Ethambutol
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| Systematic (IUPAC) name | |
| (2S,2′S)-2,2′-(ethane-1,2-diyldiimino)dibutan-1-ol | |
| Clinical data | |
| Trade names | Myambutol |
| AHFS/Drugs.com | monograph |
| MedlinePlus | a682550 |
| Pregnancy cat. | B |
| Legal status | ? |
| Routes | Oral |
| Pharmacokinetic data | |
| Bioavailability | Well-absorbed from GI tract |
| Protein binding | 20 to 30% |
| Metabolism | Liver |
| Half-life | 3-4 hr (increased in impaired renal function) |
| Excretion | Renal |
| Identifiers | |
| CAS number | 74-55-5  |
| ATC code | J04AK02 |
| PubChem | CID 14052 |
| DrugBank | APRD00957 |
| ChemSpider | 13433 |
| UNII | 8G167061QZ |
| KEGG | D07925 |
| ChEBI | CHEBI:4877 |
| ChEMBL | CHEMBL44884 |
| NIAID ChemDB | AIDSNO:007655 |
| Chemical data | |
| Formula | C10H24N2O2 |
| Mol. mass | 204.31 g/mol |
| SMILES | eMolecules & PubChem |
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Ethambutol (commonly abbreviated EMB or simply E) is a bacteriostatic antimycobacterial drug prescribed to treat tuberculosis.1 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.
Contents
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Adverse effects
- Optic neuritis.2 Hence contraindicated in children below 6 yrs of age.
- Red-green color 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
- ^ 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. http://linkinghub.elsevier.com/retrieve/pii/S0960-894X(08)00082-6.
- ^ Lim SA (April 2006). "Ethambutol-associated optic neuropathy". Ann. Acad. Med. Singap. 35 (4): 274–8. PMID 16710500. http://www.annals.edu.sg/pdf/35VolNo4200605/V35N4p274.pdf.
External links
- Medline Plus drug information
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