Details of the Drug

General Information of Drug (ID: DM8K3EI)

Drug Name

Ethionamide

Synonyms

Aethionamidum; Aetina; Aetiva; Amidazin; Amidazine; Atina; Ethatyl; Ethimide; Ethina; Ethinamide; Ethionamidum; Ethioniamide; Ethylisothiamide; Ethyonomide; Etimid; Etiocidan; Etionamid; Etionamida; Etionamide; Etioniamid; Etionid; Etionizin; Etionizina; Etionizine; Fatoliamid; Iridocin; Iridozin; Isothin; Isotiamida; Itiocide; Nicotion; Nisotin; Nizotin; Rigenicid; Sertinon; Teberus; Thianid; Thianide; Thioamide; Thiomid; Thioniden; Tianid; Tiomid; Trecator; Trekator; Trescatyl; Trescazide; Tubenamide; Tubermin; Tuberoid; Tuberoson; Ethionamid prothionamid; Etionamide [DCIT]; Iridocin Bayer; Trecator SC; Wyeth Brand of Ethionamide; Bayer 5312; Bayer5312; E0695; TH 1314; Alpha-Ethylisonicotinic acid thioamide; Alpha-Ethylisonicotinoylthioamide; Alpha-Ethylisothionicotinamide; Alpha-Ethylthioisonicotinamide; Alpha-ethylt hioisonicotinamide; Ethina (VAN); Ethionamidum [INN-Latin]; Etionamida [INN-Spanish]; Tio-Mid; Trecator-SC; Alpha-Ethyl-thioisonicotinamide; Trecator-SC (TN); Ethionamide (JP15/USP/INN); Ethionamide [USAN:INN:BAN:JAN]; 2-ETHYL-4-PYRIDINECARBOTHIOAMIDE; 2-Ethyl-4-thioamidylpyridine; 2-Ethyl-4-thiocarbamoylpyridine; 2-Ethyl-thioisonicotinamide; 2-Ethylisonicotinic acid thioamide; 2-Ethylisonicotinic thioamide; 2-Ethylisonicotinothioamide; 2-Ethylisonicotinoylthioamide; 2-Ethylisothionicotinamide; 2-Ethylthioisonicotinamide; 2-e thylisothionicotinamide; 2-ethyl-4-aminothiocarbonylpyridine; 2-ethylisonicotinic acid thiomide; 2-ethylpyridine-4-carbothioamide; 2-ethylthioisonicotinamide, Trecator SC, Amidazine, Ethionamide; 3-Ethylisothionicotinamide

Indication

Disease Entry	ICD 11	Status	REF
Tuberculosis	1B10-1B1Z	Approved	[1], [2]

Therapeutic Class

Antituberculosis Agents

Drug Type

Small molecular drug

Structure

3D MOL

2D MOL

#Ro5 Violations (Lipinski): 0

Molecular Weight (mw)

166.25

Topological Polar Surface Area (xlogp)

1.1

Rotatable Bond Count (rotbonds)

Hydrogen Bond Donor Count (hbonddonor)

Hydrogen Bond Acceptor Count (hbondacc)

ADMET Property

Bioavailability: 80% of drug becomes completely available to its intended biological destination(s) [3]
MRTD: The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 100.45336 micromolar/kg/day [4]

Chemical Identifiers

Formula: C8H10N2S
IUPAC Name: 2-ethylpyridine-4-carbothioamide
Canonical SMILES: CCC1=NC=CC(=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

Cross-matching ID

PubChem CID: 2761171
ChEBI ID: CHEBI:4885
CAS Number: 536-33-4
DrugBank ID: DB00609
TTD ID: D0P0HB
INTEDE ID: DR1752
ACDINA ID: D00253

Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
Bacterial Fatty acid synthetase I (Bact inhA)	TTVTX4N	INHA_MYCTU	Inhibitor	[5], [6]

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Drug-Metabolizing Enzyme (DME)

DME Name	DME ID	UniProt ID	MOA	REF
Dimethylaniline oxidase 3 (FMO3)	DEP76YL	FMO3_HUMAN	Substrate	[7]
Dimethylaniline oxidase 2 (FMO2)	DEIASEZ	FMO2_HUMAN	Substrate	[8]

