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
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 Date3.72038402E11 |
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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 Date3.72038402E11 |
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 |
---|---|---|
Repeated measurements of aldicarb in blood and urine in a case of nonfatal poisoning. | 2001 Dec |
|
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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Delayed post-hypoxic leukoencephalopathy. | 2001 Nov-Dec |
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Effects of alprazolam and fluoxetine on morphine sensitization in mice. | 2002 |
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Differential metabolism of alprazolam by liver and brain cytochrome (P4503A) to pharmacologically active metabolite. | 2002 |
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Augmentation of analgesic effect of ibuprofen by alprazolam in experimental model of pain. | 2002 |
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Orally delivered alprazolam, diazepam, and triazolam as reinforcers in rhesus monkeys. | 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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Utilization of psychotropic drugs in Taiwan: an overview of outpatient sector in 2000. | 2002 Aug |
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Molecular actions of (S)-desmethylzopiclone (SEP-174559), an anxiolytic metabolite of zopiclone. | 2002 Aug |
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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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Preoperative alprazolam reduces anxiety in ambulatory surgery patients: a comparison with oral midazolam. | 2002 Dec |
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Development of Cushing's syndrome after use of a herbal remedy. | 2002 Dec 7 |
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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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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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[The application of a broard spectrum automatic rapid drug identification system in acute drug poisoning]. | 2002 Jun |
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GABA(A)-benzodiazepine receptor complex sensitivity in 5-HT(1A) receptor knockout mice on a 129/Sv background. | 2002 Jun 28 |
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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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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 |
|
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 |
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Isolation and structural elucidation of degradation products of alprazolam: photostability studies of alprazolam tablets. | 2002 May |
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Acute dystonic reactions to "street Xanax". | 2002 May 30 |
|
5-ethoxymethyl-7-fluoro-3-oxo-1,2,3,5-tetrahydrobenzo[4,5]imidazo[1,2a]pyridine-4-N-(2-fluorophenyl)carboxamide (RWJ-51204), a new nonbenzodiazepine anxiolytic. | 2002 Nov |
|
Self-association and cyclodextrin solubilization of drugs. | 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 |
|
Segmental ion spray LC-MS-MS analysis of benzodiazepines in hair of psychiatric patients. | 2002 Oct |
|
Clinical inquiries. What medications are effective for treating symptoms of premenstrual syndrome (PMS)? | 2002 Oct |
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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 |
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Effects of GABA(A) compounds on mCPP drug discrimination in rats. | 2002 Oct 18 |
|
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 |
|
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 |
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Benzodiazepines and anterior pituitary function. | 2002 Sep |
|
Selective serotonin reuptake inhibitors decrease impulsive behavior as measured by an adjusting delay procedure in the pigeon. | 2002 Sep |
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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 |
|
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
by
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on
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Wed Jul 05 22:48:59 UTC 2023
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on
Wed Jul 05 22:48:59 UTC 2023
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Record UNII |
YU55MQ3IZY
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Record Status |
Validated (UNII)
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LIVERTOX |
NBK548178
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DEA NO. |
2882
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N05BA12
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N0000007542
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QN05BA12
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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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YU55MQ3IZY
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3426
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2118
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760140
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596
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SUB05370MIG
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28981-97-7
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2611
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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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PRIMARY |
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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