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*This document is like a lab demo—an example Certificate of Analysis (COA) that showcases what a COA looks like but may not match the latest batch in all its glory. Think of it as a chemistry experiment: close, but not quite the final reaction!
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Bulk Quote| IUPAC name | 2-ethylpyridine-4-carbothioamide |
| inchi | InChI=1S/C8H10N2S/c1-2-7-5-6(8(9)11)3-4-10-7/h3-5H,2H2,1H3,(H2,9,11) |
| inchi key | AEOCXXJPGCBFJA-UHFFFAOYSA-N |
| molecular formula | C8H10N2S |
| synonyms | |
| Compound Description |
| Molecular Weight: | 166.25 g/mol |
| XLogP3: | 1.1 |
| Hydrogen Bond Donor Count: | 1 |
| Hydrogen Bond Acceptor Count: | 2 |
| Rotatable Bond Count: | 2 |
| Exact Mass: | 166.05646950 g/mol |
| Monoisotopic Mass: | 166.05646950 g/mol |
| Topological Polar Surface Area: | 71 Ų |
| Heavy Atom Count: | 11 |
| Formal Charge: | 0 |
| Complexity: | 147 |
| Isotope Atom Count: | 0 |
| Defined Atom Stereocenter Count: | 0 |
| Undefined Atom Stereocenter Count: | 0 |
| Defined Bond Stereocenter Count: | 0 |
| Undefined Bond Stereocenter Count: | 0 |
| Covalently-Bonded Unit Count: | 1 |
| Compound Is Canonicalized: | Yes |
| hazard signal | Warning |
| hazard classes and categories | |
| precautionary statement codes | P203, P264, P270, P280, P301+P317, P318, P330, P405, and P501 |
| hazard statements |
| toxicity summary | IDENTIFICATION: Ethionamide is a drug for the treatment of tuberculosis. Ethionamide is a yellow crystalline powder. Soluble in 1 in 30 of alcohol. Very sparingly soluble in water. Slightly soluble in chloroform. Slightly soluble in ether. Soluble in methyl alcohol. Sparingly soluble in propylene glycol. Indications: For the treatment of pulmonary and extrapulmonary tuberculosis in conjunction with other antituberculous agents . For the treatment of leprosy, as part of multi-drug regimens. In the treatment of pulmonary disease in Mycobacterium kansasii and other atypical mycobacteria. HUMAN EXPOSURE: Main risks and target organs: Most common adverse reactions are gastrointestinal disturbances including anorexia, nausea, vomiting, excessive salivation, a metallic taste, stomatitis and diarrhoea and hepatitis. Central nervous system effects include dizziness, drowsiness, headaches, convulsions, peripheral neuropathy, tremors and paraesthesias. There is no experience in acute overdose of ethionamide. One of the metabolites resembles isoniazid and one should watch for similar symptoms. Summary of clinical effects: Gastrointestinal: Anorexia, vomiting, stomatitis, diarrhea, System: excessive salivation, metallic taste, hepatotoxicity. Central Nervous: Mental depression, anxiety or psychosis, System: encephalopathy with pellagra-like symptoms, dizziness, drowsiness, headache, convulsion, peripheral neuropathy, tremors, paresthesias. Eye: Optic neuritis, optic atrophy, diplopia. Nose: olfactory disturbances Ear: Deafness Endocrine: Hypothyroidism, gynecomastia, impotence, menorrhagia, hypoglycemia. Integumentary: Alopecia, acne, severe allergic rashes, photodermatitis. Hematology: Thrombocytopenia Skeletal system: Rheumatic pains Cardiovascular: Postural hypotension Contraindications: Ethionamide should not be given to pregnant women unless the benefits outweigh its possible risk. To be used with caution in women of child-bearing age. Individuals with severe liver disease. Severe hypersensitivity. Note: Caution is necessary in administering ethionamide to patients with depression or other psychiatric diseases, chronic alcoholism, epilepsy, hypothyroidism or diabetes mellitus. Routes of entry: Oral: This is the usual route of administration for therapeutic use. Parenteral: Ethionamide hydrochloride has been given intravenously, but there is no commercial preparation. Other: Ethionamide has been administered as rectal suppositories. Absorption by route of exposure: Approximately 80% of a gastrointestinal oral dose of ethionamide is rapidly absorbed from the gastrointestinal tract. After oral administration, the bioavailability is about 100%. Relative bioavailability after rectal administration was 57.3% of that following oral administration. Distribution by route of exposure: It is widely distributed throughout body tissues and