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Showing drug card for Triazolam (DB00897)

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Version 2.5
Creation Date 2005-06-13 13:24:05
Update Date 2009-06-23 18:08:07
Primary Accession Number DB00897
Secondary Accession Number
  • APRD00313
Name Triazolam
Drug Type
  • Approved
  • Illicit
  • Small Molecule
  • Withdrawn
Description Withdrawn in the United Kingdom due to risk of psychiatric adverse drug reactions. This drug continues to be available in the U.S. Internationally, triazolam is a Schedule IV drug under the Convention on Psychotropic Substances.
Synonyms
  1. DEA No. 2887
  2. Triazolamum [INN-Latin]
Brand Names
  1. Alti-Triazolam
  2. Apo-Triazo
  3. Clorazolam
  4. Gen-Triazolam
  5. Halcion
  6. Novidorm
  7. Novo-Triolam
  8. Novodorm
  9. Songar
Brand Mixtures Not Available
Chemical IUPAC Name 8-chloro-6-(2-chlorophenyl)-1-methyl-4H-[1,2,4]triazolo[4,3-a][1,4]benzodiazepine
Chemical Formula C17H12Cl2N4
Chemical Structure Structure
CAS Registry Number 28911-01-5
InChI Identifier InChI=1/C17H12Cl2N4/c1-10-21-22-16-9-20-17(12-4-2-3-5-14(12)19)13-8-11(18)6-7-15(13)23(10)16/h2-8H,9H2,1H3
InChI Key JOFWLTCLBGQGBO-UHFFFAOYAU
KEGG Drug D00387 Link Image
KEGG Compound Not Available
PubChem Compound 5556 Link Image
PubChem Substance 7847453 Link Image
ChEBI ID Not Available
PharmGKB ID PA451753 Link Image
HET ID Not Available
GenBank ID Not Available
Drug ID Number [DIN] 02230024 Link Image
RxList Link http://www.rxlist.com/cgi/generic/triazolam.htm Link Image
PDRhealth Link http://www.pdrhealth.com/drug_info/rxdrugprofiles/drugs/hal1192.shtml Link Image
Wikipedia Link http://en.wikipedia.org/wiki/Triazolam Link Image
FDA Label Not Available
Material Safety Data Sheet (MSDS)
Synthesis Reference J. B. Hester, U.S. Pat. 3,701,782 (1972)
Average Molecular Weight 343.2100
Monoisotopic Molecular Weight 342.0439
State Solid
Melting Point 233-235 oC
Experimental Water Solubility 4.53 mg/L Source: PhysProp
Predicted Water Solubility 1.83e-02 mg/mL Calculated using ALOGPS
Experimental LogP/Hydrophobicity 5.5 Source: PhysProp
Predicted LogP 2.94 Calculated using ALOGPS
Experimental LogS -4.08 [ADME Research, USCD]
Predicted LogS -4.27 Calculated using ALOGPS
Experimental Caco2 Permeability Not Available
pKa/Isoelectric Point Not Available
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 CC1=NN=C2CN=C(C3=CC=CC=C3Cl)C3=C(C=CC(Cl)=C3)N12
Canonical SMILES CC1=NN=C2CN=C(C3=CC=CC=C3Cl)C3=C(C=CC(Cl)=C3)N12
Drug Category
  • Adjuvants, Anesthesia
  • Anti-anxiety Agents
  • Benzodiazepines
  • GABA Modulators
ATC Codes
AHFS Codes
  • 28:24.08
Indication For the short-term treatment of insomnia.
Pharmacology A short-acting benzodiazepine used as a hypnotic agent in the treatment of insomnia. Some countries temporarily withdrew triazolam from the market because of concerns about adverse reactions, mostly psychological, associated with higher dose ranges. Its use at lower doses with appropriate care and labeling has been reaffirmed by the FDA and most other countries. Triazolam has a shorter half-life than chlordiazepoxide, flurazepam, and prazepam and does not generate active metabolites.
