Compound: primidone
SMILES: O=C1NCNC(C1(c2ccccc2)CC)=O
InChIKey: DQMZLTXERSFNPB-UHFFFAOYSA-N
Synonyms: primidone, 125-33-7, Mysoline, Primaclone, Lepimidin, Mylepsin, 2-Deoxyphenobarbital, Lepsiral, Liskantin, Milepsin, Neurosyn, Primakton, Mysedon, Hexadiona, Prilepsin, Primoline, Prysoline, Resimatil, Majsolin, Misolyne, Mizolin, Primidon, Cyral, Midone, 2-Desoxyphenobarbital, Primacone, Desoxyphenobarbitone, Pyrimidone Medi-pets, Primidona, 5-ethyl-5-phenyl-1,3-diazinane-4,6-dione, Primidonum, Roe 101, 4,6(1H,5H)-Pyrimidinedione, 5-ethyldihydro-5-phenyl-, 5-Phenyl-5-ethyl-hexahydropyrimidine-4,6-dione, 5-Ethyldihydro-5-phenyl-4,6(1H,5H)-pyrimidinedione, 5-Ethyl-5-phenylhexahydropyrimidine-4,6-dione, NCI-C56360, Hexamidine (the antispasmodic), 5-Ethylhexahydro-4,6-dioxo-5-phenylpyrimidine, 5-Ethylhexahydro-5-phenylpyrimidine-4,6-dione, 5-Aethyl-5-phenyl-hexahydropyrimidin-4,6-dion, DTXSID7023510, NSC-41701, CHEBI:8412, 13AFD7670Q, DTXCID603510, Myidone, 5-24-08-00102 (Beilstein Handbook Reference), NSC41701, Apo Primidone, Mylepsin Tablets, Neurosyn Tablets, Mysoline, Apo-Primidone, RefChem:57475, Mylepsin, Primidone Medi-Pets, N03AA03, 5-Ethyl-5-phenyl-2,3-dihydropyrimidine-4,6(1H,5H)-dione, 204-737-0, Misodine, Mizodin, Sertan, Mylepsinum, Medi-Pets, 5-ethyl-5-phenyldihydropyrimidine-4,6(1H,5H)-dione, MFCD00038662, NSC 41701, Primidone(Mysoline), 5-Phenyl-5-aethylhexahydropyrimidindion-(4,6), MLS000028593, Primacione, s1965, NCGC00015834-11, CAS-125-33-7, SMR000058501, A1AIA, Primidonum [INN-Latin], Primidona [INN-Spanish], Primidone (primaclone), 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], UNII-13AFD7670Q, Primidone CRS, Primidone [USP:INN:BAN:JAN], Primidone (Mysoline), Primidone (Standard), Spectrum_000832, Tocris-0830, Pyrimidone 'Medi-pets', PRIMIDONE [INN], PRIMIDONE [JAN], PRIMIDONE [MI], PRIMIDONE [HSDB], PRIMIDONE [IARC], Opera_ID_1083, Prestwick0_000933, Prestwick1_000933, Prestwick2_000933, Prestwick3_000933, Spectrum2_001293, Spectrum3_000553, Spectrum4_000485, Spectrum5_001144, Lopac-P-7295, PRIMIDONE [VANDF], Biomol-NT_000261, CHEMBL856, PRIMIDONE [MART.], P 7295, Pyrimidone ''Medi-pets'', PRIMIDONE [USP-RS], PRIMIDONE [WHO-DD], 5-ethyl-5-phenyl-hexahydropyrimidine-4,6-dione, Lopac0_001021, SCHEMBL34221, BSPBio_000866, BSPBio_002225, KBioGR_000969, KBioSS_001312, MLS001055411, MLS001074125, BIDD:GT0319, DivK1c_000324, Primidone, analytical standard, SPECTRUM1500501, Primidone - Bio-X trade mark, SPBio_001325, SPBio_003035, Primidone (JP18/USP/INN), PRIMIDONE [GREEN BOOK], BPBio1_000859, BPBio1_000954, GTPL5338, orb1311011, orb3025176, PRIMIDONE [EP IMPURITY], PRIMIDONE [ORANGE BOOK], PRIMIDONE [EP MONOGRAPH], HMS501A06, HY-B0339R, KBio1_000324, KBio2_001312, KBio2_003880, KBio2_006448, KBio3_001725, Primidone for peak identification, WLN: T6MV DVMTJ C2 CR, PRIMIDONE [USP