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

• ChemBase ID: 544
• Molecular Formular: C21H28N2O5
• Molecular Mass: 388.45742
• Monoisotopic Mass: 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

NAMES AND DATABASE IDS

Names

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

Database IDs

• CAS Number: 138-56-7
• PubChem SID: 160964007; 46507787
• PubChem CID: 5577
• CHEBI ID: 27796
• CHEMBL: 1201256
• Chemspider ID: 5375
• DrugBank ID: DB00662
• Unique Ingredient Identifier: W2X096QY97
• Wikipedia Title: Trimethobenzamide
• Medline Plus: a682693

CALCULATED PROPERTIES

JChem

• Acid pKa: 14.3617935
• H Acceptors: 6
• H Donor: 1
• LogD (pH = 5.5): -0.9106402
• LogD (pH = 7.4): 0.77358747
• Log P: 2.1599948
• Molar Refractivity: 108.5176 cm^3
• Polarizability: 41.72525 Å^3
• Polar Surface Area: 69.26 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 2.44
• LOG S: -3.99
• Solubility (Water): 3.98e-02 g/l

PROPERTIES

Physical Property

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

Pharmacology Properties

• Admin Routes: Oral, rectal, intramuscular
• Half Life: 7 to 9 hours (mean)
• Legal Status: Rx-only (US)

DETAILS

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

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