Identification

Name
Quazepam
Accession Number
DB01589
Description

Quazepam is a drug which is a benzodiazepine derivative. It induces impairment of motor function and has hypnotic properties. Quazepam is used to treat insomnia.

Type
Small Molecule
Groups
Approved, Illicit
Structure
Thumb
Weight
Average: 386.794
Monoisotopic: 386.026759579
Chemical Formula
C17H11ClF4N2S
Synonyms
  • Quazepam
  • Quazepamum
External IDs
  • SCH 16134
  • SCH-16134

Pharmacology

Pharmacology
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Indication

Used to treat insomnia.

Associated Conditions
Contraindications & Blackbox Warnings
Contraindications
Contraindications & Blackbox Warnings
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Pharmacodynamics

Quazepam is a benzodiazepine derivative. The main pharmacological action of quazepam is the enhancement of the neurotransmitter GABA at the GABAA receptor.

Mechanism of action
TargetActionsOrganism
AGABA(A) Receptor
positive allosteric modulator
Humans
AGABA(A) Receptor Benzodiazepine Binding Site
ligand
Humans
Absorption

Bioavailability is 29-35% following oral administration.

Volume of distribution
Not Available
Protein binding
Not Available
Metabolism

Hepatic.

Hover over products below to view reaction partners

Route of elimination
Not Available
Half-life

39 hours

Clearance
Not Available
Adverse Effects
Medicalerrors
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Toxicity
Not Available
Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
AbametapirThe serum concentration of Quazepam can be increased when it is combined with Abametapir.
AbataceptThe metabolism of Quazepam can be increased when combined with Abatacept.
AbirateroneThe metabolism of Quazepam can be decreased when combined with Abiraterone.
AcenocoumarolThe metabolism of Acenocoumarol can be decreased when combined with Quazepam.
AcetazolamideThe risk or severity of adverse effects can be increased when Acetazolamide is combined with Quazepam.
AcetohexamideThe metabolism of Quazepam can be decreased when combined with Acetohexamide.
AcetophenazineThe risk or severity of adverse effects can be increased when Acetophenazine is combined with Quazepam.
Acetyl sulfisoxazoleThe metabolism of Quazepam can be decreased when combined with Acetyl sulfisoxazole.
Acetylsalicylic acidThe metabolism of Quazepam can be decreased when combined with Acetylsalicylic acid.
AclidiniumQuazepam may increase the central nervous system depressant (CNS depressant) activities of Aclidinium.
Interactions
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Food Interactions
  • Avoid alcohol. Ingesting alcohol may increase the drowsiness and CNS depression caused by quazepam.

Products

Products
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International/Other Brands
Dormalin
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
DoralTablet15 mg/1OralNuro Pharma, Inc.1985-12-272014-12-18US flag
DoralTablet15 mg/1OralGalt Pharmaceuticals, LLC2017-07-19Not applicableUS flag
DoralTablet15 mg/1OralQuestcor Pharmaceuticals, Inc.1985-12-272013-06-20US flag
DoralTablet15 mg/1OralPhysicians Total Care, Inc.1994-03-022002-06-30US flag
QuazepamTablet15 mg/1Oralbryant ranch prepack2013-08-082016-01-29US flag
QuazepamTablet15 mg/1OralPreferreed Pharmaceuticals Inc.2013-08-152016-01-11US flag
QuazepamTablet15 mg/1OralKLE 2, Inc.2013-08-082015-10-30US flag
QuazepamTablet15 mg/1OralAtland Pharmaceuticals, Llc2018-03-20Not applicableUS flag
QuazepamTablet15 mg/1OralA S Medication Solutions2013-08-08Not applicableUS flag
QuazepamTablet15 mg/1OralLake Erie Medical Dba Quality Care Produts Llc2013-08-082015-08-24US flag

