2-ethylpyridine-4-carbothioamide

• ChemBase编号: 491
• 分子式: C8H10N2S
• 平均质量: 166.2434
• 单一同位素质量: 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

名称和登记号

名称

• IUPAC标准名: 2-ethylpyridine-4-carbothioamide
• IUPAC传统名: ethionamide
• 商标名: 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
• 别名: 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

登记号

• CAS号: 536-33-4; 536-33-4
• EC号: 208-628-9
• MDL号: MFCD00057361
• PubChem SID: 160963954; 46506077; 24894350
• PubChem CID: 2761171
• CHEBI ID: 4885
• ATC码: J04AD03
• CHEMBL: 1441
• Chemspider ID: 2041901
• DrugBank ID: DB00609
• KEGG ID: D00591
• 美国药典/FDA物质标识码: OAY8ORS3CQ
• 维基百科标题: Ethionamide
• Medline Plus: a682402

理论计算性质

JChem

• Acid pKa: 11.89397
• 质子受体: 1
• 质子供体: 1
• LogD (pH = 5.5): 1.2127073
• LogD (pH = 7.4): 1.326323
• Log P: 1.3279893
• 摩尔折射率: 50.1888 cm^3
• 极化性: 19.25215 Å^3
• 极化表面积: 38.91 Å^2
• 可自由旋转的化学键: 2
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: 1.88
• LOG S: -2.3
• 溶解度: 8.39e-01 g/l

分子性质

理化性质

• 溶解度: DMSO; Practically insoluble
• 外观: Yellow Solid
• 熔点: 160-162°C (dec.); 164°C (decomposes)
• 疏水性(logP): 0.5

安全信息

• 保存条件: -20°C; 2-8°C; Refrigerator
• RTECS编号: NS0350000
• 欧盟危险性物质标志: 有害性(Harmful) (Xn)
• 德国WGK号: 3
• 危险公开号: 63-22; R:22
• 安全公开号: 36/37; S:36/37/39
• GHS危险品标识: GHS07; GHS08
• GHS警示词: Warning
• GHS危险声明: H302-H361
• GHS警示性声明: P281
• 个人保护装置: 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
• 保存温度: 2-8°C

药理学性质

• 半衰期: 2 to 3 hours
• 蛋白结合率: Approximately 30% bound to proteins.

产品相关信息

• 成盐信息: Free Base
• Empirical Formula (Hill Notation): C8H10N2S

详细说明

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

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).

参考文献

• 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