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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
- All
- Classifications
- Links to Resources
- Names & Synonyms
- Registry Numbers
- Structure Descriptors
- Toxicity
- Physical Properties
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
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Links to Resources
NLM Resources (File Locators)
Regulatory Agencies (Superlist Locators)
Other Resources (Internet Locators)
Search for this InChIKey on the Web
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-NSmiles
CCC1(C(=O)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.