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Version 2.5
Creation Date 2005-06-13 13:24:05
Update Date 2009-02-19 16:04:51
Primary Accession Number DB00418
Secondary Accession Number
  • APRD00497
Name Secobarbital
Drug Type
  • Approved
  • Small Molecule
Description Secobarbital (marketed by Eli Lilly and Company under the brand names Seconal® and Tuinal) is a barbiturate derivative drug. It possesses anaesthetic, anticonvulsant, sedative and hypnotic properties. In the United Kingdom, it was known as Quinalbarbitone.
Synonyms
  1. (+/-)-Secobarbital
  2. Secobarbital Sodium
  3. Secobarbitale [DCIT]
  4. Secobarbitalum [INN-Latin]
  5. Sodium Secobarbital
  6. Sodium quinalbarbitone
Brand Names
  1. Barbosec
  2. Bipanal
  3. Bipinal sodium
  4. Evronal
  5. Evronal Sodium
  6. Evrronal
  7. Hypotrol
  8. Hyptran
  9. Imesonal
  10. Immenoctal
  11. Immenox
  12. Meballymal
  13. Meballymal sodium
  14. Meballymalum
  15. Novosecobarb
  16. Pramil
  17. Quinalbarbital
  18. Quinalbarbitone
  19. Quinalbarbitone sodium
  20. Quinalspan
  21. Sebar
  22. Seco 8
  23. Secobarbitone
  24. Seconal
  25. Sedutain
  26. Seotal
  27. Somosal
  28. Synate
  29. Trisomnin
Brand Mixtures Not Available
Chemical IUPAC Name 5-[(2R)-pentan-2-yl]-5-prop-2-enyl-1,3-diazinane-2,4,6-trione
Chemical Formula C12H18N2O3
Chemical Structure Structure
CAS Registry Number 76-73-3
InChI Identifier InChI=1/C12H18N2O3/c1-4-6-8(3)12(7-5-2)9(15)13-11(17)14-10(12)16/h5,8H,2,4,6-7H2,1,3H3,(H2,13,14,15,16,17)/t8-/m1/s1/f/h13-14H
InChI Key KQPKPCNLIDLUMF-UZILFIRBDI
KEGG Drug D00430 Link Image
KEGG Compound Not Available
PubChem Compound 31143 Link Image
PubChem Substance 173168 Link Image
ChEBI ID 9073 Link Image
PharmGKB ID PA451313 Link Image
HET ID Not Available
GenBank ID Not Available
Drug ID Number [DIN] 00021032 Link Image
RxList Link Not Available
PDRhealth Link Not Available
Wikipedia Link http://en.wikipedia.org/wiki/Secobarbital Link Image
FDA Label Not Available
Material Safety Data Sheet (MSDS)
Synthesis Reference Not Available
Average Molecular Weight 238.2829
Monoisotopic Molecular Weight 238.1317
State Solid
Melting Point 100 oC
Experimental Water Solubility 550 mg/L Source: PhysProp
Predicted Water Solubility 1.21e+00 mg/mL Calculated using ALOGPS
Experimental LogP/Hydrophobicity 2.3 Source: PhysProp
Predicted LogP 2.20 Calculated using ALOGPS
Experimental LogS Not Available
Predicted LogS -2.29 Calculated using ALOGPS
Experimental Caco2 Permeability Not Available
pKa/Isoelectric Point 7.8
Mass Spectrum Not Available
MOL File Show Link Image | Download Link Image
SDF File Show Link Image | Download Link Image
PDB File Show Link Image | Download Link Image
2D Structure
3D Structure
Experimental PDB ID Not Available
Isomeric SMILES CCC[C@@H](C)C1(CC=C)C(=O)NC(=O)NC1=O
Canonical SMILES CCCC(C)C1(CC=C)C(=O)NC(=O)NC1=O
Drug Category
  • Adjuvants
  • Adjuvants, Anesthesia
  • Barbiturates
  • GABA Modulators
  • Hypnotics and Sedatives
ATC Codes
AHFS Codes Not Available
Indication For the Short-term treatment of intractable insomnia for patients habituated to barbiturates
Pharmacology Secobarbital, a barbiturate, is used for the induction of anesthesia prior to the use of other general anesthetic agents and for induction of anesthesia for short surgical, diagnostic, or therapeutic procedures associated with minimal painful stimuli. Little analgesia is conferred by barbiturates; their use in the presence of pain may result in excitation.
