Alprazolam

Alprazolam
Clinical data
Pronunciation/ælˈpræzəlæm/ or /ælˈprzəlæm/
Trade namesXanax, others
AHFS/Drugs.comMonograph
MedlinePlusa684001
License data
Pregnancy
category
  • AU: C
Dependence
liability
Very high
Addiction
liability
High
Routes of
administration
By mouth
Drug classBenzodiazepine
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability80–90%
Protein binding80%
MetabolismLiver, via cytochrome P450 3A4
Metabolites
  • α-hydroxyalprazolam
  • 4-hydroxyalprazolam
Onset of action30~60 minutes
Elimination half-life
  • Instant-release:
  • 11~13 hours
  • Extended-release:
  • 11~16 hours
Duration of action
  • Instant-release:
  • 6 hours
  • Extended-release:
  • 11.3 hours
ExcretionKidney
Identifiers
  • 8-Chloro-1-methyl-6-phenyl-4H-[1,2,4]triazolo[4,3-a] [1,4]benzodiazepine
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.044.849
Chemical and physical data
FormulaC17H13ClN4
Molar mass308.77 g·mol−1
3D model (JSmol)
  • Cc1nnc2n1-c1ccc(Cl)cc1C(c1ccccc1)=NC2
  • InChI=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 Y
  • Key:VREFGVBLTWBCJP-UHFFFAOYSA-N Y
  (verify)

Alprazolam, sold under the brand name Xanax among others, is a fast-acting, potent tranquilizer of moderate duration within the triazolobenzodiazepine group of chemicals called benzodiazepines. Alprazolam is most commonly prescribed in the management of anxiety disorders, especially panic disorder and generalized anxiety disorder (GAD). Other uses include the treatment of chemotherapy-induced nausea, together with other treatments. GAD improvement occurs generally within a week. Alprazolam is generally taken orally.

Common side effects include sleepiness, depression, suppressed emotions, mild to severe decreases in motor skills, hiccups, dulling or declining of cognition, decreased alertness, dry mouth (mildly), decreased heart rate, suppression of central nervous system activity, impairment of judgment (usually in higher than therapeutic doses), marginal to severe decreases in memory formation, decreased ability to process new information, as well as partial to complete anterograde amnesia, depending on dosage. Some of the sedation and drowsiness may improve within a few days.

Benzodiazepine withdrawal symptoms may occur if use is suddenly decreased.

Alprazolam was invented by Jackson Hester Jr. at the Upjohn Company and patented in 1971 and approved for medical use in the United States in 1981. Alprazolam is a Schedule IV controlled substance and is a common drug of abuse. It is available as a generic medication. In 2022, it was the 41st most commonly prescribed medication in the United States, with more than 14 million prescriptions.