Details
Stereochemistry | ACHIRAL |
Molecular Formula | C17H13ClN4 |
Molecular Weight | 308.765 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CC1=NN=C2CN=C(C3=CC=CC=C3)C4=C(C=CC(Cl)=C4)N12
InChI
InChIKey=VREFGVBLTWBCJP-UHFFFAOYSA-N
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
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 |
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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 n = 85 Health Status: unhealthy Condition: Migraine Population Size: 85 Sources: |
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 n = 85 Health Status: unhealthy Condition: Migraine Population Size: 85 Sources: |
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 n = 85 Health Status: unhealthy Condition: Migraine Population Size: 85 Sources: |
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 n = 85 Health Status: unhealthy Condition: Migraine Population Size: 85 Sources: |
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 n = 85 Health Status: unhealthy Condition: Migraine Population Size: 85 Sources: |
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 n = 85 Health Status: unhealthy Condition: Migraine Population Size: 85 Sources: |
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 n = 85 Health Status: unhealthy Condition: Migraine Population Size: 85 Sources: |
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 n = 85 Health Status: unhealthy Condition: Migraine Population Size: 85 Sources: |
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 |
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no | ||||
no | ||||
no | ||||
no | ||||
no | ||||
no | ||||
no | ||||
no | ||||
no | ||||
no | ||||
no | ||||
no | ||||
no | ||||
no | ||||
no | ||||
no | ||||
yes |
PubMed
Title | Date | PubMed |
---|---|---|
Interactions between herbal medicines and prescribed drugs: a systematic review. | 2001 |
|
Comorbidity, neurobiology, and pharmacotherapy of social anxiety disorder. | 2001 |
|
Benzodiazepines and anticonvulsants for social phobia (social anxiety disorder). | 2001 |
|
Gabapentin use in benzodiazepine dependence and detoxification. | 2001 Apr |
|
[Does the addition of an anxiolytic drug improve the anti-emetic effectiveness of the steroid and granisetron combination in the prophylaxis of cisplatin-induced vomiting?]. | 2001 Aug 5 |
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Repeated measurements of aldicarb in blood and urine in a case of nonfatal poisoning. | 2001 Dec |
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Comparative study of tropisetron with the addition of dexamethasone or alprazolam in breast cancer patients receiving adjuvant chemotherapy with CEF (cyclophosphamide, epirubicin and 5-fluorouracil). | 2001 Dec |
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[Carotid endarterectomy under remifentanil]. | 2001 Dec |
|
Simultaneous determination of fifteen low-dosed benzodiazepines in human urine by solid-phase extraction and gas chromatography-mass spectrometry. | 2001 Dec 25 |
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Role of dopaminergic and serotonergic systems on behavioral stimulatory effects of low-dose alprazolam and lorazepam. | 2001 Feb |
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Opipramol for the treatment of generalized anxiety disorder: a placebo-controlled trial including an alprazolam-treated group. | 2001 Feb |
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Effects of alprazolam, caffeine, and zolpidem in humans trained to discriminate triazolam from placebo. | 2001 Feb 1 |
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Cyclodextrin solubilization of benzodiazepines: formulation of midazolam nasal spray. | 2001 Jan 5 |
|
No correlations between the urinary ratio of 6beta-hydroxycortisol to free cortisol and pharmacokinetics of alprazolam. | 2001 Jul |
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[Alpha-interferon and mental disorders]. | 2001 Jul-Aug |
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[Benzodiazepine consumption: survey of community pharmacies in Aquitaine]. | 2001 Jul-Aug |
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Psychosis after ultrarapid opiate detoxification. | 2001 Jun |
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In vitro/in vivo scaling of alprazolam metabolism by CYP3A4 and CYP3A5 in humans. | 2001 Mar |
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Spontaneous activity as a contingency-controlled behavior within an operant context: alprazolam concentration-effect relations after subcutaneous administration in rats. | 2001 May |
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Structural requirements of benzodiazepines for the inhibition of pig brain nitric oxide synthase. | 2001 Nov 30 |
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[Psychiatric and psychological aspects of premenstrual syndrome]. | 2001 Nov-Dec |
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Delayed post-hypoxic leukoencephalopathy. | 2001 Nov-Dec |
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Inverse agonist activity of selected ligands of platelet-activating factor receptor. | 2001 Oct |
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Full remission of panic attacks in a schizophrenic patient after switching from haloperidol to risperidone. | 2001 Winter |
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Effects of alprazolam and fluoxetine on morphine sensitization in mice. | 2002 |
