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

• ChemBase ID: 1102
• Molecular Formular: C14H22ClN3O2
• Molecular Mass: 299.79638
• Monoisotopic Mass: 299.14005464
• SMILES: Clc1cc(C(=O)NCCN(CC)CC)c(OC)cc1N
• Canonical SMILES: CCN(CCNC(=O)c1cc(Cl)c(cc1OC)N)CC
• 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)
• InChIKey: TTWJBBZEZQICBI-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-amino-5-chloro-N-[2-(diethylamino)ethyl]-2-methoxybenzamide
• IUPAC Traditional name: metoclopramide
• Brand Name: Metocobil; Metramid; Moriperan; Mygdalon; Neu-Sensamide; Nu-Metoclopramide; Octamide; Parmid; Paspertin; Peraprin; Plasil; Pms-Metoclopramide; Pramiel; Pramin; Primperan; Reclomide; Reglan; Reliveran; Terperan; Emitasol; Pramidin; Apo-Metoclop; Cerucal; Clopra; Clopra-Yellow; Clopromate; DEL; Duraclamid; Elieten; Emetid; Emperal; Eucil; Gastrese; Gastro-Timelets; Gastrobid; Gastromax; Gastronerton; Gastrosil; Gastrotablinen; Gastrotem; Imperan; Maxeran; Maxolon; Meclopran; Metamide; Metoclol; Metoclopramide Intensol; Metoclopramide Omega
• Synonyms: Metaclopramide; Metaclopromide; Methochlopramide; Methoclopramide; Metochlopramide; Metoclopramida [INN-Spanish]; Metoclopramide Hcl; Metoclopramide Hydrochloride; Metoclopramidum [INN-Latin]; metoclopramide; Metoclopramide; 4-Amino-5-chloro-N-[2-(diethylamino)ethyl]-2-methoxybenzamide; Methoxychloroprocainamide; Metoclopramide; 4-amino-5-chloro-N-[2-(diethylamino)ethyl]-2-methoxybenzamide; 甲氧氯普胺

Database IDs

• CAS Number: 364-62-5
• EC Number: 206-662-9
• MDL Number: MFCD00211338
• Beilstein Number: 1884366
• PubChem SID: 46505631; 160964565
• PubChem CID: 4168

CALCULATED PROPERTIES

JChem

• Acid pKa: 14.490737
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): -1.8242222
• LogD (pH = 7.4): -0.2508232
• Log P: 1.3972701
• Molar Refractivity: 83.5178 cm^3
• Polarizability: 31.281101 Å^3
• Polar Surface Area: 67.59 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 2.18
• LOG S: -2.99
• Solubility (Water): 3.10e-01 g/l

PROPERTIES

Physical Property

• Solubility: 200 mg/L
• Hydrophobicity(logP): 1.8; 2.229

Safety Information

• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22-64
• Safety Statements: 36/37
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302-H362
• GHS Precautionary statements: P263
• Storage Temperature: 2-8°C

Product Information

• Purity: 95%
• Grade: VETRANAL™, analytical standard
• Empirical Formula (Hill Notation): C14H22ClN3O2

DETAILS

DrugBank - DB01233

• Drug Groups: approved; investigational
• Description: A dopamine D2 antagonist that is used as an antiemetic. [PubChem]
• Indication: For the treatment of gastroesophageal reflux disease (GERD). It is also used in treating nausea and vomiting, and to increase gastric emptying.
• Pharmacology: Metoclopramide, although chemically related to procainamide, does not possess local anesthetic or antiarrhythmic properties. Metoclopramide is used to enhance GI motility, to treat diabetic gastroparesis, as an antinauseant, and to facilitate intubation of the small bowel during radiologic examination. Metoclopramide may be used to treat chemotherapy-induced emesis and as a radiosensitizing agents in the treatment of non-small cell lung carcinoma and glioblastomas in the future.
• Toxicity: Oral, mouse LD₅₀: 280 mg/kg. Signs of overdose include drowsiness, disorientation, and extrapyramidal reactions.
• Affected Organisms: Humans and other mammals
• Biotransformation: Hepatic
• Absorption: Rapidly and well absorbed (oral bioavailability 80±15.5%).
• Half Life: 5-6 hr
• Protein Binding: 30%
• Elimination: Approximately 85% of the radioactivity of an orally administered dose appears in the urine within 72 hours.
• Distribution: * 4.4±0.65 L/kg
• Clearance: * 0.67 +/- 0.14 L/hr/kg [infants (0.9-5.4 months) with gastroesophageal reflux (GER)]
• References: JUSTIN-BESANCON L, LAVILLE C: [ANTIEMETIC ACTION OF METOCLOPRAMIDE WITH RESPECT TO APOMORPHINE AND HYDERGINE.] C R Seances Soc Biol Fil. 1964;158:723-7. [Pubmed] ; Tonini M, Candura SM, Messori E, Rizzi CA: Therapeutic potential of drugs with mixed 5-HT4 agonist/5-HT3 antagonist action in the control of emesis. Pharmacol Res. 1995 May;31(5):257-60. [Pubmed]
• External Links: Wikipedia; RxList; PDRhealth; Drugs.com

Sigma Aldrich - 32473

Legal Information
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REFERENCES

• JUSTIN-BESANCON L, LAVILLE C: [ANTIEMETIC ACTION OF METOCLOPRAMIDE WITH RESPECT TO APOMORPHINE AND HYDERGINE.] C R Seances Soc Biol Fil. 1964;158:723-7. Pubmed
• Tonini M, Candura SM, Messori E, Rizzi CA: Therapeutic potential of drugs with mixed 5-HT4 agonist/5-HT3 antagonist action in the control of emesis. Pharmacol Res. 1995 May;31(5):257-60. Pubmed