File:Alprazolam_structure.svg · Wikimedia Commons · See Wikimedia Commons
alprazolam
Sign in to saveAlso known as U-31889, 8-chloro-1-methyl-6-phenyl-4H-s-triazolo(4,3-a)(1,4)benzodiazepine, 8-chloro-1-methyl-6-phenyl-4H-S-triazolo(4,3-a)(1,4)benzodiazepine
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AI-generated from the Wikipedia summary — may contain errors.
Key facts
- Drug.Cl
- 1
- Drug.N
- 4
- Drug.H
- 13
- Drug.tradename
- Xanax, others
- Drug.MedlinePlus
- a684001
- Drug.Watchedfields
- changed
- Drug.verifiedrevid
- 477164519
- Drug.image
- Alprazolam structure.svg
- Drug.image_class
- skin-invert-image
- Drug.width
- 140px
- Drug.image2
- Alprazolam ball-and-stick model.png
- Drug.image_class2
- bg-transparent
- Drug.pronounce
- or
- Drug.DailyMedID
- Alprazolam
- Drug.pregnancy_AU
- C
- Drug.dependency_liability
- Very high
- Drug.addiction_liability
- High
- Drug.routes_of_administration
- By mouth
via Wikipedia infobox
Chemical data
- Formula
- C17H13ClN4
- Molecular weight
- 308.8 g/mol
- IUPAC name
- 8-chloro-1-methyl-6-phenyl-4H-[1,2,4]triazolo[4,3-a][1,4]benzodiazepine
- SMILES
- CC1=NN=C2N1C3=C(C=C(C=C3)Cl)C(=NC2)C4=CC=CC=C4
- InChIKey
- VREFGVBLTWBCJP-UHFFFAOYSA-N
- XLogP
- 2.1
- Polar surface area
- 43.1 Ų
- H-bond donors
- 0
- H-bond acceptors
- 3
- Formal charge
- 0
via PubChem
Research
3,179 papers- A Review of Alprazolam Use, Misuse, and Withdrawal.ReviewJournal of addiction medicine · 2018Ait-Daoud N, Hamby AS, Sharma S et al.DOI: 10.1097/ADM.0000000000000350
- Alprazolam: Good for Some, Not Good for All!ReviewJournal of clinical psychopharmacology · 2023Mamtani H, Chaturvedi SKDOI: 10.1097/JCP.0000000000001669
- Alprazolam for depression.The Cochrane database of systematic reviews · 2012van Marwijk H, Allick G, Wegman F et al.DOI: 10.1002/14651858.CD007139.pub2
- Alprazolam and diazepam: addiction potential.ReviewJournal of substance abuse treatment · 1991Juergens SDOI: 10.1016/0740-5472(91)90026-7
- Alprazolam is relatively more toxic than other benzodiazepines in overdose.ReviewBritish journal of clinical pharmacology · 2004Isbister GK, O'Regan L, Sibbritt D et al.DOI: 10.1111/j.1365-2125.2004.02089.x
- Alprazolam pharmacokinetics, metabolism, and plasma levels: clinical implications.ReviewThe Journal of clinical psychiatry · 1993Greenblatt DJ, von Moltke LL, Harmatz JS et al.
- Alprazolam for tinnitus.ReviewThe Annals of pharmacotherapy · 1995Huynh L, Fields SDOI: 10.1177/106002809502900313
- Alprazolam as an antidepressant.ReviewThe Journal of clinical psychiatry · 1988Warner MD, Peabody CA, Whiteford HA et al.
via PubMed
Wikidata facts
- Mass
- 308.083
- Image
- Alprazolam.svg
Show 7 more facts
- Commons category
- Alprazolam
- chemical formula
- C₁₇H₁₃ClN₄
- World Health Organisation international non-proprietary name
- alprazolam
- canonical SMILES
- CC1=NN=C2N1C3=C(C=C(C=C3)Cl)C(=NC2)C4=CC=CC=C4
- defined daily dose
- 1
- MCN code
- 2933.91.11
- stylized name
- ALPRAZolam
Sources (10)
via Wikidata · CC0
~25 min read
Article
26 sectionsContents
- Medical uses
- Panic disorder
- Anxiety disorders
- Chemotherapy-induced nausea and vomiting
- Contraindications
- Side effects
- Paradoxical reactions
- Pregnancy and breastfeeding
- Overdose
- Dependence and withdrawal
- Interactions
- Pharmacology
- Mechanism of action
- Pharmacokinetics
- Chemistry
- Physical properties
- Synthesis
- Detection
- Dosage forms
- Legal status
- Availability
- Recreational use
- Slang terms
- In popular culture
- References
- External links
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, impairment of judgment (usually in higher than therapeutic doses), and decreased memory formation, depending on dosage. Some of the sedation and drowsiness may improve within a few days.