5-ethyl-5-phenyl-1,3-diazinane-2,4,6-trione

• ChemBase ID: 1045
• Molecular Formular: C12H12N2O3
• Molecular Mass: 232.23528
• Monoisotopic Mass: 232.08479225
• SMILES: O=C1NC(=O)NC(=O)C1(CC)c1ccccc1
• Canonical SMILES: CCC1(C(=O)NC(=O)NC1=O)c1ccccc1
• 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

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-ethyl-5-phenyl-1,3-diazinane-2,4,6-trione
• IUPAC Traditional name: phenobarbital
• Brand Name: Adonal; Aephenal; Agrypnal; Amylofene; Aphenylbarbit; Aphenyletten; Barbenyl; Barbinal; Barbiphen; Barbiphenyl; Barbipil; Barbita; Barbivis; Barbonal; Barbophen; Bardorm; Bartol; Bialminal; Blu-Phen; Cabronal; Calmetten; Calminal; Cardenal; Chinoin; Codibarbita; Coronaletta; Cratecil; Damoral; Dezibarbitur; Dormina; Dormiral; Dormital; Doscalun; Duneryl; Ensobarb; Ensodorm; Epanal; Epidorm; Epilol; Episedal; Epsylone; Eskabarb; Etilfen; Euneryl; Fenbital; Fenemal; Fenosed; Fenylettae; Gardenal; Gardepanyl; Glysoletten; Haplopan; Haplos; Helional; Hennoletten; Henotal; Hypnaletten; Hypnette; Hypno-Tablinetten; Hypnogen; Hypnolone; Hypnoltol; Hysteps; Lefebar; Leonal; Lephebar; Lepinal; Lepinaletten; Linasen; Liquital; Lixophen; Lubergal; Lubrokal; Lumen; Lumesettes; Lumesyn; Luminal; Lumofridetten; Luphenil; Luramin; Molinal; Neurobarb; Nirvonal; Noptil; Nova-Pheno; Nunol; Parkotal; Pharmetten; Phen-Bar; Phenaemal; Phenemal; Phenemalum; Phenobal; Phenobarbyl; Phenoluric; Phenolurio; Phenomet; Phenonyl; Phenoturic; Phenyletten; Phenyral; Phob; Polcominal; Promptonal; Seda-Tablinen; Sedabar; Sedicat; Sedizorin; Sedlyn; Sedofen; Sedonal; Sedonettes; Sevenal; Sinoratox; Solfoton; Solfoton Talpheno; Solu-Barb; Sombutol; Somnolens; Somnoletten; Somnosan; Somonal; Spasepilin; Starifen; Starilettae; Stental; Stental Extentabs; Talpheno; Teolaxin; Teoloxin; Thenobarbital; Theoloxin; Triabarb; Tridezibarbitur; Triphenatol; Versomnal; Zadoletten; Zadonal
• Synonyms: Phenobarbitol; Phenobarbituric Acid; Phenylethylbarbiturate; Phenylethylbarbituric Acid; Phenylethylmalonylurea; Fenobarbital; Phenobarbitone; Phenobarbital; 5-Ethyl-5-phenylbarbituric acid solution; Phenobarbital solution; 5-Ethyl-5-phenyl-2,4,6(1H,3H,5H)-pyrimidinetrione; Agrypnal; Barbiphenyl; Barbipil; Gardenal; 5-Ethyl-5-phenyl-2,4,6-pyrimidinetrione; 5-Ethyl-5-phenylbarbituric acid; Luminal; Phenobarbital

Database IDs

• CAS Number: 50-06-6
• EC Number: 200-007-0
• MDL Number: MFCD00066494
• Beilstein Number: 233363
• PubChem SID: 24898226; 160964508; 46505776
• PubChem CID: 4763

CALCULATED PROPERTIES

JChem

• Acid pKa: 8.136713
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 1.4053402
• LogD (pH = 7.4): 1.3341205
• Log P: 1.4063301
• Molar Refractivity: 59.7463 cm^3
• Polarizability: 23.17525 Å^3
• Polar Surface Area: 75.27 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 1.4
• LOG S: -2.93
• Solubility (Water): 2.76e-01 g/l

PROPERTIES

Physical Property

• Solubility: 1.11 mg/mL at 25 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)]; Alcohol; Chloroform; Water
• Apperance: White Solid
• Melting Point: 174-178 °C; 174-1780C
• Flash Point: 11 °C; 51.8 °F
• Hydrophobicity(logP): 1.47 [HANSCH,C ET AL. (1995)]

