ethambutol (CHEBI:4877)

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ChEBI Name	ethambutol

ChEBI ID	CHEBI:4877

Definition	An ethylenediamine derivative that is ethane-1,2-diamine in which one hydrogen attached to each of the nitrogens is sutstituted by a 1-hydroxybutan-2-yl group (S,S-configuration). It is a bacteriostatic antimycobacterial drug, effective against Mycobacterium tuberculosis and some other mycobacteria. It is used (as the dihydrochloride salt) in combination with other antituberculous drugs in the treatment of pulmonary and extrapulmonary tuberculosis; resistant strains of M. tuberculosis are readily produced if ethambutol is used alone.

Stars	This entity has been manually annotated by the ChEBI Team.

Secondary ChEBI IDs	CHEBI:133410, CHEBI:678172, CHEBI:659237

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Formula

C10H24N2O2

Net Charge

Average Mass

204.30980

Monoisotopic Mass

204.18378

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

InChIKey

AEUTYOVWOVBAKS-UWVGGRQHSA-N

SMILES

CC[C@@H](CO)NCCN[C@@H](CC)CO

Roles Classification
Chemical Role(s):	environmental contaminant Any minor or unwanted substance introduced into the environment that can have undesired effects. Bronsted base A molecular entity capable of accepting a hydron from a donor (Bronsted acid). (via organic amino compound )

Biological Role(s):	antitubercular agent A substance that kills or slows the growth of Mycobacterium tuberculosis and is used in the treatment of tuberculosis. xenobiotic A xenobiotic (Greek, xenos "foreign"; bios "life") is a compound that is foreign to a living organism. Principal xenobiotics include: drugs, carcinogens and various compounds that have been introduced into the environment by artificial means.

Application(s):	antitubercular agent A substance that kills or slows the growth of Mycobacterium tuberculosis and is used in the treatment of tuberculosis.

ChEBI Ontology
Outgoing	ethambutol (CHEBI:4877) has role antitubercular agent (CHEBI:33231) ethambutol (CHEBI:4877) has role environmental contaminant (CHEBI:78298) ethambutol (CHEBI:4877) has role xenobiotic (CHEBI:35703) ethambutol (CHEBI:4877) is a ethanolamines (CHEBI:23981) ethambutol (CHEBI:4877) is a ethylenediamine derivative (CHEBI:31577)

Incoming	ethambutol dihydrochloride (CHEBI:4878) has part ethambutol (CHEBI:4877)

IUPAC Name

(2S,2'S)-2,2'-(ethane-1,2-diyldiimino)dibutan-1-ol

Synonyms	Sources
(+)-2,2'-(ethylenediimino)di-1-butanol	ChemIDplus
(+)-ethambutol	ChEBI
(+)-N,N'-bis(1-(hydroxymethyl)propyl)ethylenediamine	ChemIDplus
(+)-S,S-ethambutol	ChemIDplus
(2S,7S)-2,7-diethyl-3,6-diazaoctane-1,8-diol	ChEBI
(S,S)-ethambutol	ChEBI
EMB	ChEBI
Ethambutol	KEGG COMPOUND
S,S-Ethambutol	ChEMBL

Last Modified

22 February 2017

General Comment
2014-10-29	Stravs M, Schymanski E, Singer H, Department of Environmental Chemistry, Eawag