Identification
- Summary
Quazepam is a long -acting benzodiazepine used to manage insomnia.
- Brand Names
- Doral
- Generic Name
- Quazepam
- DrugBank Accession Number
- DB01589
- Background
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
Structure for Quazepam (DB01589)
- Weight
- Average: 386.794
Monoisotopic: 386.026759579 - Chemical Formula
- C17H11ClF4N2S
- Synonyms
- Quazepam
- Quazepamum
- External IDs
- SCH 16134
- SCH-16134
Pharmacology
- Indication
Used to treat insomnia.
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- Contraindications & Blackbox Warnings
Avoid life-threatening adverse drug eventsImprove clinical decision support with information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events & improve clinical decision support.- 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
Target Actions Organism AGABA(A) Receptor positive allosteric modulatorHumans AGABA(A) Receptor Benzodiazepine Binding Site ligandHumans - Absorption
Bioavailability is 29-35% following oral administration.
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
Hepatic.
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- Route of elimination
Not Available
- Half-life
39 hours
- Clearance
Not Available
- Adverse Effects
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates.Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
Not Available
- 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.
Drug Interaction Integrate drug-drug
interactions in your software1,2-Benzodiazepine The risk or severity of adverse effects can be increased when Quazepam is combined with 1,2-Benzodiazepine. Abametapir The serum concentration of Quazepam can be increased when it is combined with Abametapir. Abatacept The metabolism of Quazepam can be increased when combined with Abatacept. Abrocitinib The metabolism of Abrocitinib can be decreased when combined with Quazepam. Acenocoumarol The metabolism of Quazepam can be decreased when combined with Acenocoumarol. Acetazolamide The risk or severity of adverse effects can be increased when Acetazolamide is combined with Quazepam. Acetohexamide The metabolism of Quazepam can be decreased when combined with Acetohexamide. Acetophenazine The risk or severity of adverse effects can be increased when Acetophenazine is combined with Quazepam. Acetyl sulfisoxazole The metabolism of Quazepam can be decreased when combined with Acetyl sulfisoxazole. Acetylsalicylic acid The metabolism of Quazepam can be decreased when combined with Acetylsalicylic acid. 
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- Avoid alcohol. Ingesting alcohol may increase the drowsiness and CNS depression caused by quazepam.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- International/Other Brands
- Dormalin
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Doral Tablet 15 mg/1 Oral Physicians Total Care, Inc. 1994-03-02 2002-06-30 US 
Doral Tablet 15 mg/1 Oral Galt Pharmaceuticals, LLC 2017-07-19 Not applicable US Doral Tablet 15 mg/1 Oral Nuro Pharma, Inc. 1985-12-27 2014-12-18 US Doral Tablet 15 mg/1 Oral Questcor Pharmaceuticals, Inc. 1985-12-27 2013-06-20 US Quazepam Tablet 15 mg/1 Oral A S Medication Solutions 2013-08-08 Not applicable US Quazepam Tablet 15 mg/1 Oral Thompson Medical Solutions Llc 2016-04-12 2018-05-23 US Quazepam Tablet 15 mg/1 Oral Unit Dose Services 2013-08-08 2015-10-30 US Quazepam Tablet 15 mg/1 Oral bryant ranch prepack 2013-08-08 2016-01-29 US Quazepam Tablet 15 mg/1 Oral Preferreed Pharmaceuticals Inc. 2013-08-15 2016-01-11 US Quazepam Tablet 15 mg/1 Oral KLE 2, Inc. 2013-08-08 2015-10-30 US
Categories
- ATC Codes
- N05CD10 — Quazepam
- Drug Categories
- Benzazepines
- Benzodiazepine hypnotics and sedatives
- Benzodiazepines and benzodiazepine derivatives
- Central Nervous System Agents
- Central Nervous System Depressants
- Cytochrome P-450 CYP2B6 Inhibitors
- Cytochrome P-450 CYP2B6 Inhibitors (strength unknown)
- Cytochrome P-450 CYP2C19 Substrates
- Cytochrome P-450 CYP2C9 Substrates
- Cytochrome P-450 CYP3A Substrates
- Cytochrome P-450 CYP3A4 Substrates
- Cytochrome P-450 Enzyme Inhibitors
- Cytochrome P-450 Substrates
- Heterocyclic Compounds, Fused-Ring
- Hypnotics and Sedatives
- Nervous System
- Psycholeptics
- 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)
- Affected organisms
- Humans and other mammals
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
- External Links
- Human Metabolome Database
- HMDB0015528
- KEGG Drug
- D00457
- KEGG Compound
- C07336
- PubChem Compound
- 4999
- PubChem Substance
- 46505952
- ChemSpider
- 4825
- 35185
- ChEBI
- 8694
- ChEMBL
- CHEMBL1200472
- ZINC
- ZINC000000538266
- Therapeutic Targets Database
- DAP000690
- PharmGKB
- PA164744373
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Quazepam
Clinical Trials
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Physicians Total Care Inc.
