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    Chemistry

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    Also known as: 536-33-4, 2-ethylpyridine-4-carbothioamide, Ethioniamide, Trecator, 2-ethylthioisonicotinamide, Ethyonomide
    Molecular Formula
    C8H10N2S
    Molecular Weight
    166.25  g/mol
    InChI Key
    AEOCXXJPGCBFJA-UHFFFAOYSA-N
    FDA UNII
    OAY8ORS3CQ
    Ethionamide
    A second-line antitubercular agent that inhibits mycolic acid synthesis.
    Ethionamide is an Antimycobacterial.
    1 2D Structure

    Ethionamide

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    2-ethylpyridine-4-carbothioamide
    2.1.2 InChI
    InChI=1S/C8H10N2S/c1-2-7-5-6(8(9)11)3-4-10-7/h3-5H,2H2,1H3,(H2,9,11)
    2.1.3 InChI Key
    AEOCXXJPGCBFJA-UHFFFAOYSA-N
    2.1.4 Canonical SMILES
    CCC1=NC=CC(=C1)C(=S)N
    2.2 Other Identifiers
    2.2.1 UNII
    OAY8ORS3CQ
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. Amidazine

    2. Ethioniamide

    3. Trecator

    4. Trecator Sc

    5. Trecator-sc

    2.3.2 Depositor-Supplied Synonyms

    1. 536-33-4

    2. 2-ethylpyridine-4-carbothioamide

    3. Ethioniamide

    4. Trecator

    5. 2-ethylthioisonicotinamide

    6. Ethyonomide

    7. Amidazine

    8. Ethinamide

    9. Etionamid

    10. Etioniamid

    11. Thioamide

    12. Ethylisothiamide

    13. Trecator-sc

    14. Nizotin

    15. 4-pyridinecarbothioamide, 2-ethyl-

    16. Amidazin

    17. Ethimide

    18. Etiocidan

    19. Etionizin

    20. Etionizina

    21. Etionizine

    22. Fatoliamid

    23. Iridocin

    24. Iridozin

    25. Isotiamida

    26. Itiocide

    27. Nicotion

    28. Rigenicid

    29. Sertinon

    30. Thianide

    31. Thioniden

    32. Trekator

    33. Trescatyl

    34. Trescazide

    35. Tubenamide

    36. Tubermin

    37. Tuberoid

    38. Tuberoson

    39. Aetina

    40. Aetiva

    41. Ethina

    42. Etimid

    43. Etionid

    44. Isothin

    45. Teberus

    46. Thianid

    47. Tianid

    48. Atina

    49. Bayer 5312

    50. Ethionamid Prothionamid

    51. Iridocin Bayer

    52. Ethionamidum

    53. Nisotin

    54. Thiomid

    55. Etionamide [dcit]

    56. Etionamida

    57. Etionamide

    58. Tiomid

    59. 2-ethylisothionicotinamide

    60. 2-ethyl-4-pyridinecarbothioamide

    61. 2-ethylisonicotinothioamide

    62. Ethionamidum [inn-latin]

    63. Etionamida [inn-spanish]

    64. 1314 Th

    65. 2-ethyl-4-thiocarbamoylpyridine

    66. 2-ethyl-4-thiopyridylamide

    67. 2-ethyl-thioisonicotinamide

    68. 2-ethylisonicotinic Acid Thioamide

    69. Th 1314

    70. Nci-c01694

    71. 1314-th

    72. F.i. 58-30

    73. 1314th

    74. 2-ethyl-4-thioamidylpyridine

    75. Isonicotinamide, 2-ethylthio-

    76. Oay8ors3cq

    77. Aethionamidum

    78. Etp

    79. Nsc-255115

    80. Tio-mid

    81. Mls000069764

    82. Chebi:4885

    83. .alpha.-ethylisothionicotinamide

    84. .alpha.-ethylthioisonicotinamide

    85. .alpha.-ethylisonicotinoylthioamide

    86. Trecator Sc

    87. Nsc255115

    88. 1314 Tn

    89. .alpha.-ethylisonicotinic Acid Thioamide

    90. Ethina (van)

    91. Ncgc00016497-05

    92. Cas-536-33-4

    93. Smr000058716

    94. Dsstox_cid_577

    95. Dsstox_rid_75669

    96. Dsstox_gsid_20577

    97. Alpha-ethylisothionicotinamide

    98. Alpha-ethylthioisonicotinamide

    99. Alpha-ethylisonicotinoylthioamide

    100. 2-ethylisonicotinic Thioamide

    101. Alpha-ethylisonicotinic Acid Thioamide

    102. Ccris 287

    103. Hsdb 7473

    104. Bayer5312

    105. Sr-01000759219

    106. Unii-oay8ors3cq

    107. Einecs 208-628-9

    108. Nsc 255115

    109. Brn 0116474

    110. Thiodine

    111. Trecator (tn)

    112. Prestwick_842

    113. Isonicotinimidic Acid, 2-ethylthio-

    114. Mfcd00057361

    115. Ethionamide [usan:usp:inn:ban:jan]

    116. Spectrum_001082

    117. Cpd001370750

    118. Opera_id_632

    119. Ethionamide [mi]

    120. Prestwick0_000526

    121. Prestwick1_000526

    122. Prestwick2_000526

    123. Prestwick3_000526

    124. Spectrum2_000994

    125. Spectrum3_000428

    126. Spectrum4_000547

    127. Spectrum5_000979

    128. 2-ethylisonicotinothiamide

    129. 2-ethylisonicotinthioamide

    130. Ethionamide [inn]

    131. Ethionamide [jan]

    132. E0695

    133. Ethionamide [hsdb]

    134. Ethionamide [iarc]

    135. Ethionamide [usan]

    136. Ethionamide [vandf]

    137. Chembl1441

    138. Ethionamide [mart.]

    139. Schembl27007

    140. Bspbio_000511

    141. Bspbio_002016

    142. Ethionamide [usp-rs]

    143. Ethionamide [who-dd]

    144. Ethionamide [who-ip]

    145. Kbiogr_001213

    146. Kbioss_001562

    147. 5-22-02-00360 (beilstein Handbook Reference)

