Details
Stereochemistry | ACHIRAL |
Molecular Formula | C17H11ClF4N2S |
Molecular Weight | 386.794 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
FC1=C(C=CC=C1)C2=NCC(=S)N(CC(F)(F)F)C3=C2C=C(Cl)C=C3
InChI
InChIKey=IKMPWMZBZSAONZ-UHFFFAOYSA-N
InChI=1S/C17H11ClF4N2S/c18-10-5-6-14-12(7-10)16(11-3-1-2-4-13(11)19)23-8-15(25)24(14)9-17(20,21)22/h1-7H,8-9H2
DescriptionCurator's Comment: description was created based on several sources, including:
https://www.drugs.com/pro/quazepam.html | https://livertox.nlm.nih.gov/Quazepam.htm | https://www.ncbi.nlm.nih.gov/pubmed/1969151
Curator's Comment: description was created based on several sources, including:
https://www.drugs.com/pro/quazepam.html | https://livertox.nlm.nih.gov/Quazepam.htm | https://www.ncbi.nlm.nih.gov/pubmed/1969151
Quazepam is indicated for the treatment of insomnia characterized by difficulty in falling asleep, frequent nocturnal awakenings, and/or early morning awakenings. Quazepam interact preferentially with the benzodiazepine-1 (BZ1) receptors. Most common adverse reactions (>1%): drowsiness, headache, fatigue, dizziness, dry mouth, dyspepsia. Downward of CAN depressant dose adjustment may be necessary due to additive effects.
CNS Activity
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL2093872 |
101.0 nM [IC50] | ||
Target ID: CHEMBL340 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15801544 |
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Target ID: CHEMBL3622 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15801544 |
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Target ID: CHEMBL3397 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15801544 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | DORAL Approved UseQUAZEPAM® (quazepam) is indicated for the treatment of insomnia characterized by difficulty in falling asleep, frequent nocturnal awakenings, and/or early morning awakenings. The effectiveness of QUAZEPAM has been established in placebo-controlled clinical studies of 5 nights duration in acute and chronic insomnia. The sustained effectiveness of QUAZEPAM has been established in chronic insomnia in a sleep lab (polysomnographic) study of 28 nights duration. Because insomnia is often transient and intermittent, the prolonged administration of QUAZEPAM Tablets is generally not necessary or recommended. Since insomnia may be a symptom of several other disorders, the possibility that the complaint may be related to a condition for which there is a more specific treatment should be considered. QUAZEPAM, a gamma-aminobutyric (GABAA ) agonist, is indicated for the treatment of insomnia characterized by difficulty falling asleep, frequent nocturnal awakenings, and/or early morning awakenings. (1) Launch Date5.04489607E11 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
28 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/12680887 |
20 mg single, oral dose: 20 mg route of administration: Oral experiment type: SINGLE co-administered: |
QUAZEPAM plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
81.2 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/12680887 |
20 mg single, oral dose: 20 mg route of administration: Oral experiment type: SINGLE co-administered: |
QUAZEPAM plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
291 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/12680887 |
20 mg single, oral dose: 20 mg route of administration: Oral experiment type: SINGLE co-administered: |
QUAZEPAM plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
468 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/12680887 |
20 mg single, oral dose: 20 mg route of administration: Oral experiment type: SINGLE co-administered: |
QUAZEPAM plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
14.3 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/12680887 |
20 mg single, oral dose: 20 mg route of administration: Oral experiment type: SINGLE co-administered: |
QUAZEPAM plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
15.5 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/12680887 |
20 mg single, oral dose: 20 mg route of administration: Oral experiment type: SINGLE co-administered: |
QUAZEPAM plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED |
Funbound
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
5% |
QUAZEPAM plasma | Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
Doses
Dose | Population | Adverse events |
---|---|---|
15 mg 1 times / day steady, oral Recommended Dose: 15 mg, 1 times / day Route: oral Route: steady Dose: 15 mg, 1 times / day Sources: |
healthy, 19 - 39 years n = 11 Health Status: healthy Age Group: 19 - 39 years Sex: M Population Size: 11 Sources: |
|
30 mg 1 times / day steady, oral Highest studied dose Dose: 30 mg, 1 times / day Route: oral Route: steady Dose: 30 mg, 1 times / day Sources: |
