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Showing toxin card for Hexobarbital (T3D3039)

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Version 1.0
Creation Date 2009-07-21 20:28:47
Update Date 2010-03-18 21:59:40
Accession Number T3D3039
Name Hexobarbital
Compound Type
  • Adjuvant
  • Barbiturate
  • Drug
  • GABA Modulator
  • Hypnotic and Sedative
Description A barbiturate that is effective as a hypnotic and sedative. [PubChem]
Synonyms
  1. 5-(1-cyclohexen-1-yl)-1,5-dimethylbarbituric Acid
  2. Hexobarbitone
  3. Methexenyl
  4. Methylhexabital
Chemical IUPAC Name 5-(cyclohex-1-en-1-yl)-1,5-dimethyl-1,3-diazinane-2,4,6-trione
Chemical Formula C12H16N2O3
Chemical Structure Structure
CAS Registry Number 56-29-1
InChI Identifier InChI=1S/C12H16N2O3/c1-12(8-6-4-3-5-7-8)9(15)13-11(17)14(2)10(12)16/h6H,3-5,7H2,1-2H3,(H,13,15,17)
InChI Key InChIKey=UYXAWHWODHRRMR-UHFFFAOYSA-N
PubChem Compound ID 3608 Link Image
KEGG ID C11723 Link Image
UniProt ID Not Available
OMIM ID Not Available
ChEBI ID 5706 Link Image
BioCyc ID Not Available
SuperToxic ID Not Available
CTD ID Not Available
Stitch ID Hexobarbital Link Image
DrugBank ID DB01355 Link Image
PDB ID Not Available
ACToR ID Not Available
Wikipedia Link http://en.wikipedia.org/wiki/Hexobarbital Link Image
Monoisotopic Mass 236.116092
MOL File Show
PDB File Show
SDF File Show
SMILES CN1C(=O)NC(=O)C(C)(C1=O)C1=CCCCC1
Appearance Not Available
Melting Point 146.5 oC
Solubility 0.435 mg/mL at 25 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)]
Predicted LogP 1.2476
Route of Exposure Oral
Mechanism of Action Hexobarbital binds at a distinct binding site associated with a Cl- ionopore at the GABA-A 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.
Metabolism Hepatic.
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 Not Available
General References
  • V229 - Dall V, Orntoft U, Schmidt A, Nordholm L: Interaction of the competitive AMPA receptor antagonist NBQX with hexobarbital. Pharmacol Biochem Behav. 1993 Sep;46(1):73-6. [PubMed Link Image]
  • V227 - Wahlstrom G: A study of the duration of acute tolerance induced with hexobarbital in male rats. Pharmacol Biochem Behav. 1998 Apr;59(4):945-8. [PubMed Link Image]
  • V228 - Korkmaz S, Ljungblad E, Wahlstrom G: Interaction between flumaze and the anesthetic effects of hexobarbital in the rat. Brain Res. 1995 Apr 10;676(2):371-7. [PubMed Link Image]
  • V226 - Takenoshita R, Toki S: [New aspects of hexobarbital metabolism: stereoselective metabolism, new metabolic pathway via GSH conjugation, and 3-hydroxyhexobarbital dehydrogenases] Yakugaku Zasshi. 2004 Dec;124(12):857-71. [PubMed Link Image]
Targets
  1. Gamma-aminobutyric acid receptor subunit alpha-1
  2. Methyl-CpG-binding domain protein 2
Target 1 [top]
Target 1 ID 36
Target 1 Name Gamma-aminobutyric acid receptor subunit alpha-1
Target 1 Mechanism of Action Hexobarbital binds at a distinct binding site associated with a Cl- ionopore at the GABA-A 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.
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
Target 2 [top]
Target 2 ID 1322
Target 2 Name Methyl-CpG-binding domain protein 2
Target 2 Mechanism of Action Hexobarbital binds at a distinct binding site associated with a Cl- ionopore at the GABA-A 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.
