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IdentificationPharmacologyInteractionsReferencesTrialsEconomicsPropertiesSpectraTaxonomyCinolazepam
Identification
- Name
- Cinolazepam
- Accession Number
- DB01594
- Type
- Small Molecule
- Groups
- Experimental
- Description
Cinolazepam is a benzodiazepine derivative with anxiolytic, anticonvulsant, sedative and skeletal muscle relaxant activity. It is not approved in Canada or America.
- Structure
Structure for Cinolazepam (DB01594)
- 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
- International/Other Brands
- Gerodorm
- Categories
- UNII
- 68P0556B0U
- CAS number
- 75696-02-5
- Weight
- Average: 357.766
Monoisotopic: 357.068032587 - Chemical Formula
- C18H13ClFN3O2
- 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
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.
- 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.
- 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
- Toxicity
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.
- 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.
Drug Interaction Unlock Additional Data2,5-Dimethoxy-4-ethylthioamphetamine The risk or severity of adverse effects can be increased when Cinolazepam is combined with 2,5-Dimethoxy-4-ethylthioamphetamine. 3-isobutyl-1-methyl-7H-xanthine The therapeutic efficacy of Cinolazepam can be decreased when used in combination with 3-isobutyl-1-methyl-7H-xanthine. 4-Bromo-2,5-dimethoxyamphetamine The risk or severity of adverse effects can be increased when 4-Bromo-2,5-dimethoxyamphetamine is combined with Cinolazepam. 4-Methoxyamphetamine The risk or severity of adverse effects can be increased when 4-Methoxyamphetamine is combined with Cinolazepam. 5-methoxy-N,N-dimethyltryptamine The risk or severity of adverse effects can be increased when Cinolazepam is combined with 5-methoxy-N,N-dimethyltryptamine. 6-O-benzylguanine The therapeutic efficacy of Cinolazepam can be decreased when used in combination with 6-O-benzylguanine. 7-Deazaguanine The therapeutic efficacy of Cinolazepam can be decreased when used in combination with 7-Deazaguanine. 7-Nitroindazole The risk or severity of adverse effects can be increased when Cinolazepam is combined with 7-Nitroindazole. 7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline The risk or severity of adverse effects can be increased when Cinolazepam is combined with 7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline. 7,9-Dimethylguanine The therapeutic efficacy of Cinolazepam can be decreased when used in combination with 7,9-Dimethylguanine. Additional Data Available- Extended DescriptionExtended Description
Extended description of the mechanism of action and particular properties of each drug interaction.
Learn more - Severity
- Evidence Level
- ActionAction
An effect category for each drug interaction. Know how this interaction affects the subject drug.
Learn more
- Food Interactions
- Avoid alcohol.
- Limit caffeine intake.
- Take with food.
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
- ATC Codes
- N05CD13 — Cinolazepam
Clinical Trials
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage forms
- Not Available
- 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 34.12 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 Not Available 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
Taxonomy
- 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 / Alpha-amino acid or derivatives / Fluorobenzene / Halobenzene / Aryl chloride / Aryl fluoride / Aryl halide / Monocyclic benzene moiety / Benzenoid / Tertiary carboxylic acid amide show 23 more
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- organochlorine compound, 1,4-benzodiazepinone (CHEBI:59514)
Targets
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Potentiator
- 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...
- Gene Name
- GABRA1
- Uniprot ID
- P14867
- Uniprot Name
- Gamma-aminobutyric acid receptor subunit alpha-1
- Molecular Weight
- 51801.395 Da
References
- Amin J, Brooks-Kayal A, Weiss DS: Two tyrosine residues on the alpha subunit are crucial for benzodiazepine binding and allosteric modulation of gamma-aminobutyric acidA receptors. Mol Pharmacol. 1997 May;51(5):833-41. [PubMed:9145922]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Potentiator
- General Function
- Inhibitory extracellular ligand-gated ion channel activity
- Specific Function
- GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel.
- Gene Name
- GABRA2
- Uniprot ID
- P47869
- Uniprot Name
- Gamma-aminobutyric acid receptor subunit alpha-2
- Molecular Weight
- 51325.85 Da
References
- Walash MI, Belal F, Metwally ME, Hefnawy MM: A selective fluorimetric method for the determination of some 1,4-benzodiazepine drugs containing a hydroxyl group at C-3. J Pharm Biomed Anal. 1994 Nov;12(11):1417-23. [PubMed:7849137]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Potentiator
- General Function
- Inhibitory extracellular ligand-gated ion channel activity
- Specific Function
- GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel.
