Details of the Active Pharmaceutical Ingredient (API)

General Information of API (ID: D00555)
Name
Primidone
Synonyms    Click to Show/Hide the Synonyms of This API
primidone; 125-33-7; Primaclone; Mysoline; 2-Deoxyphenobarbital; Lepimidin; Liskantin; Mylepsinum; Lepsiral; Misodine; Mizodin; Mylepsin; Neurosyn; Primidon; Sertan; 2-Desoxyphenobarbital; Hexadiona; Majsolin; Milepsin; Misolyne; Prilepsin; Primakton; Primoline; Prysoline; Midone; Mizolin; Mysedon; Medi-Pets; Primacone; Desoxyphenobarbitone; Pyrimidone Medi-pets; 5-ethyl-5-phenyl-1,3-diazinane-4,6-dione; Primidona; Primidonum; Roe 101; 5-Phenyl-5-ethyl-hexahydropyrimidine-4,6-dione; 4,6(1H,5H)-Pyrimidinedione, 5-ethyldihydro-5-phenyl-; 5-ethyl-5-phenyldihydropyrimidine-4,6(1H,5H)-dione; NCI-C56360; Primidone (primaclone); 5-Ethyl-5-phenylhexahydropyrimidine-4,6-dione; 5-Ethyldihydro-5-phenyl-4,6(1H,5H)-pyrimidinedione; 5-Ethylhexahydro-4,6-dioxo-5-phenylpyrimidine; 5-Ethylhexahydro-5-phenylpyrimidine-4,6-dione; NSC 41701; 5-Aethyl-5-phenyl-hexahydropyrimidin-4,6-dion; UNII-13AFD7670Q; CHEBI:8412; Resimatil; 5-Phenyl-5-aethylhexahydropyrimidindion-(4,6); MLS000028593; Primacione; 13AFD7670Q; NSC-41701; NCGC00015834-11; CAS-125-33-7; SMR000058501; DSSTox_CID_3510; Primidonum [INN-Latin]; DSSTox_RID_77058; DSSTox_GSID_23510; Primidona [INN-Spanish]; 5-ethyldihydro-5-phenyl-4,6[1H,5H]-pyrimidinedione; Hexamidine (the antispasmodic); CCRIS 54; Mysoline (TN); HSDB 3169; SR-01000003162; EINECS 204-737-0; BRN 0218034; 5-ethyl-5-phenyl-1,2,3,5-tetrahydropyrimidine-4,6-dione; Hexamidine(the antispasmodic); 5-Aethyl-5-phenyl-hexahydropyrimidin-4,6-dion [German]; 5-Phenyl-5-aethylhexahydropyrimidindion-(4,6) [German]; Primidone [USP:INN:BAN:JAN]; Primidone solution; Primidone(Mysoline); Sodiumtrimetaphosphate; Primidone (Mysoline); Spectrum_000832; Tocris-0830; Pyrimidone 'Medi-pets'; Opera_ID_1083; Prestwick0_000933; Prestwick1_000933; Prestwick2_000933; Prestwick3_000933; Spectrum2_001293; Spectrum3_000553; Spectrum4_000485; Spectrum5_001144; Lopac-P-7295; Biomol-NT_000261; CHEMBL856; P 7295; Pyrimidone ''Medi-pets''; Lopac0_001021; SCHEMBL34221; BSPBio_000866; BSPBio_002225; KBioGR_000969; KBioSS_001312; 5-24-08-00102 (Beilstein Handbook Reference); MLS001055411; MLS001074125; BIDD:GT0319; DivK1c_000324; Primidone, analytical standard; SPECTRUM1500501; SPBio_001325; SPBio_003035; Primidone (JP17/USP/INN); BPBio1_000859; BPBio1_000954; GTPL5338; ZINC1979; DTXSID7023510; HMS501A06; KBio1_000324; KBio2_001312; KBio2_003880; KBio2_006448; KBio3_001725; WLN: T6MV DVMTJ C2 CR; NINDS_000324; HMS1570L08; HMS1920J20; HMS2092A21; HMS2097L08; HMS2236G03; HMS3259K04; HMS3263M03; HMS3266H18; HMS3369J12; HMS3411N13; HMS3655L05; HMS3675N13; HMS3714L08; HMS3884A18; Pharmakon1600-01500501; HY-B0339; NSC41701; Tox21_110238; Tox21_201948; Tox21_303194; Tox21_501021; ANW-42020; BDBM50248152; CCG-39231; MFCD00038662; NSC757291; SBB017254; AKOS003368409; Tox21_110238_1; DB00794; KS-5217; LP01021; MCULE-2519004832; NC00532; NSC-757291; SDCCGSBI-0050994.P005; IDI1_000324; SMP1_000135; NCGC00015834-01; NCGC00015834-02; NCGC00015834-03; NCGC00015834-04; NCGC00015834-05; NCGC00015834-06; NCGC00015834-07; NCGC00015834-08; NCGC00015834-09; NCGC00015834-10; NCGC00015834-12; NCGC00015834-13; NCGC00015834-14; NCGC00015834-15; NCGC00015834-16; NCGC00015834-17; NCGC00015834-19; NCGC00015834-28; NCGC00016377-01; NCGC00023254-02; NCGC00023254-04; NCGC00023254-05; NCGC00023254-06; NCGC00023254-07; NCGC00023254-08; NCGC00023254-09; NCGC00023254-10; NCGC00257146-01; NCGC00259497-01; NCGC00261706-01; AK546499; ST076725; SBI-0050994.P004; AB0013274; AB00052079; EU-0101021; FT-0603328; FT-0674032; SW196576-3; 5-Ethyldihydro-5-phenyl-4,5H)-pyrimidinedione; C07371; D00474; K-1838; AB00052079-14; AB00052079_15; AB00052079_16; 125P337; 4,5H)-Pyrimidinedione, 5-ethyldihydro-5-phenyl-; A805374; Q420383; J-005215; SR-01000003162-2; SR-01000003162-4; SR-01000003162-5; SR-01000003162-8; BRD-K32247306-001-05-4; BRD-K32247306-001-17-9; 5-Ethyl-5-phenyldihydro-4,6(1H,5H)-pyrimidinedione #; Primidone, European Pharmacopoeia (EP) Reference Standard; Primidone, United States Pharmacopeia (USP) Reference Standard; 5-Ethyl-5-phenylhexahydropyrimidine-4,6-dione / 2-Deoxyphenobarbital