    148. Mls001074114

    149. Mls002454402

    150. Divk1c_000145

    151. Spectrum1500292

    152. Wln: T6nj B2 Dyzus

    153. Spbio_001087

    154. Spbio_002432

    155. Bpbio1_000563

    156. Ethionamide (jp17/usp/inn)

    157. Dtxsid0020577

    158. Aeocxxjpgcbfja-uhfffaoysa-

    159. Hms500h07

    160. Kbio1_000145

    161. Kbio2_001562

    162. Kbio2_004130

    163. Kbio2_006698

    164. Kbio3_001236

    165. .alpha.-ethyl-thioisonicotinamide

    166. Ethionamide [orange Book]

    167. Isonicotinamide, 2-ethyl, Thio-

    168. Ethionamide For System Suitability

    169. Ninds_000145

    170. Ethionamide [ep Monograph]

    171. Hms1569j13

    172. Hms1920m22

    173. Hms2091f03

    174. Hms2096j13

    175. Hms2231f10

    176. Hms2233j11

    177. Hms3259k17

    178. Hms3370i18

    179. Hms3371d12

    180. Hms3655m10

    181. Hms3713j13

    182. Pharmakon1600-01500292

    183. Ethionamide [usp Monograph]

    184. Bcp29626

    185. Ethionamidum [who-ip Latin]

    186. Hy-b0276

    187. Zinc3872520

    188. Tox21_110458

    189. Tox21_202409

    190. Tox21_302769

    191. Ccg-40212

    192. Nsc757028

    193. S1777

    194. Akos006220662

    195. Tox21_110458_1

    196. Db00609

    197. Fs-1770

    198. Nc00508

    199. Nsc-757028

    200. Idi1_000145

    201. Ncgc00016497-01

    202. Ncgc00016497-02

    203. Ncgc00016497-03

    204. Ncgc00016497-04

    205. Ncgc00016497-06

    206. Ncgc00016497-08

    207. Ncgc00016497-09

    208. Ncgc00091074-01

    209. Ncgc00091074-02

    210. Ncgc00091074-03

    211. Ncgc00091074-04

    212. Ncgc00256600-01

    213. Ncgc00259958-01

    214. Ac-13715

    215. Smr001370750

    216. Sbi-0051377.p003

    217. Db-049945

    218. 2-ethylpyridine-4-carbothioamide;ethionamide

    219. Ab00051990

    220. Sw196973-3

    221. C07665

    222. D00591

    223. F15438

    224. Ab00051990-09

    225. Ab00051990_10

    226. Ab00051990_11

    227. A829694

    228. Q414767

    229. Sr-01000759219-2

    230. Sr-01000759219-5

    231. W-105719

    232. Brd-k33710385-001-05-4

    233. Brd-k51207550-001-09-9

    234. Ethionamide, European Pharmacopoeia (ep) Reference Standard

    235. Ethionamide, United States Pharmacopeia (usp) Reference Standard

    236. Ethinamide; 2-ethylthioisonicotinamide; 2-ethylpyridine-4-carbothioamide

    237. Ethionamide For System Suitability, European Pharmacopoeia (ep) Reference Standard

    238. Trecator;2-ethylthioisonicotinamide;ethinamide; Ethioniamide; Trecator Sc; Trecator-sc

    2.4 Create Date
    2005-03-25
    3 Chemical and Physical Properties
    Molecular Weight 166.25 g/mol
    Molecular Formula C8H10N2S
    XLogP31.1
    Hydrogen Bond Donor Count1
    Hydrogen Bond Acceptor Count2
    Rotatable Bond Count2
    Exact Mass166.05646950 g/mol
    Monoisotopic Mass166.05646950 g/mol
    Topological Polar Surface Area71 Ų
    Heavy Atom Count11
    Formal Charge0
    Complexity147
    Isotope Atom Count0
    Defined Atom Stereocenter Count0
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Drug and Medication Information
