Alprazolam

Alprazolam
Clinical data
Pronunciation	/ælˈpræzəlæm/ or /ælˈpreɪzəlæm/
Trade names	Xanax, Xanor, Niravam, others
AHFS/Drugs.com	Monograph
MedlinePlus	a684001
License data	US DailyMed: Alprazolam;
Pregnancy; category	AU: C;
Dependence; liability	Very high
Addiction; liability	High
Routes of; administration	Oral
Drug class	Benzodiazepine
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; US: WARNINGSchedule 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	20~60 minutes
Elimination half-life	Full release: 11~13 hours; Extended release: 11~16 hours
Duration of action	Full release: 6 hours; Extended release: 11.3 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 ;
PubChem CID	2118;
IUPHAR/BPS	7111;
DrugBank	DB00404 ;
ChemSpider	2034 ;
UNII	YU55MQ3IZY;
KEGG	D00225 ;
ChEBI	CHEBI:2611 ;
ChEMBL	ChEMBL661 ;
CompTox Dashboard (EPA)	DTXSID4022577 ;
ECHA InfoCard	100.044.849
Chemical and physical data
Formula	C17H13ClN4
Molar mass	308.77 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 ; Key:VREFGVBLTWBCJP-UHFFFAOYSA-N ;
	(verify)

Alprazolam, sold under the brand name Xanax, is a fast-acting, potent tranquilizer of moderate duration within the triazolobenzodiazepine group of chemicals called benzodiazepines. Alprazolam is most commonly used in management of anxiety disorders, specifically panic disorder or 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 (by mouth).

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) depending on dosage. Some of the sedation and tiredness may improve within a few days.

Alprazolam withdrawal may occur if use is suddenly decreased.

Alprazolam was invented by Jackson Hester Jr. at the Upjohn Company and patented in 1971 and approved for medical use in the United States in 1981. Alprazolam is a Schedule IV controlled substance and is a common drug of abuse. It is available as a generic medication. In 2021, it was the 42nd most-commonly-prescribed medication in the United States, with more than 15 million prescriptions for over 3.9 million patients.

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