Mechanism of Action Benzodiazepines bind nonspecifically to bezodiazepine receptors BNZ1, which mediates sleep, and BNZ2, which affects affects muscle relaxation, anticonvulsant activity, motor coordination, and memory. As benzodiazepine receptors are thought to be coupled to gamma-aminobutyric acid-A (GABAA) receptors, this enhances the effects of GABA by increasing GABA affinity for the GABA receptor. Binding of GABA to the site opens the chloride channel, resulting in a hyperpolarized cell membrane that prevents further excitation of the cell.
Absorption Bioavailability is 44% (oral) and 53% (sublingual).
Toxicity Symptoms of overdose include drowsiness, slurred speech, motor inco-ordination, coma, and respiratory depression.
Protein Binding Not Available
Biotransformation Hepatic. Small amounts of unmetabolized triazolam appear in the urine.
Half Life 1.5-5.5 hours
Dosage Forms
Form Route
Tablet Oral
Patient Information Show Link Image
Contraindications Show Link Image
Interactions Show Link Image
Drug Interactions
Drug Interaction
Amprenavir Amprenavir increases the effect and toxicity of benzodiazepine
Aprepitant Aprepitant increases the effect and toxicity of benzodiazepine
Atazanavir Atazanavir increases the effect and toxicity of benzodiazepine
Cimetidine Cimetidine increases the effect and toxicity of benzodiazepine
Clarithromycin The macrolide increases the effect of the benzodiazepine
Clozapine Increased risk of toxicity
Delavirdine The antiviral agent increases the effect and toxicity of benzodiazepine
Diltiazem The calcium channel blocker increases the effect and toxicity of the benzodiazepine
Efavirenz The antiviral agent increases the effect and toxicity of benzodiazepine
Erythromycin The macrolide increases the effect of the benzodiazepine
Ethotoin Possible increased levels of the hydantoin, decrease of benzodiazepine
Fluconazole Fluconazole increases the effect of the benzodiazepine
Fosamprenavir Amprenavir increases the effect and toxicity of benzodiazepine
Fosphenytoin Possible increased levels of the hydantoin, decrease of benzodiazepine
Indinavir The protease inhibitor increases the effect of the benzodiazepine
Itraconazole The imidazole increases the effect of the benzodiazepine
Josamycin The macrolide increases the effect of the benzodiazepine
Kava Kava increases the effect of the benzodiazepine
Ketoconazole The imidazole increases the effect of the benzodiazepine
Mephenytoin Possible increased levels of the hydantoin, decrease of benzodiazepine
Modafinil Modafinil decreases the effect of triazolam
Nefazodone Nefazodone increases the effect of triazolam
Nelfinavir The protease inhibitor increases the effect of the benzodiazepine
Omeprazole Omeprazole increases the effect of the benzodiazepine
Phenytoin Possible increased levels of the hydantoin, decrease of benzodiazepine
Rifampin Rifampin decreases the effect of the benzodiazepine
Ritonavir The protease inhibitor increases the effect of the benzodiazepine
Saquinavir The protease inhibitor increases the effect of the benzodiazepine
St. John's Wort St. John's Wort could reduce the benzodiazepine effect
Telithromycin Telithromycin increases the effect/toxicity of the benzodiazepine
