Details
Stereochemistry | ACHIRAL |
Molecular Formula | C17H13ClN4.2H2O |
Molecular Weight | 344.795 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
O.O.CC1=NN=C2CN=C(C3=CC=CC=C3)C4=C(C=CC(Cl)=C4)N12
InChI
InChIKey=BTXVPVVNJNBVPC-UHFFFAOYSA-N
InChI=1S/C17H13ClN4.2H2O/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;2*1H2
Molecular Formula | H2O |
Molecular Weight | 18.0153 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
Molecular Formula | C17H13ClN4 |
Molecular Weight | 308.765 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
DescriptionCurator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/14978513
Curator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/14978513
Alprazolam, a benzodiazepine, is used to treat panic disorder and anxiety disorder. Unlike chlordiazepoxide, clorazepate, and prazepam, alprazolam has a shorter half-life and metabolites with minimal activity. Alprazolam may have significant drug interactions involving the hepatic cytochrome P-450 3A4 isoenzyme. Clinically, all benzodiazepines cause a dose-related central nervous system depressant activity varying from mild impairment of task performance to hypnosis. Unlike other benzodiazepines, alprazolam may also have some antidepressant activity, although clinical evidence of this is lacking. CNS agents of the 1,4 benzodiazepine class presumably exert their effects by binding at stereo specific receptors at several sites within the central nervous system. Their exact mechanism of action is unknown. Benzodiazepines bind nonspecifically to benzodiazepine receptors BNZ1, which mediates sleep, and BNZ2, which affects muscle relaxation, anticonvulsant activity, motor coordination, and memory. As benzodiazepine receptors are thought to be coupled to gamma-aminobutyric acid-A (GABAA) receptors, this enhances the effects of GABA by increasing GABA affinity for the GABA receptor. Binding of the inhibitory neurotransmitter GABA to the site opens the chloride channel, resulting in a hyperpolarized cell membrane that prevents further excitation of the cell.
CNS Activity
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL2093872 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18384456 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Palliative | XANAX Approved UseXANAX Tablets (alprazolam) are indicated for the management of anxiety disorder (a condition corresponding most closely to the APA Diagnostic and Statistical Manual [DSMIII-R] diagnosis of generalized anxiety disorder) or the short-term relief of symptoms of anxiety. Anxiety or tension associated with the stress of everyday life usually does not require treatment with an anxiolytic. XANAX is also indicated for the treatment of panic disorder, with or without agoraphobia. Studies supporting this claim were conducted in patients whose diagnoses corresponded closely to the DSM-III-R/IV criteria for panic disorder Launch Date1981 |
|||
Primary | XANAX Approved UseXANAX Tablets (alprazolam) are indicated for the management of anxiety disorder (a condition corresponding most closely to the APA Diagnostic and Statistical Manual [DSMIII-R] diagnosis of generalized anxiety disorder) or the short-term relief of symptoms of anxiety. Anxiety or tension associated with the stress of everyday life usually does not require treatment with an anxiolytic. XANAX is also indicated for the treatment of panic disorder, with or without agoraphobia. Studies supporting this claim were conducted in patients whose diagnoses corresponded closely to the DSM-III-R/IV criteria for panic disorder Launch Date1981 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
17.4 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6152055/ |
1 g single, oral dose: 1 g route of administration: Oral experiment type: SINGLE co-administered: |
ALPRAZOLAM plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
261 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6152055/ |
1 g single, oral dose: 1 g route of administration: Oral experiment type: SINGLE co-administered: |
ALPRAZOLAM plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
11.8 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6152055/ |
1 g single, oral dose: 1 g route of administration: Oral experiment type: SINGLE co-administered: |
ALPRAZOLAM plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
2.2 h |
unknown |
ALPRAZOLAM plasma | Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
Funbound
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
20% |
unknown |
ALPRAZOLAM plasma | Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
Doses
Dose | Population | Adverse events |
---|---|---|
1 mg 1 times / week multiple, oral Dose: 1 mg, 1 times / week Route: oral Route: multiple Dose: 1 mg, 1 times / week Sources: |
unhealthy |
Other AEs: Nausea, Fatigue... Other AEs: Nausea (below serious, 3 patients) Sources: Fatigue (below serious, 14 patients) Dizziness (below serious, 26 patients) Headache (below serious, 6 patients) Lethargy (below serious, 3 patients) Somnolence (below serious, 45 patients) Hiccups (below serious, 5 patients) |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Fatigue | below serious, 14 patients | 1 mg 1 times / week multiple, oral Dose: 1 mg, 1 times / week Route: oral Route: multiple Dose: 1 mg, 1 times / week Sources: |
unhealthy |
Dizziness | below serious, 26 patients | 1 mg 1 times / week multiple, oral Dose: 1 mg, 1 times / week Route: oral Route: multiple Dose: 1 mg, 1 times / week Sources: |