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Molecular Interaction Atlas (MIA)

MIA Detail

Jump to Detail Molecular Interaction Atlas of This Drug

Drug Inactive Ingredient(s) (DIG) and Formulation(s) of This Drug

DIG

DIG Name	DIG ID	PubChem CID	Functional Classification
Sunset yellow FCF	E00255	17730	Colorant
Carmellose sodium	E00625	Not Available	Disintegrant
Magnesium stearate	E00208	11177	lubricant
Silicon dioxide	E00670	Not Available	Anticaking agent; Opacifying agent; Viscosity-controlling agent
Talc	E00520	16211421	Anticaking agent; Diluent; Glidant; lubricant
Titanium dioxide	E00322	26042	Coating agent; Colorant; Opacifying agent
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⏷ Show the Full List of 6 Pharmaceutical Excipients of This Drug

Pharmaceutical Formulation

Formulation Name	Drug Dosage	Dosage Form	Route
Ethionamide 250 mg tablet	250 mg	Oral Tablet	Oral

Jump to Detail Pharmaceutical Formulation Page of This Drug

References

1	Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services. 2015
2	Novel agents in the management of Mycobacterium tuberculosis disease. Curr Med Chem. 2007;14(18):2000-8.
3	Critical Evaluation of Human Oral Bioavailability for Pharmaceutical Drugs by Using Various Cheminformatics Approaches
4	Estimating the safe starting dose in phase I clinical trials and no observed effect level based on QSAR modeling of the human maximum recommended daily dose
5	Mechanism of thioamide drug action against tuberculosis and leprosy. J Exp Med. 2007 Jan 22;204(1):73-8.
6	Calcium-activated conductance in skate electroreceptors: current clamp experiments. J Gen Physiol. 1977 Feb;69(2):121-43.
7	Physiologically based pharmacokinetic modeling approach to predict drug-drug interactions with ethionamide involving impact of genetic polymorphism on FMO3. J Clin Pharmacol. 2019 Jun;59(6):880-889.
8	Drug metabolism by flavin-containing monooxygenases of human and mouse. Expert Opin Drug Metab Toxicol. 2017 Feb;13(2):167-181.
9	Identification of the human enzymes involved in the oxidative metabolism of dasatinib: an effective approach for determining metabolite formation kinetics. Drug Metab Dispos. 2008 Sep;36(9):1828-39.
10	Identification of the human liver enzymes involved in the metabolism of the antimigraine agent almotriptan. Drug Metab Dispos. 2003 Apr;31(4):404-11.
11	FDA label of Fedratinib. The 2020 official website of the U.S. Food and Drug Administration.
12	Development of a physiologically based pharmacokinetic model to predict the effects of flavin-containing monooxygenase 3 (FMO3) polymorphisms on itopride exposure. Biopharm Drug Dispos. 2017 Sep;38(6):389-393.
13	Human FMO2-based microbial whole-cell catalysts for drug metabolite synthesis. Microb Cell Fact. 2015 Jun 12;14:82.
14	Diversity in enoyl-acyl carrier protein reductases. Cell Mol Life Sci. 2009 May;66(9):1507-17.
15	Pyrazinamide inhibits the eukaryotic-like fatty acid synthetase I (FASI) of Mycobacterium tuberculosis. Nat Med. 2000 Sep;6(9):1043-7.
16	Affinium Pharmaceuticals Announces the Initiation of a Phase 1 Intravenous Clinical Trial of a New Antibiotic Prodrug, and the Closing of a Follow-on Financing Round. PR Newswire Sep. 4, 2013 10:16 PM.
17	SAR and pharmacophore models for the rhodanine inhibitors of Plasmodium falciparum enoyl-acyl carrier protein reductase. IUBMB Life. 2010 Mar;62(3):204-13.
18	How many drug targets are there Nat Rev Drug Discov. 2006 Dec;5(12):993-6.
19	2-Hexadecynoic acid inhibits plasmodial FAS-II enzymes and arrests erythrocytic and liver stage Plasmodium infections. Bioorg Med Chem. 2010 Nov 1;18(21):7475-85.