Mechanism of Action Secobarbital 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.
Absorption Not Available
Toxicity Not Available
Protein Binding Not Available
Biotransformation Not Available
Half Life Not Available
Dosage Forms Not Available
Patient Information Not Available
Contraindications Not Available
Interactions Show Link Image
Drug Interactions Not Available
Food Interactions Not Available
Pathways Not Available
General References
  1. Drugs.com Link Image
  2. Wikipedia Link Image
Organisms Affected
  • Humans and other mammals
Targets
  1. Gamma-aminobutyric-acid receptor subunit alpha-1
Drug Target 1 [top]
Target 1 ID 872
Target 1 Name Gamma-aminobutyric-acid receptor subunit alpha-1
Target 1 Synonyms
  1. Gamma-aminobutyric-acid receptor subunit alpha-1 precursor
Target 1 Gene Name GABRA1
Target 1 Protein Sequence >Gamma-aminobutyric-acid receptor subunit alpha-1 precursor 
MRKSPGLSDCLWAWILLLSTLTGRSYGQPSLQDELKDNTTVFTRILDRLLDGYDNRLRPG
LGERVTEVKTDIFVTSFGPVSDHDMEYTIDVFFRQSWKDERLKFKGPMTVLRLNNLMASK
IWTPDTFFHNGKKSVAHNMTMPNKLLRITEDGTLLYTMRLTVRAECPMHLEDFPMDAHAC
PLKFGSYAYTRAEVVYEWTREPARSVVVAEDGSRLNQYDLLGQTVDSGIVQSSTGEYVVM
TTHFHLKRKIGYFVIQTYLPCIMTVILSQVSFWLNRESVPARTVFGVTTVLTMTTLSISA
RNSLPKVAYATAMDWFIAVCYAFVFSALIEFATVNYFTKRGYAWDGKSVVPEKPKKVKDP
LIKKNNTYAPTATSYTPNLARGDPGLATIAKSATIEPKEVKPETKPPEPKKTFNSVSKID
RLSRIAFPLLFGIFNLVYWATYLNREPQLKAPTPHQ
Target 1 Number of Residues 463
Target 1 Molecular Weight 51802
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 GABA-A receptor activity
Target 1 Specific Function 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 Pathways Not Available
Target 1 Reactions Not Available
Target 1 Pfam Domain Function
Target 1 Signals
  • 1-27
Target 1 Transmembrane Regions
  • 252-273
  • 279-300
  • 313-334
  • 422-443
Target 1 Essentiality Non-Essential
Target 1 GenBank ID Protein 31631 Link Image
Target 1 UniProtKB/Swiss-Prot ID P14867 Link Image
Target 1 UniProtKB/Swiss-Prot Entry Name GBRA1_HUMAN Link Image
Target 1 PDB ID Not Available
Target 1 Cellular Location
  • Membrane
  • multi-pass membrane protein
Target 1 Gene Sequence >1371 bp 
ATGAGGAAAAGTCCAGGTCTGTCTGACTGTCTTTGGGCCTGGATCCTCCTTCTGAGCACA
CTGACTGGAAGAAGCTATGGACAGCCGTCATTACAAGATGAACTTAAAGACAATACCACT
GTCTTCACCAGGATTTTGGACAGACTCCTAGATGGTTATGACAATCGCCTGAGACCAGGA
TTGGGAGAGCGTGTAACCGAAGTGAAGACTGATATCTTCGTCACCAGTTTCGGACCCGTT
TCAGACCATGATATGGAATATACAATAGATGTATTTTTCCGTCAAAGCTGGAAGGATGAA
