| Version |
1.0 |
| Creation Date |
2009-07-05 03:14:44 |
| Update Date |
2010-05-18 20:58:07 |
| Accession Number |
T3D2564 |
| Name |
Triazolam |
| Compound Type |
- Adjuvant, Anesthesia
- Anti-Anxiety Agent
- Benzodiazepine
- Drug
- GABA Modulator
|
| Description |
Triazolam is a benzodiazepine derivative drug. It possesses pharmacological properties similar to that of other benzodiazepines, but it is generally only used as a sedative to treat insomnia. It was withdrawn in the United Kingdom due to risk of psychiatric adverse drug reactions.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.[wikipedia] |
| Synonyms |
- Triazolamum [inn-latin]
|
| Chemical IUPAC Name |
12-chloro-9-(2-chlorophenyl)-3-methyl-2,4,5,8-tetraazatricyclo[8.4.0.0^{2,6}]tetradeca-1(14),3,5,8,10,12-hexaene |
| Chemical Formula |
C17H12Cl2N4 |
| Chemical Structure |
 |
| CAS Registry Number |
28911-01-5 |
| InChI Identifier |
InChI=1S/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 |
InChIKey=JOFWLTCLBGQGBO-UHFFFAOYSA-N |
| PubChem Compound ID |
5556  |
| KEGG ID |
Not Available |
| UniProt ID |
Not Available |
| OMIM ID |
Not Available |
| ChEBI ID |
9674 |
| BioCyc ID |
Not Available |
| SuperToxic ID |
Not Available |
| CTD ID |
Not Available |
| Stitch ID |
Triazolam |
| DrugBank ID |
DB00897 |
| PDB ID |
Not Available |
| ACToR ID |
Not Available |
| Wikipedia Link |
http://en.wikipedia.org/wiki/Triazolam |
| Monoisotopic Mass |
342.043902 |
| MOL File |
Show |
| PDB File |
Show |
| SDF File |
Show |
| SMILES |
CC1=NN=C2CN=C(C3=CC=CC=C3Cl)C3=CC(Cl)=CC=C3N12 |
| Appearance |
White crystalline powder (RxList, S405). |
| Melting Point |
233-235 oC |
| Solubility |
4.53 mg/L |
| Predicted LogP |
2.6921 |
| Route of Exposure |
Inhalation; dermal or skin contact; ingestion (MSDS, S405). |
| 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. |
| Metabolism |
Triazolam undergoes hepatic microsomal oxidation to inactive hydroxylated metabolites that are eliminated primarily as glucuronide conjugates (S599). |
| Toxicity Values |
LD50: >1000 mg/kg (Oral, Mouse)
LD50: >5000 mg/kg (Oral, Rat) |
| Lethal Dose |
Not Available |
| Carcinogenicity (IARC Classification) |
Not Available |
| Uses/Sources |
For the short-term treatment of insomnia (S405). |
| Minimum Risk Level |
Not Available |
| Health Effects |
Following acute overdose, clinical symptoms or manifestations may include sleepiness, which, following larger overdose can range from stage zero to stage one coma. Initially, excitement may be seen as a result of the disinhibition effects of these drugs, which then progresses to central nervous system depression, hypotension, respiratory depression, and coma (S598). |
| Symptoms |
Symptoms of overdose include drowsiness, slurred speech, motor inco-ordination, coma, and respiratory depression. |
| Treatment |
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. Prior to the administration of flumazenil, necessary measures should be instituted to secure airway, ventilation and intravenous access. (V650) |
| General References |
- T345 - Oelschlager H: [Chemical and pharmacologic aspects of benzodiazepines] Schweiz Rundsch Med Prax. 1989 Jul 4;78(27-28):766-72. [PubMed ]
- S598 - Amdur, MO, Doull J, Klaasen CD (eds) (1991). Casarett and Doull's Toxicology. 4th ed. New York, NY: Pergamon Press.
