Details
Stereochemistry | ACHIRAL |
Molecular Formula | C8H10N2S |
Molecular Weight | 166.243 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CCC1=NC=CC(=C1)C(N)=S
InChI
InChIKey=AEOCXXJPGCBFJA-UHFFFAOYSA-N
InChI=1S/C8H10N2S/c1-2-7-5-6(8(9)11)3-4-10-7/h3-5H,2H2,1H3,(H2,9,11)
DescriptionCurator's Comment: Description was created using several sources including:
http://www.ncbi.nlm.nih.gov/pubmed/13741471;
https://www.ncbi.nlm.nih.gov/pubmed/17220416;
http://www.ncbi.nlm.nih.gov/pubmed/26435990
Curator's Comment: Description was created using several sources including:
http://www.ncbi.nlm.nih.gov/pubmed/13741471;
https://www.ncbi.nlm.nih.gov/pubmed/17220416;
http://www.ncbi.nlm.nih.gov/pubmed/26435990
Ethionamide is a second-line agent, structurally similar to isoniazid, used as a second-line therapy for the treatment of multidrug-resistant tuberculosis or active tuberculosis in case of patient intolerance to other drugs. Depending on its the concentration at the infected site and the susceptibility of the infecting organism it may be bacteriostatic or bactericidal. When used alone rapidly develops bacterial resistance. Ethionamide was approved by FDA in 1965 as TRECATOR manufactured by Wyeth Pharmaceuticals Inc. (purchased by Pfizer in 2009). Ethionamide is specific for Mycobacteria and is thought to exert a toxic effect on mycolic acid components of the bacterial cell wall when activated through intermediate S-oxidation by EtaA. Mycolic acid synthesis was shown to be inhibited by ethionamide in the EthA protein-overexpressing mycobacteria,
CNS Activity
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: P9WIE5|||Q50553 Gene ID: 885638.0 Gene Symbol: katG Target Organism: Mycobacterium tuberculosis (strain ATCC 25618 / H37Rv) Sources: http://www.drugbank.ca/drugs/DB00609 |
|||
Target ID: CHEMBL1849 Sources: http://www.ncbi.nlm.nih.gov/pubmed/10944230 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Curative | TRECATOR Approved UseTrecator is primarily indicated for the treatment of active tuberculosis in patients with M. tuberculosis resistant to isoniazid or rifampin, or when there is intolerance on the part of the patient to other drugs. Its use alone in the treatment of tuberculosis results in the rapid development of resistance. It is essential, therefore, to give a suitable companion drug or drugs, the choice being based on the results of susceptibility tests. If the susceptibility tests indicate that the patient's organism is resistant to one of the first-line antituberculosis drugs (i.e., isoniazid or rifampin) yet susceptible to ethionamide, ethionamide should be accompanied by at least one drug to which the M. tuberculosis isolate is known to be susceptible.3 If the tuberculosis is resistant to both isoniazid and rifampin, yet susceptible to ethionamide, ethionamide should be accompanied by at least two other drugs to which the M. tuberculosis isolate is known to be susceptible.3 Patient nonadherence to prescribed treatment can result in treatment failure and in the development of drug-resistant tuberculosis, which can be life-threatening and lead to other serious health risks. It is, therefore, essential that patients adhere to the drug regimen for the full duration of treatment. Directly observed therapy is recommended for all patients receiving treatment for tuberculosis. Patients in whom drug-resistant M. tuberculosis organisms are isolated should be managed in consultation with an expert in the treatment of drug-resistant tuberculosis. Launch Date-1.47484803E11 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
2.16 μg/mL |
250 mg single, oral dose: 250 mg route of administration: Oral experiment type: SINGLE co-administered: |
ETHIONAMIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: FASTED |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
7.67 μg × h/mL |
250 mg single, oral dose: 250 mg route of administration: Oral experiment type: SINGLE co-administered: |
ETHIONAMIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: FASTED |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
1.92 h |
250 mg single, oral dose: 250 mg route of administration: Oral experiment type: SINGLE co-administered: |
ETHIONAMIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: FASTED |
Funbound
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
70% |
250 mg single, oral dose: 250 mg route of administration: Oral experiment type: SINGLE co-administered: |
ETHIONAMIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: FASTED |
Doses
Dose | Population | Adverse events |
---|---|---|
