ChemicalBook > Product Catalog >API >Synthetic Anti-infective Drugs >Anti-tuberculous mycobacterium leprae drugs >Ethionamide

Ethionamide

Ethionamide Suppliers list
Company Name: Hebei Weibang Biotechnology Co., Ltd
Tel: +8615531157085
Email: abby@weibangbio.com
Products Intro: Product Name:Ethionamide
CAS:536-33-4
Purity:99% Package:1KG;9.90;USD
Company Name: Capot Chemical Co.,Ltd.
Tel: +86-(0)57185586718 +86-13336195806
Email: sales@capot.com
Products Intro: Product Name:Ethionamide
CAS:536-33-4
Purity:98%(Min,GC) Package:100g;1kg;5kg,10kg,25kg,50kg
Company Name: Beijing Cooperate Pharmaceutical Co.,Ltd
Tel: 010-60279497
Email: sales01@cooperate-pharm.com
Products Intro: Product Name:Ethinamide
CAS:536-33-4
Purity:98% Package:100G;1KG;5KG;10KG;25KG;50KG;100KG
Company Name: Henan Tianfu Chemical Co.,Ltd.
Tel: +86-0371-55170693 +86-19937530512
Email: info@tianfuchem.com
Products Intro: Product Name:EthionaMide
CAS:536-33-4
Purity:99% Package:25KG;5KG;1KG
Company Name: career henan chemical co
Tel: +86-0371-86658258 +8613203830695
Email: sales@coreychem.com
Products Intro: Product Name:Ethionamide
CAS:536-33-4
Purity:99% Package:1KG;1USD

Ethionamide manufacturers

  • Ethionamide
  • Ethionamide pictures
  • $0.00 / 1Kg/Bag
  • 2024-12-13
  • CAS:536-33-4
  • Min. Order: 1KG
  • Purity: 98%min
  • Supply Ability: 20 tons
  • Ethionamide
  • Ethionamide pictures
  • $9.90 / 1KG
  • 2024-12-04
  • CAS:536-33-4
  • Min. Order: 1KG
  • Purity: 99%
  • Supply Ability: 5tons
  • Ethionamide
  • Ethionamide pictures
  • $51.00 / 500mg
  • 2024-11-19
  • CAS:536-33-4
  • Min. Order:
  • Purity: 99.92%
  • Supply Ability: 10g