- U532 - 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 ]
- T785 - 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 ]
- U531 - Drugs.com
- S405 - DrugBank: a knowledgebase for drugs, drug actions and drug targets. Wishart DS, Knox C, Guo AC, Cheng D, Shrivastava S, Tzur D, Gautam B, Hassanali M. Nucleic Acids Res. 2008 Jan;36(Database issue):D901-6. [PubMed ]
- U533 - 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 ]
- T344 - 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 ]
- S599 - Thomson.Micromedex. Drug Information for the Health Care Professional. 24th ed. Volume 1. Plus Updates. Content Reviewed by the United States Pharmacopeial Convention, Inc. Greenwood Village, CO. 2004., p. 520.
|
| Targets |
- Translocator protein
|
|
Target 1
[top]
|
| Target 1 ID |
1151 |
| Target 1 Name |
Translocator protein |
| Target 1 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. |
| Target 1 Description |
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. Plays a role in the transport of cholesterol across mitochondrial membranes in steroidogenic cells (By similarity) |
| Target 1 Synonyms |
- Peripheral-type benzodiazepine receptor; PBR; PKBS; Mitochondrial benzodiazepine receptor
|
| Target 1 Gene Name |
TSPO |
| Target 1 Protein Sequence |
>Translocator protein
MAPPWVPAMGFTLAPSLGCFVGSRFVHGEGLRWYAGLQKPSWHPPHWVLGPVWGTLYSAM
GYGSYLVWKELGGFTEKAVVPLGLYTGQLALNWAWPPIFFGARQMGWALVDLLLVSGAAA
ATTVAWYQVSPLAARLLYPYLAWLAFATTLNYCVWRDNHGWHGGRRLPE
|
| Target 1 Number of Residues |
169 |
| Target 1 Molecular Weight |
18778.7 |
| 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 Pathways |
Not Available |
| Target 1 Reactions |
Not Available |
| Target 1 Signals |
|
| Target 1 Transmembrane Regions |
- 6-26
- 47-67
- 80-100
- 106-126
- 135-155
|
| Target 1 Essentiality |
Non Essential |
| Target 1 Domain Function |
PF03073:TspO_MBR |
| Target 1 GenBank ID Protein |
Not Available |
| Target 1 UniProtKB ID |
P30536 |
| Target 1 Cellular Location |
Mitochondrion membrane |
| Target 1 Gene Sequence |
>510 bp
CCCCTGAACAGCAGCTGCAGCAGCCATGGCCCCGCCCTGGGTGCCCGCCATGGGCTTCAC
GCTGGCGCCCAGCCTGGGGTGCTTCGTGGGCTCCCGCTTTGTCCACGGCGAGGGTCTCCG
CTGGTACGCCGGCCTGCAGAAGCCCTCGTGGCACCCGCCCCACTGGGTGCTGGGCCCTGT
CTGGGGCACGCTCTACTCAGCCATGGGGTACGGCTCCTACCTGGTCTGGAAAGAGCTGGG
AGGCTTCACAGAGAAGGCTGTGGTTCCCCTGGGCCTCTACACTGGGCAGCTGGCCCTGAA
CTGGGCATGGCCCCCCATCTTCTTTGGTGCCCGACAAATGGGCTGGGCCTTGGTGGATCT
CCTGCTGGTCAGTGGGGCGGCGGCNGCCACTACCGTGGCCTGGTACCAGGTGAGCCCGCT
GGCCGCCCGCCTGCTCTACCCCTACCTGGCCTGGCTGGCCTTCGCGACCACACTCAACTA
CTGCGTATGGCGGGACAACCATGGCTGGCA
|
| Target 1 GenBank Gene ID |
Not Available |
| Target 1 GeneCard ID |
TSPO |
| Target 1 GenAtlas ID |
TSPO |
| Target 1 HGNC ID |
HGNC:1158 |
| Target 1 Chromosome Location |
Chromosome:22 |
| Target 1 Locus |
22q13.31 |
| Target 1 SNPs |
SNPJam Report |
| Target 1 Toxin References |
- T243 - 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 ]
|
| Target 1 General References |
1847678; 7721091; 16189298; 15461802; 10591208; 15489334; 9915832; 16822554 |