0.1 g 2 times / week multiple, oral MTD Dose: 0.1 g, 2 times / week Route: oral Route: multiple Dose: 0.1 g, 2 times / week Co-administed with:: AMINOSALICYLATE SODIUM(6 g; oral; 2/week) Sources: ISONIAZID(15 mg/kg; oral; 2/week) |
unhealthy, >12 n = 27 Health Status: unhealthy Condition: pulmonary tuberculosis Age Group: >12 Sex: M+F Population Size: 27 Sources: |
|
0.5 g 2 times / week multiple, oral MTD Dose: 0.5 g, 2 times / week Route: oral Route: multiple Dose: 0.5 g, 2 times / week Co-administed with:: AMINOSALICYLATE SODIUM(6 g; oral; 2/week) Sources: ISONIAZID(15 mg/kg; oral; 2/week) |
unhealthy, >12 n = 27 Health Status: unhealthy Condition: pulmonary tuberculosis Age Group: >12 Sex: M+F Population Size: 27 Sources: |
|
0.75 g 2 times / week multiple, oral MTD Dose: 0.75 g, 2 times / week Route: oral Route: multiple Dose: 0.75 g, 2 times / week Co-administed with:: AMINOSALICYLATE SODIUM(6 g; oral; 2/week) Sources: ISONIAZID(15 mg/kg; oral; 2/week) |
unhealthy, >12 n = 27 Health Status: unhealthy Condition: pulmonary tuberculosis Age Group: >12 Sex: M+F Population Size: 27 Sources: |
|
1.25 g 2 times / week multiple, oral MTD Dose: 1.25 g, 2 times / week Route: oral Route: multiple Dose: 1.25 g, 2 times / week Co-administed with:: AMINOSALICYLATE SODIUM(6 g; oral; 2/week) Sources: ISONIAZID(15 mg/kg; oral; 2/week) |
unhealthy, >12 n = 27 Health Status: unhealthy Condition: pulmonary tuberculosis Age Group: >12 Sex: M+F Population Size: 27 Sources: |
|
1.5 g 2 times / week multiple, oral MTD Dose: 1.5 g, 2 times / week Route: oral Route: multiple Dose: 1.5 g, 2 times / week Co-administed with:: AMINOSALICYLATE SODIUM(6 g; oral; 2/week) Sources: ISONIAZID(15 mg/kg; oral; 2/week) |
unhealthy, >12 n = 27 Health Status: unhealthy Condition: pulmonary tuberculosis Age Group: >12 Sex: M+F Population Size: 27 Sources: |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Page: 4.0 |
no | |||
Page: 4.0 |
no | |||
weak | ||||
Page: 4.0 |
yes [IC50 110 uM] | |||
Page: 4.0 |
yes [IC50 195 uM] | |||
Page: 4.0 |
yes [IC50 396 uM] | |||
Page: 4.0 |
yes [IC50 524 uM] | |||
yes [IC50 78.4 uM] | ||||
yes |
PubMed
Title | Date | PubMed |
---|---|---|
Spectrum of drugs against atypical mycobacteria: how valid is the current practice of drug susceptibility testing and the choice of drugs? | 1992 Dec |
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Mycolic acid synthesis: a target for ethionamide in mycobacteria? | 1992 Jun |
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Thiolactomycin and related analogues as novel anti-mycobacterial agents targeting KasA and KasB condensing enzymes in Mycobacterium tuberculosis. | 2000 Jun 2 |
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[Components of monitoring drug resistance of tuberculosis agent in the evaluation of effectiveness of the national tuberculosis control program]. | 2001 |
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Ion interaction reagent reversed-phase high-performance liquid chromatography determination of anti-tuberculosis drugs and metabolites in biological fluids. | 2001 Apr 25 |
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High-performance liquid chromatographic-tandem mass spectrometric method for the determination of ethionamide in human plasma, bronchoalveolar lavage fluid and alveolar cells. | 2001 Apr 5 |
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[Treatment outcomes of multidrug-resistant tuberculosis--comparison between success and failure cases]. | 2001 Dec |
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Solvent effects on the thioamide rotational barrier: an experimental and theoretical study. | 2001 Mar 7 |
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Pharmacokinetics of para-aminosalicylic acid granules under four dosing conditions. | 2001 Nov |
|
[Two cases of multi-drug-resistant pulmonary tuberculosis with para-aminosalicylic acid (PAS)-induced hypothyroidism]. | 2001 Oct |
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Therapeutic drug monitoring in the treatment of tuberculosis. | 2002 |
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Comparative study on the use of solid media: Löwenstein-Jensen and Ogawa in the determination of anti-tuberculosis drug susceptibility. | 2002 |
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Long-term follow up of childhood tuberculous meningitis. | 2002 Aug |
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2-Pyridinethiol/2-pyridinethione tautomeric equilibrium. A comparative experimental and computational study. | 2002 Dec 13 |
