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Substance Name: Ethionamide [USAN:USP:INN:BAN:JAN]
RN: 536-33-4
UNII: OAY8ORS3CQ
InChIKey: AEOCXXJPGCBFJA-UHFFFAOYSA-N

Note

  • A second-line antitubercular agent that inhibits mycolic acid synthesis.

Molecular Formula

  • C8-H10-N2-S

Molecular Weight

  • 166.247
 

Classification Codes

Classification Codes

  • Anti-Bacterial Agents
  • Anti-Infective Agents
  • Antibacterial (Tuberculostatic)
  • Antimetabolites
  • Antitubercular Agents
  • Drug / Therapeutic Agent
  • Fatty Acid Synthesis Inhibitors
  • Human Data
  • Hypolipidemic Agents
  • Mutation Data
  • Reproductive Effect
  • Tumor Data

Superlist Classification Code

  • Overall Carcinogenic Evaluation: Group 3

Names and Synonyms

Name of Substance

  • Ethionamide [USAN:USP:INN:BAN:JAN]

MeSH Heading

  • Ethionamide

Synonyms

  • 1314 TH
  • 1314-TH
  • 1314TH
  • 2-Ethyl-4-pyridinecarbothioamide
  • 2-Ethyl-4-thiocarbamoylpyridine
  • 2-Ethylisonicotinic acid thioamide
  • 2-Ethylisonicotinothioamide
  • 2-Ethylisothionicotinamide
  • 2-Ethylthioisonicotinamide
  • 5-22-02-00360 (Beilstein Handbook Reference)
  • Aethionamidum
  • Aetina
  • Aetiva
  • alpha-Ethylisonicotinic acid thioamide
  • alpha-Ethylisonicotinoylthioamide
  • alpha-Ethylisothionicotinamide
  • alpha-Ethylthioisonicotinamide
  • Amidazin
  • Amidazine
  • Atina
  • Bayer 5312
  • BRN 0116474
  • CCRIS 287
  • EINECS 208-628-9
  • Ethimide
  • Ethina
  • Ethina (VAN)
  • Ethionamid prothionamid
  • Ethionamide
  • Ethionamidum
  • Ethionamidum [INN-Latin]
  • Ethioniamide
  • Ethylisothiamide
  • Ethyonomide
  • Etimid
  • Etimid (VAN)
  • Etiocidan
  • Etionamid
  • Etionamida
  • Etionamida [INN-Spanish]
  • Etionamide
  • Etionamide [DCIT]
  • Etioniamid
  • Etionid
  • Etionizin
  • Etionizina
  • Etionizine
  • F.I. 58-30
  • Fatoliamid
  • HSDB 7473
  • Iridocin
  • Iridocin Bayer
  • Iridozin
  • Isothin
  • Isotiamida
  • Itiocide
  • NCI-C01694
  • Nicotion
  • Nizotin
  • NSC 255115
  • Rigenicid
  • Sertinon
  • Teberus
  • TH 1314
  • Thianid
  • Thianide
  • Thioamide
  • Thioniden
  • Tianid
  • Tio-Mid
  • Trecator
  • Trecator-SC
  • Trekator
  • Trescatyl
  • Trescazide
  • Tubenamide
  • Tubermin
  • Tuberoid
  • Tuberoson
  • UNII-OAY8ORS3CQ

Systematic Names

  • 4-Pyridinecarbothioamide, 2-ethyl-
  • Ethionamide
  • Isonicotinamide, 2-ethylthio-
  • Isonicotinimidic acid, 2-ethylthio-

Superlist Name

  • Ethionamide

Registry Numbers

CAS Registry Number

  • 536-33-4

FDA UNII

  • OAY8ORS3CQ

Other Registry Number

  • 5261-38-1

System Generated Number

  • 0000536334

Structure Descriptors

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

Smiles

CCc1cc(ccn1)C(=S)N

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
guinea pig LD50 subcutaneous 550mg/kg (550mg/kg)   Ukrainskii Biokhimicheskii Zhurnal. Ukranian Biochemical Journal. Vol. 52, Pg. 593, 1980.
human TDLo oral 482mg/kg/5W (482mg/kg) LIVER: "JAUNDICE, OTHER OR UNCLASSIFIED"

LIVER: CHANGE IN GALL BLADDER STRUCTURE OR FUNCTION
American Review of Respiratory Disease. Vol. 87, Pg. 896, 1963.
human TDLo oral 856mg/kg (856mg/kg) LIVER: "JAUNDICE, OTHER OR UNCLASSIFIED"

LIVER: CHANGE IN GALL BLADDER STRUCTURE OR FUNCTION
American Review of Respiratory Disease. Vol. 84, Pg. 890, 1961.
mouse LD50 intraperitoneal 1350mg/kg (1350mg/kg)   Dissertationes Pharmaceuticae et Pharmacologicae. Vol. 23, Pg. 383, 1971.
mouse LD50 oral 1gm/kg (1000mg/kg)   Federation Proceedings, Federation of American Societies for Experimental Biology. Vol. 21, Pg. 452, 1962.
mouse LD50 subcutaneous 1580mg/kg (1580mg/kg)   Drugs in Japan Vol. 6, Pg. 111, 1982.
rat LD50 intraperitoneal 490mg/kg (490mg/kg)   Drugs in Japan Vol. 6, Pg. 111, 1982.
rat LD50 oral 1320mg/kg (1320mg/kg)   Drugs in Japan Vol. 6, Pg. 111, 1982.
rat LD50 subcutaneous 1350mg/kg (1350mg/kg)   Drugs in Japan Vol. 6, Pg. 111, 1982.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 163 deg C   EXP
log P (octanol-water) 1.520 (none)   EST
Atmospheric OH Rate Constant 2.41E-11 cm3/molecule-sec 25 EST

Physical property data is provided to ChemIDplus by SRC, Inc.