Alprazolam (CHEM002187)

Record Information
Version1.0
Creation Date2009-07-21 20:26:48 UTC
Update Date2026-05-14 16:37:43 UTC
Accession NumberCHEM002187
Identification
Common NameAlprazolam
ClassSmall Molecule
Description
Alprazolam is only found in individuals that have used or taken this drug. It is a triazolobenzodiazepine compound with antianxiety and sedative-hypnotic actions, that is efficacious in the treatment of panic disorders, with or without agoraphobia, and in generalized anxiety disorders. (From AMA Drug Evaluations Annual, 1994, p238) Benzodiazepines bind nonspecifically to benzodiazepine receptors BNZ1, which mediates sleep, and BNZ2, which 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 the inhibitory neurotransmitter GABA to the site opens the chloride channel, resulting in a hyperpolarized cell membrane that prevents further excitation of the cell.
Contaminant Sources
  • HMDB Contaminants - Urine
  • STOFF IDENT Compounds
  • Suspected Compounds
  • T3DB toxins
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Anti-Anxiety Agent
  • Benzodiazepine
  • Drug
  • GABA Modulator
  • Human Neurotoxin
  • Hypnotic and Sedative
  • Metabolite
  • Organic Compound
  • Organochloride
  • Synthetic Compound
Chemical Structure
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
8-Chloro-1-methyl-6-phenyl-4H-S-triazolo(4,3-a)(1,4)benzodiazepineChEBI
XanaxChEBI
TUS-1HMDB
Alphapharm brand OF alprazolamHMDB
Alprazolam orion brandHMDB
Alprazolam pfizer brandHMDB
Apotex brand OF alprazolamHMDB
KalmaHMDB
Kenral brand OF alprazolamHMDB
Nu alprazHMDB
Pfizer brand OF alprazolamHMDB
Temmler brand OF alprazolamHMDB
TrankimazinHMDB
Alprazolam kenral brandHMDB
Alprazolam novopharm brandHMDB
Alprazolam nu-pharm brandHMDB
Apo alprazHMDB
Apo-alprazHMDB
Arzneimittelwerk dresden brand OF alprazolamHMDB
CassadanHMDB
NuAlprazHMDB
Alprazolam alphapharm brandHMDB
ApoAlprazHMDB
Novo alprazolHMDB
Novo-alprazolHMDB
NovoAlprazolHMDB
Nu pharm brand OF alprazolamHMDB
Nu-pharm brand OF alprazolamHMDB
Alprazolam apotex brandHMDB
Alprazolam temmler brandHMDB
AlprazolanHMDB
AlproxHMDB
D-65MTHMDB
D65MTHMDB
EsparonHMDB
Novopharm brand OF alprazolamHMDB
Nu-alprazHMDB
Orion brand OF alprazolamHMDB
RalozamHMDB
TafilHMDB
Chemical FormulaC17H13ClN4
Average Molecular Mass308.765 g/mol
Monoisotopic Mass308.083 g/mol
CAS Registry Number28981-97-7
IUPAC Name12-chloro-3-methyl-9-phenyl-2,4,5,8-tetraazatricyclo[8.4.0.0²,⁶]tetradeca-1(10),3,5,8,11,13-hexaene
Traditional Nameneurol
SMILESCC1=NN=C2CN=C(C3=CC=CC=C3)C3=C(C=CC(Cl)=C3)N12
InChI IdentifierInChI=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
InChI KeyVREFGVBLTWBCJP-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 1,2,4-triazolo[4,3-a][1,4]benzodiazepines. These are aromatic compounds containing a 1,4-benzodiazepine fused to and sharing a nitrogen atom with a 1,2,4-triazole ring.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzodiazepines
Sub Class1,4-benzodiazepines
Direct Parent1,2,4-triazolo[4,3-a][1,4]benzodiazepines
Alternative Parents
Substituents
  • 1,2,4-triazolo[4,3-a][1,4]benzodiazepine
  • Aryl chloride
  • Aryl halide
  • Monocyclic benzene moiety
  • Benzenoid
  • Azole
  • 1,2,4-triazole
  • Heteroaromatic compound
  • Ketimine
  • Propargyl-type 1,3-dipolar organic compound
  • Organic 1,3-dipolar compound
  • Azacycle
  • Organopnictogen compound
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organochloride
  • Organohalogen compound
  • Imine
  • Hydrocarbon derivative
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cytoplasm
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
Applications
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point228-229.5°C
Boiling PointNot Available
Solubility40 mg/L at pH 7; 12 mg/mL at pH 1.2
Predicted Properties
PropertyValueSource
Water Solubility0.032 g/LALOGPS
logP2.23ALOGPS
logP2.37ChemAxon
logS-4ALOGPS
pKa (Strongest Acidic)18.3ChemAxon
pKa (Strongest Basic)5.08ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area43.07 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity98.88 m³·mol⁻¹ChemAxon
Polarizability32.22 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Toxicity Profile
Route of ExposureOral. Readily absorbed from the gastrointestinal tract. Bioavailability is 80-90%.
Mechanism of ToxicityBenzodiazepines bind nonspecifically to benzodiazepine receptors BNZ1, which mediates sleep, and BNZ2, which 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 the inhibitory neurotransmitter GABA to the site opens the chloride channel, resulting in a hyperpolarized cell membrane that prevents further excitation of the cell.
MetabolismHepatic. Hydroxylated in the liver to α-hydroxyalprazolam, which is also active. This and other metabolites are later excreted in urine as glucuronides. Route of Elimination: Alprazolam and its metabolites are excreted primarily in the urine. Half Life: 6.3-26.9 hours
Toxicity ValuesLD50: 1020 mg/kg (Oral, mouse)
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesFor the management of anxiety disorder or the short-term relief of symptoms of anxiety and for the treatment of panic disorder, with or without agoraphobia.
Minimum Risk LevelNot Available
Health EffectsThey cause slurred speech, disorientation and "drunken" behavior. They are physically and psychologically addictive.
SymptomsSymptoms of overdose include confusion, coma, impaired coordination, sleepiness, and slowed reaction time.
TreatmentAs in all cases of drug overdosage, respiration, pulse rate, and blood pressure should be monitored. General supportive measures should be employed, along with immediate gastric lavage. Intravenous fluids should be administered and an adequate airway maintained. If hypotension occurs, it may be combated by the use of vasopressors. Dialysis is of limited value. 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. (8)
Concentrations
Not Available
External Links
DrugBank IDDB00404
HMDB IDHMDB0014548
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkAlprazolam
Chemspider ID2034
ChEBI ID2611
PubChem Compound ID2118
Kegg Compound IDC06817
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis Reference