    4.1 Drug Information
    1 of 2  
    Drug NameTrecator
    PubMed HealthEthionamide (By mouth)
    Drug ClassesAntitubercular
    Drug LabelTrecator (ethionamide tablets, USP) is used in the treatment of tuberculosis. The chemical name for ethionamide is 2-ethylthioisonicotinamide with the following structural formula: Ethionamide is a yellow crystalline, nonhygroscopic compound with a...
    Active IngredientEthionamide
    Dosage FormTablet
    RouteOral
    Strength250mg
    Market StatusPrescription
    CompanyWyeth Pharms

    2 of 2  
    Drug NameTrecator
    PubMed HealthEthionamide (By mouth)
    Drug ClassesAntitubercular
    Drug LabelTrecator (ethionamide tablets, USP) is used in the treatment of tuberculosis. The chemical name for ethionamide is 2-ethylthioisonicotinamide with the following structural formula: Ethionamide is a yellow crystalline, nonhygroscopic compound with a...
    Active IngredientEthionamide
    Dosage FormTablet
    RouteOral
    Strength250mg
    Market StatusPrescription
    CompanyWyeth Pharms

    4.2 Therapeutic Uses

    Antibacterial (tuberculostatic)

    O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. 13th Edition, Whitehouse Station, NJ: Merck and Co., Inc., 2001., p. 666

    Ethionamide is indicated in combination with other antituberculosis medications in the treatment of tuberculosis, including tuberculous meningitis, after failure with the primary medications (streptomycin, isoniazid, rifampin, and ethambutol) or when these cannot be used because of toxicity or development of resistant tubercle bacilli. Ethionamide is effective only against mycobacteria. /Included in US product label/

    Thomson/Micromedex. Drug Information for the Health Care Professional. Volume 1, Greenwood Village, CO. 2006.

    Ethionamide is used in combination with other antileprosy agents in the treatment of Hansen's disease. /Not included in US product label/

    Thomson/Micromedex. Drug Information for the Health Care Professional. Volume 1, Greenwood Village, CO. 2006.

    Ethionamide is used in the treatment of atypical mycobacterial infections, such as Mycobacterium avium complex (MAC). /Not included in US product label/

    Thomson/Micromedex. Drug Information for the Health Care Professional. Volume 1, Greenwood Village, CO. 2006.

    Ethionamide and prothionamide are thioamides used as second-line antituberculosis drugs for treatment of multi-drug resistant tuberculosis.

    WHO; Guidelines for the Management of Drug-Resistant Tuberculosis (WHO/TB/96.210 REV.1) 1997. Available from, as of November 26, 2006: https://whqlibdoc.who.int/hq/1997/WHO_TB_96.210_(Rev.1).pdf

    4.3 Drug Warning

    Adverse GI effects, including nausea, vomiting, diarrhea, abdominal pain, excessive salivation, metallic taste, stomatitis, anorexia, and weight loss, are the most common adverse effects reported with ethionamide. Nausea and vomiting may be severe enough to necessitate discontinuance of ethionamide. GI effects appear to be dose related, and approximately 50% of patients are unable to tolerate a single 1-g dose of the drug.