Related articles

  • Mechanism of action of Ethionamide
  • Ethionamide (2-ethyl-4-pyridinecarbothioamide) is a derivative of isonicotinic acid that was first synthesized in France in 19....
  • Mar 29,2022
Ethionamide Basic information
Product Name:Ethionamide
Synonyms:1314 TH;1314 TN;1314th;2-Ethyl-4-thioamidylpyridine;2-Ethyl-4-thiocarbamoylpyridine;2-Ethylisonicotinic acid thioamide;2-Ethylisonicotinic thioamide;2-ethylisonicotinicacidthioamide
CAS:536-33-4
MF:C8H10N2S
MW:166.24
EINECS:208-628-9
Product Categories:TRECATOR;Intermediates & Fine Chemicals;Pharmaceuticals;Pyridines;Amines;Heterocycles;Sulfur & Selenium Compounds;Pharmaceutical Raw Materials;536-33-4
Mol File:536-33-4.mol
Ethionamide Structure
Ethionamide Chemical Properties
Melting point 164 °C
Boiling point 167 °C / 1mmHg
density 1.1332 (rough estimate)
refractive index 1.5500 (estimate)
Fp >110°(230°F)
storage temp. 2-8°C
solubility DMSO (Slightly), Methanol (Slightly)
form Solid
pkapKa 4.37(H2O t=25.0 I=0.025) (Uncertain)
color Yellow
Water Solubility Soluble in DMSO. Sparingly soluble in water
Merck 14,3737
BCS Class3/1
InChIKeyAEOCXXJPGCBFJA-UHFFFAOYSA-N
CAS DataBase Reference536-33-4(CAS DataBase Reference)
IARC3 (Vol. 13, Sup 7) 1987
NIST Chemistry ReferenceEthionamide(536-33-4)
EPA Substance Registry SystemEthionamide (536-33-4)
Safety Information
Hazard Codes Xn
Risk Statements 22-63
Safety Statements 36/37
WGK Germany 3
RTECS NS0350000
HS Code 29333990
Hazardous Substances Data536-33-4(Hazardous Substances Data)
ToxicityLD50 oral in rat: 1320mg/kg
MSDS Information
ProviderLanguage
2-Ethylpyridine-4-carbothioamide English
SigmaAldrich English
Ethionamide Usage And Synthesis
DescriptionEthionamide is an antimycobacterial compound that is active against M. tuberculosis (MICs = 0.3-1.25 μg/ml). It is activated via oxidation by flavin monooxygenase and inhibits the InhA enzyme involved in mycolic acid biosynthesis. Formulations containing ethionamide have been used in the second-line treatment of multi-drug resistant tuberculosis.
Chemical PropertiesYellow Solid
OriginatorTrecator,Theraplix,France,1959
UsesAntibacterial (tuberculostatic).
UsesEthionamide is used in antimicrobials and in potency assay of test compounds on M. tuberculosis.
DefinitionChEBI: A thiocarboxamide that is pyridine-4-carbothioamide substituted by an ethyl group at position 2. A prodrug that undergoes metabolic activation by conversion to the corresponding S-oxide.
IndicationsEthionamide (Trecator) is a derivative of isonicotinic acid and is chemically related to isoniazid. It is a secondary agent used in combination when primary agents are ineffective or contraindicated; it is a bacteriostatic antituberculosis agent. Its exact mechanism of action is unknown but is believed to involve inhibition of oxygen-dependent mycolic acid synthesis. It is thought that mutations in the region of the (inhA) gene that are involved in mycolic acid synthesis can cause both isoniazid and ethionamide resistance.
Manufacturing ProcessEthyl Propionyl-Pyruvate: 36 grams of methyl ethyl ketone and 73 grams of ethyl oxalate are condensed in the presence of sodium ethylate, the reaction mixture being refluxed in an alcoholic medium. 28 grams of the desired product having a boiling point of 100° to 105°C/6 mm are obtained.
3-Cyano-4-Carbethoxy-6-Ethyl-2-Pyridone: 205 cc of 60% alcohol, 22 grams of the product just obtained, 11 grams of cyanacetamide and 4.5 cc of piperidine are refluxed. 19 grams of product having a melting point of 211°C are obtained.
4-Carboxy-6-Ethyl-2-Pyridone: 30 grams of the cyanopyridone just obtained are refluxed with concentrated hydrochloric acid. 13.5 grams of product having a melting point of 308°C are obtained.
2-Chloro-4-Carbethoxy-6-Ethyl-Pyridine: 26 grams of the product just obtained are treated with 81 grams of phosphorus pentachloride in 45 cc of phosphorus oxychloride. The phosphorus oxychloride is distilled off in a vacuum and the residue is treated with absolute alcohol. After distillation there are obtained 24 grams of product having a boiling point of 127° to 131°C/8 mm.
Ethyl-2-Ethyl-Isonicotinate: 10 grams of the ester just obtained dissolved in 80 cc of absolute alcohol containing 5.5 grams of potassium acetate are hydrogenated catalytically on 5% palladium black. 8 grams of product having a boiling point of 120° to 124°C/14 mm are obtained.
2-Ethyl-Isonicotinic-Amide: 20 grams of the ether just obtained are agitated, with 25 cc of concentrated ammonia. 11 grams of product having a melting point of 131°C are obtained.
2-Ethyl-Isonicotinic Nitrile: The 11 grams of the amide just obtained are treated with 15 grams of phosphorus anhydride at 160° to 180°C in a vacuum. 6 grams of a liquid residue are obtained.
Alpha-Ethyl-Isonicotinic Thioamide: The 6 grams of the liquid just obtained, in solution in 15 cc of absolute alcohol containing 2 grams of triethanolamine, are treated with hydrogen sulfide. 6.5 grams of the desired product having a melting point of 166°C are obtained.
Brand nameTrecator (Wyeth.
Therapeutic FunctionAntitubercular
General DescriptionYellow crystals or canary yellow powder with a faint to moderate sulfide odor.
Air & Water ReactionsInsoluble in water.
Reactivity ProfileA thiocarbamate/amine. Thiocarbamates slowly decompose in aqueous solution to form carbon disulfide and methylamine or other amines. Such decompositions are accelerated by acids. Flammable gases are generated by the combination of thiocarbamates and dithiocarbamates with aldehydes, nitrides, and hydrides. Thiocarbamates and dithiocarbamates are incompatible with acids, peroxides, and acid halides.
Fire HazardFlash point data for Ethinamide are not available. Ethinamide is probably combustible.
Biochem/physiol ActionsEthionamide is used as an anti-tuberculosis antibiotic and an inducer of hypothyroidism.
Mechanism of actionEvidence has been presented suggesting that the mechanism of action of ethionamide is similar to that of INH. Similar to INH, ethionamide is considered to be a pro-drug, which is converted via oxidation by catalase-peroxidase to an active acylating agent, ethionamide sulfoxide, which in turn inactivates the inhA enoyl reductase enzyme. In the case of ethionamide, it has been proposed that the ethionamide sulfoxide acylates Cys-243 in inhA protein.
PharmacologyEthionamide is well absorbed following oral administration. It is rapidly and widely distributed to all body tissues and fluids, including the cerebrospinal fluid. Metabolism of ethionamide is extensive, and several dihydropyridine metabolites are produced. Less than 1% of the drug is eliminated in the urine unchanged. GI disturbances, including nausea, vomiting, and intense gastric irritation, are frequent. In addition, ethionamide may cause a wide range of neurological side effects, such as confusion, peripheral neuropathy, psychosis, and seizures. Neurological effects can be minimized by pyridoxine supplementation. Other rare side effects include gynecomastia, impotence, postural hypotension, and menorrhagia.
Clinical Use2-Ethylthioisonicotinamide (Trecator SC) occurs as a yellowcrystalline material that is sparingly soluble in water. Thisnicotinamide has weak bacteriostatic activity in vitro but, becauseof its lipid solubility, is effective in vivo. In contrast tothe isoniazid series, 2-substitution enhances activity in thethioisonicotinamide series.
Ethionamide is rapidly and completely absorbed followingoral administration. It is widely distributed throughoutthe body and extensively metabolized to predominantly inactiveforms that are excreted in the urine. Less than 1% ofthe parent drug appears in the urine.Ethionamide is considered a secondary drug for the treatmentof tuberculosis. It is used in the treatment of isoniazidresistanttuberculosis or when the patient is intolerant toisoniazid and other drugs. Because of its low potency, thehighest tolerated dose of ethionamide is usually recommended.Gastrointestinal intolerance is the most commonside effect associated with its use. Visual disturbances andhepatotoxicity have also been reported.
SynthesisEthionamide, 2-(ethyl)isonicotinthioamide (34.1.18), a derivative of isonicotinic acid, is synthesized by the following scheme. Diethyl oxalate is condensated with methylethylketone in the presence of sodium ethoxide to form the ethyl ester of propionylpyruvic acid (34.1.12). Condensation of this with cyanoacetamide results in heterocyclization, to form 3-cyano-4-carboethoxy-6-ethyl-2-pyridone (34.1.13), which is hydrolyzed with hydrochloric acid to give 4-carboxy-6-ethyl-2-pyridone (34.1.14). Reacting this with a mixture of phosphorous oxychloride and pentachloride gives 6-ethyl- 2-chloroisonicotinic acid chloride, which is subsequently treated with ethyl alcohol to obtain the ethyl ester of 6-ethyl-2-chloroisonicotinic acid (34.1.15). Reducing this with hydrogen over a palladium catalyst removes the chlorine atom at position 2 of the pyridine ring, giving the ethyl ester of 6-ethylisonicotinic acid (34.1.15). Interacting this with ammonia, followed by dehydration of the resulting amide of 6-ethylisonicotinic acid using phosphorous pentoxide gives the nitrile of 6-ethylisonicotinic acid (34.1.17). Finally, reacting this with hydrogen sulfide gives ethionamide.

