(beta-(diethylamino)ethyl)benzamide dihydrochloride monohydrate; 4-amino-5-chloro-N-(2-(diethylamino)ethyl)-o-anisamide dihydrochloride monohydrate

2-Methoxy-5-chloroprocainamide

2576-84-3 (di-hydrochloride)

364-62-5

364-62-5; C07868; Metoclopramide

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)-2-methoxybenzamide monohydrochloride; 4-Amino-5-chloro-N-(2-(diethylamino)ethyl)-o-anisamide hydrochloride; Benzamide, 4-amino-5-chloro-N-(2-(diethylamino)ethyl)-2-methoxy-, monohydrochloride; C14H22ClN3O2.HCl; C

4-Amino-5-chloro-N-(2-(diethylamino)ethyl)-o-anisamide

4-Amino-5-chloro-N-(2-(diethylamino)ethyl)-o-anisamide monohydrochloride monohydrate; AHR-3070-C; Benzamide, 4-amino-5-chloro-N-(2-(diethylamino)ethyl)-2-methoxy-, monohydrochloride, monohydrate; C14H22ClN3O2.HCl; CLOPRA; CLOPRA-"YELLOW"; LS-175536; MAXOL

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

4-amino-5-chloro-N-[2-(diethylamino)ethyl]-2-methoxybenzamide dihydrochloride

5-Chloro-2-methoxyprocainamide

54143-57-6 (mono-hydrochloride, mono-hydrate)

54143-57-6; Clopra (TN); D05008; Metoclopramide hydrochloride (USAN); Metoclopramide hydrochloride monohydrate; Reglan (TN)

5581-45-3; D02213; Metoclopramide dihydrochloride monohydrate; Metoclopramide hydrochloride (JAN); Primperan (TN); Reglan (TN)

7232-21-5 (mono-hydrochloride)

7232-21-5; Metoclopramide monohydrochloride; Prestwick_332

AB00053498

AC1L1HKD

AHR-3070-C

AKOS000280832

Apo-Metoclop

ARONIS24307

Benzamide, 4-amino-5-chloro-N-(2-(diethylamino)ethyl)-2-methoxy-

Benzamide, 4-amino-5-chloro-N-(2-(diethylamino)ethyl)-2-methoxy- (9CI)

benzamide, 4-amino-5-chloro-N-[2-(diethylamino)ethyl]-2-methoxy-

Biomol-NT_000082

bmse000779

BPBio1_000217

BPBio1_001100

BRD-K75641298-001-01-5

BRD-K75641298-003-05-2

BRN 1884366

BSPBio_000197

BSPBio_002027

C07868

C14H22ClN3O2

CAS-7232-21-5

Cerucal

CHEBI:107736

CHEBI:6898

CHEMBL86

CID4168

Clopra

CLOPRA-"YELLOW"

Clopra-Yellow

Clopromate

CPD000058471; Maxolon; SAM002554911

CPD000058471; Metoclopramide hydrochloride; SAM002554911

D00726

DAP000530

DB01233

DEL

DEL 1267

DivK1c_000069

Duraclamid

EINECS 206-662-9

Elieten

Elieten (TN)

Elieten; Reliveran

Emetid

Emetid; Gastronerton; Primperan

Emitasol

Emperal

Eucil

Gastrese

Gastro-Timelets

Gastrobid

Gastromax

Gastronerton

Gastrosil

Gastrotablinen

Gastrotem

HMS2089G16

IDI1_000069

Imperan

INN

INN); Metoclopramide HCl (FDA

JAN

JAN); Metoclopramide HCl (FDA

JAN); Metoclopramide Hydrochloride (FDA

KBio1_000069

KBio2_002118

KBio2_004686

KBio2_007254

KBio3_001527

KBioGR_001307

KBioSS_002118

L001078

LS-190225

LS-20038

Maxeran

Maxolon

Meclopran

Metaclopramide

Metaclopramide;Metaclopromide;Methochlopramide;Methoclopramide;Metochlopramide;Metoclopramida [INN-Spanish];Metoclopramidum [INN-Latin]

