Details of the Active Pharmaceutical Ingredient (API)

General Information of API (ID: D00253)
Name
Ethionamide
Synonyms    Click to Show/Hide the Synonyms of This API
ethionamide; 536-33-4; 2-ethylpyridine-4-carbothioamide; Ethioniamide; Ethyonomide; Amidazine; Ethinamide; Etionamid; Etioniamid; Thioamide; Trecator; Ethylisothiamide; 2-Ethylthioisonicotinamide; Trecator-SC; 4-Pyridinecarbothioamide, 2-ethyl-; Amidazin; Ethimide; Etiocidan; Etionizin; Etionizina; Etionizine; Fatoliamid; Iridocin; Iridozin; Isotiamida; Itiocide; Nicotion; Rigenicid; Sertinon; Thianide; Thioniden; Trekator; Trescatyl; Trescazide; Tubenamide; Tubermin; Tuberoid; Tuberoson; Aetina; Aetiva; Ethina; Etimid; Etionid; Isothin; Nizotin; Teberus; Thianid; Tianid; Bayer 5312; Ethionamid prothionamid; Iridocin Bayer; Nisotin; Thiomid; 2-ETHYL-4-PYRIDINECARBOTHIOAMIDE; Etionamide [DCIT]; Ethionamidum; Etionamida; Etionamide; Tiomid; 2-Ethylisothionicotinamide; 2-Ethylisonicotinothioamide; Ethionamidum [INN-Latin]; Etionamida [INN-Spanish]; 2-Ethyl-4-thiocarbamoylpyridine; 2-Ethyl-thioisonicotinamide; 1314 TH; 2-Ethylisonicotinic acid thioamide; TH 1314; 2-ethyl-4-thiopyridylamide; NCI-C01694; UNII-OAY8ORS3CQ; 1314-Th; F.I. 58-30; 1314TH; 2-Ethyl-4-thioamidylpyridine; Isonicotinamide, 2-ethylthio-; OAY8ORS3CQ; Aethionamidum; Tio-Mid; MLS000069764; CHEBI:4885; .alpha.-Ethylisothionicotinamide; .alpha.-Ethylthioisonicotinamide; .alpha.-Ethylisonicotinoylthioamide; Trecator SC; NSC255115; NSC-255115; 1314 TN; .alpha.-Ethylisonicotinic acid thioamide; Ethina (VAN); NCGC00016497-05; CAS-536-33-4; SMR000058716; DSSTox_CID_577; DSSTox_RID_75669; DSSTox_GSID_20577; alpha-Ethylisothionicotinamide; alpha-Ethylthioisonicotinamide; alpha-Ethylisonicotinoylthioamide; 2-Ethylisonicotinic thioamide; alpha-Ethylisonicotinic acid thioamide; CCRIS 287; amino(2-ethyl(4-pyridyl))methane-1-thione; HSDB 7473; Bayer5312; SR-01000759219; EINECS 208-628-9; NSC 255115; BRN 0116474; Thiodine; Trecator (TN); Prestwick_842; Isonicotinimidic acid, 2-ethylthio-; MFCD00057361; Ethionamide [USAN:USP:INN:BAN:JAN]; PubChem15920; Spectrum_001082; CPD001370750; Opera_ID_632; Prestwick0_000526; Prestwick1_000526; Prestwick2_000526; Prestwick3_000526; Spectrum2_000994; Spectrum3_000428; Spectrum4_000547; Spectrum5_000979; 2-Ethylisonicotinothiamide; 2-Ethylisonicotinthioamide; CHEMBL1441; SCHEMBL27007; BSPBio_000511; BSPBio_002016; KBioGR_001213; KBioSS_001562; 5-22-02-00360 (Beilstein Handbook Reference); MLS001074114; MLS002454402; DivK1c_000145; SPECTRUM1500292; WLN: T6NJ B2 DYZUS; SPBio_001087; SPBio_002432; BPBio1_000563; Ethionamide (JP17/USP/INN); DTXSID0020577; AEOCXXJPGCBFJA-UHFFFAOYSA-; HMS500H07; KBio1_000145; KBio2_001562; KBio2_004130; KBio2_006698; KBio3_001236; .alpha.