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

• ChemBase编号: 1102
• 分子式: C14H22ClN3O2
• 平均质量: 299.79638
• 单一同位素质量: 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

名称和登记号

名称

• IUPAC标准名: 4-amino-5-chloro-N-[2-(diethylamino)ethyl]-2-methoxybenzamide
• IUPAC传统名: metoclopramide
• 商标名: 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
• 别名: 甲氧氯普胺; 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

登记号

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

理论计算性质

JChem

• Acid pKa: 14.490737
• 质子受体: 4
• 质子供体: 2
• LogD (pH = 5.5): -1.8242222
• LogD (pH = 7.4): -0.2508232
• Log P: 1.3972701
• 摩尔折射率: 83.5178 cm^3
• 极化性: 31.281101 Å^3
• 极化表面积: 67.59 Å^2
• 可自由旋转的化学键: 7
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: 2.18
• LOG S: -2.99
• 溶解度: 3.10e-01 g/l

分子性质

理化性质

• 溶解度: 200 mg/L
• 疏水性(logP): 1.8; 2.229

安全信息

• 欧盟危险性物质标志: 有害性(Harmful) (Xn)
• 德国WGK号: 3
• 危险公开号: 22-64
• 安全公开号: 36/37
• GHS危险品标识: GHS07
• GHS警示词: Warning
• GHS危险声明: H302-H362
• GHS警示性声明: P263
• 保存温度: 2-8°C

产品相关信息

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

详细说明

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

法律信息
VETRANAL 商标 Sigma-Aldrich Co. LLC

参考文献

• 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