Ethambutol

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Ethambutol
Ethambutol.svg
Ethambutol substance photo.jpg
Ethambutol ball-and-stick.png
Identifiers
CAS number74-55-5 YesY
PubChem14052
ChemSpider13433 YesY
UNII8G167061QZ YesY
EC number200-810-26
DrugBankDB00330
KEGGD07925 YesY
MeSHEthambutol
ChEBICHEBI:4877 YesY
ChEMBLCHEMBL44884 YesY
ATC codeJ04AK02
Jmol-3D imagesImage 1
Properties
Molecular formulaC10H24N2O2
Molar mass204.31 g mol−1
AppearanceWhite crystals
OdorOdourless
log P−0.291
Pharmacology
Routes of
administration
Oral
MetabolismHepatic
Elimination
half-life
3–4 hours
Protein binding20–30%
ExcretionRenal
Pregnancy
category
B
Related compounds
Related compounds
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references
 
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Ethambutol
Ethambutol.svg
Ethambutol substance photo.jpg
Ethambutol ball-and-stick.png
Identifiers
CAS number74-55-5 YesY
PubChem14052
ChemSpider13433 YesY
UNII8G167061QZ YesY
EC number200-810-26
DrugBankDB00330
KEGGD07925 YesY
MeSHEthambutol
ChEBICHEBI:4877 YesY
ChEMBLCHEMBL44884 YesY
ATC codeJ04AK02
Jmol-3D imagesImage 1
Properties
Molecular formulaC10H24N2O2
Molar mass204.31 g mol−1
AppearanceWhite crystals
OdorOdourless
log P−0.291
Pharmacology
Routes of
administration
Oral
MetabolismHepatic
Elimination
half-life
3–4 hours
Protein binding20–30%
ExcretionRenal
Pregnancy
category
B
Related compounds
Related compounds
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Ethambutol (commonly abbreviated EMB or simply E) is a bacteriostatic antimycobacterial drug prescribed to treat tuberculosis.[2] It is usually given in combination with other tuberculosis drugs, such as isoniazid, rifampicin and pyrazinamide.

It is sold under the trade names Myambutol and Servambutol.

Adverse effects[edit]

Mechanism of action[edit]

Ethambutol is bacteriostatic against actively growing TB bacilli. It works by obstructing the formation of cell wall. Mycolic acids attach to the 5'-hydroxyl groups of D-arabinose residues of arabinogalactan and form mycolyl-arabinogalactan-peptidoglycan complex in the cell wall. It disrupts arabinogalactan synthesis by inhibiting the enzyme arabinosyl transferase. Disruption of the arabinogalactan synthesis inhibits the formation of this complex and leads to increased permeability of the cell wall.

Pharmacokinetics[edit]

It is well absorbed from the gastrointestinal tract and well distributed in body tissues and fluids. 50% is excreted unchanged in urine.

References[edit]

  1. ^ "ethambutol (CHEBI:4877)". Chemical Entities of Biological Interest. UK: European Bioinformatics Institute. 18 August 2010. Main. Retrieved 26 April 2012. 
  2. ^ Yendapally R, Lee RE (March 2008). "Design, synthesis, and evaluation of novel ethambutol analogues". Bioorg. Med. Chem. Lett. 18 (5): 1607–11. doi:10.1016/j.bmcl.2008.01.065. PMC 2276401. PMID 18242089. 
  3. ^ Lim SA (April 2006). "Ethambutol-associated optic neuropathy". Ann. Acad. Med. Singap. 35 (4): 274–8. PMID 16710500. 

External links[edit]