ethambutol   Click here for help

GtoPdb Ligand ID: 12996

Synonyms: Myambutol®
Approved drug PDB Ligand
ethambutol is an approved drug (FDA (1967))
Compound class: Synthetic organic
Comment: Ethambutol is used in the treatment of active tuberculosis (TB), usually in conjunction with other antituberculosis agents [1]. The clinical formulation was originally a racemic mixture, but now contains only the active (S,S)-(+)-enantiomer.

ethambutol is commercially available from our sponsors

2D Structure
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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.

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Physico-chemical Properties
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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.

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Hydrogen bond acceptors 4
Hydrogen bond donors 4
Rotatable bonds 9
Topological polar surface area 64.52
Molecular weight 204.31
XLogP -0.34
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
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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/)

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Canonical SMILES CC[C@@H](CO)NCCN[C@@H](CC)CO
Isomeric SMILES CC[C@@H](CO)NCCN[C@@H](CC)CO
InChI InChI=1S/C10H24N2O2/c1-3-9(7-13)11-5-6-12-10(4-2)8-14/h9-14H,3-8H2,1-2H3/t9-,10-/m0/s1
InChI Key AEUTYOVWOVBAKS-UWVGGRQHSA-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 (1967)
WHO Essential Medicine WHO Essential Medicines List (EML) (23rd List, 2023). Access PDF version.
Click to view more information about the WHO Model Lists of Essential Medicines.
IUPAC Name Click here for help
(2S)-2-[2-[[(2S)-1-hydroxybutan-2-yl]amino]ethylamino]butan-1-ol
International Nonproprietary Names Click here for help
INN number INN
1074 ethambutol
Synonyms Click here for help
Myambutol®
Database Links Click here for help
Specialist databases
Antibiotic DB Antibiotic DB Database logo Ethambutol
Other databases
BindingDB Ligand 50448407
CAS Registry No. 74-55-5 (source: Scifinder)
ChEBI CHEBI:4877
ChEMBL Ligand CHEMBL44884
DrugBank Ligand DB00330
DrugCentral Ligand 1073
GtoPdb PubChem SID 485206117
PubChem CID 14052
RCSB PDB Ligand 95E
Search Google for chemical match using the InChIKey AEUTYOVWOVBAKS-UWVGGRQHSA-N
Search Google for chemicals with the same backbone AEUTYOVWOVBAKS
Search PubMed clinical trials ethambutol
Search PubMed titles ethambutol
Search PubMed titles/abstracts ethambutol
UniChem Compound Search for chemical match using the InChIKey AEUTYOVWOVBAKS-UWVGGRQHSA-N
UniChem Connectivity Search for chemical match using the InChIKey AEUTYOVWOVBAKS-UWVGGRQHSA-N
Wikipedia Ethambutol

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MedChemExpress
Ethambutol (links to external site)
Cat. No. HY-B0535