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=CC(Cl)=CC=C4N12
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 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 |
|||
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 |
|
Alprozolam poisoning. | 2001 Apr |
|
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 |
|
[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 |
|
Open study of effects of alprazolam on seasonal affective disorder. | 2001 Feb |
|
Role of dopaminergic and serotonergic systems on behavioral stimulatory effects of low-dose alprazolam and lorazepam. | 2001 Feb |
|
Opipramol for the treatment of generalized anxiety disorder: a placebo-controlled trial including an alprazolam-treated group. | 2001 Feb |
|
Cyclodextrin solubilization of benzodiazepines: formulation of midazolam nasal spray. | 2001 Jan 5 |
|
Psychotropic drug use in Italy, 1984-99: the impact of a change in reimbursement status. | 2001 Jul |
|
Psychosis after ultrarapid opiate detoxification. | 2001 Jun |
|
Delayed post-hypoxic leukoencephalopathy. | 2001 Nov-Dec |
|
[Two case reports of cerebral autosomal dominant arteriophaty with subcortical infarctions and leukoencephalopathy (CADASIL)]. | 2001 Oct |
|
Differential effects of alprazolam on the baseline and fear-potentiated startle reflex in humans: a dose-response study. | 2001 Oct |
|
Alprazolam withdrawal and tolerance measured in the social conflict test in mice. | 2001 Sep |
|
Recruiting phobic research subjects: effectiveness and cost. | 2001 Winter |
|
Full remission of panic attacks in a schizophrenic patient after switching from haloperidol to risperidone. | 2001 Winter |
|
Differential metabolism of alprazolam by liver and brain cytochrome (P4503A) to pharmacologically active metabolite. | 2002 |
|
Augmentation of analgesic effect of ibuprofen by alprazolam in experimental model of pain. | 2002 |
|
Orally delivered alprazolam, diazepam, and triazolam as reinforcers in rhesus monkeys. | 2002 Apr |
|
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 |
|
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 |
|
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 |
|
[The application of a broard spectrum automatic rapid drug identification system in acute drug poisoning]. | 2002 Jun |
|
GABA(A)-benzodiazepine receptor complex sensitivity in 5-HT(1A) receptor knockout mice on a 129/Sv background. | 2002 Jun 28 |
|
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 |
|
Isolation and structural elucidation of degradation products of alprazolam: photostability studies of alprazolam tablets. | 2002 May |
|
Nightmares and panic disorder associated with carvedilol overdose. | 2002 Nov |
|
Self-association and cyclodextrin solubilization of drugs. | 2002 Nov |
|
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 |
|
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 |
|
Spectrofluorimetric assay for the photodegradation products of alprazolam. | 2002 Oct 15 |
|
Effects of GABA(A) compounds on mCPP drug discrimination in rats. | 2002 Oct 18 |
|
The effects of alprazolam and buspirone in light and moderate female social drinkers. | 2002 Sep |
|
Don't ask, don't tell, but benzodiazepines are still the leading treatments for anxiety disorder. | 2002 Sep |
|
Target-controlled infusion of propofol induction with or without plasma concentration constraint in high-risk adult patients undergoing cardiac surgery. | 2002 Sep |
|
Suppression of monocyte chemoattractant protein 1, but not IL-8, by alprazolam: effect of alprazolam on c-Rel/p65 and c-Rel/p50 binding to the monocyte chemoattractant protein 1 promoter region. | 2002 Sep 15 |
|
Assay sensitivity, failed clinical trials, and the conduct of science. | 2002 Sep-Oct |
|
Discriminative stimulus effects of zolpidem in squirrel monkeys: role of GABA(A)/alpha1 receptors. | 2003 Jan |
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
by
admin
on
Edited
Fri Dec 15 19:39:22 GMT 2023
by
admin
on
Fri Dec 15 19:39:22 GMT 2023
|
Record UNII |
2I8KVA57TM
|
Record Status |
Validated (UNII)
|
Record Version |
|
-
Download
Name | Type | Language | ||
---|---|---|---|---|
|
Common Name | English |
Code System | Code | Type | Description | ||
---|---|---|---|---|---|
|
135748-32-2
Created by
admin on Fri Dec 15 19:39:22 GMT 2023 , Edited by admin on Fri Dec 15 19:39:22 GMT 2023
|
PRIMARY | |||
|
2I8KVA57TM
Created by
admin on Fri Dec 15 19:39:22 GMT 2023 , Edited by admin on Fri Dec 15 19:39:22 GMT 2023
|
PRIMARY | |||
|
178274
Created by
admin on Fri Dec 15 19:39:22 GMT 2023 , Edited by admin on Fri Dec 15 19:39:22 GMT 2023
|
PRIMARY | |||
|
DTXSID00159507
Created by
admin on Fri Dec 15 19:39:22 GMT 2023 , Edited by admin on Fri Dec 15 19:39:22 GMT 2023
|
PRIMARY |
Related Record | Type | Details | ||
---|---|---|---|---|
|
PARENT -> SALT/SOLVATE | |||
|
ANHYDROUS->SOLVATE |