Trimethobenzamide

• Catalog No.: DB00662
• CAS Number: 138-56-7
• M. F.: C21H28N2O5
• M. W.: 388.45742

SYNONYMS

• IUPAC name: N-({4-[2-(dimethylamino)ethoxy]phenyl}methyl)-3,4,5-trimethoxybenzamide
• IUPAC Traditional name: trimethobenzamide
• Brand Name: Tigan; Nauseton; Ametik hydrochloride; Benzacot; Stemetic; Tebamide; Tribenzagan; Trimazide
• Synonyms: Trimetobenzamida [INN-Spanish]; Trimethobenzamide HCL; Trimethobenzamide hydrochloride; Trimethobenzamidum [INN-Latin]

DATABASE IDS

• PubChem CID: 5577
• CAS Number: 138-56-7
• PubChem SID: 46507787

PROPERTIES

• Hydrophobicity(logP): 2.2
• Solubility: 40 mg/L

DETAILS

Description (English)

• 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

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