QUAZEPAM

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

Structure Search

SMILES

FC1=CC=CC=C1C2=NCC(=S)N(CC(F)(F)F)C3=CC=C(Cl)C=C23

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	386.794
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2016/018708s023lbl.pdf
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	Potency
GABA-A receptor; anion channel 203 Target ID: CHEMBL2093872 Sources: https://www.ncbi.nlm.nih.gov/pubmed/1969151 \| https://www.ncbi.nlm.nih.gov/pubmed/12420154	Positive Allosteric Modulator 186	101.0 nM [IC50]
Cytochrome P450 3A4 127 Target ID: CHEMBL340 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15801544	Substrate 661
Cytochrome P450 2C19 51 Target ID: CHEMBL3622 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15801544	Substrate 661
Cytochrome P450 2C9 50 Target ID: CHEMBL3397 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15801544	Substrate 661

Conditions

Condition	Modality	Targets	Highest Phase	Product
Insomnia 111 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2016/018708s023lbl.pdf	Primary		Approved 8583	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 1985

C_max

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

T_1/2

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

F_unbound

Value	Dose	Co-administered	Analyte	Population
5% DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/018708s018lbl.pdf			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: https://pubmed.ncbi.nlm.nih.gov/6705450/	healthy, 19 - 39 years Health Status: healthy Age Group: 19 - 39 years Sex: M Sources: https://pubmed.ncbi.nlm.nih.gov/6705450/	Sources: https://pubmed.ncbi.nlm.nih.gov/6705450/
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: https://pubmed.ncbi.nlm.nih.gov/6113910/	unhealthy, 22 -58 years Health Status: unhealthy Age Group: 22 -58 years Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/6113910/	Sources: https://pubmed.ncbi.nlm.nih.gov/6113910/
20 mg single, oral Dose: 20 mg Route: oral Route: single Dose: 20 mg Sources: https://pubmed.ncbi.nlm.nih.gov/15385836/	healthy, 30.6 years Health Status: healthy Age Group: 30.6 years Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/15385836/	Sources: https://pubmed.ncbi.nlm.nih.gov/15385836/
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: https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/018708s023lbl.pdf	unhealthy, adult Health Status: unhealthy Age Group: adult Sex: unknown Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/018708s023lbl.pdf	Other AEs: Drowsiness, Headache... Other AEs: Drowsiness (12%) Headache (5%) Fatigue (2%) Dizziness (2%) Dry mouth (2%) Dyspepsia (1%) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/018708s023lbl.pdf

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: https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/018708s023lbl.pdf	unhealthy, adult Health Status: unhealthy Age Group: adult Sex: unknown Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/018708s023lbl.pdf
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: https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/018708s023lbl.pdf	unhealthy, adult Health Status: unhealthy Age Group: adult Sex: unknown Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/018708s023lbl.pdf
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: https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/018708s023lbl.pdf	unhealthy, adult Health Status: unhealthy Age Group: adult Sex: unknown Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/018708s023lbl.pdf
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: https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/018708s023lbl.pdf	unhealthy, adult Health Status: unhealthy Age Group: adult Sex: unknown Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/018708s023lbl.pdf
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: https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/018708s023lbl.pdf	unhealthy, adult Health Status: unhealthy Age Group: adult Sex: unknown Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/018708s023lbl.pdf
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: https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/018708s023lbl.pdf	unhealthy, adult Health Status: unhealthy Age Group: adult Sex: unknown Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/018708s023lbl.pdf

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1946	substrate 1193

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP2B6 926 CYP2C8 1057 CYP2E1 1060	CYP2C19 1119

Drug as perpetrator

Target	Modality	Activity	Clinical evidence
CYP2B6 1160	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/018708s018lbl.pdf#page=2; https://patentimages.storage.googleapis.com/f0/4e/2b/bb4627286b330a/US7608616.pdf Page: 2.0	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 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/018708s018lbl.pdf#page=2; https://patentimages.storage.googleapis.com/f0/4e/2b/bb4627286b330a/US7608616.pdf Page: 2.0
CYP2C8 1117	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/018708s018lbl.pdf#page=2 Page: 2.0	no
CYP2E1 1146	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/018708s018lbl.pdf#page=2 Page: 2.0	no

Drug as victim

Target	Modality	Activity	Clinical evidence
CYP3A4 1946	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/15801544/; https://journals.lww.com/drug-monitoring/Abstract/2003/08000/Effects_of_Itraconazole_on_the_Plasma_Kinetics_of.10.aspx	major	no (co-administration study) Comment: Itraconazole treatment did not change the plasma kinetics of quazepam Sources: https://pubmed.ncbi.nlm.nih.gov/15801544/; https://journals.lww.com/drug-monitoring/Abstract/2003/08000/Effects_of_Itraconazole_on_the_Plasma_Kinetics_of.10.aspx
CYP2C19 1119	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/15801544/	minor
CYP2C9 1193	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/15801544/	minor