Metaclopromide

Metamide

Methochlopramide

Methoclopramide

Metochlopramide

Metoclol

Metoclopramida

Metoclopramida [INN-Spanish]

metoclopramida; metoclopramide; metoclopramidum

Metoclopramide

Metoclopramide (BAN

Metoclopramide (JP15/INN)

metoclopramide dihydrochloride monohydrate

MetoclopraMide HCl

Metoclopramide HCl monohydrate

Metoclopramide Hydrochloride

Metoclopramide hydrochloride monohydrate

Metoclopramide Intensol

Metoclopramide monohydrochloride

Metoclopramide Monohydrochloride, Monohydrate

Metoclopramide Omega

Metoclopramide [INN:BAN:JAN]

Metoclopramidum

Metoclopramidum [INN-Latin]

Metocobil

Metramid

MFCD00058011

MFCD00150634

MFCD00211338

MolPort-000-883-854

Moriperan

Mygdalon

N-(Diethylaminoethyl)-2-methoxy-4-amino-5-chlorobenzamide

n-Anisamide, 4-amino-5-chloro-N-(2-(diethylamino)ethyl)-

N/A

NCGC00015643-01

NCGC00015643-02

NCGC00015643-03

NCGC00015643-08

NCGC00024440-03

NCGC00024440-04

NCI60_003185

Neu-Sensamide

NINDS_000069

Nu-Metoclopramide

o-Anisamide, 4-amino-5-chloro-N-(2-(diethylamino)ethyl)-

o-Anisamide, 4-amino-5-chloro-N-(2-(diethylamino)ethyl)- (8CI)

o-Anisamide, 4-amino-5-chloro-N-[2-(diethylamino)ethyl]-

Octamide

Parmid

Paspertin

Peraprin

Plasil

Plasil (pharmaceutical)

Pms-Metoclopramide

Pramidin

Pramiel

Pramin

Prestwick0_000209

Prestwick1_000209

Prestwick2_000209

Prestwick3_000209

Primperan

QA-6300

Reclomide

Reglan

Reliveran

SPBio_001740

SPBio_002118

Spectrum2_001720

Spectrum3_000504

Spectrum4_000964

Spectrum5_001449

Spectrum_001638

ST024773

Terperan

Terperan (TN)

UNII-L4YEB44I46

USAN

USP)

Download: MOL2 SDF SMILES Flexibase

Annotations

Vendors

Physical Representations

Type pH range xlogP Des A‑Pol Apolar desolvation (kcal/mol) Des Pol Polar desolvation (kcal/mol) H Don H-bond donors H Acc H-bond acceptors Chg Net charge tPSA (Ų) MWT Molecular weight (g/mol) RB Rotatable bonds DL
Ref Reference (pH 7) 2.54 5.3 -40.76 4 5 1 69 300.81 7

Vendor Notes

Note Type Comments Provided By
ALOGPS_SOLUBILITY 3.10e-01 g/l DrugBank-approved
Therapy 5-HT3 Serotonin receptor antagonist; D2 dopamine receptor antagonist; anti-emetic SMDC Iconix
purity 9.500000000000000e+001 Enamine Building Blocks Enamine Building Blocks
therap antiemetic MicroSource Spectrum
Indications antiemetic, gastroesophageal reflux disease (GERD) KeyOrganics Bioactives
Indications antiemetic, gastroprokinetic KeyOrganics Bioactives
Target Dopamine Receptor Selleck Chemicals
PUBCHEM_SUBSTANCE_COMMENT NCC_SAMPLE_SUPPLIER : LightBiologicals; NCC_SUPPLIER_STRUCTURE_ID : M-6903; NCC_SUPPLIER_SAMPLE_COMMENTS : OFF-WHITE POWDER; 1 hydrogen chloride NIH Clinical Collection via PubChem
UniProt Database Links OAR1_LOCMI ChEBI
PUBCHEM_SUBSTANCE_COMMENT SAMPLE_SUPPLIER: LightBiologicals; SUPPLIER_STRUCTURE_ID: M-6903; SALT: 1 hydrogen chloride; SUPPLIER_COMMENTS: OFF-WHITE POWDER NIH Clinical Collection via PubChem