Synthesis_536-33-4

MetabolismEthionamide is orally active but is not well tolerated in a single large dose (>500 mg). The GI irritation can be reduced by administration with meals. Additional side effects may include central nervous system (CNS) effects, hepatitis, and hypersensitivities. Less than 1% of the drug is excreted in the free form, with the remainder of the drug appearing as one of six metabolites. Among the metabolites are ethionamide sulfoxide, 2-ethylisonicotinamide, and the N-methylated- 6-oxodihydropyridines.
Purification MethodsIt crystallises from EtOH as lemon yellow needles. The hydrochloride crystallises from EtOH (+ few drops of HCl) as orange yellow needles with m 212-214o. [Kutscherowa et al. J Gen Chem USSR (English transl) 29 915 1959, Beilstein 22 III/IV 737.] It causes peripheral and occular neuropathy and is carcinogenic and teratogenic.
Tag:Ethionamide(536-33-4) Related Product Information
Benzamide 2-Ethylpyridine Chlorantraniliprole THIOFORMAMIDE Formamide Protionamide N,N-Dimethylformamide Ethambutol 4-Aminosalicylic acid Ethyl acetimidate hydrochloride ar-ethoxybenzamide ETHIRIMOL Acetamidine hydrochloride ETHYL HYDRAZINE OXALATE Dacarbazine Sodium 1-heptanesulfonate Thioacetamide Diethylamine