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Alprazolam is extensively metabolized in humans, primarily by the enzyme CYP3A4 to two major metabolites in plasma: 4-hydroxyalprazolam and α- hydroxyalprazolam. A benzophenone derived from alprazolam is also found in humans. Half-lives are similar to that of alprazolam. The plasma concentrations of 4-hydroxyalprazolam and α-hydroxyalprazolam relative to unchanged alprazolam concentration were always less than 4%. The reported relative potencies in benzodiazepines receptor binding experiments and in animals models of induced seizure inhibition are 0.2 and 0.66, respectively, for 4-hydroxyalprazolam and α-hydroxyalprazolam. Such low concentrations and lesser potencies of 4-hydroxyalprazolam and α-hydroxyalprazolam suggest that they are unlikely to contribute much to the pharmacological effects of alprazolam. The benzophenone metabolite is essentially inactive.
Alprazolam and its metabolites are excreted primarily in the urine.
Forms of alprazolam[edit]
Alprazolam regular release and orally disintegrating tablets are available as 0.25 mg, 0.5 mg, 1 mg, 2 mg strength tablets.[84]
Alprazolam extended release tablets are available as 0.5 mg, 1 mg, 2 mg, and 3 mg strength tablets.
Alprazolam oral solutions are available as 0.5 mg/5 mL and as 1 mg/1 mL oral solutions.
Active ingredient: alprazolam
Inactive ingredients: microcrystalline cellulose, corn starch, docusate sodium, povidone, sodium starch glycollate, lactose monohydrate, magnesium stearate, colloidal silicon dioxide and sodium benzoate. In addition, the 0.25 mg tablet contains D&C Yellow No. 10 and the 0.5 mg tablet contains FD&C Yellow No. 6 and D&C Yellow No. 10
Society and culture[edit]
Patent[edit]
It is covered under U.S. Patent 3,987,052, which was filed on 29 October 1969, granted on 19 October 1976, and expired in September 1993.
Recreational use[edit]
See also: Benzodiazepine misuse
There is a risk of misuse and dependence in both patients and non-medical users of alprazolam; the pharmacological properties of alprazolam such as high affinity binding, high potency, being short-acting and having a rapid onset of action increase the abuse potential of alprazolam. The physical dependence and withdrawal syndrome of alprazolam also adds to the addictive nature of alprazolam. In the small subgroup of individuals who escalate their doses there is usually a history of alcohol or other substance use disorders.[10] Despite this, most prescribed alprazolam users do not use their medication recreationally, and the long-term use of benzodiazepines does not generally correlate with the need for dose escalation.[85] However, based on US findings from the Treatment Episode Data Set (TEDS), an annual compilation of patient characteristics in substance abuse treatment facilities in the United States, admissions due to "primary tranquilizer" (including, but not limited to, benzodiazepine-type) drug use increased 79% from 1992 to 2002, suggesting that misuse of benzodiazepines may be on the rise.[86] The New York Times also reported in 2011 that "The Centers for Disease Control and Prevention last year reported an 89 percent increase in emergency room visits nationwide related to nonmedical benzodiazepine use between 2004 and 2008."[87]
Alprazolam is one of the most commonly prescribed and misused benzodiazepines in the United States.[12][15] A large-scale nationwide U.S. government study conducted by SAMHSA found that, in the U.S., benzodiazepines are recreationally the most frequently used pharmaceuticals due to their widespread availability, accounting for 35% of all drug-related visits to hospital emergency and urgent care facilities. Men and women are equally likely to use benzodiazepines recreationally. The report found that alprazolam is the most common benzodiazepine for recreational use followed by clonazepam, lorazepam, and diazepam. The number of emergency room visits due to benzodiazepines increased by 36% between 2004 and 2006.[15]
Regarding the significant increases detected, it is worthwhile to consider that the number of pharmaceuticals dispensed for legitimate therapeutic uses may be increasing over time, and DAWN estimates are not adjusted to take such increases into account. Nor do DAWN estimates take into account the increases in the population or in ED use between 2004 and 2006.[15]
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Product Name:	Alprazolam
Synonyms:	8-CHLORO-1-METHYL-6-PHENYL-4H-1,2,4-TRIAZOLO(3,4-A)(1,4)BENZODIAZEPINE;8-CHLORO-1-METHYL-6-PHENYL-4H-[1,2,4]TRIAZOLO[4,3-A][1,4]BENZODIAZEPINE;8-chloro-1-methyl-6-phenyl-4h-s-triazolo[4,3-a][1,4]benzodiazepine;3-a)(1,4)benzodiazepine,8-chloro-1-methyl-6-phenyl-4h-s-triazolo(;4H-[1,2,4]Triazolo[4,3-a][1,4]benzodiazepine, 8-chloro-1-methyl-6-phenyl-;4H-s-Triazolo(4,3-a)(1,4)benzodiazepine, 8-chloro-1-methyl-6-phenyl-;8-Chloro-1-methyl-6-phenyl-4H-s-triazolo [4,3-alpha]-1,4-benzodiazepine;Alplax
CAS:	28981-97-7
MF:	C17H13ClN4
MW:	308.76
EINECS:	249-349-2
Product Categories:	Active Pharmaceutical Ingredients;API;Intermediates & Fine Chemicals;Pharmaceuticals;Aromatics;Heterocycles
Mol File:	28981-97-7.mol