Identification
- Summary
Cinolazepam is a benzodiazepine used to manage severe and debilitating forms of sleep disorders of various origins in adults.
- Generic Name
- Cinolazepam
- DrugBank Accession Number
- DB01594
- Background
Cinolazepam is a benzodiazepine derivative with anxiolytic, anticonvulsant, sedative and skeletal muscle relaxant activity. It is not approved in Canada or America.
- Type
- Small Molecule
- Groups
- Experimental
- Structure
Structure for Cinolazepam (DB01594)
- Weight
- Average: 357.766
Monoisotopic: 357.068032587 - Chemical Formula
- C18H13ClFN3O2
- Synonyms
- 1-(2-cyanoethyl)-7-chloro-3-hydroxy-5-(2'-fluorophenyl)-1,3-dihydro-2H-1,4-benzodiazepin-2-one
- 7-chloro-5-(2-fluorophenyl)-2,3-dihydro-3-hydroxy-2-oxo-1H-1,4-benzodiazepine-1-propanenitrile
- 7-chloro-5-(o-fluorophenyl)-2,3-dihydro-3-hydroxy-2-oxo-1H-1,4-benzodiazepine-1-propionitrile
- Cinolazepam
- Cinolazepamum
- External IDs
- OX 373
- OX-373
Pharmacology
- Indication
For the management of anxiety disorders or for the short-term relief of the symptoms of anxiety or anxiety associated with depressive symptoms.
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Associated Conditions
Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Treatment of Insomnia •••••••••••• ••••• •••••• Treatment of Sleep disorder •••••••••••• ••••• •••••• - Contraindications & Blackbox Warnings
Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- Pharmacodynamics
Cinolazepam is a benzodiazepine derivative with anxiolytic, anticonvulsant, sedative and skeletal muscle relaxant activity. It is not approved in Canada or America.
- Mechanism of action
Cinolazepam binds to central benzodiazepine receptors which interact allosterically with GABA receptors. This potentiates the effects of the inhibitory neurotransmitter GABA, increasing the inhibition of the ascending reticular activating system and blocking the cortical and limbic arousal that occurs following stimulation of the reticular pathways.
Target Actions Organism AGABA(A) Receptor positive allosteric modulatorHumans AGABA(A) Receptor Benzodiazepine Binding Site ligandHumans - Absorption
Bioavailability following oral administration is 90-100%.
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
Hepatic.
- Route of elimination
Not Available
- Half-life
9 hours
- Clearance
Not Available
- Adverse Effects
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The onset of impairment of consciousness is relatively rapid in benzodiazepine poisoning. Onset is more rapid following larger doses and with agents of shorter duration of action. The most common and initial symptom is somnolence. This may progress to coma Grade I or Grade II following very large ingestions.
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
- Not Available
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
- 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 CNS depression can be increased when Cinolazepam is combined with 1,2-Benzodiazepine. Acetazolamide The risk or severity of CNS depression can be increased when Acetazolamide is combined with Cinolazepam. Acetophenazine The risk or severity of CNS depression can be increased when Acetophenazine is combined with Cinolazepam. Agomelatine The risk or severity of CNS depression can be increased when Cinolazepam is combined with Agomelatine. Alfentanil The risk or severity of adverse effects can be increased when Alfentanil is combined with Cinolazepam. - Food Interactions
- Avoid alcohol.
- Limit caffeine intake.
- Take with food.
