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

ID: ALA86

Chembl Id: CHEMBL86

Cas Number: 364-62-5

PubChem CID: 4168

Product Number: M124440

Max Phase: Approved

First Approval: 1979

Molecular Formula: C14H22ClN3O2

Molecular Weight: 299.80

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Clopra | Clopra-"Yellow" | Elieten | Maxolon | Methoxyclopramide | Metoclopramide | Reglan | Terperan | metoclopramide|364-62-5|Methochlopramide|Metochlopramide|Metaclopramide|Reliveran|Primperan|Metaclopromide|Elieten|Reglan|Metoclol|Moriperan|Terperan|Plasil|Metoclopramida|Metoclopramidum|2-Methoxy-5-chloroprocainamide|Maxolon|4-Amino-5-chloro-N-(2-(diethylamino)ethyl)-2-methoxybenzamide|Plasil (pharmaceutical)|4-amino-5-chloro-N-[2-(diethylamino)ethyl]-2-methoxybenzamide|Methoclopramide|5-ChlShow More⌵

Synonyms from Alternative Forms(29): Metoclopramide hydrochloride | Metoclopramide monohydrochloride monohydrate | Metipamid | Metoclopramide dihydrochloride monohydrate | Metoclopramide hcl monohydrate | Metoclopramide hydrochloride monohydrate | Metoclopramidi hydrochloridum | AHR-3070-C | NSC-757117 | "clopra-""yellow""" | Clopra | Clopra-"Yellow" | Gastrese l.a. | Gastrobid continus | Gastroflux | Gastromax | Gimoti | Maxolon | Maxolon sr | Metoclomex | Metoclopramide intensol | Metox | Metozolv odt | Metramid | Mygdalon | Parmid | Primperan | Reglan | Reglan odt

Canonical SMILES:  CCN(CC)CCNC(=O)c1cc(Cl)c(N)cc1OC

Standard 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)

Standard InChI Key:  TTWJBBZEZQICBI-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA86

   METOCLOPRAMIDE

2. Alternative Forms:

   

   ALA86

   metoclopramide hydrochloride
3. 

   ALA86

   Metoclopramide hydrochloride

Molecule Features

Natural Product: Yes

Oral: Yes

Chemical Probe: No

Parenteral: Yes

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: Yes

Chirality: Yes

Availability: Yes

Prodrug: No

Calculated Properties

Molecular Weight: 299.80

Molecular Weight (Monoisotopic): 299.1401

AlogP: 2.00

#Rotatable Bonds: 7

Polar Surface Area: 67.59

Molecular Species: BASE

HBA: 4

HBD: 2

#RO5 Violations: 0

HBA (Lipinski): 5

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 0

CX Acidic pKa:

CX Basic pKa: 9.04

CX LogP: 1.40

CX LogD: -0.25

Aromatic Rings: 1

Heavy Atoms: 20

QED Weighted: 0.76

Np Likeness Score: -1.54

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Source

Source(11):

• Scientific Literature
• PubChem BioAssays
• Clinical Candidates
• DrugMatrix
• AstraZeneca Deposited Data
• BindingDB Database
• WHO Anatomical Therapeutic Chemical Classification
• SARS-CoV-2 Screening Data 2020-21
• IMI-CARE SARS-CoV-2 Data
• Fraunhofer HDAC6
• Zimmerman Lab Biotransformation data Dec 2023