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76-74-4 molecular structure
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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 and InChIs

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

Cite this record

CBID:197 http://www.chembase.cn/molecule-197.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

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

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID Price
Sigma Aldrich
P3636 external link Add to cart Please log in.

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 8.482022  H Acceptors
H Donor LogD (pH = 5.5) 1.892804 
LogD (pH = 7.4) 1.8591163  Log P 1.8932513 
Molar Refractivity 58.0029 cm3 Polarizability 22.809618 Å3
Polar Surface Area 75.27 Å2 Rotatable Bonds
Lipinski's Rule of Five true 
Log P 2.16  LOG S -2.42 
Solubility (Water) 8.64e-01 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Solubility
679 mg/L expand Show data source
Hydrophobicity(logP)
2.1 expand Show data source
RTECS
CQ5775000 expand Show data source
European Hazard Symbols
Toxic Toxic (T) expand Show data source
UN Number
2811 expand Show data source
MSDS Link
Download expand Show data source
German water hazard class
3 expand Show data source
Hazard Class
6.1 expand Show data source
Packing Group
3 expand Show data source
Risk Statements
63-25 expand Show data source
Safety Statements
22-36/37/39-45 expand Show data source
GHS Pictograms
GHS06 expand Show data source
GHS08 expand Show data source
GHS Signal Word
Danger expand Show data source
GHS Hazard statements
H301-H361 expand Show data source
GHS Precautionary statements
P281-P301 + P310 expand Show data source
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 expand Show data source
RID/ADR
UN 2811 6.1/PG 3 expand Show data source
Drug Control
USDEA Schedule II; Home Office Schedule 3; psychotrope; kontrollierte Droge in Deutschland; regulated under CDSA - not available from Sigma-Aldrich Canada expand Show data source
Admin Routes
Oral, Intravenous, Intramuscular, Rectal; also Intraperitoneal & Intracardiac (for animal euthanasia) expand Show data source
Bioavailability
70-90% oral; 90% rectal expand Show data source
Excretion
Renal expand Show data source
Half Life
15-48 hours expand Show data source
Metabolism
Hepatic expand Show data source
Protein Bound
20-45% expand Show data source
Legal Status
USA: Schedule II (oral and parenteral); Schedule III (rectal), UK: Class B Controlled Substance expand Show data source
Pregnancy Category
D (USA) expand Show data source
Empirical Formula (Hill Notation)
C11H18N2O3 expand Show data source

DETAILS

DETAILS

DrugBank DrugBank Wikipedia Wikipedia
DrugBank - DB00312 external link
Item Information
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

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • 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
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PATENTS

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