unhealthy |
Lethargy | below serious, 3 patients | 1 mg 1 times / week multiple, oral Dose: 1 mg, 1 times / week Route: oral Route: multiple Dose: 1 mg, 1 times / week Sources: |
unhealthy |
Nausea | below serious, 3 patients | 1 mg 1 times / week multiple, oral Dose: 1 mg, 1 times / week Route: oral Route: multiple Dose: 1 mg, 1 times / week Sources: |
unhealthy |
Somnolence | below serious, 45 patients | 1 mg 1 times / week multiple, oral Dose: 1 mg, 1 times / week Route: oral Route: multiple Dose: 1 mg, 1 times / week Sources: |
unhealthy |
Hiccups | below serious, 5 patients | 1 mg 1 times / week multiple, oral Dose: 1 mg, 1 times / week Route: oral Route: multiple Dose: 1 mg, 1 times / week Sources: |
unhealthy |
Headache | below serious, 6 patients | 1 mg 1 times / week multiple, oral Dose: 1 mg, 1 times / week Route: oral Route: multiple Dose: 1 mg, 1 times / week Sources: |
unhealthy |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
major | ||||
minor | ||||
minor | ||||
minor | yes (pharmacogenomic study) Comment: [PMID:16765147]:CYP3A5*3 genotype affects the disposition of alprazolam and thus influences the plasma levels of alprazolam |
|||
no | ||||
no | ||||
no | ||||
no | ||||
no | ||||
no | ||||
no | ||||
no | ||||
no | ||||
no | ||||
no | ||||
no | ||||
no | ||||
no | ||||
no | ||||
no | ||||
yes |
PubMed
Title | Date | PubMed |
---|---|---|
Alprazolam and hypotension. | 1999 May |
|
Comorbidity, neurobiology, and pharmacotherapy of social anxiety disorder. | 2001 |
|
High-speed liquid chromatography/tandem mass spectrometry using a monolithic column for high-throughput bioanalysis. | 2001 |
|
Simultaneous determination of fifteen low-dosed benzodiazepines in human urine by solid-phase extraction and gas chromatography-mass spectrometry. | 2001 Dec 25 |
|
Sensitive gas chromatographic--mass spectrometric screening of acetylated benzodiazepines. | 2001 Feb 23 |
|
In vitro/in vivo scaling of alprazolam metabolism by CYP3A4 and CYP3A5 in humans. | 2001 Mar |
|
Analytical methodology for the detection of benzodiazepine consumption in opioid-dependent subjects. | 2001 Mar |
|
Spontaneous activity as a contingency-controlled behavior within an operant context: alprazolam concentration-effect relations after subcutaneous administration in rats. | 2001 May |
|
A benzodiazepine mood effect scale: reliability and validity determined for alcohol-dependent subjects and adults with a parental history of alcoholism. | 2001 May |
|
[Psychiatric and psychological aspects of premenstrual syndrome]. | 2001 Nov-Dec |
|
The influence of stimulants, sedatives, and fatigue on tunnel vision: risk factors for driving and piloting. | 2001 Summer |
|
Effects of alprazolam and fluoxetine on morphine sensitization in mice. | 2002 |
|
Influence of the 5-HT2C receptor antagonist, SB-242084, in tests of anxiety. | 2002 Apr |
|
Utilization of psychotropic drugs in Taiwan: an overview of outpatient sector in 2000. | 2002 Aug |
|
Preoperative alprazolam reduces anxiety in ambulatory surgery patients: a comparison with oral midazolam. | 2002 Dec |
|
Development of Cushing's syndrome after use of a herbal remedy. | 2002 Dec 7 |
|
The comorbidity of bipolar and anxiety disorders: prevalence, psychobiology, and treatment issues. | 2002 Feb |
|
Behavioral, psycho-physiological and salivary cortisol modifications after short-term alprazolam treatment in patients with recent myocardial infarction. | 2002 Jan |
|
A comparative evaluation of the effects of oral lorazepam, alprazolam and diazepam on venous admixture. | 2002 Mar |
|
The orphanin receptor agonist RO 64-6198 does not induce place conditioning in rats. | 2002 Mar 25 |
|
Alprazolam, a benzodiazepine, does not modify the ACTH and cortisol response to hCRH and AVP, but blunts the cortisol response to ACTH in humans. | 2002 May |
|
Segmental ion spray LC-MS-MS analysis of benzodiazepines in hair of psychiatric patients. | 2002 Oct |
|
Neurobehavior effects in four strains of mice offspring exposed prenatally to alprazolam. | 2002 Oct |
|
Discriminative stimulus effects of zolpidem in squirrel monkeys: role of GABA(A)/alpha1 receptors. | 2003 Jan |
|
Determination of hypnotic benzodiazepines (alprazolam, estazolam, and midazolam) and their metabolites in rat hair and plasma by reversed-phase liquid-chromatography with electrospray ionization mass spectrometry. | 2003 Jan 15 |
Patents
Sample Use Guides
Tablets may be administered once daily, preferably in the morning. The tablets should be taken intact; they should not be chewed, crushed, or broken. The suggested total daily dose ranges between 3 to 6 mg/day. Dosage should be individualized for maximum beneficial effect
Route of Administration:
Oral
Substance Class |
Chemical
Created
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admin
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Edited
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Record UNII |
2I8KVA57TM
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Record Status |
Validated (UNII)
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Record Version |
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2I8KVA57TM
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178274
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DTXSID00159507
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