Details of the Active Pharmaceutical Ingredient (API)

General Information of API (ID: D00254)
Name
Ethosuximide
Synonyms    Click to Show/Hide the Synonyms of This API
ethosuximide; 77-67-8; Zarontin; Etosuximida; 2-Ethyl-2-methylsuccinimide; Ethosuxide; Ethosuccimide; Ethosuccinimide; Etosuximid; Petnidan; Suxinutin; Atysmal; Emeside; Ethymal; Suxilep; Pentinimid; Peptinimid; Petinimid; Pyknolepsinum; Succimitin; Zaraondan; Capitus; Mesentol; Pemalin; Simatin; Succimal; Suximal; Thetamid; Zarodan; Zarondan; Zartalin; Asamid; Etomal; Ronton; Aethosuximide; Piknolepsin; Thilopemal; Epileo Petit MAL; 3-Ethyl-3-methylpyrrolidine-2,5-dione; Zarondan-Saft; Simatin(E); Ethosuximidum; 3-Ethyl-3-methyl-2,5-pyrrolidinedione; 3-Methyl-3-ethylsuccinimide; 2-Methyl-2-ethylsuccinimide; 2,5-Pyrrolidinedione, 3-ethyl-3-methyl-; CI-366; Succinimide, 2-ethyl-2-methyl-; 3-Ethyl-3-methylsuccinimide; PM 671; PM-671; CN-10,395; 3-Methyl-3-ethylpyrrolidine-2,5-dione; alpha-Ethyl-alpha-methylsuccinimide; alpha-Methyl-alpha-ethylsuccinimide; gamma-Methyl-gamma-ethyl-succinimide; C.I. 366; Cl 366; (+-)-2-Ethyl-2-methylsuccinimide; CN-10395; gamma-ethyl-gamma-methyl-succinimide; NSC-64013; 3-Ethyl-3-methylpyrroline-2,5-dione; CHEMBL696; .alpha.-Ethyl-.alpha.-methylsuccinimide; 3-ethyl-3-methyl-pyrrolidine-2,5-dione; CHEBI:4887; Aethosuccimidum; Etosuximide; NSC64013; MFCD00072123; .gamma.-Methyl-.gamma.-ethylsuccinimide; Etosuccimide; Etosuccimide [DCIT]; Aethosuximide [German]; DSSTox_CID_3019; N-Ethyl methylsuccinimide; DSSTox_RID_76832; DSSTox_GSID_23019; Ethosuximidum [INN-Latin]; Etosuximida [INN-Spanish]; Pyknole.psi.num; Piknole.psi.n; Zarontin (TN); HSDB 1119; SR-01000075863; EINECS 201-048-7; CI 366; NSC 64013; BRN 0117054; CAS-77-67-8; NCGC00016320-01; Prestwick_611; Zorontin,Ethosuximide; Ethosuximide [USAN:USP:INN:BAN:JAN]; Spectrum_001385; Prestwick0_000165; Prestwick1_000165; Prestwick2_000165; Prestwick3_000165; Spectrum2_001483; Spectrum3_000944; Spectrum4_001051; Spectrum5_001073; (.+/-.)-Ethosuximide; 2, 3-ethyl-3-methyl-; E 7138; NCIOpen2_000014; Lopac0_000532; SCHEMBL34212; BSPBio_000029; KBioGR_001342; KBioSS_001865; 5-21-09-00595 (Beilstein Handbook Reference); DivK1c_000218; SPECTRUM1502196; 2,5-Pyrrolidinedione, 3-ethyl-3-methyl-, (+-)-; SPBio_001465; SPBio_001950; BPBio1_000033; GTPL7182; WLN: T5VMVTJ D2 D1; DTXSID7023019; SCHEMBL20541518; Ethosuximide (JP17/USP/INN); Ethosuximide, analytical standard; HMS500K20; KBio1_000218; KBio2_001865; KBio2_004433; KBio2_007001; KBio3_002008; AOB5337; NINDS_000218; HMS1568B11; HMS1921L14; HMS2092D20; HMS2095B11; HMS3261L05; HMS3712B11; HMS3885D12; Pharmakon1600-01502196; HY-B1378; Ethosuximide 1.0 mg/ml in Methanol; Tox21_110370; Tox21_500532; (+/-)-2-ethyl-2-methylsuccinimide; ANW-41860; BDBM50240424; CCG-39217; NSC758192; 3-ethyl-3-methylazolidine-2,5-dione; AKOS005261742; Tox21_110370_1; CS-7976; DB00593; LP00532; MCULE-4034034545; NE54559; NSC-758192; SDCCGSBI-0050515.P004; .alpha.-Methyl-.alpha.-ethylsuccinimide; IDI1_000218; NCGC00015418-02; NCGC00015418-03; NCGC00015418-04; NCGC00015418-05; NCGC00015418-06; NCGC00015418-08; NCGC00015418-09; NCGC00015418-15; NCGC00093923-01; NCGC00093923-02; NCGC00093923-03; NCGC00093923-04; NCGC00261217-01; 3-Ethyl-3-methyl-2, 5-pyrrolidinedione; AS-16859; SBI-0050515.P003; 2, 5-Pyrrolidinedione, 3-ethyl-3-methyl-; AB00052288; AK01050738; EU-0100532; FT-0668060; FT-0668061; ST51037248; C07505; D00539; AB00052288_04; zarontin3-Ethyl-3-methyl-pyrrolidine-2,5-dione; Q421567; SR-01000075863-1; SR-01000075863-3; SR-01000075863-5; W-109273; 3-Ethyl-3-methyl-pyrrolidine-2,5-dione(Ethosuximide); BRD-A99633051-001-04-7; BRD-A99633051-001-05-4; 3-Ethyl-3-methyl-pyrrolidine-2,5-dione (ethosuximide); Z2379802739; 3-ethyl-5-hydroxy-3-methyl-3,4-dihydro-2H-pyrrol-2-one; 4-ethyl-5-hydroxy-4-methyl-3,4-dihydro-2H-pyrrol-2-one; Ethosuximide, European Pharmacopoeia (EP) Reference Standard; Ethosuximide, United States Pharmacopeia (USP) Reference Standard
Clinical Status
Approved
Disease Indication Epilepsy ICD-11: 8A60 [1]
PubChem CID
3291
Formula
C7H11NO2
Canonical SMILES
CCC1(CC(=O)NC1=O)C
InChI
