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Substance Name: Phenobarbital [USP:INN:BAN:JAN]
RN: 50-06-6
UNII: YQE403BP4D
InChIKey: DDBREPKUVSBGFI-UHFFFAOYSA-N

Note

  • A barbituric acid derivative that acts as a nonselective central nervous system depressant. It potentiates GAMMA-AMINOBUTYRIC ACID action on GABA-A RECEPTORS, and modulates chloride currents through receptor channels. It also inhibits glutamate induced depolarizations.

Molecular Formula

  • C12-H12-N2-O3

Molecular Weight

  • 232.2378
 

Classification Codes

Classification Codes

  • Anticonvulsant
  • Anticonvulsants
  • Central Nervous System Agents
  • Central Nervous System Depressants
  • Cytochrome P-450 CYP2B6 Inducers
  • Cytochrome P-450 CYP3A Inducers
  • Drug / Therapeutic Agent
  • Excitatory Amino Acid Agents
  • Excitatory Amino Acid Antagonists
  • GABA Agents
  • GABA Modulators
  • Human Data
  • Hypnotics and Sedatives
  • Metabolic Side Effects of Drugs and Substances
  • Mutation Data
  • Neurotransmitter Agents
  • Reproductive Effect
  • Sedative-Hypnotic
  • Tumor Data

Superlist Classification Codes

  • DEA Schedule IV
  • Overall Carcinogenic Evaluation: Group 2B

Names and Synonyms

Name of Substance

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

MeSH Heading

  • Phenobarbital

Synonyms

  • 2,4,6(1H,3H,5H)-Pyrimidinetrione, 5-ethyl-5-phenyl-
  • 5-Ethyl-5-phenyl-2,4,6-(1H,3H,5H)pyrimidinetrione
  • 5-Ethyl-5-phenylbarbituric acid
  • 5-Phenyl-5-ethylbarbituric acid
  • Acido 5-fenil-5-etilbarbiturico
  • Acido 5-fenil-5-etilbarbiturico [Italian]
  • Adonal
  • Aephenal
  • Agrypnal
  • AI3-02726
  • Amylofene
  • Aphenylbarbit
  • Aphenyletten
  • Austrominal
  • Barbenyl
  • Barbinol
  • Barbiphenyl
  • Barbipil
  • Barbita
  • Barbituric acid, 5-ethyl-5-phenyl-
  • Barbivis
  • Barbonal
  • Barbophen
  • Bardorm
  • Bartol
  • Bialminal
  • Blu-phen
  • Cabronal
  • Calmetten
  • Calminal
  • Cardenal
  • CCRIS 502
  • Chinoin
  • Codibarbita
  • Coronaletta
  • Cratecil
  • Dezibarbitur
  • Dormiral
  • Doscalun
  • Duneryl
  • EINECS 200-007-0
  • Elixir of phenobarbital
  • Ensobarb
  • Ensodorm
  • Epanal
  • Epidorm
  • Epilol
  • Episedal
  • Epsylone
  • Eskabarb
  • Etilfen
  • Euneryl
  • Fenbital
  • Fenemal
  • Fenobarbital
  • Fenobarbital [INN-Spanish]
  • Fenobarbitale
  • Fenobarbitale [DCIT]
  • Fenosed
  • Fenylettae
  • Gardenal
  • Gardepanyl
  • Glysoletten
  • Haplopan
  • Haplos
  • Helional
  • Hennoletten
  • Henotal
  • HSDB 3157
  • Hypnaletten
  • Hypnette
  • Hypno-Tablinetten
  • Hypnogen
  • Hypnolone
  • Hypnoltol
  • Hysteps
  • Leonal
  • Lepinal
  • Lepinaletten
  • Linasen
  • Liquital
  • Lixophen
  • Lubergal
  • Lubrokal
  • Lumen
  • Lumesettes
  • Lumesyn
  • Luminal
  • Lumofridetten
  • Luphenil
  • Luramin
  • Molinal
  • Neurobarb
  • Nirvonal
  • Noptil
  • Nova-pheno
  • NSC 128143
  • Nunol
  • Parkotal
  • Pharmetten
  • Phen-Bar
  • Phenaemal
  • Phenemal
  • Phenemalum
  • Phenobal
  • Phenobarb
  • Phenobarbital
  • Phenobarbitalum
  • Phenobarbitalum [INN-Latin]
  • Phenobarbitalum [INN]
  • Phenobarbitol
  • Phenobarbitone
  • Phenobarbitonum
  • Phenobarbituric acid
  • Phenobarbyl
  • Phenoluric
  • Phenolurio
  • Phenomet
  • Phenonyl
  • Phenoturic
  • Phenyl-ethyl-barbituric acid
  • Phenylethyl barbituric acid
  • Phenylethylbarbiturate
  • Phenylethylbarbituric Acid
  • Phenylethylmalonylurea
  • Phenyletten
  • Phenyral
  • Phob
  • Polcominal
  • Promptonal
  • Seda-Tablinen
  • Sedabar
  • Sedicat
  • Sedizorin
  • Sedlyn
  • Sedofen
  • Sedonal
  • Sedonettes
  • Sedophen
  • Sevenal
  • SK-Phenobarbital
  • Solfoton
  • Solu-Barb
  • Sombutol
  • Somnolens
  • Somnoletten
  • Somnosan
  • Somonal
  • Spasepilin
  • Starifen
  • Starilettae
  • Stental Extentabs
  • Talpheno
  • Teolaxin
  • UNII-YQE403BP4D

