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
OverviewAI-generated
Alprazolam is a chemical compound with the formula C₁₇H₁₃ClN₄. Its IUPAC name is 8-chloro-1-methyl-6-phenyl-4H-[1,2,4]triazolo[4,3-a][1,4]benzodiazepine. The substance has a mass of 308.083 and a weight of 308.8. It possesses a defined daily dose of 1 and an xlogp value of 2.1. The compound contains 0 hydrogen bond donors and 3 hydrogen bond acceptors, with a topological polar surface area of 43.1.
The stylized name for the compound is ALPRAZolam. It is assigned the MCN code 2933.91.11. In scientific literature, alprazolam is the subject of 3,179 PubMed entries. Additionally, the compound is referenced by 1,059 other encyclopedia articles.
Synthesized by Vinony from 20 facts across 4 sources: Wikidata, PubChem, PubMed, Vinony graph. Generated from structured data (not the Wikipedia text) and checked against those facts — may still 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
~25 min read
Encyclopedic overview
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.
Excerpted from Wikipedia’s “alprazolam” article, available under the CC BY-SA 4.0 licence.