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Transition metal complexes with thiosemicarbazide-based ligands. XLIII. Chlorobis(3-methylisoemicarbazide-kappa(2)N(1),N(4))zinc(II) chloride. | 2002 Jun |
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Feasibility and cost-effectiveness of standardised second-line drug treatment for chronic tuberculosis patients: a national cohort study in Peru. | 2002 Jun 8 |
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Direct sensitivity test of the MB/BacT system. | 2002 Mar |
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Effects of thioamide substitutions on the conformation and stability of alpha- and 3(10)-helices. | 2002 May 8 |
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Identifying the sources of tuberculosis in young children: a multistate investigation. | 2002 Nov |
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Molecular epidemiology of tuberculosis in a sentinel surveillance population. | 2002 Nov |
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Heterocyclic benzazole derivatives with antimycobacterial in vitro activity. | 2002 Nov 18 |
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Overexpression of inhA, but not kasA, confers resistance to isoniazid and ethionamide in Mycobacterium smegmatis, M. bovis BCG and M. tuberculosis. | 2002 Oct |
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Drugs that inhibit mycolic acid biosynthesis in Mycobacterium tuberculosis. | 2002 Sep |
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Diversity in the oxidation of substrates by cytochrome P450 2D6: lack of an obligatory role of aspartate 301-substrate electrostatic bonding. | 2002 Sep 10 |
|
The 2,3-bis(2-methoxy-4-nitro-5-sulfophenyl)-2H-tetrazolium-5-carboxanilide (XTT) assay as rapid colorimetric method for determination of antibiotic susceptibility of clinical Mycobacterium tuberculosis isolates in liquid medium. | 2003 |
|
Vibrational study of the secondary thioamide function, the intramolecular resonance assisted and intermolecular hydrogen bonding in NN'-hydroxyalkyl dithiooxamides. | 2003 Apr |
|
Lepromatous leprosy in a heart transplant recipient. | 2003 Dec |
|
Activities of moxifloxacin alone and in combination with other antimicrobial agents against multidrug-resistant Mycobacterium tuberculosis infection in BALB/c mice. | 2003 Jan |
|
Vibrational characterization of the peptide bond. | 2003 Jan 1 |
|
Vibrational characterization of the tertiary amide and thioamide group. | 2003 Mar 1 |
|
Preparation of thioamide building blocks via microwave-promoted three-component kindler reactions. | 2003 Mar-Apr |
|
Pharmacokinetics and relative bioavailability of clofazimine in relation to food, orange juice and antacid. | 2004 |
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Synthesis and antimycobacterial activity of 1,2,4-triazole 3-benzylsulfanyl derivatives. | 2004 Apr |
|
Use of MGIT 960 for rapid quantitative measurement of the susceptibility of Mycobacterium tuberculosis complex to ciprofloxacin and ethionamide. | 2004 Apr |
|
Pharmacy data for tuberculosis surveillance and assessment of patient management. | 2004 Aug |
|
Antituberculous activity of some aryl semicarbazone derivatives. | 2004 Aug 2 |
|
Synthesis and antibacterial activity of arylpiperazinyl oxazolidinones with diversification of the N-substituents. | 2004 Aug 2 |
|
New agents active against Mycobacterium avium complex selected by molecular topology: a virtual screening method. | 2004 Jan |
|
Covalent binding of the 13C-labeled skin sensitizers 5-chloro-2-methylisothiazol-3-one (MCI) and 2-methylisothiazol-3-one (MI) to a model peptide and glutathione. | 2004 Jan 19 |
|
Computational study of conformational preferences of thioamide-containing azaglycine peptides. | 2004 Jan 30 |
|
Treatment and follow-up of HIV-negative multidrug-resistant tuberculosis patients in an infectious diseases reference hospital, Buenos Aires, Argentina. | 2004 Jun |
|
Drug susceptibility of Brazilian strains of Mycobacterium bovis using traditional and molecular techniques. | 2004 Nov |
|
Axially dissymmetric N-thioacylated (S)-(-)-1,1'-binaphthyl-2,2'-diamine ligands for copper-catalyzed asymmetric Michael addition of diethylzinc to alpha,beta-unsaturated ketone. | 2004 Nov |
|
Mycobacterium triplex pulmonary disease in immunocompetent host. | 2004 Oct |
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Multidrug resistant miliary tuberculosis and Pott's disease in an immunocompetent patient. | 2004 Oct |
|
Structure of EthR in a ligand bound conformation reveals therapeutic perspectives against tuberculosis. | 2004 Oct 22 |