Systematic Names

  • 2,4,6(1H,3H,5H)-Pyrimidinetrione, 5-ethyl-5-phenyl-
  • Barbituric acid, 5-ethyl-5-phenyl-
  • Phenobarbital

Superlist Names

  • DEA No. 2285
  • Phenobarbital

Mixture Names

  • Antrocol
  • Barbidonna
  • Bronkotabs
  • Chardonna-2
  • Donnatal
  • Donnazyme
  • Hydantal
  • Kinesed
  • Levsin PB Drops and Tablets
  • Quadrinal
  • Tedral

Registry Numbers

CAS Registry Number

  • 50-06-6

FDA UNII

  • YQE403BP4D

Other Registry Numbers

  • 11097-06-6
  • 46755-67-3

Related Registry Number

  • 57-30-7 (mono-hydrochloride salt)

System Generated Number

  • 0000050066

Structure Descriptors

InChI

InChI=1S/C12H12N2O3/c1-2-12(8-6-4-3-5-7-8)9(15)13-11(17)14-10(12)16/h3-7H,2H2,1H3,(H2,13,14,15,16,17)

InChIKey

DDBREPKUVSBGFI-UHFFFAOYSA-N

Smiles

CCC1(C(=O)NC(=O)NC1=O)c2ccccc2

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
cat LDLo oral 125mg/kg (125mg/kg)   "Abdernalden's Handbuch der Biologischen Arbeitsmethoden." Vol. 4, Pg. 1289, 1935.
cat LDLo subcutaneous 125mg/kg (125mg/kg)   "Abdernalden's Handbuch der Biologischen Arbeitsmethoden." Vol. 4, Pg. 1289, 1935.
child TDLo oral 10mg/kg (10mg/kg) BEHAVIORAL: ATAXIA

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)		 American Journal of Diseases of Children. Vol. 130, Pg. 507, 1976.
child TDLo oral 20mg/kg/I (20mg/kg) BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY)

SENSE ORGANS AND SPECIAL SENSES: OTHER: EYE

BEHAVIORAL: ATAXIA		 Clinical Pediatrics Vol. 31, Pg. 252, 1992.
dog LD50 oral 150mg/kg (150mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) Schweizerische Medizinische Wochenschrift. Vol. 85, Pg. 305, 1955.
dog LDLo subcutaneous 150mg/kg (150mg/kg)   "Abdernalden's Handbuch der Biologischen Arbeitsmethoden." Vol. 4, Pg. 1289, 1935.
frog LDLo subcutaneous 500mg/kg (500mg/kg)   "Abdernalden's Handbuch der Biologischen Arbeitsmethoden." Vol. 4, Pg. 1289, 1935.
guinea pig LD50 oral 130mg/kg (130mg/kg)   Archives Internationales de Pharmacodynamie et de Therapie. Vol. 91, Pg. 437, 1952.
human TDLo oral 18mg/kg (18mg/kg) SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE"

LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES		 JAMA, Journal of the American Medical Association. Vol. 116, Pg. 700, 1941.
infant TDLo intramuscular 50mg/kg (50mg/kg) BEHAVIORAL: COMA Pediatrics. Vol. 77, Pg. 848, 1986.
man LDLo oral 6485ug/kg/2W- (6.485mg/kg)   Annals of Internal Medicine. Vol. 13, Pg. 1243, 1940.
man LDLo oral 6485ug/kg/2W- (6.485mg/kg) SKIN AND APPENDAGES (SKIN): "DERMATITIS, ALLERGIC: AFTER SYSTEMIC EXPOSURE" Annals of Internal Medicine. Vol. 13, Pg. 1243, 1940.
mouse LD50 intramuscular 175mg/kg (175mg/kg)   Gekkan Yakuji. Pharmaceuticals Monthly. Vol. 23, Pg. 2215, 1981.
mouse LD50 intraperitoneal 88mg/kg (88mg/kg)   Pharmazie. Vol. 52, Pg. 926, 1997.
mouse LD50 intravenous 218mg/kg (218mg/kg) PERIPHERAL NERVE AND SENSATION: LOCAL ANESTHETIC Archives Internationales de Pharmacodynamie et de Therapie. Vol. 191, Pg. 405, 1971.
mouse LD50 oral 137mg/kg (137mg/kg)   Pharmaceutical Chemistry Journal Vol. 10, Pg. 41, 1976.
mouse LD50 subcutaneous 228mg/kg (228mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 30, Pg. 477, 1980.
rabbit LD50 intravenous 187mg/kg (187mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION		 Arzneimittel-Forschung. Drug Research. Vol. 33, Pg. 1168, 1983.
rabbit LD50 oral 185mg/kg (185mg/kg)   Neuropatologia Polska. Vol. 15, Pg. 545, 1977.
rabbit LDLo intraperitoneal 150mg/kg (150mg/kg)   Journal of Pharmacology and Experimental Therapeutics. Vol. 44, Pg. 325, 1932.
rabbit LDLo subcutaneous 150mg/kg (150mg/kg)   Journal of the American Chemical Society. Vol. 45, Pg. 243, 1923.
rat LC inhalation > 4100ug/m3/4H (4.1mg/m3) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BLOOD: OTHER CHANGES		 Toksikologicheskii Vestnik. Vol. (1), Pg. 39, 2000.
rat LD50 intraperitoneal 110mg/kg (110mg/kg)   French Medicament Patent Document. Vol. #7157M,
rat LD50 intravenous 209mg/kg (209mg/kg)   Archives of Toxicology. Vol. 40, Pg. 211, 1978.
rat LD50 oral 162mg/kg (162mg/kg)   Toxicology and Applied Pharmacology. Vol. 18, Pg. 185, 1971.
rat LD50 rectal 284mg/kg (284mg/kg) BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)

BEHAVIORAL: GENERAL ANESTHETIC		 Anesthesia and Analgesia Vol. 46, Pg. 395, 1967.
rat LD50 subcutaneous 200mg/kg (200mg/kg)   Naunyn-Schmiedeberg's Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 152, Pg. 341, 1930.
women LDLo oral 25272ug/kg/13 (25.272mg/kg)   Canadian Medical Association Journal. Vol. 33, Pg. 635, 1935.
women LDLo oral 25272ug/kg/13 (25.272mg/kg) BEHAVIORAL: COMA

SKIN AND APPENDAGES (SKIN): "DERMATITIS, ALLERGIC: AFTER SYSTEMIC EXPOSURE"		 Canadian Medical Association Journal. Vol. 33, Pg. 635, 1935.
women TDLo oral 46mg/kg (46mg/kg) LUNGS, THORAX, OR RESPIRATION: DYSPNEA

BEHAVIORAL: COMA		 Clinical Pediatrics Vol. 24, Pg. 678, 1985.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 174 deg C   EXP
pKa Dissociation Constant 7.3 (none)   EXP
log P (octanol-water) 1.47 (none)   EXP
Water Solubility 1110 mg/L 25 EXP
Vapor Pressure 1.98E-12 mm Hg 25 EST
Henry's Law Constant 3.80E-16 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 1.01E-11 cm3/molecule-sec 25 EST

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