Categories

ATC Codes
N05CD10 — Quazepam
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as 1,4-benzodiazepines. These are organic compounds containing a benzene ring fused to a 1,4-azepine.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Benzodiazepines
Sub Class
1,4-benzodiazepines
Direct Parent
1,4-benzodiazepines
Alternative Parents
Fluorobenzenes / Aryl fluorides / Aryl chlorides / Thiolactams / Ketimines / Propargyl-type 1,3-dipolar organic compounds / Azacyclic compounds / Thiocarbonyl compounds / Organopnictogen compounds / Organofluorides
show 3 more
Substituents
1,4-benzodiazepine / Alkyl fluoride / Alkyl halide / Aromatic heteropolycyclic compound / Aryl chloride / Aryl fluoride / Aryl halide / Azacycle / Benzenoid / Fluorobenzene
show 16 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
benzodiazepine (CHEBI:8694)

Chemical Identifiers

UNII
JF8V0828ZI
CAS number
36735-22-5
InChI Key
IKMPWMZBZSAONZ-UHFFFAOYSA-N
InChI
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
IUPAC Name
7-chloro-5-(2-fluorophenyl)-1-(2,2,2-trifluoroethyl)-2,3-dihydro-1H-1,4-benzodiazepine-2-thione
SMILES
FC1=CC=CC=C1C1=NCC(=S)N(CC(F)(F)F)C2=C1C=C(Cl)C=C2

References

General References
Not Available
Human Metabolome Database
HMDB0015528
KEGG Drug
D00457
KEGG Compound
C07336
PubChem Compound
4999
PubChem Substance
46505952
ChemSpider
4825
RxNav
35185
ChEBI
8694
ChEMBL
CHEMBL1200472
ZINC
ZINC000000538266
Therapeutic Targets Database
DAP000690
PharmGKB
PA164744373
Drugs.com
Drugs.com Drug Page
Wikipedia
Quazepam

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
Not Available
Packagers
  • Physicians Total Care Inc.
  • Questcor
Dosage Forms
FormRouteStrength
TabletOral15 mg/1
TabletOral15 MG
Prices
Not Available
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)Region
US7608616No2009-10-272028-06-03US flag

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)137.5-139 °CPhysProp
logP4.03SANGSTER (1994)
Predicted Properties
PropertyValueSource
Water Solubility0.00231 mg/mLALOGPS
logP4.76ALOGPS
logP5.06ChemAxon
logS-5.2ALOGPS
pKa (Strongest Acidic)18.93ChemAxon
pKa (Strongest Basic)2.59ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area15.6 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity93.47 m3·mol-1ChemAxon
Polarizability33.99 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9385
Blood Brain Barrier+0.9789
Caco-2 permeable+0.5748
P-glycoprotein substrateSubstrate0.5341
P-glycoprotein inhibitor IInhibitor0.9324
P-glycoprotein inhibitor IIInhibitor0.8253
Renal organic cation transporterInhibitor0.6883
CYP450 2C9 substrateNon-substrate0.8255
CYP450 2D6 substrateNon-substrate0.8135
CYP450 3A4 substrateSubstrate0.5133
CYP450 1A2 substrateInhibitor0.7023
CYP450 2C9 inhibitorInhibitor0.5757
CYP450 2D6 inhibitorNon-inhibitor0.6337
CYP450 2C19 inhibitorInhibitor0.688
CYP450 3A4 inhibitorInhibitor0.7937
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.9484
Ames testNon AMES toxic0.6683
CarcinogenicityNon-carcinogens0.7273
BiodegradationNot ready biodegradable1.0
Rat acute toxicity1.9195 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.978
hERG inhibition (predictor II)Inhibitor0.6396
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Mass Spectrum (Electron Ionization)MSsplash10-05aa-3988000000-ca1cf29da979ef46dd6c
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Targets

Kind
Protein group
Organism
Humans
Pharmacological action
Yes
Actions
Positive allosteric modulator
Curator comments
The GABA(A) receptor is pentameric (i.e. comprising 5 subunit proteins) and therefore has a multitude of potential isoforms. The above target is a collection of all possible GABA(A) subunits that may participate in the formation of the pentameric receptor and is not meant to imply direct a drug-protein interaction for each individual subunit.
General Function
Inhibitory extracellular ligand-gated ion channel activity
Specific Function
Component of the heteropentameric receptor for GABA, the major inhibitory neurotransmitter in the vertebrate brain. Functions also as histamine receptor and mediates cellular responses to histamine...