Safety Information

• Storage Condition: Controlled Substance, -20°C Freezer
• RTECS: CQ6825000
• European Hazard Symbols: Flammable (F); Toxic (T)
• UN Number: 1230; 2811
• German water hazard class: 1; 3
• Hazard Class: 3; 6.1
• Packing Group: 2; 3
• Risk Statements: 11-23/24/25-39/23/24/25; 61-25-40-43
• Safety Statements: 16-36/37-45; 53-36/37-45
• GHS Pictograms: GHS02; GHS06; GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H225-H301-H311-H331-H370; H301-H317-H351-H360D
• GHS Precautionary statements: P201-P280-P301 + P310-P308 + P313; P210-P260-P280-P301 + P310-P311
• Personal Protective Equipment: Eyeshields, Faceshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges; Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US)
• RID/ADR: UN 1230 3/PG 2; UN 2811 6.1/PG 3
• Drug Control: Home Office Schedule 3; psychotrope; kontrollierte Droge in Deutschlandregulated under CDSA - not available from Sigma-Aldrich Canada; USDEA Schedule IV; Home Office Schedule 3; psychotrope; kontrollierte Droge in Deutschland; regulated under CDSA - not available from Sigma-Aldrich Canada; USDEA Schedule IV; regulated under CDSA - not available from Sigma-Aldrich Canada
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥99.0% (T)
• Concentration: 1.0 mg/mL±5% in methanol
• Grade: drug standard; purum
• Empirical Formula (Hill Notation): C12H12N2O3

DETAILS

DrugBank - DB01174

• Drug Groups: approved
• Description: A barbituric acid derivative that acts as a nonselective central nervous system depressant. It promotes binding to inhibitory gamma-aminobutyric acid subtype receptors, and modulates chloride currents through receptor channels. It also inhibits glutamate induced depolarizations. [PubChem]
• Indication: For the treatment of all types of seizures except absence seizures.
• Pharmacology: Phenobarbital, the longest-acting barbiturate, is used for its anticonvulsant and sedative-hypnotic properties in the management of all seizure disorders except absence (petit mal).
• Toxicity: CNS and respiratory depression which may progress to Cheyne-Stokes respiration, areflexia, constriction of the pupils to a slight degree (though in severe poisoning they may wshow paralytic dilation), oliguria, tachycardia, hypotension, lowered body temperature, and coma. Typical shock syndrome (apnea, circulatory collapse, respiratory arrest, and death) may occur.
• Affected Organisms: Humans and other mammals
• Biotransformation: Hepatic (mostly via CYP2C19).
• Absorption: Absorbed in varying degrees following oral, rectal or parenteral administration. The salts are more rapidly absorbed than are the acids. The rate of absorption is increased if the sodium salt is ingested as a dilute solution or taken on an empty stomach.
• Half Life: 53 to 118 hours (mean 79 hours)
• Protein Binding: 20 to 45%
• References: Kwan P, Brodie MJ: Phenobarbital for the treatment of epilepsy in the 21st century: a critical review. Epilepsia. 2004 Sep;45(9):1141-9. [Pubmed] ; Taylor S, Tudur Smith C, Williamson PR, Marson AG: Phenobarbitone versus phenytoin monotherapy for partial onset seizures and generalized onset tonic-clonic seizures. Cochrane Database Syst Rev. 2001;(4):CD002217. [Pubmed] ; Tudur Smith C, Marson AG, Williamson PR: Carbamazepine versus phenobarbitone monotherapy for epilepsy. Cochrane Database Syst Rev. 2003;(1):CD001904. [Pubmed] ; Kalviainen R, Eriksson K, Parviainen I: Refractory generalised convulsive status epilepticus : a guide to treatment. CNS Drugs. 2005;19(9):759-68. [Pubmed] ; Booth D, Evans DJ: Anticonvulsants for neonates with seizures. Cochrane Database Syst Rev. 2004 Oct 18;(4):CD004218. [Pubmed]
• External Links: Wikipedia; RxList; PDRhealth; Drugs.com

Sigma Aldrich - P1636

Biochem/physiol Actions
Anesthetic; sedative; hypnotic; anticonvulsant

Sigma Aldrich - 04710

Biochem/physiol Actions
Anesthetic; sedative; hypnotic; anticonvulsant
Other Notes
Sales restrictions may apply

Toronto Research Chemicals - P316760

This is a controlled substance (depressant). Anticonvulsant; sedative; hypnotic.

REFERENCES

• Kwan P, Brodie MJ: Phenobarbital for the treatment of epilepsy in the 21st century: a critical review. Epilepsia. 2004 Sep;45(9):1141-9. Pubmed
• Taylor S, Tudur Smith C, Williamson PR, Marson AG: Phenobarbitone versus phenytoin monotherapy for partial onset seizures and generalized onset tonic-clonic seizures. Cochrane Database Syst Rev. 2001;(4):CD002217. Pubmed
• Tudur Smith C, Marson AG, Williamson PR: Carbamazepine versus phenobarbitone monotherapy for epilepsy. Cochrane Database Syst Rev. 2003;(1):CD001904. Pubmed
• Kalviainen R, Eriksson K, Parviainen I: Refractory generalised convulsive status epilepticus : a guide to treatment. CNS Drugs. 2005;19(9):759-68. Pubmed
• Booth D, Evans DJ: Anticonvulsants for neonates with seizures. Cochrane Database Syst Rev. 2004 Oct 18;(4):CD004218. Pubmed
• Goldenthal, E.I., et al.: Toxicol. Appl. Pharmacol., 18, 185 (1971)
• Chao, M.K.C., et al.: Anal. Profiles Drug Subs., 7, 359 (1971)