Clinical Status
Approved
Disease Indication Epilepsy ICD-11: 8A60 [1]
PubChem CID
4909
Formula
C12H14N2O2
Canonical SMILES
CCC1(C(=O)NCNC1=O)C2=CC=CC=C2
InChI
1S/C12H14N2O2/c1-2-12(9-6-4-3-5-7-9)10(15)13-8-14-11(12)16/h3-7H,2,8H2,1H3,(H,13,15)(H,14,16)
InChIKey
DQMZLTXERSFNPB-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=4909"></iframe>
3D MOL 2D MOL
Physicochemical Properties Molecular Weight 218.25 Topological Polar Surface Area 58.2
XlogP 0.9 Complexity 279
Heavy Atom Count 16 Rotatable Bond Count 2
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 2
Full List of Drug Formulations (DFMs) Containing This API
          Primidone 250 mg tablet Click to Show/Hide the Full List of Formulation(s):        11 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
Stearic acid; Sodium benzoate; Docusate sodium; Magnesium stearate; Silicon dioxide; Cellulose, microcrystalline; Sodium starch glycolate type a potato
                   Dosage Form Oral Tablet
                   Company Actavis Pharma
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Stearic acid DIG Info Phosphodiesterase 3A (IC50 = 3.1 uM) [2]
Sodium benzoate DIG Info Carbonic anhydrase II (Ki = 30000 nM) [3]
Docusate sodium DIG Info Solute carrier SLCO2B1 (Ki = 2.3 uM) [2]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [4]
Silicon dioxide DIG Info Albendazole monooxygenase (Protein expression downregulation) [4]
             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
Lactose monohydrate; Sodium lauryl sulfate; Fd&c yellow no. 5; Magnesium stearate; Talc; Povidone; Cellulose, microcrystalline; Sodium starch glycolate type a potato
                   Dosage Form Oral Tablet
                   Company Global Pharmaceuticals
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Hydrazine yellow DIG Info GABA(A) receptor alpha-1 (IC50 = 13 uM) [2]
Sodium lauryl sulfate DIG Info Solute carrier SLCO2B1 (Ki = 1.98 uM) [5]
Povidone DIG Info Cholesterol 25-hydroxylase (IC50 = 78.3 uM) [6]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [4]
             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
Lactose monohydrate; Sodium lauryl sulfate; D&c yellow no. 10; Fd&c yellow no. 5; Magnesium stearate; Talc; Cellulose, microcrystalline; Hypromelloses; Sodium starch glycolate type a potato
                   Dosage Form Oral Tablet
                   Company Par Pharmaceutical
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Hydrazine yellow DIG Info GABA(A) receptor alpha-1 (IC50 = 13 uM) [2]
Sodium lauryl sulfate DIG Info Solute carrier SLCO2B1 (Ki = 1.98 uM) [5]
Quinoline yellow WS DIG Info Estrogen receptor alpha (IC50 = 18 uM) [2]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [4]
             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
Stearic acid; Lactose monohydrate; Sodium lauryl sulfate; Magnesium stearate; Povidone; Cellulose, microcrystalline; Sodium starch glycolate type a potato
                   Dosage Form Oral Tablet
                   Company NCS HealthCare of KY, Inc dba Vangard Labs; West-Ward Pharmaceticals
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Stearic acid DIG Info Phosphodiesterase 3A (IC50 = 3.1 uM) [2]
Sodium lauryl sulfate DIG Info Solute carrier SLCO2B1 (Ki = 1.98 uM) [5]
Povidone DIG Info Cholesterol 25-hydroxylase (IC50 = 78.3 uM) [6]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [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
Lactose monohydrate; Sodium lauryl sulfate; Magnesium stearate; Ferric oxide yellow; Talc; Water; Sodium starch glycolate type a potato
                   Dosage Form Oral Tablet
                   Company Dr Reddy's Laboratories