Activity (Go SEA)

Clustered Target Annotations
Code Description Organism Class Affinity (nM) LE (kcal/mol/atom) Type
5HT1A-1-E Serotonin 1a (5-HT1a) Receptor (cluster #1 Of 4), Eukaryotic Eukaryotes 7800 0.36 Binding ≤ 10μM
5HT1B-1-E Serotonin 1b (5-HT1b) Receptor (cluster #1 Of 2), Eukaryotic Eukaryotes 7800 0.36 Binding ≤ 10μM
5HT1D-1-E Serotonin 1d (5-HT1d) Receptor (cluster #1 Of 2), Eukaryotic Eukaryotes 7800 0.36 Binding ≤ 10μM
5HT1F-1-E Serotonin 1f (5-HT1f) Receptor (cluster #1 Of 2), Eukaryotic Eukaryotes 7800 0.36 Binding ≤ 10μM
5HT3A-1-E Serotonin 3a (5-HT3a) Receptor (cluster #1 Of 5), Eukaryotic Eukaryotes 995 0.42 Binding ≤ 10μM
5HT3B-2-E Serotonin 3b (5-HT3b) Receptor (cluster #2 Of 4), Eukaryotic Eukaryotes 995 0.42 Binding ≤ 10μM
5HT4R-1-E Serotonin 4 (5-HT4) Receptor (cluster #1 Of 1), Eukaryotic Eukaryotes 975 0.42 Binding ≤ 10μM
ADA2A-1-E Alpha-2a Adrenergic Receptor (cluster #1 Of 4), Eukaryotic Eukaryotes 7700 0.36 Binding ≤ 10μM
ADA2B-1-E Alpha-2b Adrenergic Receptor (cluster #1 Of 4), Eukaryotic Eukaryotes 7700 0.36 Binding ≤ 10μM
ADA2C-1-E Alpha-2c Adrenergic Receptor (cluster #1 Of 4), Eukaryotic Eukaryotes 7700 0.36 Binding ≤ 10μM
DRD3-1-E Dopamine D3 Receptor (cluster #1 Of 2), Eukaryotic Eukaryotes 27 0.53 Binding ≤ 10μM
5HT4R-1-E Serotonin 4 (5-HT4) Receptor (cluster #1 Of 1), Eukaryotic Eukaryotes 1920 0.40 Functional ≤ 10μM
CP2D6-1-E Cytochrome P450 2D6 (cluster #1 Of 3), Eukaryotic Eukaryotes 960 0.42 ADME/T ≤ 10μM
DRD2-3-E Dopamine D2 Receptor (cluster #3 Of 24), Eukaryotic Eukaryotes 820 0.43 Binding ≤ 10μM
ChEMBL Target Annotations
Uniprot Swissprot Description Affinity (nM) LE (kcal/mol/atom) Type
DRD2_RAT P61169 Dopamine D2 Receptor, Rat 104 0.49 Binding ≤ 1μM
DRD2_BOVIN P20288 Dopamine D2 Receptor, Bovin 80 0.50 Binding ≤ 1μM
DRD3_HUMAN P35462 Dopamine D3 Receptor, Human 27 0.53 Binding ≤ 1μM
DRD3_RAT P19020 Dopamine D3 Receptor, Rat 61.3 0.50 Binding ≤ 1μM
5HT3A_RAT P35563 Serotonin 3a (5-HT3a) Receptor, Rat 210 0.47 Binding ≤ 1μM
5HT3A_MOUSE P23979 Serotonin 3a (5-HT3a) Receptor, Mouse 200 0.47 Binding ≤ 1μM
5HT3B_RAT Q9JJ16 Serotonin 3b (5-HT3b) Receptor, Rat 210 0.47 Binding ≤ 1μM