    McEvoy, G.K. (ed.). American Hospital Formulary Service. AHFS Drug Information. American Society of Health-System Pharmacists, Bethesda, MD. 2006., p. 567

    Psychotic disturbances, mental depression, restlessness, drowsiness, dizziness, headache, postural hypotension, and asthenia occur occasionally with ethionamide. Rarely, peripheral neuritis, paresthesia, seizures, tremors, a pellagra-like syndrome, hallucinations, diplopia, optic neuritis, blurred vision, and olfactory disturbances have been reported.

    McEvoy, G.K. (ed.). American Hospital Formulary Service. AHFS Drug Information. American Society of Health-System Pharmacists, Bethesda, MD. 2006., p. 567

    The manufacturer of ethionamide recommends concomitant use of pyridoxine to prevent or relieve neurotoxic effects during ethionamide treatment.

    McEvoy, G.K. (ed.). American Hospital Formulary Service. AHFS Drug Information. American Society of Health-System Pharmacists, Bethesda, MD. 2006., p. 568

    Transient increases in serum bilirubin, AST (SGOT), and ALT (SGPT) concentrations have been reported in patients receiving ethionamide. Hepatitis (with or without jaundice) also has been reported. Hepatotoxicity generally is reversible following discontinuance of the drug.

    McEvoy, G.K. (ed.). American Hospital Formulary Service. AHFS Drug Information. American Society of Health-System Pharmacists, Bethesda, MD. 2006., p. 568

    For more Drug Warnings (Complete) data for ETHIONAMIDE (22 total), please visit the HSDB record page.

    4.4 Drug Indication

    For use in the treatment of pulmonary and extrapulmonary tuberculosis when other antitubercular drugs have failed.

    FDA Label

    5 Pharmacology and Biochemistry
    5.1 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.

    5.2 MeSH Pharmacological Classification

    Antitubercular Agents

    Drugs used in the treatment of tuberculosis. They are divided into two main classes: "first-line" agents, those with the greatest efficacy and acceptable degrees of toxicity used successfully in the great majority of cases; and "second-line" drugs used in drug-resistant cases or those in which some other patient-related condition has compromised the effectiveness of primary therapy. (See all compounds classified as Antitubercular Agents.)

    Fatty Acid Synthesis Inhibitors

    Compounds that interfere with FATTY ACID SYNTHASE resulting in a reduction of FATTY ACIDS. This is a target mechanism in humans of some ANTINEOPLASTIC AGENTS and ANTI-OBESITY AGENTS and of some ANTI-INFECTIVE AGENTS which interfere with CELL WALL and CELL MEMBRANE formation. (See all compounds classified as Fatty Acid Synthesis Inhibitors.)

    5.3 FDA Pharmacological Classification
    5.3.1 Active Moiety
    ETHIONAMIDE
    5.3.2 FDA UNII
    OAY8ORS3CQ
    5.3.3 Pharmacological Classes
    Antimycobacterial [EPC]
    5.4 ATC Code

    J - Antiinfectives for systemic use

    J04 - Antimycobacterials

    J04A - Drugs for treatment of tuberculosis

    J04AD - Thiocarbamide derivatives

    J04AD03 - Ethionamide

    5.5 Absorption, Distribution and Excretion

    Absorption

    Essentially completely absorbed following oral administration and not subjected to any appreciable first pass metabolism. Bioavailability approximately 100%.

    Route of Elimination

    Less than 1% of the oral dose is excreted as ethionamide in urine. Ethionamide is extensively metabolized to active and inactive metabolites.

    Volume of Distribution

    93.5 L [healthy volunteers]

    Rapidly absorbed from the gastrointestinal tract following oral administration. Bioavailability approximately 100%.

    Thomson/Micromedex. Drug Information for the Health Care Professional. Volume 1, Greenwood Village, CO. 2006.

    Ethionamide is essentially completely absorbed following oral administration and does not undergo any appreciable first-pass metabolism.

    McEvoy, G.K. (ed.). American Hospital Formulary Service. AHFS Drug Information. American Society of Health-System Pharmacists, Bethesda, MD. 2006., p. 568

    Following a single 250-mg oral dose of ethionamide given as film-coated tablets in fasting adults, peak plasma concentrations of ethionamide average 2.16 mcg/mL and are attained within 1 hour. When a single 250-mg oral dose of ethionamide is given as sugar-coated tablets (Trecator-SC; no longer commercially available in the US) in healthy adults, peak plasma concentrations average 1.48 mcg/mL and are attained within 1.5 hours.