fluids. It crosses the placenta and penetrates the meninges, appearing in the CSF in concentrations equivalent to those in the serum. Protein binding is low . Biological half-life by route of exposure: Half-life is 2 to 3 hours. Ethionamide is extensively metabolized, probably in the liver, to ethionamide sulfoxide, 2-ethylisonicotinic acid and 2-ethylisonicotinamide. The sulfoxide is the main active metabolite. Elimination by route of exposure: Less than 1% of a dose appears in the urine as unchanged drug, the remainder is excreted in the urine as inactive metabolites. Mode of action: Toxicodynamics: In view of the structural similarity of the metabolite 2-methylisonicotinic acid to isoniazid, it has been suggested that toxicity is due to pyridoxine deficiency. Pharmacodynamics: Ethionamide inhibits the synthesis of mycolic acids and stimulates oxidation reduction reactions. Treated cells lose acid fastness. Both the drug and the sulfoxide metabolite are active against M.tuberculosis. 2-ethylisonicotinic acid and 2-ethylisonicotinamide are not active metabolites. It is bacteriostatic against M. tuberculosis at therapeutic concentrations, but may be bactericidal at higher concentrations. It is bactericidal against M. lepra. Resistance develops rapidly if used alone and there is complete cross-resistance with prothionamide, thiacetazone and thiambutosine. Toxicity: Adults: In clinical use, neuropsychiatric symptoms, such as headache, sleeping, insomnia, depression and paresthesia may occur. Elevation of liver transaminase enzymes has been known to develop. No special precautions are required due to age, as doses are adjusted according to patient response. However, dose should be modified depending on liver and renal status. Interactions: Ethionamide taken with pyrazinamide may lead to abnormalities of liver function and the use of these two agents together should be avoided. The use of rifampicin with the thioamides as part of the treatment of multibacillary leprosy has been associated with an unexpectedly high incidence of hepatotoxicity. Adverse nervous system effects of ethionamide, cylcoserine and isoniazid may be additive. The side effects of other tuberculostatic agents may be enhanced when ethionamide is administered concomitantly. Alcohol may contribute to psychotropic reactions in an ethionamide treated patient. More study is needed to clarify the clinical significance of this interaction. Main adverse effects: The most common adverse effects are dose-related, viz: gastrointestinal disturbances, including anorexia, excessive salivation, a metallic taste, nausea, vomiting, stomatitis, diarrhea and hepatitis. Dizziness, drowsiness, headache, postural hypotension and asthenia may also occur occasionally. Other side effects reported include acne, allergic reactions alopecia, convulsions, deafness, dermatitis , visual disturbances, tremors, gynecomastia, impotence, menstrual disturbances, olfactory disorders, peripheral and optic neuropathy, thrombocytopenia and rheumatic pains. Mental disturbances, including depression, anxiety and psychosis have been provoked. A pellagra-like syndrome with encephalopathy has been reported rarely. A tendency towards hypoglycemia may occur and could be of significance in patients with diabetes mellitus. Hypothyroidism has also occurred. Racial differences in tolerance may occur, e.g. Chinese and Africans are often more tolerant of ethionamide than are Europeans. ANIMAL/PLANT STUDIES: A rat study showed the sublethal neurotoxicity which included paralysis, loss of screen grip and decreased motor activity. Teratogenicity: Teratogenic effects have been reported in rabbits, mice and rats, in which high doses have led to abortions and some malformations. Mutagenicity: Ethionamide was not found to be mutagenic as shown by Ames Salmonella and micronuclei assay test. |
| symptoms |
| carcinogen classification | IARC Carcinogenic Agent: Ethionamide |
| carcinogen classification | IARC Carcinogenic Classes: Group 3: Not classifiable as to its carcinogenicity to humans |
| carcinogen classification | IARC Monographs: Volume 13: Some Miscellaneous Pharmaceutical SubstancesVolume Sup 7: Overall Evaluations of Carcinogenicity: An Updating of IARC Monographs Volumes 1 to 42, 1987; 440 pages; ISBN 92-832-1411-0 |
