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Showing toxin card for Chlordiazepoxide (T3D2804)

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Version 1.0
Creation Date 2009-07-21 20:27:00
Update Date 2010-05-18 21:00:02
Accession Number T3D2804
Name Chlordiazepoxide
Compound Type
  • Adjuvant, Anesthesia
  • Anti-Anxiety Agent
  • Benzodiazepine
  • Drug
  • GABA Modulator
  • Hypnotic and Sedative
Description An anxiolytic benzodiazepine derivative with anticonvulsant, sedative, and amnesic properties. It has also been used in the symptomatic treatment of alcohol withdrawal. [PubChem]
Synonyms
  1. 7-Chlor-2-methylamino-5-phenyl-3H-1,4-benzodiazepin-4-oxid
  2. 7-Cloro-2-metilamino-5-fenil-3H-1,4-benzodiazepina 4-ossido
  3. Abboxide
  4. Apo Chlordiazepoxide Hcl Cap 10mg
  5. Apo Chlordiazepoxide Hcl Cap 25mg
  6. Apo Chlordiazepoxide Hcl Cap 5mg
  7. Balance
  8. Balance (pharmaceutical)
  9. CDO
  10. CDP
  11. Chloradiazepoxide
  12. Chlordiazepoxide (JP15/USP/INN)
  13. Chlordiazepoxide Cap 10mg
  14. Chlordiazepoxide Cap 5mg
  15. Chlordiazepoxide [usan:inn:ban:jan]
  16. Chlordiazepoxide and amitriptyline HCL
  17. Chlordiazepoxide monohydrochloride
  18. Chlordiazepoxidum
  19. Chlordiazepoxidum [inn-latin]
  20. Chlordiazepoxyde Hcl Cap 25mg
  21. Chlordiazepoxydum
  22. Chloridazepoxide
  23. Chloridiazepide
  24. Chloridiazepoxide
  25. Chlorodiazepoxide
  26. Chlozepid
  27. Clopoxide
  28. Clordiazepossido
  29. Clordiazepossido [italian]
  30. Clordiazepoxido
  31. Clordiazepoxido [inn-spanish]
  32. Contol
  33. Control
  34. Decacil
  35. Disarim
  36. EDEN
  37. Eden-psich
  38. Elenium
  39. Helogaphen
  40. Ifibrium
  41. Kalmocaps
  42. Librax
  43. Librelease
  44. Librinin
  45. Libritabs
  46. Libritabs (TN)
  47. Librium
  48. Limbitrol
  49. Limbitrol DS
  50. MENRIUM 10-4
  51. MENRIUM 5-2
  52. MENRIUM 5-4
  53. Menrium
  54. Mesural
  55. Methaminodiazepoxide
  56. Mildmen
  57. Mixture name
  58. Multum
  59. Napoton
  60. Napton
  61. Psicosan
  62. Radepur
  63. Risolid
  64. Silibrin
  65. Sonimen
  66. Tropium
  67. UNII-6RZ6XEZ3CR
  68. Viopsicol
  69. Zeisin
  70. Zetran
  71. nchembio747-comp24
Chemical IUPAC Name 7-chloro-2-(methylimino)-5-phenyl-3,4-dihydro-2H-1,4-benzodiazepin-4-ol
Chemical Formula C16H14ClN3O
Chemical Structure Structure
CAS Registry Number 58-25-3
InChI Identifier InChI=1S/C16H14ClN3O/c1-18-15-10-20(21)16(11-5-3-2-4-6-11)13-9-12(17)7-8-14(13)19-15/h2-9,21H,10H2,1H3
InChI Key InChIKey=BUCORZSTKDOEKQ-UHFFFAOYSA-N
PubChem Compound ID 2712 Link Image
KEGG ID Not Available
UniProt ID Not Available
OMIM ID Not Available
ChEBI ID 3611 Link Image
BioCyc ID Not Available
SuperToxic ID Not Available
CTD ID Not Available
Stitch ID Chlordiazepoxide Link Image
DrugBank ID DB00475 Link Image
PDB ID Not Available
ACToR ID Not Available
Wikipedia Link http://en.wikipedia.org/wiki/Chlordiazepoxide Link Image
Monoisotopic Mass 299.08254
MOL File Show
PDB File Show
SDF File Show
SMILES CN=C1CN(O)C(C2=CC=CC=C2)=C2C=C(Cl)C=CC2=N1
Appearance Not Available
Melting Point 236.2 oC
Solubility 2000 mg/L
Predicted LogP 1.6284
Route of Exposure Oral
Mechanism of Action Chlordiazepoxide binds to stereospecific benzodiazepine (BZD) binding sites on GABA (A) receptor complexes at several sites within the central nervous system, including the limbic system and reticular formation. BZDs enhance GABA-mediated chloride influx through GABA receptor channels, causing membrane hyperpolarization. The net neuro-inhibitory effects result in the observed sedative, hypnotic, anxiolytic, and muscle relaxant properties.
Metabolism Hepatic.
Toxicity Values LD50: 537 mg/kg (Oral, Rat) (S405)
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.
Symptoms Signs of overdose include respiratory depression, muscle weakness, somnolence (general depressed activity).
Treatment General supportive measures should be employed, along with immediate gastric lavage. Intravenous fluids should be administered and an adequate airway maintained. Hypotension may be combated by the use of Levophed (norepinephrine) or Aramine (metaraminol). Flumazenil, a specific benzodiazepine-receptor antagonist, is indicated for the complete or partial reversal of the sedative effects of benzodiazepines and may be used in situations when an overdose with a benzodiazepine is known or suspected. (V650)
General References
  • T346 - Vozeh S: [Pharmacokinetic of benzodiazepines in old age] Schweiz Med Wochenschr. 1981 Nov 21;111(47):1789-93. [PubMed Link Image]
  • T841 - Olive G, Dreux C: [Pharmacologic bases of use of benzodiazepines in pereinatal medicine] Arch Fr Pediatr. 1977 Jan;34(1):74-89. [PubMed Link Image]
  • T838 - Skerritt JH, Johnston GA: Enhancement of GABA binding by benzodiazepines and related anxiolytics. Eur J Pharmacol. 1983 May 6;89(3-4):193-8. [PubMed Link Image]
  • T837 - Drugs.com
  • T839 - Oishi R, Nishibori M, Itoh Y, Saeki K: Diazepam-induced decrease in histamine turnover in mouse brain. Eur J Pharmacol. 1986 May 27;124(3):337-42. [PubMed Link Image]
  • T840 - Earley JV, Fryer RI, Ning RY: Quinazolines and 1,4-benzodiazepines. LXXXIX: Haptens useful in benzodiazepine immunoassay development. J Pharm Sci. 1979 Jul;68(7):845-50. [PubMed Link Image]
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 Chlordiazepoxide binds to stereospecific benzodiazepine (BZD) binding sites on GABA (A) receptor complexes at several sites within the central nervous system, including the limbic system and reticular formation. BZDs enhance GABA-mediated chloride influx through GABA receptor channels, causing membrane hyperpolarization. The net neuro-inhibitory effects result in the observed sedative, hypnotic, anxiolytic, and muscle relaxant properties.
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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