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Substance Name: Primidone [USP:INN:BAN:JAN]
RN: 125-33-7
UNII: 13AFD7670Q
InChIKey: DQMZLTXERSFNPB-UHFFFAOYSA-N

Note

  • An antiepileptic agent related to the barbiturates; it is partly metabolized to PHENOBARBITAL in the body and owes some of its actions to this metabolite. Adverse effects are reported to be more frequent than with PHENOBARBITAL. (From Martindale, The Extra Pharmacopoeia, 30th ed, p309)

Molecular Formula

  • C12-H14-N2-O2

Molecular Weight

  • 218.2546
 

Classification Codes

  • Anticonvulsant
  • Anticonvulsants
  • Central Nervous System Agents
  • Drug / Therapeutic Agent
  • GABA Agents
  • GABA Modulators
  • Human Data
  • Mutation Data
  • Neurotransmitter Agents
  • Reproductive Effect
  • Tumor Data

Names and Synonyms

Name of Substance

  • Primidone
  • Primidone [USP:INN:BAN:JAN]

MeSH Heading

  • Primidone

Synonyms

  • 2-Deoxyphenobarbital
  • 2-Desoxyphenobarbital
  • 4,4'-(Hexamethylenedioxy)dibenzamidine
  • 4,6(1H,5H)-Pyrimidinedione, 5-ethyldihydro-5-phenyl-
  • 5-24-08-00102 (Beilstein Handbook Reference)
  • 5-Aethyl-5-phenyl-hexahydropyrimidin-4,6-dion
  • 5-Aethyl-5-phenyl-hexahydropyrimidin-4,6-dion [German]
  • 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
  • 5-Phenyl-5-aethylhexahydropyrimidindion-(4,6)
  • 5-Phenyl-5-aethylhexahydropyrimidindion-(4,6) [German]
  • 5-Phenyl-5-ethyl-hexahydropyrimidine-4,6-dione
  • BRN 0218034
  • CCRIS 54
  • Cyral
  • Desoxyphenobarbitone
  • EINECS 204-737-0
  • Hexadiona
  • Hexamidine
  • Hexamidine (the antispasmodic)
  • HSDB 3169
  • Lepimidin
  • Lepsiral
  • Liskantin
  • Majsolin
  • Medi-Pets
  • Midone
  • Milepsin
  • Misodine
  • Misolyne
  • Mizodin
  • Mizolin
  • Mylepsin
  • Mylepsinum
  • Mysedon
  • Mysoline
  • NCI-C56360
  • Neurosyn
  • NSC 41701
  • Prilepsin
  • Primaclone
  • Primakton
  • Primidon
  • Primidona
  • Primidona [INN-Spanish]
  • Primidone
  • Primidonum
  • Primidonum [INN-Latin]
  • Primoline
  • Prysoline
  • Pyrimidone medi-pets
  • ROE 101
  • Sertan
  • UNII-13AFD7670Q

Systematic Names

  • 4,6(1H,5H)-Pyrimidinedione, 5-ethyldihydro-5-phenyl-
  • Primaclone
  • Primidone

Superlist Name

  • Primidone

Registry Numbers

CAS Registry Number

  • 125-33-7

FDA UNII

  • 13AFD7670Q

System Generated Number

  • 0000125337

Structure Descriptors

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

Smiles

CCC1(C(=O)NCNC1=O)c2ccccc2

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
child TDLo oral 625mg/kg (625mg/kg) BEHAVIORAL: SLEEP

BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)

BEHAVIORAL: GENERAL ANESTHETIC		 British Medical Journal. Vol. 1, Pg. 90, 1957.
mouse LD50 intraperitoneal 332mg/kg (332mg/kg) BEHAVIORAL: ANTICONVULSANT Pharmaceutical Chemistry Journal Vol. 15, Pg. 403, 1981.
mouse LD50 oral 280mg/kg (280mg/kg)   Toxicology and Applied Pharmacology. Vol. 34, Pg. 271, 1975.
mouse LD50 unreported 340mg/kg (340mg/kg) BEHAVIORAL: ANTICONVULSANT Russian Pharmacology and Toxicology Vol. 43, Pg. 73, 1980.
rat LD50 intraperitoneal 240mg/kg (240mg/kg)   Pharmaceutical Chemistry Journal Vol. 25, Pg. 305, 1991.
rat LD50 oral 1500mg/kg (1500mg/kg)   Drugs in Japan Vol. 6, Pg. 691, 1982.
rat LD50 unreported > 2gm/kg (2000mg/kg)   British Journal of Pharmacology and Chemotherapy. Vol. 8, Pg. 230, 1953.
women TDLo oral 5mg/kg (5mg/kg) GASTROINTESTINAL: NAUSEA OR VOMITING

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: HEADACHE		 Lancet. Vol. 266, Pg. 102, 1954.
women TDLo oral 450mg/kg (450mg/kg) BEHAVIORAL: ANTIPSYCHOTIC

BEHAVIORAL: ATAXIA

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)		 Archives of Neurology Vol. 30, Pg. 255, 1974.
women TDLo oral 38gm/kg/7Y-I (38000mg/kg) BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS"

BEHAVIORAL: TOXIC PSYCHOSIS		 Drug Intelligence and Clinical Pharmacy. Vol. 17, Pg. 551, 1983.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 281.5 deg C   EXP
log P (octanol-water) 0.91 (none)   EXP
Water Solubility 500 mg/L 22 EXP
Vapor Pressure 3.64E-09 mm Hg 25 EST
Henry's Law Constant 1.94E-10 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 3.48E-11 cm3/molecule-sec 25 EST

Physical property data is provided to ChemIDplus by SRC, Inc.