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Sodium lauryl sulfate DIG Info Solute carrier SLCO2B1 (Ki = 1.98 uM) [5]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [4]
             Drug Formulation 6 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
Lactose monohydrate; Sodium lauryl sulfate; Magnesium stearate; Ferric oxide yellow; Talc; Cellulose, microcrystalline; Methylcellulose (15 cps); Sodium starch glycolate type a potato
                   Dosage Form Oral Tablet
                   Company Valeant Pharmaceuticals
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Sodium lauryl sulfate DIG Info Solute carrier SLCO2B1 (Ki = 1.98 uM) [5]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [4]
             Drug Formulation 7 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
Lactose monohydrate; Sodium lauryl sulfate; Magnesium stearate; Cellulose, microcrystalline; Methylcellulose (100 cps); Sodium starch glycolate type a potato; Starch, corn
                   Dosage Form Oral Tablet
                   Company AvKARE
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Sodium lauryl sulfate DIG Info Solute carrier SLCO2B1 (Ki = 1.98 uM) [5]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [4]
             Drug Formulation 8 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
Lactose monohydrate; Sodium lauryl sulfate; Magnesium stearate; Cellulose, microcrystalline; Methylcellulose (100 cps); Sodium starch glycolate type a potato; Starch, corn
                   Dosage Form Oral Tablet
                   Company Major Pharmaceuticals
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Sodium lauryl sulfate DIG Info Solute carrier SLCO2B1 (Ki = 1.98 uM) [5]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [4]
             Drug Formulation 9 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
Lactose monohydrate; Magnesium stearate; Acacia; Methylcellulose (400 cps); Sodium starch glycolate type a potato
                   Dosage Form Oral Tablet
                   Company Lannett Company; Physicians Total Care
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [4]
             Drug Formulation 10 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
Lactose monohydrate; Magnesium stearate; Acacia; Methylcellulose (400 mpa.s); Sodium starch glycolate type a potato
                   Dosage Form Oral Tablet
                   Company Major Pharmaceuticals; Marlex Pharmaceuticals; NCS HealthCare of KY, Inc dba Vangard Labs
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [4]
             Drug Formulation 11 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
Lactose monohydrate; Magnesium stearate; Acacia; Methylcellulose (400 mpa.s); Sodium starch glycolate type a potato
                   Dosage Form Oral Tablet
                   Company American Health Packaging
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [4]
          Primidone 50 mg tablet Click to Show/Hide the Full List of Formulation(s):          9 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
Stearic acid; Lactose monohydrate; Sodium lauryl sulfate; Magnesium stearate; Povidone; Cellulose, microcrystalline; Sodium starch glycolate type a potato
                   Dosage Form Oral Tablet
                   Company West-Ward Pharmaceticals
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Stearic acid DIG Info Phosphodiesterase 3A (IC50 = 3.1 uM) [2]
Sodium lauryl sulfate DIG Info Solute carrier SLCO2B1 (Ki = 1.98 uM) [5]
Povidone DIG Info Cholesterol 25-hydroxylase (IC50 = 78.3 uM) [6]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [4]
             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
Lactose monohydrate; Sodium lauryl sulfate; Magnesium stearate; Talc; Povidone; Cellulose, microcrystalline; Sodium starch glycolate type a potato
                   Dosage Form Oral Tablet
                   Company Global Pharmaceuticals
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Sodium lauryl sulfate DIG Info Solute carrier SLCO2B1 (Ki = 1.98 uM) [5]
