Home > Compound List > Compound details
536-33-4 molecular structure
click picture or here to close

2-ethylpyridine-4-carbothioamide

ChemBase ID: 491
Molecular Formular: C8H10N2S
Molecular Mass: 166.2434
Monoisotopic Mass: 166.05646933
SMILES and InChIs

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

Cite this record

CBID:491 http://www.chembase.cn/molecule-491.html

Collapse All Expand All

NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
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
CAS Number
536-33-4
536-33-4
EC Number
208-628-9
MDL Number
MFCD00057361
PubChem SID
160963954
46506077
24894350
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

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 11.89397  H Acceptors
H Donor LogD (pH = 5.5) 1.2127073 
LogD (pH = 7.4) 1.326323  Log P 1.3279893 
Molar Refractivity 50.1888 cm3 Polarizability 19.25215 Å3
Polar Surface Area 38.91 Å2 Rotatable Bonds
Lipinski's Rule of Five true 
Log P 1.88  LOG S -2.3 
Solubility (Water) 8.39e-01 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Solubility
DMSO expand Show data source
Practically insoluble expand Show data source
Apperance
Yellow Solid expand Show data source
Melting Point
160-162°C (dec.) expand Show data source
164°C (decomposes) expand Show data source
Hydrophobicity(logP)
0.5 expand Show data source
Storage Condition
-20°C expand Show data source
2-8°C expand Show data source
Refrigerator expand Show data source
RTECS
NS0350000 expand Show data source
European Hazard Symbols
Harmful Harmful (Xn) expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
Download expand Show data source
German water hazard class
3 expand Show data source
Risk Statements
63-22 expand Show data source
R:22 expand Show data source
Safety Statements
36/37 expand Show data source
S:36/37/39 expand Show data source
GHS Pictograms
GHS07 expand Show data source
GHS08 expand Show data source
GHS Signal Word
Warning expand Show data source
GHS Hazard statements
H302-H361 expand Show data source
GHS Precautionary statements
P281 expand Show data source
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 expand Show data source
Storage Temperature
2-8°C expand Show data source
Half Life
2 to 3 hours expand Show data source
Protein Bound
Approximately 30% bound to proteins. expand Show data source
Salt Data
Free Base expand Show data source
Certificate of Analysis
Download expand Show data source
Download expand Show data source
Empirical Formula (Hill Notation)
C8H10N2S expand Show data source

DETAILS

DETAILS

MP Biomedicals MP Biomedicals DrugBank DrugBank Selleck Chemicals Selleck Chemicals Wikipedia Wikipedia Sigma Aldrich Sigma Aldrich TRC TRC
DrugBank - DB00609 external link
Item Information
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 external link
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 external link
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 external link
Antibacterial (tuberculostatic).

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • •  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
  • Searching...Please wait...

PATENTS

PATENTS

PubChem iconPubChem Patent Google Patent Search IconGoogle Patent

INTERNET

INTERNET

Baidu iconBaidu google iconGoogle