unhealthy, 22 -58 years n = 18 Health Status: unhealthy Condition: insomnia Age Group: 22 -58 years Sex: M+F Population Size: 18 Sources: |
|
20 mg single, oral |
healthy, 30.6 years n = 20 Health Status: healthy Age Group: 30.6 years Sex: M+F Population Size: 20 Sources: |
|
15 mg 1 times / day steady, oral Recommended Dose: 15 mg, 1 times / day Route: oral Route: steady Dose: 15 mg, 1 times / day Sources: |
unhealthy, adult n = 267 Health Status: unhealthy Condition: insomnia Age Group: adult Sex: unknown Population Size: 267 Sources: |
Other AEs: Drowsiness, Headache... Other AEs: Drowsiness (12%) Sources: Headache (5%) Fatigue (2%) Dizziness (2%) Dry mouth (2%) Dyspepsia (1%) |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Dyspepsia | 1% | 15 mg 1 times / day steady, oral Recommended Dose: 15 mg, 1 times / day Route: oral Route: steady Dose: 15 mg, 1 times / day Sources: |
unhealthy, adult n = 267 Health Status: unhealthy Condition: insomnia Age Group: adult Sex: unknown Population Size: 267 Sources: |
Drowsiness | 12% | 15 mg 1 times / day steady, oral Recommended Dose: 15 mg, 1 times / day Route: oral Route: steady Dose: 15 mg, 1 times / day Sources: |
unhealthy, adult n = 267 Health Status: unhealthy Condition: insomnia Age Group: adult Sex: unknown Population Size: 267 Sources: |
Dizziness | 2% | 15 mg 1 times / day steady, oral Recommended Dose: 15 mg, 1 times / day Route: oral Route: steady Dose: 15 mg, 1 times / day Sources: |
unhealthy, adult n = 267 Health Status: unhealthy Condition: insomnia Age Group: adult Sex: unknown Population Size: 267 Sources: |
Dry mouth | 2% | 15 mg 1 times / day steady, oral Recommended Dose: 15 mg, 1 times / day Route: oral Route: steady Dose: 15 mg, 1 times / day Sources: |
unhealthy, adult n = 267 Health Status: unhealthy Condition: insomnia Age Group: adult Sex: unknown Population Size: 267 Sources: |
Fatigue | 2% | 15 mg 1 times / day steady, oral Recommended Dose: 15 mg, 1 times / day Route: oral Route: steady Dose: 15 mg, 1 times / day Sources: |
unhealthy, adult n = 267 Health Status: unhealthy Condition: insomnia Age Group: adult Sex: unknown Population Size: 267 Sources: |
Headache | 5% | 15 mg 1 times / day steady, oral Recommended Dose: 15 mg, 1 times / day Route: oral Route: steady Dose: 15 mg, 1 times / day Sources: |
unhealthy, adult n = 267 Health Status: unhealthy Condition: insomnia Age Group: adult Sex: unknown Population Size: 267 Sources: |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
likely | likely (co-administration study) Comment: mechanism based inhibition; Increased plasma concentrations of drugs that are substrates of CYP2B6 may result if coadministered with DORAL; Bupropion (a CYP2B6 substrate): Co-administration of a single dose of 150 mg Bupropion Hydrochloride XL with steady state quazepam did not significantly affect the AUC and Cmax of bupropion or its primary metabolite, hydroxybupropion Page: 2.0 |
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Page: 2.0 |
no | |||
Page: 2.0 |
no |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
major | no (co-administration study) Comment: Itraconazole treatment did not change the plasma kinetics of quazepam |
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minor | ||||
minor |
PubMed
Title | Date | PubMed |
---|---|---|
Quazepam versus triazolam in patients with sleep disorders: a double-blind study. | 1993 |
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Feasibility of an every-other-night regimen in insomniac patients: subjective hypnotic effectiveness of quazepam, triazolam, and placebo. | 1993 Jan |
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Effect of dietary fat content in meals on pharmacokinetics of quazepam. | 2002 Dec |
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[Cytochrome P450 3A4 and Benzodiazepines]. | 2003 |
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Time effects of food intake on the pharmacokinetics and pharmacodynamics of quazepam. | 2003 Apr |
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Effects of itraconazole on the plasma kinetics of quazepam and its two active metabolites after a single oral dose of the drug. | 2003 Aug |
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Interaction study between fluvoxamine and quazepam. | 2003 Dec |
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Discriminative stimulus effects of zolpidem in squirrel monkeys: role of GABA(A)/alpha1 receptors. | 2003 Jan |
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Comparison of hangover effects among triazolam, flunitrazepam and quazepam in healthy subjects: a preliminary report. | 2003 Jun |
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Effects of foods on the pharmacokinetics and clinical efficacy of quazepam. | 2003 Oct |