5HT3B_MOUSE Q9JHJ5 Serotonin 3b (5-HT3b) Receptor, Mouse 200 0.47 Binding ≤ 1μM
5HT4R_RAT Q62758 Serotonin 4 (5-HT4) Receptor, Rat 900 0.42 Binding ≤ 1μM
5HT4R_HUMAN Q13639 Serotonin 4 (5-HT4) Receptor, Human 546 0.44 Binding ≤ 1μM
ADA2A_RAT P22909 Alpha-2a Adrenergic Receptor, Rat 7700 0.36 Binding ≤ 10μM
ADA2B_RAT P19328 Alpha-2b Adrenergic Receptor, Rat 7700 0.36 Binding ≤ 10μM
ADA2C_RAT P22086 Alpha-2c Adrenergic Receptor, Rat 7700 0.36 Binding ≤ 10μM
DRD2_BOVIN P20288 Dopamine D2 Receptor, Bovin 80 0.50 Binding ≤ 10μM
DRD2_RAT P61169 Dopamine D2 Receptor, Rat 104 0.49 Binding ≤ 10μM
DRD3_RAT P19020 Dopamine D3 Receptor, Rat 61.3 0.50 Binding ≤ 10μM
DRD3_HUMAN P35462 Dopamine D3 Receptor, Human 27 0.53 Binding ≤ 10μM
5HT1A_RAT P19327 Serotonin 1a (5-HT1a) Receptor, Rat 7800 0.36 Binding ≤ 10μM
5HT1B_RAT P28564 Serotonin 1b (5-HT1b) Receptor, Rat 7800 0.36 Binding ≤ 10μM
5HT1D_RAT P28565 Serotonin 1d (5-HT1d) Receptor, Rat 7800 0.36 Binding ≤ 10μM
5HT1F_RAT P30940 Serotonin 1f (5-HT1f) Receptor, Rat 7800 0.36 Binding ≤ 10μM
5HT3A_MOUSE P23979 Serotonin 3a (5-HT3a) Receptor, Mouse 200 0.47 Binding ≤ 10μM
5HT3A_RAT P35563 Serotonin 3a (5-HT3a) Receptor, Rat 210 0.47 Binding ≤ 10μM
5HT3B_RAT Q9JJ16 Serotonin 3b (5-HT3b) Receptor, Rat 210 0.47 Binding ≤ 10μM
5HT3B_MOUSE Q9JHJ5 Serotonin 3b (5-HT3b) Receptor, Mouse 200 0.47 Binding ≤ 10μM
5HT4R_RAT Q62758 Serotonin 4 (5-HT4) Receptor, Rat 900 0.42 Binding ≤ 10μM
5HT4R_HUMAN Q13639 Serotonin 4 (5-HT4) Receptor, Human 546 0.44 Binding ≤ 10μM
5HT4R_HUMAN Q13639 Serotonin 4 (5-HT4) Receptor, Human 5.7 0.58 Functional ≤ 10μM
5HT4R_RAT Q62758 Serotonin 4 (5-HT4) Receptor, Rat 1920 0.40 Functional ≤ 10μM
CP2D6_HUMAN P10635 Cytochrome P450 2D6, Human 960 0.42 ADME/T ≤ 10μM

Reactome Annotations from Targets (via Uniprot)

Description Species
Adrenaline signalling through Alpha-2 adrenergic receptor
Adrenaline,noradrenaline inhibits insulin secretion
Adrenoceptors
CYP2E1 reactions
Dopamine receptors
Fatty acids
G alpha (i) signalling events
G alpha (s) signalling events
G alpha (z) signalling events
Miscellaneous substrates
Serotonin receptors
Xenobiotics

Analogs ( Draw Identity 99% 90% 80% 70% )