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Alprazolam information


Alprazolam
Clinical data
Pronunciation/ælˈpræzəlæm/ or /ælˈprzəlæm/
Trade namesXanax, Xanor, Niravam, others
AHFS/Drugs.comMonograph
MedlinePlusa684001
License data
  • US DailyMed: Alprazolam
Pregnancy
category
  • AU: C[1]
Dependence
liability
Very high[2]
Addiction
liability
High[2]
Routes of
administration
Oral
Drug classBenzodiazepine
ATC code
  • N05BA12 (WHO)
Legal status
Legal status
  • AU: S8 (Controlled drug)
  • BR: Class B1 (Psychoactive drugs)
  • CA: Schedule IV
  • DE: Anlage III (Special prescription form required) (in doses higher than 1 mg)
  • UK: POM (Prescription only) / Class C[4][5]
  • US: WARNING[3]Schedule IV[6][7]
  • UN: Psychotropic Schedule IV
  • In general: ℞ (Prescription only)
Pharmacokinetic data
Bioavailability80–90%
Protein binding80%
MetabolismLiver, via cytochrome P450 3A4
Metabolites• Alpha-hydroxyalprazolam

• 4-hydroxyalprazolam

• beta-hydroxyalprazolam
Onset of action20~60 minutes[8]
Elimination half-lifeFull release: 11~13 hours[9]
Extended release: 11~16 hours[9]
Duration of actionFull release: 6 hours[8]
Extended release: 11.3 hours
ExcretionKidney
Identifiers
IUPAC name
  • 8-Chloro-1-methyl-6-phenyl-4H-[1,2,4]triazolo[4,3-a] [1,4]benzodiazepine
CAS Number
  • 28981-97-7 checkY
PubChem CID
  • 2118
IUPHAR/BPS
  • 7111
DrugBank
  • DB00404 checkY
ChemSpider
  • 2034 checkY
UNII
  • YU55MQ3IZY
KEGG
  • D00225 checkY
ChEBI
  • CHEBI:2611 checkY
ChEMBL
  • ChEMBL661 checkY
CompTox Dashboard (EPA)
  • DTXSID4022577 Edit this at Wikidata
ECHA InfoCard100.044.849 Edit this at Wikidata
Chemical and physical data
FormulaC17H13ClN4
Molar mass308.77 g·mol−1
3D model (JSmol)
  • Interactive image
SMILES
  • Cc1nnc2n1-c1ccc(Cl)cc1C(c1ccccc1)=NC2
InChI
  • 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 checkY
  • Key:VREFGVBLTWBCJP-UHFFFAOYSA-N checkY
  (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.[10] Alprazolam is most commonly used in management of anxiety disorders, specifically panic disorder or generalized anxiety disorder (GAD).[6] Other uses include the treatment of chemotherapy-induced nausea, together with other treatments.[9] GAD improvement occurs generally within a week.[11][12] Alprazolam is generally taken orally (by mouth).[9]

Common side effects include sleepiness, depression or suppressed emotions, mild to severe decreases in motor skills, hiccups, dulling or declining of cognition as well as alertness or general awareness of one's surroundings or even behavior, dry mouth (mildly), decreased heart rate, suppression (physiological inhibition) of general central nervous system activity (opposite of physiological excitation), 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 amnesia (anterograde amnesia[13]) depending on dosage.[9] Some of the sedation and tiredness may improve within a few days.[14]

Alprazolam withdrawal may occur if use is suddenly decreased.[9][11]

Alprazolam was invented by Jackson Hester Jr. at the Upjohn Company[15] and patented in 1971 and approved for medical use in the United States in 1981.[9][16] Alprazolam is a Schedule IV controlled substance and is a common drug of abuse.[2][17] It is available as a generic medication.[6] In 2021, it was the 42nd most-commonly-prescribed medication in the United States, with more than 15 million prescriptions.[18][19]

