Ethionamide

Base Information

• Chemical Name: Ethionamide
• CAS No.: 536-33-4
• Deprecated CAS: 5261-38-1
• Molecular Formula: C8H10N2S
• Molecular Weight: 166.247
• Hs Code.: 29333990
• European Community (EC) Number: 208-628-9
• NSC Number: 757028,255115
• UNII: OAY8ORS3CQ
• DSSTox Substance ID: DTXSID0020577
• Nikkaji Number: J2.066D
• Wikipedia: Ethionamide
• Wikidata: Q414767
• NCI Thesaurus Code: C47522
• RXCUI: 4127
• Metabolomics Workbench ID: 42938
• ChEMBL ID: CHEMBL1441
• Mol file: 536-33-4.mol

Synonyms:Amidazine;Ethionamide;Ethioniamide;Trecator;Trecator SC;Trecator-SC

Chemical Property of Ethionamide

Chemical Property:

• Appearance/Colour: yellow solid
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 164 °C
• Refractive Index: 1.599
• Boiling Point: 296.6 °C at 760 mmHg
• PKA: pKa 4.37(H2O t=25.0 I=0.025) (Uncertain)
• Flash Point: 133.2 °C
• PSA: 71.00000
• Density: 1.17 g/cm³
• LogP: 1.97850
• Storage Temp.: 2-8°C
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• Water Solubility.: Soluble in DMSO. Sparingly soluble in water
• XLogP3: 1.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 166.05646950
• Heavy Atom Count: 11
• Complexity: 147

Purity/Quality:

99% ^*data from raw suppliers

Ethionamide ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22-63
• Safety Statements: 36/37

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Drug Classes: Antituberculosis Agents
• Canonical SMILES: CCC1=NC=CC(=C1)C(=S)N
• Recent ClinicalTrials: A Phase 2 Trial to Evaluate the EBA, Safety and Tolerability of Eto Alone and in Combination With BVL-GSK098
• Description: Ethionamide 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.
• Uses: Ethionamide is used in antimicrobials and in potency assay of test compounds on M. tuberculosis. Antibacterial (tuberculostatic).
• Indications: Ethionamide (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.
• Therapeutic Function: Antitubercular
• Clinical Use: 2-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.

Technology Process of Ethionamide

There total 11 articles about Ethionamide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 82.0%

2-ethylpyridine-4-carboxamide (3376-95-2) → ethionamide (536-33-4,5261-38-1)

Guidance literature:

With pyridin-1-ium-1-yl[pyridin-1-ium-1-yl(sulfido)phosphinothioyl]sulfanyl-sulfido-thioxo-phosphane; In acetonitrile; for 0.5h; Reflux;

DOI:10.1021/jo101865y

Reference yield: 82.0%

→ ethionamide (536-33-4,5261-38-1)

Guidance literature:

Reference yield: 80.0%

2-ethyl-4-pyridinecarbonitrile (1531-18-6) → ethionamide (536-33-4,5261-38-1)

Guidance literature:

With 2,3,4,5,7,8,9,10-octahydropyrimido[1,2-a]azepin-1-ium acetate; sodiumsulfide nonahydrate; In neat (no solvent); at 20 ℃; for 2h; Green chemistry;

DOI:10.1039/c7ra11259a

upstream raw materials:

2-ethyl-4-pyridinecarbonitrile

2-ethylpyridine-4-carboxamide

methyl 2-ethylpyridine-4-carboxylate

2-ethyl-6-chloro-isonicotinic acid methyl ester

Downstream raw materials:

2-ethyl-4-pyridinecarbonitrile

2-ethylpyridine-4-carboxamide

1-(2-ethylpyridin-4-yl)methanamine

4-(4-chlorophenyl)-2-(ethylpyridin-4-yl)thiazole

Refernces

• 1、 Cao, Xian Ting,Yang, Huiyong,Zheng, Hui,Zhang, Pengfei. "A simple method for synthesis of thioamides and application in synthesis of 1,2,4-thiadiazoles". . p. 509 - 517. Retrieved 2018/03/27.
• 2、 Bellale, Eknath,Naik, Maruti,Vb, Varun,Ambady, Anisha,Narayan, Ashwini,Ravishankar, Sudha,Ramachandran, Vasanthi,Kaur, Parvinder,McLaughlin, Robert,Whiteaker, James,Morayya, Sapna,Guptha, Supreeth,Sharma, Sreevalli,Raichurkar, Anandkumar,Awasthy, Disha,Achar, Vijayshree,Vachaspati, Prakash,Bandodkar, Balachandra,Panda, Manoranjan,Chatterji, Monalisa. "Diarylthiazole: An antimycobacterial scaffold potentially targeting PrrB-PrrA two-component system". supporting information. p. 6572 - 6582. Retrieved 2014/10/15.