N-({4-[2-(dimethylamino)ethoxy]phenyl}methyl)-3,4,5-trimethoxybenzamide

• ChemBase编号: 544
• 分子式: C21H28N2O5
• 平均质量: 388.45742
• 单一同位素质量: 388.19982201
• SMILES: O(CCN(C)C)c1ccc(CNC(=O)c2cc(OC)c(OC)c(OC)c2)cc1
• Canonical SMILES: COc1cc(cc(c1OC)OC)C(=O)NCc1ccc(cc1)OCCN(C)C
• InChI: InChI=1S/C21H28N2O5/c1-23(2)10-11-28-17-8-6-15(7-9-17)14-22-21(24)16-12-18(25-3)20(27-5)19(13-16)26-4/h6-9,12-13H,10-11,14H2,1-5H3,(H,22,24)
• InChIKey: FEZBIKUBAYAZIU-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: N-({4-[2-(dimethylamino)ethoxy]phenyl}methyl)-3,4,5-trimethoxybenzamide
• IUPAC传统名: trimethobenzamide
• 商标名: Ametik hydrochloride; Benzacot; Nauseton; Stemetic; Tebamide; Tigan; Tribenzagan; Trimazide
• 别名: Trimethobenzamide hydrochloride; Trimethobenzamide HCL; Trimethobenzamidum [INN-Latin]; Trimetobenzamida [INN-Spanish]; Trimethobenzamide

登记号

• CAS号: 138-56-7
• PubChem SID: 160964007; 46507787
• PubChem CID: 5577
• CHEBI ID: 27796
• CHEMBL: 1201256
• Chemspider ID: 5375
• DrugBank ID: DB00662
• 美国药典/FDA物质标识码: W2X096QY97
• 维基百科标题: Trimethobenzamide
• Medline Plus: a682693

理论计算性质

JChem

• Acid pKa: 14.3617935
• 质子受体: 6
• 质子供体: 1
• LogD (pH = 5.5): -0.9106402
• LogD (pH = 7.4): 0.77358747
• Log P: 2.1599948
• 摩尔折射率: 108.5176 cm^3
• 极化性: 41.72525 Å^3
• 极化表面积: 69.26 Å^2
• 可自由旋转的化学键: 10
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: 2.44
• LOG S: -3.99
• 溶解度: 3.98e-02 g/l

分子性质

理化性质

• 溶解度: 40 mg/L
• 疏水性(logP): 2.2

药理学性质

• 给药途径: Oral, rectal, intramuscular
• 半衰期: 7 to 9 hours (mean)
• 法定药品分级: Rx-only (US)

详细说明

DrugBank - DB00662

• Drug Groups: approved
• Description: Trimethobenzamide is a novel antiemetic which prevents nausea and vomiting in humans. Its actions are unclear but most likely involves the chemoreceptor trigger zone (CTZ). In dogs pretreated with trimethobenzamide HCl, the emetic response to apomorphine is inhibited, while little or no protection is afforded against emesis induced by intragastric copper sulfate.
• Indication: For the treatment of postoperative nausea and vomiting and for nausea associated with gastroenteritis.
• Pharmacology: Trimethobenzamide is a novel antiemetic which prevents nausea and vomiting in humans. Its actions are unclear but most likely involves the chemoreceptor trigger zone (CTZ). In dogs pretreated with trimethobenzamide HCl, the emetic response to apomorphine is inhibited, while little or no protection is afforded against emesis induced by intragastric copper sulfate.
• Toxicity: Oral LD₅₀ in mice is 1600 mg/kg.
• Affected Organisms: Humans and other mammals
• Biotransformation: Hepatic.
• Absorption: The relative bioavailability of the capsule formulation compared to the solution is 100%.
• Half Life: The mean elimination half-life of trimethobenzamide is 7 to 9 hours.
• Elimination: Between 30 – 50% of a single dose in humans is excreted unchanged in the urine within 48–72 hours.
• References: Hurley JD, Eshelman FN: Trimethobenzamide HCl in the treatment of nausea and vomiting associated with antineoplastic chemotherapy. J Clin Pharmacol. 1980 May-Jun;20(5-6 Pt 1):352-6. [Pubmed] ; Hurley JD, Eshelman FN: Trimethobenzamide HCl in the treatment of nausea and vomiting associated with antineoplastic chemotherapy. J Clin Pharmacol. 1980 May-Jun;20(5-6 Pt 1):352-6. [Pubmed] ; Dundee JW, Halliday F, Nicholl RM, Moore J: Studies of drugs given before anaesthesia. X. Two non-phenothiazine anti-emetics--cyclizine and trimethobenzamide. Br J Anaesth. 1966 Jan;38(1):50-7. [Pubmed]
• External Links: Wikipedia; RxList; PDRhealth; Drugs.com

参考文献

• Hurley JD, Eshelman FN: Trimethobenzamide HCl in the treatment of nausea and vomiting associated with antineoplastic chemotherapy. J Clin Pharmacol. 1980 May-Jun;20(5-6 Pt 1):352-6. Pubmed
• Hurley JD, Eshelman FN: Trimethobenzamide HCl in the treatment of nausea and vomiting associated with antineoplastic chemotherapy. J Clin Pharmacol. 1980 May-Jun;20(5-6 Pt 1):352-6. Pubmed
• Dundee JW, Halliday F, Nicholl RM, Moore J: Studies of drugs given before anaesthesia. X. Two non-phenothiazine anti-emetics--cyclizine and trimethobenzamide. Br J Anaesth. 1966 Jan;38(1):50-7. Pubmed