Verapamil The calcium channel blocker increases the effect and toxicity of the benzodiazepine
Voriconazole The imidazole increases the effect of the benzodiazepine
Food Interactions Not Available
Pathways Not Available
General References
  1. Noguchi H, Kitazumi K, Mori M, Shiba T: Electroencephalographic properties of zaleplon, a non-benzodiazepine sedative/hypnotic, in rats. J Pharmacol Sci. 2004 Mar;94(3):246-51. [PubMed Link Image]
  2. Tokunaga S, Takeda Y, Shinomiya K, Hirase M, Kamei C: Effects of some H1-antagonists on the sleep-wake cycle in sleep-disturbed rats. J Pharmacol Sci. 2007 Feb;103(2):201-6. Epub 2007 Feb 8. [PubMed Link Image]
  3. Oelschlager H: [Chemical and pharmacologic aspects of benzodiazepines] Schweiz Rundsch Med Prax. 1989 Jul 4;78(27-28):766-72. [PubMed Link Image]
  4. Veje JO, Andersen K, Gjesing S, Kielgast H: [Prescription of tranquilizers and hypnotics in the municipality of Holbaek] Ugeskr Laeger. 1989 Aug 21;151(34):2134-6. [PubMed Link Image]
  5. Rickels K: The clinical use of hypnotics: indications for use and the need for a variety of hypnotics. Acta Psychiatr Scand Suppl. 1986;332:132-41. [PubMed Link Image]
  6. Drugs.com Link Image
  7. Wikipedia Link Image
  8. RxList Link Image
  9. PDRhealth Link Image
Organisms Affected
  • Humans and other mammals
Phase 1 Metabolizing Enzymes
  1. Cytochrome P450 3A4 (CYP3A4)
Targets
  1. Translocator protein
Phase 1 Metabolizing Enzyme 1 [top]
Enzyme 1 Name Cytochrome P450 3A4 (CYP3A4)
Enzyme 1 Gene Name CYP3A4
Enzyme 1 SwissProt ID P08684 Link Image
Enzyme 1 SNPs SNPJam Report Link Image
Enzyme 1 Protein Sequence >sp|P08684|CP3A4_HUMAN Cytochrome P450 3A4 (EC 1.14.13.67) 
ALIPDLAMETWLLLAVSLVLLYLYGTHSHGLFKKLGIPGPTPLPFLGNILSYHKGFCMFD
MECHKKYGKVWGFYDGQQPVLAITDPDMIKTVLVKECYSVFTNRRPFGPVGFMKSAISIA
EDEEWKRLRSLLSPTFTSGKLKEMVPIIAQYGDVLVRNLRREAETGKPVTLKDVFGAYSM
DVITSTSFGVNIDSLNNPQDPFVENTKKLLRFDFLDPFFLSITVFPFLIPILEVLNICVF
PREVTNFLRKSVKRMKESRLEDTQKHRVDFLQLMIDSQNSKETESHKALSDLELVAQSII
FIFAGYETTSSVLSFIMYELATHPDVQQKLQEEIDAVLPNKAPPTYDTVLQMEYLDMVVN
ETLRLFPIAMRLERVCKKDVEINGMFIPKGWVVMIPSYALHRDPKYWTEPEKFLPERFSK
KNKDNIDPYIYTPFGSGPRNCIGMRFALMNMKLALIRVLQNFSFKPCKETQIPLKLSLGG
LLQPEKPVVLKVESRDGTVSGA
Drug Target 1 [top]
Target 1 ID 811
Target 1 Name Translocator protein
Target 1 Synonyms
  1. Mitochondrial benzodiazepine receptor
  2. PBR
  3. PKBS
  4. Peripheral-type benzodiazepine receptor
Target 1 Gene Name BZRP
Target 1 Protein Sequence >Peripheral-type benzodiazepine receptor 
MAPPWVPAMGFTLAPSLGCFVGSRFVHGEGLRWYAGLQKPSWHPPHWVLGPVWGTLYSAM
GYGSYLVWKELGGFTEKAVVPLGLYTGQLALNWAWPPIFFGARQMGWALVDLLLVSGAAA
ATTVAWYQVSPLAARLLYPYLAWLAFATTLNYCVWRDNHGWHGGRRLPE
Target 1 Number of Residues 171
Target 1 Molecular Weight 18779
Target 1 Theoretical pI 9.33
Target 1 GO Classification
Function
Not Available
Process
Not Available
Component
cell
membrane
intrinsic to membrane
integral to membrane
Target 1 General Function Signal transduction mechanisms
Target 1 Specific Function Responsible for the manifestation of peripheral-type benzodiazepine recognition sites and is most likely to comprise binding domains for benzodiazepines and isoquinoline carboxamides. May play a role in the transport of porphyrins and heme
