Ethionamide

Structural formula
General
Non-proprietary name	Ethionamide
other names	2-ethylpyridine-4-carbothioamide
Molecular formula	C 8 H 10 N 2 S
Brief description	yellow, crystalline powder or small, yellow crystals
External identifiers / databases
CAS number 536-33-4 EC number 208-628-9 ECHA InfoCard 100,007,846 PubChem 2761171 DrugBank DB00609 Wikidata Q414767
Drug information
ATC code	J04 AD03
Drug class	Tuberculostatic
properties
Molar mass	166.24 g · mol -1
solubility	practically insoluble in water, soluble in methanol , slightly soluble in ethanol
safety instructions
Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed GHS labeling of hazardous substances Caution H and P phrases H: 302-361 P: 281
Toxicological data	1320 mg kg −1 ( LD 50 ,  rat ,  oral )
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

1. ↑ ^{a b c} data sheet ETHIONAMIDE CRS (PDF) at EDQM , accessed on December 19, 2009.
2. ↑ ^{a b} Data sheet Ethionamide from Sigma-Aldrich , accessed on March 31, 2011 ( PDF ).
3. ↑ WHO Model List of Essential Medicines (PDF; 442 kB); Retrieved September 20, 2012.

This article is about a health issue. It is not used for self-diagnosis and does not replace a diagnosis by a doctor. Please note the information on health issues !