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Alprazolam, sold under the brand name Xanax, among others, is a short-acting tranquilizer of the triazolobenzodiazepine (TBZD) class, which are benzodiazepines (BZDs) fused with a triazole ring.[6]It is most commonly used in short-term management of anxiety disorders, specifically panic disorder or generalized anxiety disorder (GAD).[7]Other uses include the treatment of chemotherapy-induced nausea, together with other treatments.[5]GAD improvement occurs generally within a week.[8][9] Alprazolam is generally taken by mouth.[5]

Alprazolam structure.svg
Alprazolam ball-and-stick model.png
Clinical data
Pronunciation Alprazolam /ælˈpræzəlæm/or /ælˈprzəlæm/, Xanax /ˈzænæks/
Trade names Xanax, Xanor, Niravam, others
AHFS/ Monograph
MedlinePlus a684001
License data
Routes of
By mouth
Drug class Benzodiazepine
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability 80–90%
Protein binding 80%
Metabolism Liver, via cytochrome P450 3A4
Metabolites alpha-hydroxyalprazolam, 4-hydroxyalprazolam, beta-hydroxyalprazolam
Onset of action less than an hour[4]
Elimination half-life Immediate release: 11–13 hours[5]
Extended release: 11–16 hours[5]
Duration of action 6 hours[4]
Excretion Kidney
  • 8-Chloro-1-methyl-6-phenyl-4H-[1,2,4]triazolo[4,3-a] [1,4]benzodiazepine
CAS Number
PubChem CID
CompTox Dashboard(EPA)
ECHA InfoCard 100.044.849 Edit this at Wikidata
Chemical and physical data
Formula C17H13ClN4
Molar mass 308.77 g·mol−1
3D model (JSmol)
  • ClC1=CC2=C(C=C1)N3C(C)=NN=C3CN=C2C4=CC=CC=C4
  • 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 check

Common side effects include sleepiness, depression, headaches, feeling tired, dry mouth, and memory problems.[5] Some of the sedation and tiredness may improve within a few days.[10] Due to concerns about misuse, some do not recommend alprazolam as an initial treatment for panic disorder.[11] Withdrawal or rebound symptoms may occur if use is suddenly decreased;[5] gradually decreasing the dose over weeks or months may be required.[8] Other rare risks include suicide, possibly due to loss of inhibition.[12] Alprazolam, like other benzodiazepines, acts through the GABAAreceptor.[5]

Alprazolam was patented in 1971 and approved for medical use in the United States in 1981.[5][13]Alprazolam is a Schedule IV controlled substance and is a common drug of abuse.[2][14] It is available as a generic medication.[7] In 2018, it was the 37th most commonly prescribed medication in the United States, with more than 20 million prescriptions.[15][16]

Medical uses

Alprazolam 0.5mg pills

Alprazolam is mostly used in short term management of anxiety disorders, panic disorders, and nausea due to chemotherapy.[5] Alprazolam may also be indicated for the treatment of generalized anxiety disorder, as well as for the treatment of anxiety conditions with co-morbiddepression.[17] The FDA label advises that the physician should periodically reassess the usefulness of the drug.[18]

Panic disorderEdit

Alprazolam is effective in the relief of moderate to severe anxiety and panic attacks.[18] However, it is not a first line treatment since the development of selective serotonin reuptake inhibitors. Alprazolam is no longer recommended in Australia for the treatment of panic disorder due to concerns regarding tolerance, dependence, and abuse.[11]Most evidence shows that the benefits of alprazolam in treating panic disorder last only 4 to 10 weeks. However, people with panic disorder have been treated on an open basis for up to 8 months without apparent loss of benefit.[17][18]

In the United States, alprazolam is FDA-approved for the treatment of panic disorder with or without agoraphobia.[18] Alprazolam is recommended by the World Federation of Societies of Biological Psychiatry (WFSBP) for treatment-resistant cases of panic disorder where there is no history of toleranceor dependence.[19]

Anxiety disordersEdit

Anxiety associated with depression is responsive to alprazolam. Clinical studies have shown that the effectiveness is limited to 4 months for anxiety disorders.[18] However, the research into antidepressant properties of alprazolam is poor and has only assessed its short-term effects against depression.[20] In one study, some long term, high-dosage users of alprazolam developed reversible depression.[21] In the US, alprazolam is FDA-approved for the management of anxiety disorders (a condition corresponding most closely to the APA Diagnostic and Statistical Manual DSM-IV-TRdiagnosis of generalized anxiety disorder) or the short-term relief of symptoms of anxiety. In the UK, alprazolam is recommended for the short-term treatment (2–4 weeks) of severe acute anxiety.[17][22][23]

Nausea due to chemotherapyEdit

Alprazolam may be used in combination with other medications for chemotherapy-induced nausea and vomiting.[5]

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