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Influence of the 5-HT2C receptor antagonist, SB-242084, in tests of anxiety. | 2002 Apr |
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Sensitive method for the detection of 22 benzodiazepines by gas chromatography-ion trap tandem mass spectrometry. | 2002 Apr 19 |
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Comparative metabolic capabilities of CYP3A4, CYP3A5, and CYP3A7. | 2002 Aug |
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Effects of alprazolam on driving ability, memory functioning and psychomotor performance: a randomized, placebo-controlled study. | 2002 Aug |
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The comorbidity of bipolar and anxiety disorders: prevalence, psychobiology, and treatment issues. | 2002 Feb |
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Accidental ingestion of alprazolam in 415 dogs. | 2002 Feb |
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What did she want with Xanax? | 2002 Feb 11 |
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Behavioral, psycho-physiological and salivary cortisol modifications after short-term alprazolam treatment in patients with recent myocardial infarction. | 2002 Jan |
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Effects of commonly used benzodiazepines on the fetus, the neonate, and the nursing infant. | 2002 Jan |
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Alprazolam-induced panic disorder. | 2002 Jan-Feb |
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Tonic immobility in guinea pigs: a behavioural response for detecting an anxiolytic-like effect? | 2002 Jul |
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Effects of psychological stress and alprazolam on development of oral candidiasis in rats. | 2002 Jul |
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Street drug toxicity resulting from opiates combined with anticholinergics. | 2002 Jul-Sep |
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A comparative evaluation of the effects of oral lorazepam, alprazolam and diazepam on venous admixture. | 2002 Mar |
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Neuropeptide Y-Y2 receptors mediate anxiety in the amygdala. | 2002 Mar |
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A population-based case-control teratologic study of nitrazepam, medazepam, tofisopam, alprazolum and clonazepam treatment during pregnancy. | 2002 Mar 10 |
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The orphanin receptor agonist RO 64-6198 does not induce place conditioning in rats. | 2002 Mar 25 |
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Determination of estazolam in plasma by high-performance liquid chromatography with solid-phase extraction. | 2002 May |
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Segmental ion spray LC-MS-MS analysis of benzodiazepines in hair of psychiatric patients. | 2002 Oct |
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The stimulatory effect of canrenoate, a mineralocorticoid antagonist, on the activity of the hypothalamus-pituitary-adrenal axis is abolished by alprazolam, a benzodiazepine, in humans. | 2002 Oct |
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Effects of GABA(A) compounds on mCPP drug discrimination in rats. | 2002 Oct 18 |
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The effects of alprazolam and buspirone in light and moderate female social drinkers. | 2002 Sep |
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Don't ask, don't tell, but benzodiazepines are still the leading treatments for anxiety disorder. | 2002 Sep |
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Benzodiazepines and anterior pituitary function. | 2002 Sep |
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Selective serotonin reuptake inhibitors decrease impulsive behavior as measured by an adjusting delay procedure in the pigeon. | 2002 Sep |
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
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LIVERTOX |
NBK548178
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DEA NO. |
2882
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WHO-ATC |
N05BA12
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NDF-RT |
N0000007542
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WHO-VATC |
QN05BA12
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NDF-RT |
N0000175694
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NCI_THESAURUS |
C1012
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7111
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7207
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100000091908
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C227
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DB00404
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ALPRAZOLAM
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3426
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SUB05370MIG
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28981-97-7
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2611
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CHEMBL661
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D000525
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Alprazolam
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m1578
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249-349-2
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ACTIVE MOIETY
METABOLITE ACTIVE (PARENT)
METABOLITE LESS ACTIVE (PARENT)
SALT/SOLVATE (PARENT)