CAS 536-33-4|CAS 536-33-4|Ethionamide|2-ethylthioisonicotinamide|ethionamide|Trecator SC|2-ethylpyridine-4-carbothioamide|2-Ethyl-4-pyridinecarbothioamide|Ethionamide|Nisotin|Sertinon|Etionizine|Tub...

General Information

Structure

Molecular Formula

C₈H₁₀N₂S

Molecular Mass

166.2434

Exact Mass

166.05646933

Charge

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

Canonic Smiles

CCc1nccc(c1)C(=S)N

Isomeric Smiles

S=C(N)c1cc(ncc1)CC

Calculated Properties

JChem

LogD (pH = 7.4)

1.33

LogD (pH = 5.5)

1.21

Log P

1.33

Rotatable Bonds

H Donor

H Acceptors

Lipinski's Rule of Five

true

Acid pKa

5.00

Polar Surface Area

38.91

Polarizability

17.99

Molar Refractivity

50.19

LOG S

-1.96

Data Source

Names and Identifiers

Synonyms

Ethionamide2-ethylthioisonicotinamideTrecator SC2-Ethyl-4-pyridinecarbothioamideEthionamideEthyonomideETHETEtioniamidEtionamida [INN-Spanish]EthioniamideETPEthionamid prothionamidEthinamideEthylisothiamideEthionamidum [INN-Latin]EtionamidEtionamide [DCIT]TeberusTrekatorα-EthylisothionicotinamideIridocinα-EthylthioisonicotinamideNSC 255115TianidTrescatylTrecatorThiodine2-Ethyl-4-pyridine-carbothioamide2-Ethyl-4-thiocarbamoylpyridineTiomidThianideAmidazineEtionizineNizotinEtimidSertinonIridozinEthionamide2-Ethylisonicotinic Acid ThioamideEtionizinEtionidEthinamideEtionamidEtioniamidethionamideEthylisothiamideEthionamideEthioniamideEthyonomideethionamide2-ethyl-4-thiopyridylamideETHEtionamideETP

IUPAC Traditional name

ethionamide

IUPAC name

2-ethylpyridine-4-carbothioamide

Brand Name

NisotinSertinonEtionizineTuberoidAetivaEtimidIsothinTuberosonTrecatorThianidTrescatylIridozinTianidFatoliamidTio-MidIsotiamidaAmidazineEthimideTrescazideTeberusNizotinThianideEtionidEtionizinaItiocideThioamideTiomidBayer 5312Trecator-SCNicotionIridocinEtiocidanRigenicidAmidazinTuberminAethionamidumThionidenEthinaAtinaThiomidTrekatorEtionizinAetinaTubenamide

International Nonproprietary Name (INN)

ethionamidumetionamida

Names and Identifiers

Registration numbers

Properties

Physical Property

Product Information

Salt Data

Free Base

Certificate of Analysis

Download link

Empirical Formula (Hill Notation)

C8H10N2S

Pharmacology Properties

Half Life

2 to 3 hours

Protein Bound

Approximately 30% bound to proteins.

Properties

Related Proteins

No Data Available

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Molecular Spectra

No Data Available

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Molecule Details

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]

Crystalline

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.

TRC

E890420

Antibacterial (tuberculostatic).

ChEBI

CHEBI:4885

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.

Molecule Details

References

PubChem Literature

From Data Sources

• http://en.wikipedia.org/wiki/Ethionamide

• Banerjee, A., et al.: Science, 263, 227 (1994)

• Baulard, A., et al.: J. Biol. Chem., 275, 28326 (1994)

• Newton, G., et al.: J. Bacteriol., 178, 1990 (1994)

• Koledin, T., et al.: Arch. Microbiol., 178, 331 (1994)

• Cardoso, R., et al.: Antimicrob. Agents Ch

References

Bioactivity

PubChem BioAssay

Bioactivity

Names and Identifiers

Synonyms

IUPAC Traditional name

ethionamide

IUPAC name

2-ethylpyridine-4-carbothioamide

Brand Name

International Nonproprietary Name (INN)

ethionamidumetionamida

Molecule Details

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

Toxicity

Symptoms of overdose include convulsions, nausea, and vomiting.

Affected Organisms

Mycobacteria

Biotransformation

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]

S1777

Crystalline

E6005

E890420

Antibacterial (tuberculostatic).

ChEBI

CHEBI:4885

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.

References

PubChem Literature

From Data Sources

• http://en.wikipedia.org/wiki/Ethionamide

• Banerjee, A., et al.: Science, 263, 227 (1994)

• Baulard, A., et al.: J. Biol. Chem., 275, 28326 (1994)

• Newton, G., et al.: J. Bacteriol., 178, 1990 (1994)

• Koledin, T., et al.: Arch. Microbiol., 178, 331 (1994)

• Cardoso, R., et al.: Antimicrob. Agents Ch

Bioactivity

PubChem BioAssay

Properties

Physical Property

Product Information

Salt Data

Free Base

Certificate of Analysis

Download link

Empirical Formula (Hill Notation)

C8H10N2S

Pharmacology Properties

Half Life

2 to 3 hours

Protein Bound

Approximately 30% bound to proteins.

Molecule

ID:491