Alprazolam

Alprazolam, better known by its trade name Xanax, is a short-acting drug. The drug is made to treat people who get panic attacks or other anxiety disorders.

Alprazolam

140px
Clinical data
Pronunciation	Alprazolam /ælˈpræzəlæm/ or /ælˈpreɪzəlæm/, Xanax /ˈzænæks/
Trade names	Xanax, Xanor, Niravam, others
AHFS/Drugs.com	Monograph
MedlinePlus	a684001
Pregnancy category	US: D (Evidence of risk)
Dependence liability	High
Routes of administration	By mouth
ATC code	N05BA12 (WHO)
Legal status
Legal status	AU: S8 (Controlled) 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
Elimination half-life	Immediate release: 4–6 hours Extended release: 11–16 hours
Duration of action	6 hours
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 7pxY
PubChem CID	2118
IUPHAR/BPS	7111
DrugBank	DB00404 7pxY
ChemSpider	2034 7pxY
UNII	YU55MQ3IZY
KEGG	D00225 7pxY
ChEBI	CHEBI:2611 7pxY
ChEMBL	ChEMBL661 7pxY
E number
ECHA InfoCard
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 7pxY Key:VREFGVBLTWBCJP-UHFFFAOYSA-N 7pxY
(verify)

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.

Alprazolam Media

• Alprazolam pills in boxes, as sold in France; both the original Pfizer brand product Xanax and various generic forms of alprazolam are depicted here.

• Xanax 2 mg.jpg

  A prescription bottle of Xanax

• Alprazolam Tablets China.jpg

  Alprazolam tablets sold in China

• Xanax 0.25, 0.5 & 1 mg.jpg

  Xanax 0.25 mg (top row), 0.5 mg (middle row), and 1 mg (bottom row) tablets

• Alprazolam binds at the α1β3γ2 GABAA receptor.*Alprazolam with red space-filling carbon atoms. γ2 receptor subunit in mint green. The α1' subunit is hidden.

• Alprazolam metabolism.svg

  Alprazolam metabolized into 4-hydroxyalprazolam (top) and α-hydroxyalprazolam (bottom)