Sourcing

Vendor/Aggregator	ID	URL
ABI Chem	AC1L1JE0
Alfa Chemistry	36735-22-5	https://www.alfa-chemistry.com/quazepam-civ-200-mg-cas-36735-22-5-item-291703.htm
Ambinter	Amb13889656	http://www.ambinter.com/reference/13889656
Chemieliva Pharmaceutical Co., Ltd	PBCM0529451
ChemTik	CTK6H1725
Clearsynth	CS-EB-01820	https://www.clearsynth.com/en/CSEB01820.html
Clearsynth	CS-ER-01811	https://www.clearsynth.com/en/CSER01811.html
Compound Cloud	4999
iChemical	EBD23735	http://www.ichemical.com/chemicals/cas-36735-22-5
mcule	MCULE-9166809561
MuseChem	I008860	https://www.musechem.com/product/I008860.html
NovoSeek	4999
OChem	18282	http://www.ocheminc.com/index.php?act=psearch&pid=735Q225
PI Chemicals	PI-33655
Smolecule	S540818	http://www.smolecule.com/products/s540818
THE BioTek	bt-281199	https://www.thebiotek.com/product/inhibitors/bt-281199
Toronto Research Chemicals	KIT7213
ZINC	ZINC000000538266	http://zinc15.docking.org/substances/ZINC000000538266

PubMed

Title	Date	PubMed
Development of a list of potentially inappropriate drugs for the korean elderly using the delphi method.	2010-12	21818443
Inappropriate prescribing in the hospitalized elderly patient: defining the problem, evaluation tools, and possible solutions.	2010-04-07	20396637
Diagnosis and treatment of chronic insomnia.	2010-04	20814491
Neuronal network pharmacodynamics of GABAergic modulation in the human cortex determined using pharmaco-magnetoencephalography.	2010-04	19937723
Insomnia medication use and the probability of an accidental event in an older adult population.	2010	21701634
Algorithms for the assessment and management of insomnia in primary care.	2009-11-03	19936140
Benzodiazepine prescription and length of hospital stay at a Japanese university hospital.	2009-10-09	19818119
Drugs associated with more suicidal ideations are also associated with more suicide attempts.	2009-10-02	19798416
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.	2009-04	18937304
Interactions between herbal medicines and prescribed drugs: an updated systematic review.	2009	19719333
Community-based randomised controlled trial evaluating falls and osteoporosis risk management strategies.	2008-11-04	18983670
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.	2008-07	18603831
Indiplon in the treatment of sleep disorders.	2007-12	19300612
Insomnia in the elderly.	2007-10-01	19450355
Effects of genetic polymorphism of cytochrome P450 enzymes on the pharmacokinetics of benzodiazepines.	2007-08	17635335
Different effects of light food on pharmacokinetics and pharmacodynamics of three benzodiazepines, quazepam, nitrazepam and diazepam.	2007-02	17286787
Effects of quazepam as a preoperative night hypnotic: comparison with brotizolam.	2007	17285406
Sleep maintenance insomnia: strengths and weaknesses of current pharmacologic therapies.	2006-03-07	16517453
Interaction between grapefruit juice and hypnotic drugs: comparison of triazolam and quazepam.	2006-03	16416305
Safety and tolerability of oral antifungal agents in the treatment of fungal nail disease: a proven reality.	2005-12	18360572
Inhibitory effects of psychotropic drugs on mexiletine metabolism in human liver microsomes: prediction of in vivo drug interactions.	2005-06	16192107
[Pharmacological profiles of benzodiazepinergic hypnotics and correlations with receptor subtypes].	2005-06	16045197
In vitro metabolism of quazepam in human liver and intestine and assessment of drug interactions.	2005-04-02	15801544
Relative abuse liability of hypnotic drugs: a conceptual framework and algorithm for differentiating among compounds.	2005	16336040
Risk and benefit of drug use during pregnancy.	2005	16007261
Single oral dose pharmacokinetics of quazepam is influenced by CYP2C19 activity.	2004-10	15385836
Drug interaction between St John's Wort and quazepam.	2004-10	15373933
[Studies of time-course changes in human body balance after ingestion of long-acting hypnotics].	2004-02	15032004
Interaction study between fluvoxamine and quazepam.	2003-12	14615476
Effects of foods on the pharmacokinetics and clinical efficacy of quazepam.	2003-10	14653226
Effects of itraconazole on the plasma kinetics of quazepam and its two active metabolites after a single oral dose of the drug.	2003-08	12883232
Comparison of hangover effects among triazolam, flunitrazepam and quazepam in healthy subjects: a preliminary report.	2003-06	12753571
Time effects of food intake on the pharmacokinetics and pharmacodynamics of quazepam.	2003-04	12680887
Discriminative stimulus effects of zolpidem in squirrel monkeys: role of GABA(A)/alpha1 receptors.	2003-01	12420154
Pharmacokinetics and drug interactions of the sedative hypnotics.	2003	14561946
[Cytochrome P450 3A4 and Benzodiazepines].	2003	12875231
Effect of dietary fat content in meals on pharmacokinetics of quazepam.	2002-12	12463728
Feasibility of an every-other-night regimen in insomniac patients: subjective hypnotic effectiveness of quazepam, triazolam, and placebo.	1993-01	8428895
Quazepam versus triazolam in patients with sleep disorders: a double-blind study.	1993	7901174
Bidirectional effects of beta-carbolines in reflex epilepsy.	1987-09	3119161

Patents

Sample Use Guides

In Vivo Use Guide

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 `Mon Mar 31 18:10:11 GMT 2025` Edited by `admin` on `Mon Mar 31 18:10:11 GMT 2025`
Record UNII	JF8V0828ZI
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

QUAZEPAM

Official Name

English

QUAZEPAM CIV

Preferred 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 [WHO-DD]

Common Name

English

QUAZEPAM [MART.]

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