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Pharmacokinetics and drug interactions of the sedative hypnotics. | 2003 Winter |
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[Studies of time-course changes in human body balance after ingestion of long-acting hypnotics]. | 2004 Feb |
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In vitro metabolism of quazepam in human liver and intestine and assessment of drug interactions. | 2004 Nov-Dec |
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Drug interaction between St John's Wort and quazepam. | 2004 Oct |
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Relative abuse liability of hypnotic drugs: a conceptual framework and algorithm for differentiating among compounds. | 2005 |
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Risk and benefit of drug use during pregnancy. | 2005 |
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Safety and tolerability of oral antifungal agents in the treatment of fungal nail disease: a proven reality. | 2005 Dec |
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Interaction between grapefruit juice and hypnotic drugs: comparison of triazolam and quazepam. | 2006 Mar |
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Effects of quazepam as a preoperative night hypnotic: comparison with brotizolam. | 2007 |
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Effects of genetic polymorphism of cytochrome P450 enzymes on the pharmacokinetics of benzodiazepines. | 2007 Aug |
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Different effects of light food on pharmacokinetics and pharmacodynamics of three benzodiazepines, quazepam, nitrazepam and diazepam. | 2007 Feb |
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Insomnia in the elderly. | 2007 Oct 1 |
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Comparison of short- and long-acting benzodiazepine-receptor agonists with different receptor selectivity on motor coordination and muscle relaxation following thiopental-induced anesthesia in mice. | 2008 Jul |
|
Community-based randomised controlled trial evaluating falls and osteoporosis risk management strategies. | 2008 Nov 4 |
|
Algorithms for the assessment and management of insomnia in primary care. | 2009 Nov 3 |
|
Diagnosis and treatment of chronic insomnia. | 2010 Apr |
|
Development of a list of potentially inappropriate drugs for the korean elderly using the delphi method. | 2010 Dec |
Sample Use Guides
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/2892106
IC50 values obtained with quazepam as the competing ligand were 101 nM in cortex
and 258 nM in rat cerebellum.
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Classification Tree | Code System | Code | ||
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NDF-RT |
N0000175694
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LIVERTOX |
NBK548297
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NDF-RT |
N0000007542
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DEA NO. |
2881
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WHO-VATC |
QN05CD10
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NCI_THESAURUS |
C1012
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WHO-ATC |
N05CD10
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CHEMBL1200472
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2336
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7288
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SUB10188MIG
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4018
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4999
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C47699
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1592205
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Quazepam
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309702
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JF8V0828ZI
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JF8V0828ZI
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DB01589
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m9415
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35185
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C025130
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36735-22-5
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QUAZEPAM
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28934
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DTXSID60190193
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253-179-4
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100000081100
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ACTIVE MOIETY
METABOLITE (PARENT)
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