U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C17H11ClF4N2S
Molecular Weight 386.7959
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of QUAZEPAM

SMILES

c1ccc(c(c1)C2=NCC(=S)N(CC(F)(F)F)c3ccc(cc32)Cl)F

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

HIDE SMILES / InChI

Molecular Formula C17H11ClF4N2S
Molecular Weight 386.7959
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
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.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
DORAL

Approved Use

QUAZEPAM® (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 Date

5.04489607E11
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
28 ng/mL
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
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

AUC

ValueDoseCo-administeredAnalytePopulation
291 ng × h/mL
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
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

T1/2

ValueDoseCo-administeredAnalytePopulation
14.3 h
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
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

Funbound

ValueDoseCo-administeredAnalytePopulation
5%
QUAZEPAM plasma
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse 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
Dose: 20 mg
Route: oral
Route: single
Dose: 20 mg
Sources:
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%)
Headache (5%)
Fatigue (2%)
Dizziness (2%)
Dry mouth (2%)
Dyspepsia (1%)
Sources:
AEs

AEs

AESignificanceDosePopulation
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

Overview

CYP3A4CYP2C9CYP2D6hERG


OverviewOther

Other InhibitorOther SubstrateOther Inducer




Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical 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
no
no
Drug as victim
PubMed

PubMed

TitleDatePubMed
Bidirectional effects of beta-carbolines in reflex epilepsy.
1987 Sep
Quazepam versus triazolam in patients with sleep disorders: a double-blind study.
1993
Feasibility of an every-other-night regimen in insomniac patients: subjective hypnotic effectiveness of quazepam, triazolam, and placebo.
1993 Jan
Effect of dietary fat content in meals on pharmacokinetics of quazepam.
2002 Dec
[Cytochrome P450 3A4 and Benzodiazepines].
2003
Effects of itraconazole on the plasma kinetics of quazepam and its two active metabolites after a single oral dose of the drug.
2003 Aug
Interaction study between fluvoxamine and quazepam.
2003 Dec
Discriminative stimulus effects of zolpidem in squirrel monkeys: role of GABA(A)/alpha1 receptors.
2003 Jan
Effects of foods on the pharmacokinetics and clinical efficacy of quazepam.
2003 Oct
Pharmacokinetics and drug interactions of the sedative hypnotics.
2003 Winter
In vitro metabolism of quazepam in human liver and intestine and assessment of drug interactions.
2004 Nov-Dec
Single oral dose pharmacokinetics of quazepam is influenced by CYP2C19 activity.
2004 Oct
Drug interaction between St John's Wort and quazepam.
2004 Oct
Risk and benefit of drug use during pregnancy.
2005
Safety and tolerability of oral antifungal agents in the treatment of fungal nail disease: a proven reality.
2005 Dec
Inhibitory effects of psychotropic drugs on mexiletine metabolism in human liver microsomes: prediction of in vivo drug interactions.
2005 Jun
[Pharmacological profiles of benzodiazepinergic hypnotics and correlations with receptor subtypes].
2005 Jun
Effects of quazepam as a preoperative night hypnotic: comparison with brotizolam.
2007
Effects of genetic polymorphism of cytochrome P450 enzymes on the pharmacokinetics of benzodiazepines.
2007 Aug
Indiplon in the treatment of sleep disorders.
2007 Dec
Different effects of light food on pharmacokinetics and pharmacodynamics of three benzodiazepines, quazepam, nitrazepam and diazepam.
2007 Feb
Insomnia in the elderly.
2007 Oct 1
Community-based randomised controlled trial evaluating falls and osteoporosis risk management strategies.
2008 Nov 4
Interactions between herbal medicines and prescribed drugs: an updated systematic review.
2009
Simultaneous determination of benzodiazepines and their metabolites in human serum by liquid chromatography-tandem mass spectrometry using a high-resolution octadecyl silica column compatible with aqueous compounds.
2009 Apr
Algorithms for the assessment and management of insomnia in primary care.
2009 Nov 3
Drugs associated with more suicidal ideations are also associated with more suicide attempts.
2009 Oct 2
Benzodiazepine prescription and length of hospital stay at a Japanese university hospital.
2009 Oct 9
Insomnia medication use and the probability of an accidental event in an older adult population.
2010
Diagnosis and treatment of chronic insomnia.
2010 Apr
Neuronal network pharmacodynamics of GABAergic modulation in the human cortex determined using pharmaco-magnetoencephalography.
2010 Apr
Inappropriate prescribing in the hospitalized elderly patient: defining the problem, evaluation tools, and possible solutions.
2010 Apr 7
Development of a list of potentially inappropriate drugs for the korean elderly using the delphi method.
2010 Dec
Patents

