Ethambutol
| Ethambutol | |
|---|---|
 | |
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| Other names (2S,2’S)-2,2’-(Ethane-1,2-diyldiimino)dibutan-1-ol[1] | |
| Identifiers | |
| CAS number | 74-55-5  |
| PubChem | 14052 |
| ChemSpider | 13433 |
| UNII | 8G167061QZ |
| EC number | 200-810-26 |
| DrugBank | DB00330 |
| KEGG | D07925 |
| MeSH | Ethambutol |
| ChEBI | CHEBI:4877 |
| ChEMBL | CHEMBL44884 |
| ATC code | J04 |
| Jmol-3D images | {{#if:CC[C@@H](CO)NCCN[C@@H](CC)CO|Image 1 |
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| Properties | |
| Molecular formula | C10H24N2O2 |
| Molar mass | 204.31 g mol−1 |
| Appearance | White crystals |
| Odor | Odourless |
| log P | −0.291 |
| Pharmacology | |
| Routes of administration |
Oral |
| Metabolism | Hepatic |
| Elimination half-life |
3–4 hours |
| Protein binding | 20–30% |
| Excretion | Renal |
| Pregnancy category |
B |
| Related compounds | |
| Related compounds |
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| 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
- Optic neuritis[3] (hence contraindicated in children below six years of age)
- Red-green colour blindness
- Peripheral neuropathy
- Arthralgia
- Hyperuricaemia
- Vertical nystagmus
- Milk skin reaction
Mechanism of action
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
It is well absorbed from the gastrointestinal tract and well distributed in body tissues and fluids. 50% is excreted unchanged in urine.
References
- ↑ "ethambutol (CHEBI:4877)". Chemical Entities of Biological Interest. UK: European Bioinformatics Institute. 18 August 2010. Main. Retrieved 26 April 2012.
- ↑ 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.
- ↑ Lim SA (April 2006). "Ethambutol-associated optic neuropathy". Ann. Acad. Med. Singap. 35 (4): 274–8. PMID 16710500.
External links
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