Povidone DIG Info Cholesterol 25-hydroxylase (IC50 = 78.3 uM) [6]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [4]
             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
Lactose monohydrate; Sodium lauryl sulfate; Magnesium stearate; Talc; Water; Sodium starch glycolate type a potato
                   Dosage Form Oral Tablet
                   Company Dr Reddy's Laboratories
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Sodium lauryl sulfate DIG Info Solute carrier SLCO2B1 (Ki = 1.98 uM) [5]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [4]
             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
Lactose monohydrate; Sodium lauryl sulfate; Magnesium stearate; Talc; Cellulose, microcrystalline; Hypromelloses; Sodium starch glycolate type a potato
                   Dosage Form Oral Tablet
                   Company Aphena Pharma Solutions-Tennessee; NCS HealthCare of KY, Inc dba Vangard Labs; Par Pharmaceutical
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Sodium lauryl sulfate DIG Info Solute carrier SLCO2B1 (Ki = 1.98 uM) [5]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [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
Lactose monohydrate; Sodium lauryl sulfate; Magnesium stearate; Talc; Cellulose, microcrystalline; Methylcellulose (15 cps); Sodium starch glycolate type a potato
                   Dosage Form Oral Tablet
                   Company Valeant Pharmaceuticals
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Sodium lauryl sulfate DIG Info Solute carrier SLCO2B1 (Ki = 1.98 uM) [5]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [4]
             Drug Formulation 6 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
Lactose monohydrate; Sodium lauryl sulfate; Magnesium stearate; Cellulose, microcrystalline; Methylcellulose (100 cps); Sodium starch glycolate type a potato; Starch, corn
                   Dosage Form Oral Tablet
                   Company AvKARE
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Sodium lauryl sulfate DIG Info Solute carrier SLCO2B1 (Ki = 1.98 uM) [5]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [4]
             Drug Formulation 7 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
Lactose monohydrate; Magnesium stearate; Acacia; Methylcellulose (400 cps); Sodium starch glycolate type a potato
                   Dosage Form Oral Tablet
                   Company Lannett Company; McKesson; Physicians Total Care; Stat Rx USA
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [4]
             Drug Formulation 8 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
Lactose monohydrate; Magnesium stearate; Acacia; Methylcellulose (400 mpa.s); Sodium starch glycolate type a potato
                   Dosage Form Oral Tablet
                   Company Major Pharmaceuticals; Marlex Pharmaceuticals; NCS HealthCare of KY, Inc dba Vangard Labs
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [4]
             Drug Formulation 9 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
Lactose monohydrate; Magnesium stearate; Acacia; Methylcellulose (400 mpa.s); Sodium starch glycolate type a potato
                   Dosage Form Oral Tablet
                   Company American Health Packaging
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [4]
References
1 FDA label for approved primidone 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 Carbonic anhydrase inhibitors. Interaction of isozymes I, II, IV, V, and IX with carboxylates. Bioorg Med Chem Lett. 2005 Feb 1; 15(3):573-8.
4 Effects of commonly used excipients on the expression of CYP3A4 in colon and liver cells. Pharm Res. 2010 Aug;27(8):1703-12.
5 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.
6 Mediation of in vitro cytochrome p450 activity by common pharmaceutical excipients. Mol Pharm. 2013 Jul 1;10(7):2739-48.

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