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
- Gerodorm
Categories
- ATC Codes
- N05CD13 — Cinolazepam
- 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
- Alpha amino acids and derivatives / Fluorobenzenes / Aryl chlorides / Aryl fluorides / Tertiary carboxylic acid amides / Ketimines / Lactams / Alkanolamines / Propargyl-type 1,3-dipolar organic compounds / Azacyclic compounds show 7 more
- Substituents
- 1,4-benzodiazepine / Alkanolamine / Alpha-amino acid or derivatives / Aromatic heteropolycyclic compound / Aryl chloride / Aryl fluoride / Aryl halide / Azacycle / Benzenoid / Carbonitrile show 23 more
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- organochlorine compound, 1,4-benzodiazepinone (CHEBI:59514)
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- 68P0556B0U
- CAS number
- 75696-02-5
- InChI Key
- XAXMYHMKTCNRRZ-UHFFFAOYSA-N
- InChI
- InChI=1S/C18H13ClFN3O2/c19-11-6-7-15-13(10-11)16(12-4-1-2-5-14(12)20)22-17(24)18(25)23(15)9-3-8-21/h1-2,4-7,10,17,24H,3,9H2
- IUPAC Name
- 3-[7-chloro-5-(2-fluorophenyl)-3-hydroxy-2-oxo-2,3-dihydro-1H-1,4-benzodiazepin-1-yl]propanenitrile
- SMILES
- OC1N=C(C2=CC=CC=C2F)C2=C(C=CC(Cl)=C2)N(CCC#N)C1=O
References
- General References
- Not Available
- External Links
- Human Metabolome Database
- HMDB0015533
- KEGG Drug
- D07328
- PubChem Compound
- 3033621
- PubChem Substance
- 46508803
- ChemSpider
- 2298251
- ChEBI
- 59514
- ChEMBL
- CHEMBL2104926
- Therapeutic Targets Database
- DAP001250
- PharmGKB
- PA164748034
- Wikipedia
- Cinolazepam
Clinical Trials
- Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Tablet Oral 40 mg - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 0.012 mg/mL ALOGPS logP 2.42 ALOGPS logP 2.7 Chemaxon logS -4.5 ALOGPS pKa (Strongest Acidic) 10.68 Chemaxon pKa (Strongest Basic) -2.5 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 4 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 76.69 Å2 Chemaxon Rotatable Bond Count 3 Chemaxon Refractivity 90.99 m3·mol-1 Chemaxon Polarizability 34.13 Å3 Chemaxon Number of Rings 3 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9872 Blood Brain Barrier + 0.9778 Caco-2 permeable + 0.5712 P-glycoprotein substrate Substrate 0.5264 P-glycoprotein inhibitor I Inhibitor 0.7371 P-glycoprotein inhibitor II Inhibitor 0.9286 Renal organic cation transporter Inhibitor 0.5421 CYP450 2C9 substrate Non-substrate 0.6806 CYP450 2D6 substrate Non-substrate 0.8239 CYP450 3A4 substrate Substrate 0.7105 CYP450 1A2 substrate Inhibitor 0.6771 CYP450 2C9 inhibitor Inhibitor 0.5139 CYP450 2D6 inhibitor Non-inhibitor 0.8453 CYP450 2C19 inhibitor Inhibitor 0.5565 CYP450 3A4 inhibitor Inhibitor 0.6491 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.6814 Ames test Non AMES toxic 0.757 Carcinogenicity Non-carcinogens 0.8621 Biodegradation Not ready biodegradable 1.0 Rat acute toxicity 2.0412 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9948 hERG inhibition (predictor II) Non-inhibitor 0.5099
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS splash10-0iki-0397000000-6dc71c0e52cf323c4249 Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-0a4i-0009000000-508b871e341874c6aee5 Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-001i-1095000000-ae32d6ecfb72216be082 Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-0a4i-0009000000-d88758ae57aa88ce1f38 Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-0k9j-5049000000-543fd0ad1a98c511ae04 Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-0hjr-2049000000-cde7d9354937555f336a Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-00ec-7091000000-668a85b483439e4ad701 Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 185.1064336 predictedDarkChem Lite v0.1.0 [M-H]- 169.14244 predictedDeepCCS 1.0 (2019) [M+H]+ 185.6802336 predictedDarkChem Lite v0.1.0 [M+H]+ 171.50044 predictedDeepCCS 1.0 (2019) [M+Na]+ 185.3119336 predictedDarkChem Lite v0.1.0 [M+Na]+ 178.23618 predictedDeepCCS 1.0 (2019)
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]
Drug created at August 29, 2007 17:43 / Updated at May 05, 2021 20:30