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Showing toxin card for Pentobarbital (T3D2745)

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Version 1.0
Creation Date 2009-07-21 20:26:33
Update Date 2010-03-18 21:58:00
Accession Number T3D2745
Name Pentobarbital
Compound Type
  • Adjuvant, Anesthesia
  • Barbiturate
  • Drug
  • GABA Modulator
  • Hypnotic and Sedative
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)
Synonyms
  1. Pentabarbital
  2. Pentabarbitone
  3. Pentobarbital Sodium
  4. Pentobarbitone
  5. Pentobarbiturate
  6. Pentobarbituric Acid
  7. Sodium Pentobarbital
Chemical IUPAC Name 5-ethyl-5-(pentan-2-yl)-1,3-diazinane-2,4,6-trione
Chemical Formula C11H18N2O3
Chemical Structure Structure
CAS Registry Number 76-74-4
InChI Identifier 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)
InChI Key InChIKey=WEXRUCMBJFQVBZ-UHFFFAOYSA-N
PubChem Compound ID 4737 Link Image
KEGG ID C07422 Link Image
UniProt ID Not Available
OMIM ID Not Available
ChEBI ID 7983 Link Image
BioCyc ID Not Available
SuperToxic ID Not Available
CTD ID Not Available
Stitch ID Pentobarbital Link Image
DrugBank ID DB00312 Link Image
PDB ID Not Available
ACToR ID Not Available
Wikipedia Link http://en.wikipedia.org/wiki/Pentobarbital Link Image
Monoisotopic Mass 226.131742
MOL File Show
PDB File Show
SDF File Show
SMILES CCCC(C)C1(CC)C(=O)NC(=O)NC1=O
Appearance Not Available
Melting Point 129.5 oC
Solubility 679 mg/L
Predicted LogP 1.8933
Route of Exposure Intravenous
Mechanism of Action Pentobarbital binds at a distinct binding site associated with a Cl- ionopore at the GABAA receptor, increasing the duration of time for which the Cl- ionopore is open. The post-synaptic inhibitory effect of GABA in the thalamus is, therefore, prolonged. All of these effects are associated with marked decreases in GABA-sensitive neuronal calcium conductance (gCa). The net result of barbiturate action is acute potentiation of inhibitory GABAergic tone. Barbiturates also act through potent (if less well characterized) and direct inhibition of excitatory AMPA-type glutamate receptors, resulting in a profound suppression of glutamatergic neurotransmission.
Metabolism by hepatic microsomal enzyme system
Toxicity Values Not Available
Lethal Dose Not Available
Carcinogenicity (IARC Classification) Not Available
Uses/Sources Not Available
Minimum Risk Level Not Available
Health Effects They cause slurred speech, disorientation and "drunken" behavior. They are physically and psychologically addictive. They cause slurred speech, disorientation and "drunken" behavior. They are physically and psychologically addictive.
Symptoms Not Available
Treatment Treatment of overdosage is mainly supportive and consists of maintaining an adequate airway, with assisted respiration and oxygen administration as necessary, monitoring of vital signs and fluid balance, and fluid therapy and other standard treatment for shock, if needed. If renal function is normal, forced diuresis may aid in the elimination of the barbiturate. Alkalinization of the urine increases renal excretion of some barbiturates, especially phenobarbital, also aprobarbital and mephobarbital (which is metabolized to phenobarbital). Although not recommended as a routine procedure, hemodialysis may be used in severe barbiturate intoxications or if the patient is anuric or in shock. The patient should be rolled from side to side every 30 minutes and antibiotics should be given if pneumonia is suspected. Appropriate nursing care to prevent hypostatic pneumonia, decubiti, aspiration, and other complications of patients with altered states of consciousness. (V650)
General References
  • T502 - 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 Link Image]
  • T501 - Drugs.com
Targets
  1. Gamma-aminobutyric acid receptor subunit alpha-1
Target 1 [top]
Target 1 ID 36
Target 1 Name Gamma-aminobutyric acid receptor subunit alpha-1
Target 1 Mechanism of Action Pentobarbital binds at a distinct binding site associated with a Cl- ionopore at the GABAA receptor, increasing the duration of time for which the Cl- ionopore is open. The post-synaptic inhibitory effect of GABA in the thalamus is, therefore, prolonged. All of these effects are associated with marked decreases in GABA-sensitive neuronal calcium conductance (gCa). The net result of barbiturate action is acute potentiation of inhibitory GABAergic tone. Barbiturates also act through potent (if less well characterized) and direct inhibition of excitatory AMPA-type glutamate receptors, resulting in a profound suppression of glutamatergic neurotransmission.