Components:
References
  1. Sigel E, Steinmann ME: Structure, function, and modulation of GABA(A) receptors. J Biol Chem. 2012 Nov 23;287(48):40224-31. doi: 10.1074/jbc.R112.386664. Epub 2012 Oct 4. [PubMed:23038269]
  2. Zhu S, Noviello CM, Teng J, Walsh RM Jr, Kim JJ, Hibbs RE: Structure of a human synaptic GABAA receptor. Nature. 2018 Jul;559(7712):67-72. doi: 10.1038/s41586-018-0255-3. Epub 2018 Jun 27. [PubMed:29950725]
Kind
Protein group
Organism
Humans
Pharmacological action
Yes
Actions
Ligand
Curator comments
Benzodiazepines modulate GABA(A) function by binding at the interface between alpha (α) and gamma (γ) subunits. Of the 6 α-subunits, only 4 (α-1, -2, -3, and -5) participate in the formation of this binding site. The above target is a collection of all α- and γ-subunits that are known to participate in the formation of the benzodiazepine binding site.
General Function
Inhibitory extracellular ligand-gated ion channel activity
Specific Function
Component of the heteropentameric receptor for GABA, the major inhibitory neurotransmitter in the vertebrate brain. Functions also as histamine receptor and mediates cellular responses to histamine...

Components:
References
  1. Sigel E, Steinmann ME: Structure, function, and modulation of GABA(A) receptors. J Biol Chem. 2012 Nov 23;287(48):40224-31. doi: 10.1074/jbc.R112.386664. Epub 2012 Oct 4. [PubMed:23038269]
  2. Zhu S, Noviello CM, Teng J, Walsh RM Jr, Kim JJ, Hibbs RE: Structure of a human synaptic GABAA receptor. Nature. 2018 Jul;559(7712):67-72. doi: 10.1038/s41586-018-0255-3. Epub 2018 Jun 27. [PubMed:29950725]

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Steroid hydroxylase activity
Specific Function
Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and im...
Gene Name
CYP2C19
Uniprot ID
P33261
Uniprot Name
Cytochrome P450 2C19
Molecular Weight
55930.545 Da
References
  1. Miura M, Ohkubo T: In vitro metabolism of quazepam in human liver and intestine and assessment of drug interactions. Xenobiotica. 2004 Nov-Dec;34(11-12):1001-11. [PubMed:15801544]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Steroid hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP2C9
Uniprot ID
P11712
Uniprot Name
Cytochrome P450 2C9
Molecular Weight
55627.365 Da
References
  1. Sugimoto K, Araki N, Ohmori M, Harada K, Cui Y, Tsuruoka S, Kawaguchi A, Fujimura A: Interaction between grapefruit juice and hypnotic drugs: comparison of triazolam and quazepam. Eur J Clin Pharmacol. 2006 Mar;62(3):209-15. doi: 10.1007/s00228-005-0071-1. Epub 2006 Jan 17. [PubMed:16416305]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Vitamin d3 25-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. Sugimoto K, Araki N, Ohmori M, Harada K, Cui Y, Tsuruoka S, Kawaguchi A, Fujimura A: Interaction between grapefruit juice and hypnotic drugs: comparison of triazolam and quazepam. Eur J Clin Pharmacol. 2006 Mar;62(3):209-15. doi: 10.1007/s00228-005-0071-1. Epub 2006 Jan 17. [PubMed:16416305]
  2. Kawaguchi A, Ohmori M, Tsuruoka S, Nishiki K, Harada K, Miyamori I, Yano R, Nakamura T, Masada M, Fujimura A: Drug interaction between St John's Wort and quazepam. Br J Clin Pharmacol. 2004 Oct;58(4):403-10. doi: 10.1111/j.1365-2125.2004.02171.x. [PubMed:15373933]
  3. Miura M, Ohkubo T: In vitro metabolism of quazepam in human liver and intestine and assessment of drug interactions. Xenobiotica. 2004 Nov-Dec;34(11-12):1001-11. [PubMed:15801544]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Steroid hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP2B6
Uniprot ID
P20813
Uniprot Name
Cytochrome P450 2B6
Molecular Weight
56277.81 Da
References
  1. Quazepam FDA Label [File]

Drug created on August 29, 2007 15:30 / Updated on February 21, 2021 18:51