- Questcor
- Dosage Forms
Form Route Strength Tablet Oral 15 mg/1 Tablet Oral - Prices
- Not Available
- Patents
Patent Number Pediatric Extension Approved Expires (estimated) Region US7608616 No 2009-10-27 2028-06-03 US
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 137.5-139 °C PhysProp logP 4.03 SANGSTER (1994) - Predicted Properties
Property Value Source Water Solubility 0.00231 mg/mL ALOGPS logP 4.76 ALOGPS logP 5.06 ChemAxon logS -5.2 ALOGPS pKa (Strongest Acidic) 18.93 ChemAxon pKa (Strongest Basic) 2.59 ChemAxon Physiological Charge 0 ChemAxon Hydrogen Acceptor Count 1 ChemAxon Hydrogen Donor Count 0 ChemAxon Polar Surface Area 15.6 Å2 ChemAxon Rotatable Bond Count 3 ChemAxon Refractivity 93.47 m3·mol-1 ChemAxon Polarizability 33.99 Å3 ChemAxon Number of Rings 3 ChemAxon Bioavailability 1 ChemAxon Rule of Five No ChemAxon Ghose Filter Yes ChemAxon Veber's Rule Yes ChemAxon MDDR-like Rule No ChemAxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9385 Blood Brain Barrier + 0.9789 Caco-2 permeable + 0.5748 P-glycoprotein substrate Substrate 0.5341 P-glycoprotein inhibitor I Inhibitor 0.9324 P-glycoprotein inhibitor II Inhibitor 0.8253 Renal organic cation transporter Inhibitor 0.6883 CYP450 2C9 substrate Non-substrate 0.8255 CYP450 2D6 substrate Non-substrate 0.8135 CYP450 3A4 substrate Substrate 0.5133 CYP450 1A2 substrate Inhibitor 0.7023 CYP450 2C9 inhibitor Inhibitor 0.5757 CYP450 2D6 inhibitor Non-inhibitor 0.6337 CYP450 2C19 inhibitor Inhibitor 0.688 CYP450 3A4 inhibitor Inhibitor 0.7937 CYP450 inhibitory promiscuity High CYP Inhibitory Promiscuity 0.9484 Ames test Non AMES toxic 0.6683 Carcinogenicity Non-carcinogens 0.7273 Biodegradation Not ready biodegradable 1.0 Rat acute toxicity 1.9195 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.978 hERG inhibition (predictor II) Inhibitor 0.6396
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS Not Available Mass Spectrum (Electron Ionization) MS splash10-05aa-3988000000-ca1cf29da979ef46dd6c Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available
Targets
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- 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
- 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. [Article]
- 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. [Article]
- 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
- 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. [Article]
- 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. [Article]
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
- 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. [Article]
- 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
- 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. [Article]
- 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
- 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. [Article]
- 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. [Article]
- 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. [Article]
- 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
- Quazepam FDA Label [File]
Drug created at August 29, 2007 15:30 / Updated at February 21, 2021 18:51