MONOGRAPH], NINDS_000324, HMS1570L08, HMS1920J20, HMS2092A21, HMS2097L08, HMS2236G03, HMS3259K04, HMS3263M03, HMS3266H18, HMS3369J12, HMS3411N13, HMS3655L05, HMS3675N13, HMS3714L08, HMS3884A18, HMS5080L09, Pharmakon1600-01500501, HY-B0339, MSK10256, Tox21_110238, Tox21_201948, Tox21_303194, Tox21_501021, BDBM50248152, CCG-39231, EBC-04191, NSC757291, SBB017254, AKOS003368409, Tox21_110238_1, DB00794, FP05584, KS-5217, LP01021, 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, BP166193, ST076725, SY052118, SBI-0050994.P004, AB00052079, EU-0101021, NS00000208, P1906, SW196576-3, 5-Ethyldihydro-5-phenyl-4,5H)-pyrimidinedione, C07371, C71997, D00474, AB00052079-14, AB00052079_15, AB00052079_16, 4,5H)-Pyrimidinedione, 5-ethyldihydro-5-phenyl-, Q420383, SR-01000003162-2, SR-01000003162-4, SR-01000003162-5, SR-01000003162-8, BRD-K32247306-001-05-4, BRD-K32247306-001-17-9, BRD-K32247306-001-27-8, BRD-K32247306-001-28-6, BRD-K32247306-001-29-4, 5-Ethyl-5-phenyldihydro-4,6(1H,5H)-pyrimidinedione #, Z1509139960, Primidone, European Pharmacopoeia (EP) Reference Standard, Primidone, United States Pharmacopeia (USP) Reference Standard, Primidone for peak identification, European Pharmacopoeia (EP) Reference Standard
Theoretical properties:
molecular_formula: C12H14N2O2
molecular_weight: 218.25 g/mol
exact_mass: 218.105527694 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 2
hydrogen_bond_acceptor_count: 2
rotatable_bond_count: 2
heavy_atom_count: 16
topological_polar_surface_area: 58.2 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
physical_state: Crystals
color: Crystals
odor: Odorless
melting_point: 538 to 540 °F (NTP, 1992)
solubility: less than 1 mg/mL at 66 °F (NTP, 1992)
Descriptions:
pubchem: Primidone can cause cancer according to The National Toxicology Program.
chebi: A pyrimidone that is dihydropyrimidine-4,6(1<em>H</em>,5<em>H</em>)-dione substituted by an ethyl and a phenyl group at position 5. It is used as an  anticonvulsant for treatment of various types of seizures.
chembl: PRIMIDONE is a small molecule listed in the ChEMBL database and has reached clinical trial phase 4.0.
wikipedia: Primidone, sold under various brand names (including Mysoline), is a barbiturate medication that is used to treat partial and generalized seizures and essential tremors. It is taken by mouth.
Its common side effects include sleepiness, poor coordination, nausea, and loss of appetite. Severe side effects may include suicide and psychosis. Use during pregnancy may result in harm to the fetus. Primidone is an anticonvulsant of the barbiturate class; however, its long-term effect in raising the seizure threshold is likely due to its active metabolite, phenobarbital. The drug’s other active metabolite is Phenylethylmalonamide (PEMA).
Primidone was approved for medical use in the United States in 1954. It is available as a generic medication. In 2023, it was the 239th most commonly prescribed medication in the United States, with more than 1 million prescriptions.