    McEvoy, G.K. (ed.). American Hospital Formulary Service. AHFS Drug Information. American Society of Health-System Pharmacists, Bethesda, MD. 2006., p. 568

    Time to peak concentration: Approximately 1.8 hours; Peak serum concentration: Approximately 2.2 mcg/mL after a single oral 500-mg dose.

    Thomson/Micromedex. Drug Information for the Health Care Professional. Volume 1, Greenwood Village, CO. 2006.

    For more Absorption, Distribution and Excretion (Complete) data for ETHIONAMIDE (11 total), please visit the HSDB record page.

    5.6 Metabolism/Metabolites

    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.

    Ethionamide is extensively metabolized to active and inactive metabolites. Metabolism is presumed to occur in the liver and thus far 6 metabolites have been isolated: 2-ethylisonicotinamide, carbonyl-dihydropyridine, thiocarbonyl-dihydropyridine, S-oxocarbamoyl dihydropyridine, 2-ethylthioiso-nicotinamide, and ethionamide sulphoxide. The sulphoxide metabolite has been demonstrated to have antimicrobial activity against Mycobacterium tuberculosis .

    Physicians Desk Reference 60th ed, Thomson PDR, Montvale, NJ 2006., p. 3482

    5.7 Biological Half-Life

    2 to 3 hours

    The plasma half-life of ethionamide following a 250-mg oral dose given as film-coated tablets is 1.92 hours.

    McEvoy, G.K. (ed.). American Hospital Formulary Service. AHFS Drug Information. American Society of Health-System Pharmacists, Bethesda, MD. 2006., p. 568

    Half-life: Approximately 2 to 3 hours.

    Thomson/Micromedex. Drug Information for the Health Care Professional. Volume 1, Greenwood Village, CO. 2006.

    5.8 Mechanism of Action

    Ethionamide may be bacteriostatic or bactericidal in action, depending on the concentration of the drug attained at the site of infection and the susceptibility of the infecting organism. Ethionamide, like prothionamide and pyrazinamide, is a nicotinic acid derivative related to isoniazid. It is thought that ethionamide undergoes intracellular modification and acts in a similar fashion to isoniazid. Isoniazid inhibits the synthesis of mycoloic acids, an essential component of the bacterial cell wall. Specifically isoniazid inhibits InhA, the enoyl reductase from Mycobacterium tuberculosis, by forming a covalent adduct with the NAD cofactor. It is the INH-NAD adduct that acts as a slow, tight-binding competitive inhibitor of InhA.

    Ethionamide may be bacteriostatic or bactericidal in action, depending on the concentration of the drug attained at the site of infection and the susceptibility of the infecting organism. The exact mechanism of action of ethionamide has not been fully elucidated, but the drug appears to inhibit peptide synthesis in susceptible organisms.

    McEvoy, G.K. (ed.). American Hospital Formulary Service. AHFS Drug Information. American Society of Health-System Pharmacists, Bethesda, MD. 2006., p. 568

    API Reference Price

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ROAD,"},{"dataSource":"API Import","activeIngredients":"","year":"2024","qtr":"Q4","strtotime":1727893800,"product":"ETHIONAMIDE","address":"G\/6, INDL ESTATE, GORWA","city":"GUJARAT","supplier":"BEIJING MESOCHEM TECHNOLOGY CO., LT","supplierCountry":"CHINA","foreign_port":"BEIJING","customer":"CENTURION LABORATORIES","customerCountry":"INDIA","quantity":"100.00","actualQuantity":"100","unit":"KGS","unitRateFc":"182","totalValueFC":"18324.2","currency":"USD","unitRateINR":"15397.2","date":"03-Oct-2024","totalValueINR":"1539720","totalValueInUsd":"18324.2","indian_port":"Bombay Air","hs_no":"29339990","bill_no":"5926813","productDescription":"API","marketType":"REGULATED MARKET","country":"CHINA","selfForZScoreResived":"Pharma Grade","supplierPort":"BEIJING","supplierAddress":"D.FLOOR 23, BUILDING 9, LIPPO PLAZA ,ECONOMIC AND TECHNOLOGICALDEVELOPM ENT ZONE, BEIJING CHINA","customerAddress":"G\/6, INDL ESTATE, GORWA"}]
    16-Mar-2021
    03-Oct-2024
    KGS
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