Hester, J.B., Jr.; US. Patent 3,681,343; August 1,1972; assigned to The Upjohn Company. Hester, J.B., Jr.; US.Patent 3,781,289; December 25,1973;assigned to The Upjohn Company. Hester, J.B., Jr.; U S . Patent 3,709898; January 9,1973; assigned to The Upjohn Company.

MSDSLink
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=10350361
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=10443648
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=10631626
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=10963939
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=10997633
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=11304902
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=11824768
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=12035937
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=15647704
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=15725773
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=15830221
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=16103667
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=16139113
14. https://www.ncbi.nlm.nih.gov/pubmed/?term=16572266
15. https://www.ncbi.nlm.nih.gov/pubmed/?term=17631455
16. https://www.ncbi.nlm.nih.gov/pubmed/?term=24361783
17. https://www.ncbi.nlm.nih.gov/pubmed/?term=24464531
18. https://www.ncbi.nlm.nih.gov/pubmed/?term=24629629
19. https://www.ncbi.nlm.nih.gov/pubmed/?term=24840273
20. https://www.ncbi.nlm.nih.gov/pubmed/?term=24977401
21. https://www.ncbi.nlm.nih.gov/pubmed/?term=25032127
22. https://www.ncbi.nlm.nih.gov/pubmed/?term=25139178
23. https://www.ncbi.nlm.nih.gov/pubmed/?term=25199955
24. https://www.ncbi.nlm.nih.gov/pubmed/?term=25300043
25. https://www.ncbi.nlm.nih.gov/pubmed/?term=25427652
26. https://www.ncbi.nlm.nih.gov/pubmed/?term=25581490
27. https://www.ncbi.nlm.nih.gov/pubmed/?term=25620535
28. https://www.ncbi.nlm.nih.gov/pubmed/?term=7907366
29. https://www.ncbi.nlm.nih.gov/pubmed/?term=9050091
30. Wolf B, Griffiths RR: Physical dependence on benzodiazepines: differences within the class. Drug Alcohol Depend. 1991 Dec 31;29(2):153-6.
31. Haque W, Watson DJ, Bryant SG: Death following suspected alprazolam withdrawal seizures: a case report. Tex Med. 1990 Jan;86(1):44-7.
32. Risse SC, Whitters A, Burke J, Chen S, Scurfield RM, Raskind MA: Severe withdrawal symptoms after discontinuation of alprazolam in eight patients with combat-induced posttraumatic stress disorder. J Clin Psychiatry. 1990 May;51(5):206-9.
33. Hori A: Pharmacotherapy for personality disorders. Psychiatry Clin Neurosci. 1998 Feb;52(1):13-9.
34. Garcia-Algar O, Lopez-Vilchez MA, Martin I, Mur A, Pellegrini M, Pacifici R, Rossi S, Pichini S: Confirmation of gestational exposure to alprazolam by analysis of biological matrices in a newborn with neonatal sepsis. Clin Toxicol (Phila). 2007;45(3):295-8.