Target 1 Pathways Not Available
Target 1 Reactions Not Available
Target 1 Pfam Domain Function
Target 1 Signals
  • None
Target 1 Transmembrane Regions
  • 6-26
  • 47-67
  • 80-100
  • 106-126
  • 135-155
Target 1 Essentiality Non-Essential
Target 1 GenBank ID Protein 306883 Link Image
Target 1 UniProtKB/Swiss-Prot ID P30536 Link Image
Target 1 UniProtKB/Swiss-Prot Entry Name BZRP_HUMAN Link Image
Target 1 PDB ID Not Available
Target 1 Cellular Location
  • Mitochondrion
  • mitochondrial membrane
  • multi-pass membrane protein
Target 1 Gene Sequence >510 bp 
ATGGCCCCGCCCTGGGTGCCCGCCATGGGCTTCACGCTGGCGCCCAGCCTGGGGTGCTTC
GTGGGCTCCCGCTTTGTCCACGGCGAGGGTCTCCGCTGGTACGCCGGCCTGCAGAAGCCC
TCGTGGCACCCGCCCCACTGGGTGCTGGGCCCTGTCTGGGGCACGCTCTACTCAGCCATG
GGGTACGGCTCCTACCTGGTCTGGAAAGAGCTGGGAGGCTTCACAGAGAAGGCTGTGGTT
CCCCTGGGCCTCTACACTGGGCAGCTGGCCCTGAACTGGGCATGGCCCCCCATCTTCTTT
GGTGCCCGACAAATGGGCTGGGCCTTGGTGGATCTCCTGCTGGTCAGTGGGGCGGCGGCN
GCCACTACCGTGGCCTGGTACCAGGTGAGCCCGCTGGCCGCCCGCCTGCTCTACCCCTAC
CTGGCCTGGCTGGCCTTCGCGACCACACTCAACTACTGCGTATGGCGGGACAACCATGGC
TGGCATGGGGGACGGCGGCTGCCAGAGTGA
Target 1 GenBank Gene ID
Target 1 GeneCard ID TSPO Link Image
Target 1 GenAtlas ID TSPO Link Image
Target 1 HGNC ID HGNC:1158 Link Image
Target 1 Chromosome Location 22
Target 1 Locus 22q13.31
Target 1 SNPs SNPJam Report Link Image
Target 1 General References
  1. Dunham I, Shimizu N, Roe BA, Chissoe S, Hunt AR, Collins JE, Bruskiewich R, Beare DM, Clamp M, Smink LJ, Ainscough R, Almeida JP, Babbage A, Bagguley C, Bailey J, Barlow K, Bates KN, Beasley O, Bird CP, Blakey S, Bridgeman AM, Buck D, Burgess J, Burrill WD, O'Brien KP, et al.: The DNA sequence of human chromosome 22. Nature. 1999 Dec 2;402(6761):489-95. [PubMed Link Image]
  2. Kurumaji A, Nomoto H, Yoshikawa T, Okubo Y, Toru M: An association study between two missense variations of the benzodiazepine receptor (peripheral) gene and schizophrenia in a Japanese sample. J Neural Transm. 2000;107(4):491-500. [PubMed Link Image]
  3. Kurumaji A, Nomoto H, Yamada K, Yoshikawa T, Toru M: No association of two missense variations of the benzodiazepine receptor (peripheral) gene and mood disorders in a Japanese sample. Am J Med Genet. 2001 Mar 8;105(2):172-5. [PubMed Link Image]
  4. Riond J, Mattei MG, Kaghad M, Dumont X, Guillemot JC, Le Fur G, Caput D, Ferrara P: Molecular cloning and chromosomal localization of a human peripheral-type benzodiazepine receptor. Eur J Biochem. 1991 Jan 30;195(2):305-11. [PubMed Link Image]
  5. Yakovlev AG, Ruffo M, Jurka J, Krueger KE: Comparison of repetitive elements in the third intron of human and rodent mitochondrial benzodiazepine receptor-encoding genes. Gene. 1995 Apr 3;155(2):201-5. [PubMed Link Image]
  6. Galiegue S, Jbilo O, Combes T, Bribes E, Carayon P, Le Fur G, Casellas P: Cloning and characterization of PRAX-1. A new protein that specifically interacts with the peripheral benzodiazepine receptor. J Biol Chem. 1999 Jan 29;274(5):2938-52. [PubMed Link Image]
Target 1 Drug References
  1. Park CH, Carboni E, Wood PL, Gee KW: Characterization of peripheral benzodiazepine type sites in a cultured murine BV-2 microglial cell line. Glia. 1996 Jan;16(1):65-70. [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.