Alprazolam

Alprazolam, better known by its trade name Xanax, is a short-acting drug. The drug is used to treat people with anxiety disorders and panic attacks.

Alprazolam

Clinical data
Pronunciation	Alprazolam /ælˈpræzəlæm/ or /ælˈpreɪzəlæm/, Xanax /ˈzænæks/
Trade names	Xanax, Xanor, Niravam, others
AHFS/Drugs.com	Monograph
MedlinePlus	a684001
Pregnancy category
Dependence liability	High
Routes of administration	By mouth
ATC code	N05BA12 (WHO)
Legal status
Legal status	AU: S8 (Controlled drug) CA: Schedule IV DE: Prescription only (Anlage III for higher doses) UK: Class C US: Schedule IV UN: Psychotropic Schedule IV In general: ℞ (Prescription only)
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[1]
Elimination half-life	Immediate release: 4–6 hours Extended release: 11–16 hours
Duration of action	6 hours[1]
Excretion	Kidney
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 Y
PubChem CID	2118
IUPHAR/BPS	7111
DrugBank	DB00404 Y
ChemSpider	2034 Y
UNII	YU55MQ3IZY
KEGG	D00225 Y
ChEBI	CHEBI:2611 Y
ChEMBL	ChEMBL661 Y
ECHA InfoCard	100.044.849
Chemical and physical data
Formula	C17H13ClN4
Molar mass	308.77 g·mol−1
3D model (JSmol)	Interactive image
SMILES ClC1=CC2=C(C=C1)N3C(C)=NN=C3CN=C2C4=CC=CC=C4
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 Y Key:VREFGVBLTWBCJP-UHFFFAOYSA-N Y
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Alprazolam is the most commonly misused benzodiazepine (the drug's class) in the United States; but the majority of prescribed users do not develop a substance-use disorder. Alprazolam is a prescription drug in the United States.