AGGTTAAAATTTAAAGGACCTATGACAGTCCTCCGGTTAAATAACCTAATGGCAAGTAAA
ATCTGGACTCCGGACACATTTTTCCACAATGGAAAGAAGTCAGTGGCCCACAACATGACC
ATGCCCAACAAACTCCTGCGGATCACAGAGGATGGCACCTTGCTGTACACCATGAGGCTG
ACAGTGAGAGCTGAATGTCCGATGCATTTGGAGGACTTCCCTATGGATGCCCATGCTTGC
CCACTAAAATTTGGAAGTTATGCTTATACAAGAGCAGAAGTTGTTTATGAATGGACCAGA
GAGCCAGCACGCTCAGTGGTTGTAGCAGAAGATGGATCACGTCTAAACCAGTATGACCTT
CTTGGACAAACAGTAGACTCTGGAATTGTCCAGTCAAGTACAGGAGAATATGTTGTTATG
ACCACTCATTTCCACTTGAAGAGAAAGATTGGCTACTTTGTTATTCAAACATACCTGCCA
TGCATAATGACAGTGATTCTCTCACAAGTCTCCTTCTGGCTCAACAGAGAGTCTGTACCA
GCAAGAACTGTCTTTGGAGTAACAACTGTGCTCACCATGACAACATTGAGCATCAGTGCC
AGAAACTCCCTCCCTAAGGTGGCTTATGCAACAGCTATGGATTGGTTTATTGCCGTGTGC
TATGCCTTTGTGTTCTCAGCTCTGATTGAGTTTGCCACAGTAAACTATTTCACTAAGAGA
GGTTATGCATGGGATGGCAAAAGTGTGGTTCCAGAAAAGCCAAAGAAAGTAAAGGATCCT
CTTATTAAGAAAAACAACACTTACGCTCCAACAGCAACCAGCTACACCCCTAATTTGGCC
AGGGGCGACCCGGGCTTAGCCACCATTGCTAAAAGTGCAACCATAGAACCTAAAGAGGTC
AAGCCCGAAACAAAACCACCAGAACCCAAGAAAACCTTTAACAGTGTCAGCAAAATTGAC
CGACTGTCAAGAATAGCCTTCCCGCTGCTATTTGGAATCTTTAACTTAGTCTACTGGGCT
ACGTATTTAAACAGAGAGCCTCAGCTAAAAGCCCCCACACCACATCAATAG
Target 1 GenBank Gene ID
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 5
Target 1 Locus 5q34-q35
Target 1 SNPs SNPJam Report Link Image
Target 1 General References
  1. Cossette P, Liu L, Brisebois K, Dong H, Lortie A, Vanasse M, Saint-Hilaire JM, Carmant L, Verner A, Lu WY, Wang YT, Rouleau GA: Mutation of GABRA1 in an autosomal dominant form of juvenile myoclonic epilepsy. Nat Genet. 2002 Jun;31(2):184-9. Epub 2002 May 6. [PubMed Link Image]
  2. Schofield PR, Pritchett DB, Sontheimer H, Kettenmann H, Seeburg PH: Sequence and expression of human GABAA receptor alpha 1 and beta 1 subunits. FEBS Lett. 1989 Feb 27;244(2):361-4. [PubMed Link Image]
  3. Garrett KM, Duman RS, Saito N, Blume AJ, Vitek MP, Tallman JF: Isolation of a cDNA clone for the alpha subunit of the human GABA-A receptor. Biochem Biophys Res Commun. 1988 Oct 31;156(2):1039-45. [PubMed Link Image]
Target 1 Drug References
  1. 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]
  2. 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]

This project is supported by Genome Alberta & Genome Canada, a not-for-profit organization that is leading Canada's national genomics strategy with $600 million in funding from the federal government. This project is also supported in part by GenomeQuest, Inc., an enterprise genomic information company serving the life science community.