|
Outcome of treatment of multidrug resistant tuberculosis. | 2004 Sep |
|
Altered NADH/NAD+ ratio mediates coresistance to isoniazid and ethionamide in mycobacteria. | 2005 Feb |
|
Electron transfer kinetics and mechanistic study of the thionicotinamide coordinated to the pentacyanoferrate(III)/(II) complexes: a model system for the in vitro activation of thioamides anti-tuberculosis drugs. | 2005 Feb |
|
Analysis of Mycobacterium tuberculosis isolates from treatment failure patients living in East Timor. | 2005 Jan |
Sample Use Guides
In Vivo Use Guide
Curator's Comment: If patient exhibits poor gastrointestinal tolerance, TRECATOR has to be administered in divided doses, with a maximum daily dosage of 1 gram
15 to 20 mg/kg/day, administered once daily
Route of Administration:
Oral
In Vitro Use Guide
Curator's Comment: Standardized in vitro susceptibility method for testing ethionamide against
M. tuberculosis organisms: after 2 to 3 weeks of incubation, MIC99 values are calculated.
Two standardized in vitro susceptibility methods are available for testing ethionamide against M. tuberculosis organisms. The modified proportion method (CDC or NCCLS M24-P) utilizes Middlebrook and Cohn 7H10 agar medium impregnated with ethionamide at a final concentration of 5.0 ug/mL. After 2 to 3 weeks of incubation, MIC99 values are calculated by comparing the quantity of organisms growing in the medium containing drug to the control
cultures. Mycobacterial growth in the presence of drug, of at least 1% of the growth in the control culture, indicates resistance.
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Classification Tree | Code System | Code | ||
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WHO-VATC |
QJ04AD03
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WHO-ESSENTIAL MEDICINES LIST |
6.2.4
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LIVERTOX |
NBK548025
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NDF-RT |
N0000175483
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NCI_THESAURUS |
C280
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WHO-ATC |
J04AD03
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Code System | Code | Type | Description | ||
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OAY8ORS3CQ
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PRIMARY | |||
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100000082598
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DTXSID0020577
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CHEMBL1441
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255115
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1261004
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Ethionamide
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D005000
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DB00609
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SUB07278MIG
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ETHIONAMIDE
Created by
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PRIMARY | Description: Small yellow crystals or a yellow, crystalline powder; odour, slight.Solubility: Practically insoluble in water; soluble in methanol R; sparingly soluble in ethanol (~750 g/l) TS; slightly soluble in ether R.Category: Antileprosy drug.Storage: Ethionamide should be kept in a tightly closed container.Additional information: Ethionamide darkens on exposure to light.Definition: Ethionamide contains not less than 98.0% and not more than 101.0% of C8H10N2S, calculated with reference to the dried substance. | ||
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536-33-4
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1083
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2761171
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C47522
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m5061
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PRIMARY | Merck Index | ||
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ETHIONAMIDE
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7473
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208-628-9
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867
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4127
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4885
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OAY8ORS3CQ
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ACTIVE MOIETY
METABOLITE (PARENT)
METABOLITE (PARENT)
METABOLITE (PARENT)
SALT/SOLVATE (PARENT)