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QuickView for ethambutol (compound)
PubChem
| Name: | Ethambutol |
|---|---|
| PubChem Compound ID: | 14051 |
| Description: | An antitubercular agent that inhibits the transfer of mycolic acids into the cell wall of the tubercle bacillus. It may also inhibit the synthesis of spermidine in mycobacteria. The action is usually bactericidal, and the drug can penetrate human cell membranes to exert its lethal effect. (From Smith and Reynard, Textbook of Pharmacology, 1992, p863) |
| Molecular formula: | C10H26Cl2N2O2 |
| Molecular weight: | 277.231 g/mol |
| Synonyms: |
1-Butanol, 2,2'-(1,2-ethanediyldiimino)bis-, dihydrochloride, (R-(R*,R*))- (9CI); 1-Butanol, 2,2'-(1,2-ethanediyldiimino)bis-, dihydrochloride, (S-(R*,R*))-; Ethambutol dihydrochloride; CL 40881; Ethambutol hydrochloride [USAN:JAN]; Ethambutol hydrochloride (JP15/USP); (S-(R*,R*))-2,2'-(Ethylenediimino)dibutan-1-ol dihydrochloride; Dadibutol; CCRIS 6606; 1-BUTANOL, 2,2'-(ETHYLENEDIIMINO)DI-, DIHYDROCHLORIDE, (+)-.
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DrugBank
Identification
| Name: | Ethambutol |
|---|---|
| Name (isomeric): | DB00330 |
| Drug Type: | small molecule |
| Description: | An antitubercular agent that inhibits the transfer of mycolic acids into the cell wall of the tubercle bacillus. It may also inhibit the synthesis of spermidine in mycobacteria. The action is usually bactericidal, and the drug can penetrate human cell membranes to exert its lethal effect. (From Smith and Reynard, Textbook of Pharmacology, 1992, p863) |
| Synonyms: |
D-Ethambutol; Ethambutolum [INN-Latin]; Aethambutolum; Ethambutol HCL; Etambutol [INN-Spanish]; Ethambutol dihydrochloride; Ethambutol Hydrochloride; Etambutolo [DCIT]; EMB; Ethambutol, racemic mixture
|
| Brand: | Etibi, Tibutol, Diambutol, Dadibutol, Myambutol |
| Category: | Antitubercular Agents |
| CAS number: | 74-55-5 |
Pharmacology
| Indication: | For use, as an adjunct, in the treatment of pulmonary tuberculosis. |
|---|---|
| Pharmacology: |
Ethambutol is an oral chemotherapeutic agent which is specifically effective against actively growing microorganisms of the genus Mycobacterium, including M. tuberculosis. Ethambutol inhibits RNA synthesis and decreases tubercle bacilli replication. Nearly all strains of M. tuberculosis and M. kansasii as well as a number of st...
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| Mechanism of Action: | Ethambutol inhibits arabinosyl transferases which is involved in cell wall biosynthesis. By inhibiting this enzyme, the bacterial cell wall complex production is inhibited. This leads to an increase in cell wall permeability. |
| Absorption: | About 75% to 80% of an orally administered dose of ethambutol is absorbed from the gastrointestinal tract. |
| Protein binding: | 20-30% |
| Biotransformation: | Hepatic. Up to 15% of administered drug is metabolized to inactive metabolites. The main path of metabolism appears to be an initial oxidation of the alcohol to an aldehydic intermediate, followed by conversion to a dicarboxylic acid. |
| Route of elimination: | During the 24-hour period following oral administration of ethambutol hydrochloride approximately 50 percent of the initial dose is excreted unchanged in the urine, while an additional 8 to 15 percent appears in the form of metabolites. From 20 to 22 percent of the initial dose is excreted in the feces as unchanged drug. |
| Half Life: | In patients with normal renal function, 3 to 4 hours. In patients with impaired renal function, up to 8 hours. |
| Toxicity: | The most commonly recognized toxic effect of ethambutol is optic neuropathy, which generally is considered uncommon and reversible in medical literature. Other side effects that have been observed are pruritus, joint pain, gastrointestinal upset, abdominal pain, malaise, headache, dizziness, mental confusion, disorientation, and possible hallucinations. |
| Affected organisms: | Humans and other mammals |
Interactions
| Food interaction: |
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Targets
