5-ethyl-5-(pentan-2-yl)-1,3-diazinane-2,4,6-trione

• ChemBase ID: 197
• Molecular Formular: C11H18N2O3
• Molecular Mass: 226.27222
• Monoisotopic Mass: 226.13174245
• SMILES: O=C1NC(=O)NC(=O)C1(C(CCC)C)CC
• Canonical SMILES: CCCC(C1(CC)C(=O)NC(=O)NC1=O)C
• InChI: InChI=1S/C11H18N2O3/c1-4-6-7(3)11(5-2)8(14)12-10(16)13-9(11)15/h7H,4-6H2,1-3H3,(H2,12,13,14,15,16)
• InChIKey: WEXRUCMBJFQVBZ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-ethyl-5-(pentan-2-yl)-1,3-diazinane-2,4,6-trione
• IUPAC Traditional name: @pentobarbital; pentobarbital
• Brand Name: Dorsital; Ethaminal; Mebubarbital; Mebumal; Nebralin; Nembutal; Nembutal Sodium; Neodorm; Rivadorm
• Synonyms: Pentobarbital Sodium; Pentabarbitone; Pentabarbital; Pentobarbitone; Pentobarbiturate; Pentobarbituric acid; Sodium Pentobarbital; Pentobarbital; 5-Ethyl-5-(1-methylbutyl)-2,4,6-trioxohexahydropyrimidine; Nembutal; Pentobarbital

Database IDs

• CAS Number: 76-74-4
• EC Number: 200-983-8
• MDL Number: MFCD00057561
• PubChem SID: 160963660; 46508399
• PubChem CID: 4737
• CHEBI ID: 7983
• ATC CODE: QN51AA01; N05CA01
• CHEMBL: 448
• Chemspider ID: 4575
• DrugBank ID: DB00312
• KEGG ID: D00499
• Unique Ingredient Identifier: I4744080IR
• Wikipedia Title: Pentobarbital
• Medline Plus: a682416

CALCULATED PROPERTIES

JChem

• Acid pKa: 8.482022
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 1.892804
• LogD (pH = 7.4): 1.8591163
• Log P: 1.8932513
• Molar Refractivity: 58.0029 cm^3
• Polarizability: 22.809618 Å^3
• Polar Surface Area: 75.27 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 2.16
• LOG S: -2.42
• Solubility (Water): 8.64e-01 g/l

PROPERTIES

Physical Property

• Solubility: 679 mg/L
• Hydrophobicity(logP): 2.1

Safety Information

• RTECS: CQ5775000
• European Hazard Symbols: Toxic (T)
• UN Number: 2811
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 3
• Risk Statements: 63-25
• Safety Statements: 22-36/37/39-45
• GHS Pictograms: GHS06; GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H301-H361
• GHS Precautionary statements: P281-P301 + P310
• 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
• RID/ADR: UN 2811 6.1/PG 3
• Drug Control: USDEA Schedule II; Home Office Schedule 3; psychotrope; kontrollierte Droge in Deutschland; regulated under CDSA - not available from Sigma-Aldrich Canada

Pharmacology Properties

• Admin Routes: Oral, Intravenous, Intramuscular, Rectal; also Intraperitoneal & Intracardiac (for animal euthanasia)
• Bioavailability: 70-90% oral; 90% rectal
• Excretion: Renal
• Half Life: 15-48 hours
• Metabolism: Hepatic
• Protein Bound: 20-45%
• Legal Status: USA: Schedule II (oral and parenteral); Schedule III (rectal), UK: Class B Controlled Substance
• Pregnancy Category: D (USA)

Product Information

• Empirical Formula (Hill Notation): C11H18N2O3

DETAILS

DrugBank - DB00312

• Drug Groups: approved
• Description: A short-acting barbiturate that is effective as a sedative and hypnotic (but not as an anti-anxiety) agent and is usually given orally. It is prescribed more frequently for sleep induction than for sedation but, like similar agents, may lose its effectiveness by the second week of continued administration. (From AMA Drug Evaluations Annual, 1994, p236)
• Indication: For the short-term treatment of insomnia.
• Pharmacology: Pentobarbital, a barbiturate, is used for the treatment of short term insomnia. It belongs to a group of medicines called central nervous system (CNS) depressants that induce drowsiness and relieve tension or nervousness. Little analgesia is conferred by barbiturates; their use in the presence of pain may result in excitation.
• Toxicity: Symptoms of an overdose typically include sluggishness, incoordination, difficulty in thinking, slowness of speech, faulty judgment, drowsiness or coma, shallow breathing, staggering, and in severe cases coma and death.
• Affected Organisms: Humans and other mammals
• Biotransformation: by hepatic microsomal enzyme system
• Absorption: Barbiturates are absorbed in varying degrees following oral, rectal, or parenteral administration.
• Half Life: 5 to 50 hours (dose dependent)
• Elimination: Barbiturates are metabolized primarily by the hepatic microsomal enzyme system, and the metabolic products are excreted in the urine, and less commonly, in the feces. Approximately 25 to 50 percent of a dose of aprobarbital or phenobarbital is eliminated unchanged in the urine, whereas the amount of other barbiturates excreted unchanged in the urine is negligible.
• References: Knodell RG, Spector MH, Brooks DA, Keller FX, Kyner WT: Alterations in pentobarbital pharmacokinetics in response to parenteral and enteral alimentation in the rat. Gastroenterology. 1980 Dec;79(6):1211-6. [Pubmed]
• External Links: Wikipedia; RxList; Drugs.com

REFERENCES

• Knodell RG, Spector MH, Brooks DA, Keller FX, Kyner WT: Alterations in pentobarbital pharmacokinetics in response to parenteral and enteral alimentation in the rat. Gastroenterology. 1980 Dec;79(6):1211-6. Pubmed