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=CC(Cl)=CC=C4N12
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
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 |
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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 |
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 |
|
Interactions between herbal medicines and prescribed drugs: a systematic review. | 2001 |
|
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 |
|
Gabapentin use in benzodiazepine dependence and detoxification. | 2001 Apr |
|
Effect of alosetron on the pharmacokinetics of alprazolam. | 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 |
|
Repeated measurements of aldicarb in blood and urine in a case of nonfatal poisoning. | 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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Negligible tolerance produced by chronic intravenous alprazolam administration: a low serum drug concentration effect. | 2001 Feb |
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Electrospray ionization gas-phase electrophoresis under ambient conditions and it's potential or high-speed separations. | 2001 Feb |
|
Anxiety-like behavior in elevated plus-maze tests in repeatedly cold-stressed mice. | 2001 Feb |
|
Effects of alprazolam, caffeine, and zolpidem in humans trained to discriminate triazolam from placebo. | 2001 Feb 1 |
|
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 |
|
[Psychiatric and psychological aspects of premenstrual syndrome]. | 2001 Nov-Dec |
|
Delayed post-hypoxic leukoencephalopathy. | 2001 Nov-Dec |
|
Augmentation of analgesic effect of ibuprofen by alprazolam in experimental model of pain. | 2002 |
|
Sensitive method for the detection of 22 benzodiazepines by gas chromatography-ion trap tandem mass spectrometry. | 2002 Apr 19 |
|
Utilization of psychotropic drugs in Taiwan: an overview of outpatient sector in 2000. | 2002 Aug |
|
Molecular actions of (S)-desmethylzopiclone (SEP-174559), an anxiolytic metabolite of zopiclone. | 2002 Aug |
|
Comparative metabolic capabilities of CYP3A4, CYP3A5, and CYP3A7. | 2002 Aug |
|
Effects of alprazolam on driving ability, memory functioning and psychomotor performance: a randomized, placebo-controlled study. | 2002 Aug |
|
The comorbidity of bipolar and anxiety disorders: prevalence, psychobiology, and treatment issues. | 2002 Feb |
|
Accidental ingestion of alprazolam in 415 dogs. | 2002 Feb |
|
What did she want with Xanax? | 2002 Feb 11 |
|
Behavioral, psycho-physiological and salivary cortisol modifications after short-term alprazolam treatment in patients with recent myocardial infarction. | 2002 Jan |
|
Effects of commonly used benzodiazepines on the fetus, the neonate, and the nursing infant. | 2002 Jan |
|
Alprazolam-induced panic disorder. | 2002 Jan-Feb |
|
Effects of psychological stress and alprazolam on development of oral candidiasis in rats. | 2002 Jul |
|
Street drug toxicity resulting from opiates combined with anticholinergics. | 2002 Jul-Sep |
|
GABA(A)-benzodiazepine receptor complex sensitivity in 5-HT(1A) receptor knockout mice on a 129/Sv background. | 2002 Jun 28 |
|
A comparative evaluation of the effects of oral lorazepam, alprazolam and diazepam on venous admixture. | 2002 Mar |
|
Neuropeptide Y-Y2 receptors mediate anxiety in the amygdala. | 2002 Mar |
|
A population-based case-control teratologic study of nitrazepam, medazepam, tofisopam, alprazolum and clonazepam treatment during pregnancy. | 2002 Mar 10 |
|
The orphanin receptor agonist RO 64-6198 does not induce place conditioning in rats. | 2002 Mar 25 |
|
Investigation of excipient type and level on drug release from controlled release tablets containing HPMC. | 2002 May |
|
Determination of estazolam in plasma by high-performance liquid chromatography with solid-phase extraction. | 2002 May |
|
Acute dystonic reactions to "street Xanax". | 2002 May 30 |
|
Nightmares and panic disorder associated with carvedilol overdose. | 2002 Nov |
|
Synthesis and biological evaluation of 7,8,9,10-tetrahydroimidazo[1,2-c]pyrido[3,4-e]pyrimdin-5(6H)-ones as functionally selective ligands of the benzodiazepine receptor site on the GABA(A) receptor. | 2002 Nov 7 |
|
Clinical inquiries. What medications are effective for treating symptoms of premenstrual syndrome (PMS)? | 2002 Oct |
|
Neurobehavior effects in four strains of mice offspring exposed prenatally to alprazolam. | 2002 Oct |
|
Prenatal exposure to diazepam and alprazolam, but not to zolpidem, affects behavioural stress reactivity in handling-naïve and handling-habituated adult male rat progeny. | 2002 Oct 25 |
|
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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Record UNII |
YU55MQ3IZY
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Validated (UNII)
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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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SUB05370MIG
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28981-97-7
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DTXSID4022577
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1015008
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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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Related Record | Type | Details | ||
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DERIVATIVE -> PARENT | |||
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BASIS OF STRENGTH->SUBSTANCE |
ASSAY (HPLC)
USP
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SOLVATE->ANHYDROUS | |||
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METABOLIC ENZYME -> SUBSTRATE | |||
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SALT/SOLVATE -> PARENT |
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BASIS OF STRENGTH->SUBSTANCE |
CHROMATOGRAPHIC PURITY (TLC)
EP
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BINDER->LIGAND |
BINDING
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Related Record | Type | Details | ||
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METABOLITE ACTIVE -> PARENT |
α-Hydroxy alprazolam (α-OHALP) is the minor but pharmacologically active metabolite
MINOR
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METABOLITE ACTIVE -> PARENT |
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METABOLITE LESS ACTIVE -> PARENT |
4-hydroxy alprazolam (4-OHALP) is the major and pharmacologically less active metabolite [of alprazolam]
MAJOR
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METABOLITE LESS ACTIVE -> PARENT |
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Related Record | Type | Details | ||
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IMPURITY -> PARENT |
UNSPECIFIED
EP
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IMPURITY -> PARENT |
UNSPECIFIED
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
UNSPECIFIED
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
UNSPECIFIED
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
UNSPECIFIED
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
UNSPECIFIED
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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IMPURITY -> PARENT |
UNSPECIFIED
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
UNSPECIFIED
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
UNSPECIFIED
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
UNSPECIFIED
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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Related Record | Type | Details | ||
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ACTIVE MOIETY |
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Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
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RENAL CLEARANCE | PHARMACOKINETIC |
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MAXIMUM TOLERATED DOSE | TOXICITY |
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ROUTE OF ADMINISTRATION |
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Biological Half-life | PHARMACOKINETIC |
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EXTENDED-RELEASE |
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Volume of Distribution | PHARMACOKINETIC |
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ORAL BIOAVAILABILITY | PHARMACOKINETIC |
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IMMEDIATE-RELEASE PHARMACOKINETIC |
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Tmax | PHARMACOKINETIC |
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ORAL, IMMEDIATE-RELEASE TABLET |
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