-Ethyl-thioisonicotinamide; Isonicotinamide, 2-ethyl, thio-; NINDS_000145; HMS1569J13; HMS1920M22; HMS2091F03; HMS2096J13; HMS2231F10; HMS2233J11; HMS3259K17; HMS3370I18; HMS3371D12; HMS3655M10; HMS3713J13; Pharmakon1600-01500292; BCP29626; HY-B0276; ZINC3872520; Tox21_110458; Tox21_202409; Tox21_302769; ANW-42028; CCG-40212; NSC757028; SBB055548; AKOS006220662; Tox21_110458_1; DB00609; FS-1770; MCULE-1322319906; NC00508; NSC-757028; IDI1_000145; NCGC00016497-01; NCGC00016497-02; NCGC00016497-03; NCGC00016497-04; NCGC00016497-06; NCGC00016497-08; NCGC00016497-09; NCGC00091074-01; NCGC00091074-02; NCGC00091074-03; NCGC00091074-04; NCGC00256600-01; NCGC00259958-01; AC-13715; AK163496; SMR001370750; SBI-0051377.P003; AB0015183; DB-049945; AB00051990; ST50949989; SW196973-3; C07665; D00591; 33010-EP2286812A1; 33010-EP2287165A2; 33010-EP2287166A2; 33010-EP2292620A2; 33010-EP2297130A1; 33010-EP2301536A1; 33010-EP2301538A1; 33010-EP2305675A1; 33010-EP2305695A2; 33010-EP2305696A2; 33010-EP2305697A2; 33010-EP2305698A2; 33010-EP2305808A1; 33010-EP2308833A2; 33010-EP2308852A1; 33010-EP2308874A1; 33010-EP2311455A1; 33010-EP2311815A1; 73833-EP2308926A1; 73833-EP2309564A1; AB00051990-09; AB00051990_10; AB00051990_11; A829694; Q414767; SR-01000759219-2; SR-01000759219-5; W-105719; BRD-K33710385-001-05-4; BRD-K51207550-001-09-9; Ethionamide, European Pharmacopoeia (EP) Reference Standard; Ethionamide, United States Pharmacopeia (USP) Reference Standard
Clinical Status
Approved
Disease Indication Human immunodeficiency virus infection ICD-11: 1C60 [1]
PubChem CID
2761171
Formula
C8H10N2S
Canonical SMILES
CCC1=NC=CC(=C1)C(=S)N
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
   Click to Show/Hide the Molecular Data (Structure/Property) of This API
Structure
<iframe style="width: 300px; height: 300px;" frameborder="0" src="https://embed.molview.org/v1/?mode=balls&cid=2761171"></iframe>
3D MOL 2D MOL
Physicochemical Properties Molecular Weight 166.25 Topological Polar Surface Area 71
XlogP 1.1 Complexity 147
Heavy Atom Count 11 Rotatable Bond Count 2
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 2
Full List of Drug Formulations (DFMs) Containing This API
          Ethionamide 250 mg tablet Click to Show/Hide the Full List of Formulation(s):          1 Formulation(s)
             Drug Formulation 1 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
Fd&c yellow no. 6; Magnesium stearate; Talc; Titanium dioxide; Croscarmellose sodium; Silicon dioxide; Microcrystalline cellulose; Polyethylene glycol, unspecified; Polyvinyl alcohol, unspecified; Povidone, unspecified
                   Dosage Form Oral Tablet
                   Company Pfizer
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Sunset yellow FCF DIG Info Solute carrier SLCO2B1 (Ki = 68.4 uM) [2]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [3]
Carmellose sodium DIG Info Albendazole monooxygenase (Protein expression upregulation) [3]
Silicon dioxide DIG Info Albendazole monooxygenase (Protein expression downregulation) [3]
References
1 FDA label for approved ethionamide from the official website of the U.S. Food and Drug Administration.
2 Bacterial metabolism rescues the inhibition of intestinal drug absorption by food and drug additives. Proc Natl Acad Sci U S A. 2020 Jul 7;117(27):16009-16018.
3 Effects of commonly used excipients on the expression of CYP3A4 in colon and liver cells. Pharm Res. 2010 Aug;27(8):1703-12.

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