Chemical Component Summary

Name8-chloro-1-methyl-6-phenyl-4H-[1,2,4]triazolo[4,3-a][1,4]benzodiazepine
SynonymsALPRAZOLAM
Identifiers8-chloranyl-1-methyl-6-phenyl-4H-[1,2,4]triazolo[4,3-a][1,4]benzodiazepine
FormulaC17 H13 Cl N4
Molecular Weight308.765
TypeNON-POLYMER
Isomeric SMILESCc1nnc2n1-c3ccc(cc3C(=NC2)c4ccccc4)Cl
InChIInChI=1S/C17H13ClN4/c1-11-20-21-16-10-19-17(12-5-3-2-4-6-12)14-9-13(18)7-8-15(14)22(11)16/h2-9H,10H2,1H3
InChIKeyVREFGVBLTWBCJP-UHFFFAOYSA-N

Chemical Details

Formal Charge0
Atom Count35
Chiral Atom Count0
Bond Count38
Aromatic Bond Count17

Drug Info: DrugBank

DrugBank IDDB00404 
NameAlprazolam
Groups
  • approved
  • investigational
  • illicit
DescriptionAlprazolam is a triazolobenzodiazepine indicated for the treatment of anxiety and panic disorders.[L34783, L34788] It is mainly metabolized by CYP3As and so is contraindicated with CYP3A inhibitors like ketoconazole and itraconazole.[L34783, L34788] Benzodiazepine treatment should be stopped gradually by tapering down a patient's dose to avoid withdrawal symptoms.[A18125] Alprazolam's adverse effects are generally related to the sedation it can cause.[A18125] Alprazolam has been mixed with alcohol as a drug of abuse to potentiate the sedative effects of the drug which may lead to coma and death.[A18125] Alprazolam was given FDA approval on October 16, 1981.[L6148]
Synonyms
  • Alprazolam
  • 8-Chloro-1-methyl-6-phenyl-4H-s-triazolo(4,3-a)(1,4)benzodiazepine
Brand Names
  • Jamp Alprazolam
  • Alprazolam Extended-Release
  • Alprazolam
  • Gabazolamine-0.5
  • Nat-alprazolam
IndicationAlprazolam is indicated for the acute treatment of generalized anxiety disorder in adults.[L34783] Alprazolam is also indicated, either as a standard or extended-release formulation, for the treatment of panic disorder with or without agoraphobia in adults.[L34783, L34788] Alprazolam may also be prescribed off-label for insomnia, premenstrual syndrome, and depression.[A177973]
Categories
  • Amines
  • Anti-Anxiety Agents
  • Benzazepines
  • Benzene Derivatives
  • Benzodiazepines and benzodiazepine derivatives
ATC-CodeN05BA12
CAS number28981-97-7

Drug Targets

NameTarget SequencePharmacological ActionActions
GABA(A) ReceptorMRKSPGLSDCLWAWILLLSTLTGRSYGQPSLQDELKDNTTVFTRILDRLL...unknownpositive allosteric modulator
GABA(A) Receptor Benzodiazepine Binding SiteMRKSPGLSDCLWAWILLLSTLTGRSYGQPSLQDELKDNTTVFTRILDRLL...unknownligand
Cytochrome P450 3A7MDLIPNLAVETWLLLAVSLILLYLYGTRTHGLFKKLGIPGPTPLPFLGNA...unknownsubstrate
Cytochrome P450 3A4MALIPDLAMETWLLLAVSLVLLYLYGTHSHGLFKKLGIPGPTPLPFLGNI...unknownsubstrate
Cytochrome P450 2C9MDSLVVLVLCLSCLLLLSLWRQSSGRGKLPPGPTPLPVIGNILQIGIKDI...unknownsubstrate
View More
Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682

Related Resource References

Resource NameReference
Pharos CHEMBL661
PubChem 2118
ChEMBL CHEMBL661
ChEBI CHEBI:2611
CCDC/CSD CAKYOE, EZIFEZ, CAKZEV, CIZQAD01, EZIDIB, EZIDOH, CAKZAR, CAKZOF, EZIDUN, CAKYUK, EZIFID, MENMIB01, CAKZUL, GESJOF, EZIFAV, GESJIZ, GESKAS