Sample Use Guides

Recommended initial dose is 7.5 mg
Route of Administration: Oral
In Vitro Use Guide
IC50 values obtained with quazepam as the competing ligand were 101 nM in cortex and 258 nM in rat cerebellum.
Substance Class Chemical
Created
by admin
on Fri Jun 25 20:54:38 UTC 2021
Edited
by admin
on Fri Jun 25 20:54:38 UTC 2021
Record UNII
JF8V0828ZI
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
QUAZEPAM
INN   JAN   MART.   MI   ORANGE BOOK   USAN   USP   VANDF   WHO-DD  
USAN   INN  
Official Name English
QUAZEPAM [USP MONOGRAPH]
Common Name English
QUAZEPAM CIV [USP-RS]
Common Name English
7-CHLORO-5-(O-FLUOROPHENYL)-1,3-DIHYDRO-1-(2,2,2-TRIFLUOROETHYL)-2H-1,4-BENZODIAZEPINE-2-THIONE
Common Name English
2H-1,4-BENZODIAZEPINE-2-THIONE, 7-CHLORO-5-(2-FLUOROPHENYL)-1,3-DIHYDRO-1-(2,2,2-TRIFLUOROETHYL)-
Systematic Name English
SCH-16134
Code English
QUAZEPAM [INN]
Common Name English
QUAZEPAM CIV
USP-RS  
Common Name English
QUAZEPAM [MART.]
Common Name English
QUAZEPAM [WHO-DD]
Common Name English
DORAL
Common Name English
QUAZEPAM [USAN]
Common Name English
SCH 16134
Code English
NSC-309702
Code English
QUAZEPAM [JAN]
Common Name English
QUAZEPAM [MI]
Common Name English
QUAZEPAM [ORANGE BOOK]
Common Name English
QUAZEPAM [VANDF]
Common Name English
Classification Tree Code System Code
NDF-RT N0000175694
Created by admin on Fri Jun 25 20:54:38 UTC 2021 , Edited by admin on Fri Jun 25 20:54:38 UTC 2021
LIVERTOX 821
Created by admin on Fri Jun 25 20:54:38 UTC 2021 , Edited by admin on Fri Jun 25 20:54:38 UTC 2021
NDF-RT N0000007542
Created by admin on Fri Jun 25 20:54:38 UTC 2021 , Edited by admin on Fri Jun 25 20:54:38 UTC 2021
DEA NO. 2881
Created by admin on Fri Jun 25 20:54:38 UTC 2021 , Edited by admin on Fri Jun 25 20:54:38 UTC 2021
WHO-VATC QN05CD10
Created by admin on Fri Jun 25 20:54:38 UTC 2021 , Edited by admin on Fri Jun 25 20:54:38 UTC 2021
NCI_THESAURUS C1012
Created by admin on Fri Jun 25 20:54:38 UTC 2021 , Edited by admin on Fri Jun 25 20:54:38 UTC 2021
WHO-ATC N05CD10
Created by admin on Fri Jun 25 20:54:38 UTC 2021 , Edited by admin on Fri Jun 25 20:54:38 UTC 2021
Code System Code Type Description
ChEMBL
CHEMBL1200472
Created by admin on Fri Jun 25 20:54:38 UTC 2021 , Edited by admin on Fri Jun 25 20:54:38 UTC 2021
PRIMARY
DRUG CENTRAL
2336
Created by admin on Fri Jun 25 20:54:38 UTC 2021 , Edited by admin on Fri Jun 25 20:54:38 UTC 2021
