Ethionamide
Structural formula | |||||||||||||||||||
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General | |||||||||||||||||||
Non-proprietary name | Ethionamide | ||||||||||||||||||
other names |
2-ethylpyridine-4-carbothioamide |
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Molecular formula | C 8 H 10 N 2 S | ||||||||||||||||||
Brief description |
yellow, crystalline powder or small, yellow crystals |
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Drug information | |||||||||||||||||||
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properties | |||||||||||||||||||
Molar mass | 166.24 g · mol -1 | ||||||||||||||||||
solubility |
practically insoluble in water, soluble in methanol , slightly soluble in ethanol |
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safety instructions | |||||||||||||||||||
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Toxicological data | |||||||||||||||||||
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . |
Ethionamide is an antibiotic that structurally belongs to the thionamides . It is used to treat multidrug- resistant tuberculosis pathogens. It is an active ingredient of the second choice; it is only used in combination with other antituberculotics , as resistance quickly occurs when given alone. Ethionamide is listed as an essential drug by the World Health Organization .
Pharmacodynamics
Mechanism of action
The mechanism of action is not fully understood; ethionamide, as a bacteriostatic agent, appears to inhibit the synthesis of mycolic acids , a component of the bacterial wall . When used alone, resistances develop rapidly , with full cross-resistance to protionamide (also in the group of thionamides ).
Side effects
Frequent side effects are gastrointestinal complaints (diarrhea, abdominal pain, salivation, nausea, vomiting, loss of appetite), which occur in a dose-dependent manner. Occasionally, allergic reactions , nerve damage , reversible hepatitis , gynecomastia , menstrual disorders , joint pain, decrease in white blood cells or hypothyroidism ( hypothyroidism ) occur.
Pharmacokinetics
The bioavailability after oral ingestion as a tablet is 100%, but can be limited by digestive disorders, which can occur as a side effect. Distribution is rapid and the substance also crosses the blood-brain barrier . The liver is broken down into an active sulfoxide metabolite and other non-active breakdown products.
Contraindications
Ethionamide has shown teratogenic ( teratogenic ) effects in animal models and should not be used during pregnancy or breastfeeding. Other contraindications are porphyrias and severe liver disease. A renal failure , however, has little effect on the degradation of active ingredient.
Trade names
Trecator (USA and others), Ethatyl , Ethide , Eton , Etyomid , Myobid (other international product names, not available in Germany)
literature
- Guidelines for the programmatic management of drug-resistant tuberculosis. WHO, 2006, ISBN 978-92-4-154695-9 , pp. 135-136; who.int (PDF; 1.3 MB)
Individual evidence
- ↑ a b c data sheet ETHIONAMIDE CRS (PDF) at EDQM , accessed on December 19, 2009.
- ↑ a b Data sheet Ethionamide from Sigma-Aldrich , accessed on March 31, 2011 ( PDF ).
- ↑ WHO Model List of Essential Medicines (PDF; 442 kB); Retrieved September 20, 2012.