Target 1 Description GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel
Target 1 Synonyms
  1. GABA(A) receptor subunit alpha-1
Target 1 Gene Name GABRA1
Target 1 Protein Sequence >Gamma-aminobutyric acid receptor subunit alpha-1 
MRKSPGLSDCLWAWILLLSTLTGRSYGQPSLQDELKDNTTVFTRILDRLLDGYDNRLRPG
LGERVTEVKTDIFVTSFGPVSDHDMEYTIDVFFRQSWKDERLKFKGPMTVLRLNNLMASK
IWTPDTFFHNGKKSVAHNMTMPNKLLRITEDGTLLYTMRLTVRAECPMHLEDFPMDAHAC
PLKFGSYAYTRAEVVYEWTREPARSVVVAEDGSRLNQYDLLGQTVDSGIVQSSTGEYVVM
TTHFHLKRKIGYFVIQTYLPCIMTVILSQVSFWLNRESVPARTVFGVTTVLTMTTLSISA
RNSLPKVAYATAMDWFIAVCYAFVFSALIEFATVNYFTKRGYAWDGKSVVPEKPKKVKDP
LIKKNNTYAPTATSYTPNLARGDPGLATIAKSATIEPKEVKPETKPPEPKKTFNSVSKID
RLSRIAFPLLFGIFNLVYWATYLNREPQLKAPTPHQ
Target 1 Number of Residues 456
Target 1 Molecular Weight 51801.4
Target 1 Theoretical pI 9.61
Target 1 GO Classification
Function
neurotransmitter receptor activity
transporter activity
ion transporter activity
ion channel activity
ligand-gated ion channel activity
extracellular ligand-gated ion channel activity
signal transducer activity
receptor activity
transmembrane receptor activity
GABA receptor activity
GABA-A receptor activity
Process
cellular process
cell communication
signal transduction
cell surface receptor linked signal transduction
G-protein coupled receptor protein signaling pathway
gamma-aminobutyric acid signaling pathway
anion transport
inorganic anion transport
chloride transport
physiological process
cellular physiological process
transport
ion transport
Component
postsynaptic membrane
cell
membrane
intrinsic to membrane
integral to membrane
Target 1 General Function Involved in chloride channel activity
Target 1 Pathways Not Available
Target 1 Reactions Not Available
Target 1 Signals
  • 1-27
Target 1 Transmembrane Regions
  • 252-273
  • 279-300
  • 313-334
  • 422-443
Target 1 Essentiality Non Essential
Target 1 Domain Function PF02931:Neur_chan_LBD PF02932:Neur_chan_memb
Target 1 GenBank ID Protein Not Available
Target 1 UniProtKB ID P14867 Link Image
Target 1 Cellular Location Cell junction, synapse, postsynaptic cell membrane
Target 1 Gene Sequence Not Available
Target 1 GenBank Gene ID Not Available
Target 1 GeneCard ID GABRA1 Link Image
Target 1 GenAtlas ID GABRA1 Link Image
Target 1 HGNC ID HGNC:4075 Link Image
Target 1 Chromosome Location Not Available
Target 1 Locus 5q34-q35
Target 1 SNPs SNPJam Report Link Image
Target 1 Toxin References
  • S912 - Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed Link Image]
  • S911 - Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed Link Image]
Target 1 General References 2465923; 15489334; 2847710; 11992121; 16718694

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