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

Note

  • A barbiturate derivative that acts as a GABA modulator and anti-epileptic agent. It is partly metabolized to PHENOBARBITAL in the body and owes some of its actions to this metabolite.

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

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.