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138-56-7 molecular structure
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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 and InChIs

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

Cite this record

CBID:544 http://www.chembase.cn/molecule-544.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

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

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID Price

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 14.3617935  H Acceptors
H Donor LogD (pH = 5.5) -0.9106402 
LogD (pH = 7.4) 0.77358747  Log P 2.1599948 
Molar Refractivity 108.5176 cm3 Polarizability 41.72525 Å3
Polar Surface Area 69.26 Å2 Rotatable Bonds 10 
Lipinski's Rule of Five true 
Log P 2.44  LOG S -3.99 
Solubility (Water) 3.98e-02 g/l 

PROPERTIES

PROPERTIES

Physical Property Pharmacology Properties Bioassay(PubChem)
Solubility
40 mg/L expand Show data source
Hydrophobicity(logP)
2.2 expand Show data source
Admin Routes
Oral, rectal, intramuscular expand Show data source
Half Life
7 to 9 hours (mean) expand Show data source
Legal Status
Rx-only (US) expand Show data source

DETAILS

DETAILS

DrugBank DrugBank Wikipedia Wikipedia
DrugBank - DB00662 external link
Item Information
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
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RxList
PDRhealth
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REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • 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
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