trimethobenzamide   Click here for help

GtoPdb Ligand ID: 7614

Synonyms: Tigan® | trimethobenzamide hydrochloride
Approved drug
trimethobenzamide is an approved drug (FDA (1974))
Compound class: Synthetic organic
Comment: Marketed formulations contain trimethobenzamide hydrochloride.
2D Structure
Click here for help

2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

✖
Click here for structure editor
Physico-chemical Properties
Click here for help

Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

✖
Hydrogen bond acceptors 3
Hydrogen bond donors 1
Rotatable bonds 11
Topological polar surface area 69.26
Molecular weight 388.2
XLogP 2.38
No. Lipinski's rules broken 0

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
SMILES / InChI / InChIKey
Click here for help

SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

✖
Canonical SMILES COc1cc(cc(c1OC)OC)C(=O)NCc1ccc(cc1)OCCN(C)C
Isomeric 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)
InChI Key FEZBIKUBAYAZIU-UHFFFAOYSA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes. FDA (1974)
IUPAC Name Click here for help
N-[[4-(2-dimethylaminoethoxy)phenyl]methyl]-3,4,5-trimethoxybenzamide
International Nonproprietary Names Click here for help
INN number INN
957 trimethobenzamide
Synonyms Click here for help
Tigan® | trimethobenzamide hydrochloride
Database Links Click here for help
CAS Registry No. 138-56-7
ChEBI CHEBI:27796
ChEMBL Ligand CHEMBL1201256
DrugBank Ligand B00662
DrugCentral Ligand 2754
GtoPdb PubChem SID 223365949
PubChem CID 5577
Search Google for chemical match using the InChIKey FEZBIKUBAYAZIU-UHFFFAOYSA-N
Search Google for chemicals with the same backbone FEZBIKUBAYAZIU
Search PubMed clinical trials trimethobenzamide
Search PubMed titles trimethobenzamide
Search PubMed titles/abstracts trimethobenzamide
UniChem Compound Search for chemical match using the InChIKey FEZBIKUBAYAZIU-UHFFFAOYSA-N
UniChem Connectivity Search for chemical match using the InChIKey FEZBIKUBAYAZIU-UHFFFAOYSA-N
Wikipedia Trimethobenzamide