Ethambutol
Names | |
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Other names
(2S,2’S)-2,2’-(Ethane-1,2-diyldiimino)dibutan-1-ol[1]
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Identifiers | |
74-55-5 | |
ChEBI | CHEBI:4877 |
ChEMBL | ChEMBL44884 |
ChemSpider | 13433 |
DrugBank | DB00330 |
EC Number | 200-810-26 |
Jmol 3D model | Interactive image |
KEGG | D07925 |
MeSH | Ethambutol |
PubChem | 14052 |
UNII | 8G167061QZ |
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Properties | |
C10H24N2O2 | |
Molar mass | 204.31 g·mol−1 |
Appearance | White crystals |
Odor | Odourless |
log P | −0.291 |
Pharmacology | |
ATC code | J04 |
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Oral | |
Pharmacokinetics: | |
20–30% | |
Hepatic | |
3–4 hours | |
Renal | |
Related compounds | |
Related compounds
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references | |
Ethambutol (commonly abbreviated EMB or simply E) is a medication primarily used to treat tuberculosis.[2] It is usually given in combination with other tuberculosis drugs, such as isoniazid, rifampicin and pyrazinamide. It may also be used to treat Mycobacterium avium complex, and Mycobacterium kansasii.[3]
It can cause problems with vision, liver problems and allergies among other side effects.[3] It is pregnancy category C in the United States due to concerns with eye issues and category A in Australia meaning that they did not find evidence of harm after being taken by many pregnant women.[3][4] It is reasonable to use during breast feeding if required.[3]
It is on the World Health Organization's List of Essential Medicines, a list of the most important medication needed in a basic health system.[5] It is sold under the trade names Myambutol and Servambutol.
Contents
Medical uses
Ethambutol is used along with other medications to treat a number of infections including: tuberculosis, Mycobacterium avium complex, and Mycobacterium kansasii.[3]
Adverse effects
- Optic neuritis[6] (hence contraindicated in children below six years of age)
- Red-green color blindness[7]
- Peripheral neuropathy
- Arthralgia
- Hepatotoxicity
- 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
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