Target 2 Description Binds CpG islands in promoters where the DNA is methylated at position 5 of cytosine within CpG dinucleotides. Binds hemi-methylated DNA as well. Recruits histone deacetylases and DNA methyltransferases. Acts as transcriptional repressor and plays a role in gene silencing. Isoform 1 may enhance the activation of some unmethylated cAMP-responsive promoters. Reports about DNA demethylase activity of isoform 2 are contradictory
Target 2 Synonyms
  1. Methyl-CpG-binding protein MBD2; Demethylase; DMTase
Target 2 Gene Name MBD2
Target 2 Protein Sequence >Methyl-CpG-binding domain protein 2 
MRAHPGGGRCCPEQEEGESAAGGSGAGGDSAIEQGGQGSALAPSPVSGVRREGARGGGRG
RGRWKQAGRGGGVCGRGRGRGRGRGRGRGRGRGRGRPPSGGSGLGGDGGGCGGGGSGGGG
APRREPVPFPSGSAGPGPRGPRATESGKRMDCPALPPGWKKEEVIRKSGLSAGKSDVYYF
SPSGKKFRSKPQLARYLGNTVDLSSFDFRTGKMMPSKLQKNKQRLRNDPLNQNKGKPDLN
TTLPIRQTASIFKQPVTKVTNHPSNKVKSDPQRMNEQPRQLFWEKRLQGLSASDVTEQII
KTMELPKGLQGVGPGSNDETLLSAVASALHTSSAPITGQVSAAVEKNPAVWLNTSQPLCK
AFIVTDEDIRKQEERVQQVRKKLEEALMADILSRAADTEEMDIEMDSGDEA
Target 2 Number of Residues 411
Target 2 Molecular Weight 43254.3
Target 2 Theoretical pI 10.76
Target 2 GO Classification
Function
binding
nucleic acid binding
DNA binding
Process
Not Available
Component
Not Available
Target 2 General Function Carbohydrate transport and metabolism
Target 2 Pathways Not Available
Target 2 Reactions Not Available
Target 2 Signals
  • None
Target 2 Transmembrane Regions
  • None
Target 2 Essentiality Non Essential
Target 2 Domain Function PF01429:MBD
Target 2 GenBank ID Protein Not Available
Target 2 UniProtKB ID Q9UBB5 Link Image
Target 2 Cellular Location Nucleus
Target 2 Gene Sequence >1236 bp 
ATGCGCGCGCACCCGGGGGGAGGCCGCTGCTGCCCGGAGCAGGAGGAGGGGGAGAGTGCG
GCGGGCGGCAGCGGCGCTGGCGGCGACTCCGCCATAGAGCAGGGGGGCCAGGGCAGCGCG
CTCGCCCCGTCCCCGGTGAGCGGCGTGCGCAGGGAAGGCGCTCGGGGCGGCGGCCGTGGC
CGGGGGCGGTGGAAGCAGGCGGGCCGGGGCGGCGGCGTCTGTGGCCGTGGCCGGGGCCGG
GGCCGTGGCCGGGGACGGGGACGGGGCCGGGGCCGGGGCCGCGGCCGTCCCCCGAGTGGC
GGCAGCGGCCTTGGCGGCGACGGCGGCGGCTGCGGCGGCGGCGGCAGCGGTGGCGGCGGC
GCCCCCCGGCGGGAGCCGGTCCCTTTCCCGTCGGGGAGCGCGGGGCCGGGGCCCAGGGGA
CCCCGGGCCACGGAGAGCGGGAAGAGGATGGATTGCCCGGCCCTCCCCCCCGGATGGAAG
AAGGAGGAAGTGATCCGAAAATCTGGGCTAAGTGCTGGCAAGAGCGATGTCTACTACTTC
AGTCCAAGTGGTAAGAAGTTCAGAAGCAAGCCTCAGTTGGCAAGGTACCTGGGAAATACT
GTTGATCTCAGCAGTTTTGACTTCAGAACTGGAAAGATGATGCCTAGTAAATTACAGAAG
AACAAACAGAGACTGCGAAACGATCCTCTCAATCAAAATAAGGGTAAACCAGACTTGAAT
ACAACATTGCCAATTAGACAAACAGCATCAATTTTCAAACAACCGGTAACCAAAGTCACA
AATCATCCTAGTAATAAAGTGAAATCAGACCCACAACGAATGAATGAACAGCCACGTCAG
CTTTTCTGGGAGAAGAGGCTACAAGGACTTAGTGCATCAGATGTAACAGAACAAATTATA
AAAACCATGGAACTACCCAAAGGTCTTCAAGGAGTTGGTCCAGGTAGCAATGATGAGACC
CTTTTATCTGCTGTTGCCAGTGCTTTGCACACAAGCTCTGCGCCAATCACAGGGCAAGTC
TCCGCTGCTGTGGAAAAGAACCCTGCTGTTTGGCTTAACACATCTCAACCCCTCTGCAAA
GCTTTTATTGTCACAGATGAAGACATCAGGAAACAGGAAGAGCGAGTACAGCAAGTACGC
AAGAAATTGGAAGAAGCACTGATGGCAGACATCTTGTCGCGAGCTGCTGATACAGAAGAG
ATGGATATTGAAATGGACAGTGGAGATGAAGCCTAA
Target 2 GenBank Gene ID Not Available
Target 2 GeneCard ID MBD2 Link Image
Target 2 GenAtlas ID MBD2 Link Image
Target 2 HGNC ID HGNC:6917 Link Image
Target 2 Chromosome Location Chromosome:18
Target 2 Locus 18q21
Target 2 SNPs SNPJam Report Link Image
Target 2 Toxin References
  • V233 - Kadiiska M, Stoytchev T, Serbinova E: Effect of some heavy metal salts on hepatic monooxygenases after subchronic exposure. Arch Toxicol Suppl. 1985;8:313-5. [PubMed Link Image]
  • V232 - Sachan DS, Su PK: Effects of levels of feed restriction on in vivo and in vitro alterations in drug metabolism and associated enzymes. Drug Nutr Interact. 1986;4(4):363-70. [PubMed Link Image]
  • V230 - Koleva M, Dimova S: Effect of long-term multiple nifedipine administration on the antinociceptive activity of acetaminophen. Methods Find Exp Clin Pharmacol. 2001 Dec;23(10):537-40. [PubMed Link Image]
  • V231 - Gopinath C, Ford JH: The role of microsomal hydroxylases in the modification of chloroform hepatotoxicity in rats. Br J Exp Pathol. 1975 Oct;56(5):412-22. [PubMed Link Image]
  • V234 - Lindner E, Beyhl FE: Induction of microsomal drug-metabolizing enzymes caused by hexobarbital. Experientia. 1978 Feb 15;34(2):226-7. [PubMed Link Image]
Target 2 General References 9774669; 10441743; 15489334; 10050851; 10471499; 10947852; 10950960; 11102443; 11553631; 12183469

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