2-ethylpyridine-4-carbothioamide

• ChemBase ID: 491
• Molecular Formular: C8H10N2S
• Molecular Mass: 166.2434
• Monoisotopic Mass: 166.05646933
• SMILES: S=C(N)c1cc(ncc1)CC
• Canonical SMILES: CCc1nccc(c1)C(=S)N
• InChI: InChI=1S/C8H10N2S/c1-2-7-5-6(8(9)11)3-4-10-7/h3-5H,2H2,1H3,(H2,9,11)
• InChIKey: AEOCXXJPGCBFJA-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-ethylpyridine-4-carbothioamide
• IUPAC Traditional name: ethionamide
• Brand Name: Aethionamidum; Aetina; Aetiva; Amidazin; Amidazine; Atina; Bayer 5312; Ethimide; Ethina; Etimid; Etiocidan; Etionid; Etionizin; Etionizina; Etionizine; Fatoliamid; Iridocin; Iridozin; Isothin; Isotiamida; Itiocide; Nicotion; Nisotin; Nizotin; Rigenicid; Sertinon; Teberus; Thianid; Thianide; Thioamide; Thiomid; Thioniden; Tianid; Tio-Mid; Tiomid; Trecator; Trecator-SC; Trekator; Trescatyl; Trescazide; Tubenamide; Tubermin; Tuberoid; Tuberoson
• Synonyms: 2-Ethyl-4-pyridine-carbothioamide; 2-Ethyl-4-thiocarbamoylpyridine; 2-Ethylisonicotinic Acid Thioamide; Amidazine; Ethionamide; Etimid; Etionid; Etionizin; Etionizine; Iridocin; Iridozin; NSC 255115; Nizotin; Sertinon; Teberus; Thianide; Thiodine; Tianid; Tiomid; Trecator; Trekator; Trescatyl; α-Ethylisothionicotinamide; α-Ethylthioisonicotinamide; Etionamide [DCIT]; Etionamida [INN-Spanish]; Etionamid; Etioniamid; Ethioniamide; Ethylisothiamide; Ethyonomide; Ethionamidum [INN-Latin]; Ethionamid prothionamid; Ethinamide; ETH; ET; ETP; Ethionamide; 2-ethylthioisonicotinamide; Trecator SC; Ethionamide; 2-Ethyl-4-pyridinecarbothioamide

Database IDs

• CAS Number: 536-33-4; 536-33-4
• EC Number: 208-628-9
• MDL Number: MFCD00057361
• PubChem SID: 24894350; 46506077; 160963954
• PubChem CID: 2761171
• CHEBI ID: 4885
• ATC CODE: J04AD03
• CHEMBL: 1441
• Chemspider ID: 2041901
• DrugBank ID: DB00609
• KEGG ID: D00591
• Unique Ingredient Identifier: OAY8ORS3CQ
• Wikipedia Title: Ethionamide
• Medline Plus: a682402

CALCULATED PROPERTIES

JChem

• Acid pKa: 11.89397
• H Acceptors: 1
• H Donor: 1
• LogD (pH = 5.5): 1.2127073
• LogD (pH = 7.4): 1.326323
• Log P: 1.3279893
• Molar Refractivity: 50.1888 cm^3
• Polarizability: 19.25215 Å^3
• Polar Surface Area: 38.91 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 1.88
• LOG S: -2.3
• Solubility (Water): 8.39e-01 g/l

PROPERTIES

Physical Property

• Solubility: DMSO; Practically insoluble
• Apperance: Yellow Solid
• Melting Point: 160-162°C (dec.); 164°C (decomposes)
• Hydrophobicity(logP): 0.5

Safety Information

• Storage Condition: -20°C; 2-8°C; Refrigerator
• RTECS: NS0350000
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 63-22; R:22
• Safety Statements: 36/37; S:36/37/39
• GHS Pictograms: GHS07; GHS08
• GHS Signal Word: Warning
• GHS Hazard statements: H302-H361
• GHS Precautionary statements: P281
• Personal Protective Equipment: Eyeshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges
• Storage Temperature: 2-8°C

Pharmacology Properties

• Half Life: 2 to 3 hours
• Protein Bound: Approximately 30% bound to proteins.

Product Information

• Salt Data: Free Base
• Empirical Formula (Hill Notation): C8H10N2S

DETAILS

MP Biomedicals - 02157954

Crystalline

DrugBank - DB00609

• Drug Groups: approved
• Description: A second-line antitubercular agent that inhibits mycolic acid synthesis. It also may be used for treatment of leprosy. (From Smith and Reynard, Textbook of Pharmacology, 1992, p868)
• Indication: For use in the treatment of pulmonary and extrapulmonary tuberculosis when other antitubercular drugs have failed.
• Pharmacology: Ethinamate is bacteriostatic against M. tuberculosis. In a study examining ethionamide resistance, ethionamide administered orally initially decreased the number of culturable Mycobacterium tuberculosis organisms from the lungs of H37Rv infected mice. Drug resistance developed with continued ethionamide monotherapy, but did not occur when mice received ethionamide in combination with streptomycin or isoniazid.
• Toxicity: Symptoms of overdose include convulsions, nausea, and vomiting.
• Affected Organisms: Mycobacteria
• Biotransformation: Hepatic and extensive. Metabolized to the active metabolite sulfoxide, and several inactive metabolites. The sulphoxide metabolite has been demonstrated to have antimicrobial activity against Mycobacterium tuberculosis.
• Absorption: Essentially completely absorbed following oral administration and not subjected to any appreciable first pass metabolism. Bioavailability approximately 100%.
• Half Life: 2 to 3 hours
• Protein Binding: Approximately 30% bound to proteins.
• Elimination: Less than 1% of the oral dose is excreted as ethionamide in urine. Ethionamide is extensively metabolized to active and inactive metabolites.
• Distribution: * 93.5 L [healthy volunteers]
• External Links: Wikipedia; RxList; Drugs.com

Selleck Chemicals - S1777

Research Area: Infection
Biological Activity:
Ethionamide(2-ethylthioisonicotinamide) is an antibiotic used in the treatment of tuberculosis. It works by inhibiting or stopping the growth of TB cells, which results in cell death. [1]

Sigma Aldrich - E6005

Biochem/physiol Actions
Ethionamide is used as an anti-tuberculosis antibiotic and an inducer of hypothyroidism.
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. E6005.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Toronto Research Chemicals - E890420

Antibacterial (tuberculostatic).

REFERENCES

• http://en.wikipedia.org/wiki/Ethionamide
• Banerjee, A., et al.: Science, 263, 227 (1994)
• Newton, G., et al.: J. Bacteriol., 178, 1990 (1994)
• Baulard, A., et al.: J. Biol. Chem., 275, 28326 (1994)
• Koledin, T., et al.: Arch. Microbiol., 178, 331 (1994)
• Cardoso, R., et al.: Antimicrob. Agents Ch