1S/C7H11NO2/c1-3-7(2)4-5(9)8-6(7)10/h3-4H2,1-2H3,(H,8,9,10)
InChIKey
HAPOVYFOVVWLRS-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=3291"></iframe>
3D MOL 2D MOL
Physicochemical Properties Molecular Weight 141.17 Topological Polar Surface Area 46.2
XlogP 0.4 Complexity 188
Heavy Atom Count 10 Rotatable Bond Count 1
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 2
Full List of Drug Formulations (DFMs) Containing This API
          Ethosuximide 250 mg capsule Click to Show/Hide the Full List of Formulation(s):          5 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
Methylparaben; Fd&c red no. 40; Butyl alcohol; Fd&c yellow no. 6; Isopropyl alcohol; Propylparaben; Sorbitol; Ammonia; Glycerin; Propylene glycol; Titanium dioxide; Silicon dioxide; Dimethicone; Gelatin; Mineral oil; Polyethylene glycols; Shellac
                   Dosage Form Oral Capsule
                   Company Heritage Pharmaceuticals; Zydus Pharmaceuticals
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Allura red AC dye DIG Info Solute carrier SLCO2B1 (Ki = 4.7 uM) [2]
methylparaben DIG Info Carbonic anhydrase VII (Ki = 780 nM) [3]
Sunset yellow FCF DIG Info Solute carrier SLCO2B1 (Ki = 68.4 uM) [4]
Allura red AC dye DIG Info Solute carrier SLCO2B1 (Ki = 2.59 uM) [4]
Propyl 4-hydroxybenzoate DIG Info Estrogen receptor alpha (IC50 = 11 uM) [2]
Isopropyl alcohol DIG Info Lymphoma P388/ADR cells (IC50 = 0.22 uM) [5]
Propylene glycol DIG Info Albendazole monooxygenase (Inhibition ratio < 20 %) [6]
Silicon dioxide DIG Info Albendazole monooxygenase (Protein expression downregulation) [7]
             Drug Formulation 2 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; Sorbitol; Glycerin; Fd&c red no. 3; Polyethylene glycol 400; Gelatin
                   Dosage Form Oral Capsule
                   Company Avera McKennan Hospital; VersaPharm
                   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) [4]
FD&C red no. 3 DIG Info Phosphodiesterase 3A (IC50 = 0.092 uM) [2]
Polyethylene glycol 400 DIG Info Albendazole monooxygenase (IC50 = 10.77 mg.mL-1) [6]
             Drug Formulation 3 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
D&c yellow no. 10; Sorbitol; Glycerin; Fd&c red no. 3; Polyethylene glycol 400; Gelatin
                   Dosage Form Oral Capsule
                   Company Greenstone; Parke-Davis Div of Pfizer Inc
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Quinoline yellow WS DIG Info Estrogen receptor alpha (IC50 = 18 uM) [2]
FD&C red no. 3 DIG Info Phosphodiesterase 3A (IC50 = 0.092 uM) [2]
Polyethylene glycol 400 DIG Info Albendazole monooxygenase (IC50 = 10.77 mg.mL-1) [6]
             Drug Formulation 4 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; Glycerin; Water; Gelatin; Polyethylene glycols
                   Dosage Form Oral Capsule
                   Company Banner Life Sciences; Bionpharma
                   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) [4]
             Drug Formulation 5 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; Glycerin; Gelatin; Polyethylene glycols
                   Dosage Form Oral Capsule
                   Company Pliva
                   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) [4]
References
1 FDA label for approved ethosuximide from the official website of the U.S. Food and Drug Administration.
2 The activities of drug inactive ingredients on biological targets. Science. 2020 Jul 24;369(6502):403-413.
3 Mono-/dihydroxybenzoic acid esters and phenol pyridinium derivatives as inhibitors of the mammalian carbonic anhydrase isoforms I, II, VII, IX, XII and XIV. Bioorg Med Chem. 2013 Mar 15; 21(6):1564-9.
4 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.
5 Synthesis and evaluation of dihydropyrroloquinolines that selectively antagonize P-glycoprotein. J Med Chem. 2004 Mar 11; 47(6):1413-22.
6 Pharmaceutical excipients inhibit cytochrome P450 activity in cell free systems and after systemic administration. Eur J Pharm Biopharm. 2008 Sep;70(1):279-88.
7 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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