  1. ^ "Alprazolam Use During Pregnancy". Drugs.com. 4 May 2020. Archived from the original on 20 June 2020. Retrieved 8 June 2020.
  2. ^ a b c Ait-Daoud N, Hamby AS, Sharma S, Blevins D (2018). "A Review of Alprazolam Use, Misuse, and Withdrawal". Journal of Addiction Medicine. 12 (1): 4–10. doi:10.1097/ADM.0000000000000350. PMC 5846112. PMID 28777203.
  3. ^ "FDA-sourced list of all drugs with black box warnings (Use Download Full Results and View Query links.)". nctr-crs.fda.gov. FDA. Retrieved 22 October 2023.
  4. ^ "Xanax Summary of Product Characteristics (SmPC)". (emc). 28 July 2023. Retrieved 20 November 2023.
  5. ^ "List of most commonly encountered drugs currently controlled under the misuse of drugs legislation". GOV.UK. 20 October 2016. Retrieved 20 November 2023.
  6. ^ a b c "Xanax- alprazolam tablet". DailyMed. Archived from the original on 17 January 2021. Retrieved 19 February 2021.
  7. ^ "Xanax XR- alprazolam tablet, extended release". DailyMed. 12 March 2021. Archived from the original on 17 April 2021. Retrieved 2 June 2022.
  8. ^ a b Lilley LL, Snyder JS, Collins SR (2016). Pharmacology for Canadian Health Care Practice. Elsevier Health Sciences. p. 329. ISBN 9781771720663. Archived from the original on 10 May 2022. Retrieved 13 September 2020.
  9. ^ a b c d e f g American Society of Health-System Pharmacists (13 November 2017). "Alprazolam Monograph for Professionals". Drugs.com. Archived from the original on 7 December 2010. Retrieved 25 October 2018.
  10. ^ Goldberg R (2009). Drugs Across the Spectrum. Cengage Learning. p. 195. ISBN 9781111782009. Archived from the original on 4 June 2020. Retrieved 24 August 2017.
  11. ^ a b Verster JC, Volkerts ER (2004). "Clinical pharmacology, clinical efficacy, and behavioral toxicity of alprazolam: a review of the literature". CNS Drug Reviews. 10 (1): 45–76. doi:10.1111/j.1527-3458.2004.tb00003.x. PMC 6741717. PMID 14978513.
  12. ^ Tampi RR, Muralee S, Weder ND, Penland H, eds. (2008). Comprehensive Review of Psychiatry. Philadelphia, PA: Wolters Kluwer/ Lippincott Williams & Wilkins Health. p. 226. ISBN 978-0-7817-7176-4. Archived from the original on 19 March 2017. Retrieved 13 March 2016.
  13. ^ Chowdhury ZS, Morshed MM, Shahriar M, Bhuiyan MA, Islam SM, Bin Sayeed MS (2016). "The Effect of Chronic Alprazolam Intake on Memory, Attention, and Psychomotor Performance in Healthy Human Male Volunteers". Behavioural Neurology. 2016: 3730940. doi:10.1155/2016/3730940. PMC 4947648. PMID 27462136.
  14. ^ Pavuluri MN, Janicak PG, Marder SR (2010). Principles and Practice of Psychopharmacotherapy (5th ed.). Philadelphia, PA: Wolters Kluwer Health/ Lippincott Williams & Wilkins. p. 535. ISBN 978-1-60547-565-3. Archived from the original on 17 July 2020. Retrieved 13 March 2016.
  15. ^ Ainsworth SJ (9 December 2013). "Hester Dies At 80". Chemical & Engineering News. Retrieved 21 April 2024.
  16. ^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 536. ISBN 9783527607495. Archived from the original on 28 August 2021. Retrieved 13 September 2020.
  17. ^ Malamed SF (2009). Sedation: A Guide to Patient Management. Elsevier Health Sciences. p. 105. ISBN 978-0323075961. Archived from the original on 10 May 2022. Retrieved 13 September 2020.
  18. ^ "The Top 300 of 2021". ClinCalc. Archived from the original on 15 January 2024. Retrieved 14 January 2024.
  19. ^ "Alprazolam - Drug Usage Statistics". ClinCalc. Retrieved 14 January 2024.

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