PRIMARY
IUPHAR
7288
Created by admin on Fri Jun 25 20:54:38 UTC 2021 , Edited by admin on Fri Jun 25 20:54:38 UTC 2021
PRIMARY
EVMPD
SUB10188MIG
Created by admin on Fri Jun 25 20:54:38 UTC 2021 , Edited by admin on Fri Jun 25 20:54:38 UTC 2021
PRIMARY
INN
4018
Created by admin on Fri Jun 25 20:54:38 UTC 2021 , Edited by admin on Fri Jun 25 20:54:38 UTC 2021
PRIMARY
PUBCHEM
4999
Created by admin on Fri Jun 25 20:54:38 UTC 2021 , Edited by admin on Fri Jun 25 20:54:38 UTC 2021
PRIMARY
NCI_THESAURUS
C47699
Created by admin on Fri Jun 25 20:54:38 UTC 2021 , Edited by admin on Fri Jun 25 20:54:38 UTC 2021
PRIMARY
LACTMED
Quazepam
Created by admin on Fri Jun 25 20:54:38 UTC 2021 , Edited by admin on Fri Jun 25 20:54:38 UTC 2021
PRIMARY
FDA UNII
JF8V0828ZI
Created by admin on Fri Jun 25 20:54:38 UTC 2021 , Edited by admin on Fri Jun 25 20:54:38 UTC 2021
PRIMARY
DRUG BANK
DB01589
Created by admin on Fri Jun 25 20:54:38 UTC 2021 , Edited by admin on Fri Jun 25 20:54:38 UTC 2021
PRIMARY
MERCK INDEX
M9415
Created by admin on Fri Jun 25 20:54:38 UTC 2021 , Edited by admin on Fri Jun 25 20:54:38 UTC 2021
PRIMARY Merck Index
RXCUI
35185
Created by admin on Fri Jun 25 20:54:38 UTC 2021 , Edited by admin on Fri Jun 25 20:54:38 UTC 2021
PRIMARY RxNorm
MESH
C025130
Created by admin on Fri Jun 25 20:54:38 UTC 2021 , Edited by admin on Fri Jun 25 20:54:38 UTC 2021
PRIMARY
USP_CATALOG
1592205
Created by admin on Fri Jun 25 20:54:38 UTC 2021 , Edited by admin on Fri Jun 25 20:54:38 UTC 2021
PRIMARY USP-RS
CAS
36735-22-5
Created by admin on Fri Jun 25 20:54:38 UTC 2021 , Edited by admin on Fri Jun 25 20:54:38 UTC 2021
PRIMARY
WIKIPEDIA
QUAZEPAM
Created by admin on Fri Jun 25 20:54:38 UTC 2021 , Edited by admin on Fri Jun 25 20:54:38 UTC 2021
PRIMARY
EPA CompTox
36735-22-5
Created by admin on Fri Jun 25 20:54:38 UTC 2021 , Edited by admin on Fri Jun 25 20:54:38 UTC 2021
PRIMARY
ECHA (EC/EINECS)
253-179-4
Created by admin on Fri Jun 25 20:54:38 UTC 2021 , Edited by admin on Fri Jun 25 20:54:38 UTC 2021
PRIMARY
Related Record Type Details
BINDER->LIGAND
BINDING
Related Record Type Details
METABOLITE ACTIVE -> PARENT
MAJOR
PLASMA; URINE
METABOLITE -> PARENT
Large amount in urine
URINE
METABOLITE ACTIVE -> PARENT
MAJOR
PLASMA; URINE
METABOLITE -> PARENT
MAJOR
PLASMA; URINE
Related Record Type Details
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Biological Half-life PHARMACOKINETIC