- Gene Name
- GABRA3
- Uniprot ID
- P34903
- Uniprot Name
- Gamma-aminobutyric acid receptor subunit alpha-3
- Molecular Weight
- 55164.055 Da
References
- Walash MI, Belal F, Metwally ME, Hefnawy MM: A selective fluorimetric method for the determination of some 1,4-benzodiazepine drugs containing a hydroxyl group at C-3. J Pharm Biomed Anal. 1994 Nov;12(11):1417-23. [PubMed:7849137]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Potentiator
- General Function
- Transporter activity
- Specific Function
- GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel.
- Gene Name
- GABRA5
- Uniprot ID
- P31644
- Uniprot Name
- Gamma-aminobutyric acid receptor subunit alpha-5
- Molecular Weight
- 52145.645 Da
References
- Walash MI, Belal F, Metwally ME, Hefnawy MM: A selective fluorimetric method for the determination of some 1,4-benzodiazepine drugs containing a hydroxyl group at C-3. J Pharm Biomed Anal. 1994 Nov;12(11):1417-23. [PubMed:7849137]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Potentiator
- General Function
- Inhibitory extracellular ligand-gated ion channel activity
- Specific Function
- GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel.
- Gene Name
- GABRG1
- Uniprot ID
- Q8N1C3
- Uniprot Name
- Gamma-aminobutyric acid receptor subunit gamma-1
- Molecular Weight
- 53594.49 Da
References
- Walash MI, Belal F, Metwally ME, Hefnawy MM: A selective fluorimetric method for the determination of some 1,4-benzodiazepine drugs containing a hydroxyl group at C-3. J Pharm Biomed Anal. 1994 Nov;12(11):1417-23. [PubMed:7849137]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Potentiator
- 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...
- Gene Name
- GABRG2
- Uniprot ID
- P18507
- Uniprot Name
- Gamma-aminobutyric acid receptor subunit gamma-2
- Molecular Weight
- 54161.78 Da
References
- Walash MI, Belal F, Metwally ME, Hefnawy MM: A selective fluorimetric method for the determination of some 1,4-benzodiazepine drugs containing a hydroxyl group at C-3. J Pharm Biomed Anal. 1994 Nov;12(11):1417-23. [PubMed:7849137]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Potentiator
- General Function
- Inhibitory extracellular ligand-gated ion channel activity
- Specific Function
- GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel.
- Gene Name
- GABRG3
- Uniprot ID
- Q99928
- Uniprot Name
- Gamma-aminobutyric acid receptor subunit gamma-3
- Molecular Weight
- 54288.16 Da
References
- Walash MI, Belal F, Metwally ME, Hefnawy MM: A selective fluorimetric method for the determination of some 1,4-benzodiazepine drugs containing a hydroxyl group at C-3. J Pharm Biomed Anal. 1994 Nov;12(11):1417-23. [PubMed:7849137]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Potentiator
- General Function
- 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...
- Gene Name
- GABRB1
- Uniprot ID
- P18505
- Uniprot Name
- Gamma-aminobutyric acid receptor subunit beta-1
- Molecular Weight
- 54234.085 Da
References
- Walash MI, Belal F, Metwally ME, Hefnawy MM: A selective fluorimetric method for the determination of some 1,4-benzodiazepine drugs containing a hydroxyl group at C-3. J Pharm Biomed Anal. 1994 Nov;12(11):1417-23. [PubMed:7849137]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Potentiator
- 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...
- Gene Name
- GABRB2
- Uniprot ID
- P47870
- Uniprot Name
- Gamma-aminobutyric acid receptor subunit beta-2
- Molecular Weight
- 59149.895 Da
References
- Walash MI, Belal F, Metwally ME, Hefnawy MM: A selective fluorimetric method for the determination of some 1,4-benzodiazepine drugs containing a hydroxyl group at C-3. J Pharm Biomed Anal. 1994 Nov;12(11):1417-23. [PubMed:7849137]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Potentiator
- General Function
- Gaba-gated chloride 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...
- Gene Name
- GABRB3
- Uniprot ID
- P28472
- Uniprot Name
- Gamma-aminobutyric acid receptor subunit beta-3
- Molecular Weight
- 54115.04 Da
References
- Walash MI, Belal F, Metwally ME, Hefnawy MM: A selective fluorimetric method for the determination of some 1,4-benzodiazepine drugs containing a hydroxyl group at C-3. J Pharm Biomed Anal. 1994 Nov;12(11):1417-23. [PubMed:7849137]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Potentiator
- General Function
- Gaba-a receptor activity
- Specific Function
- GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel.
- Gene Name
- GABRD
- Uniprot ID
- O14764
- Uniprot Name
- Gamma-aminobutyric acid receptor subunit delta
- Molecular Weight
- 50707.835 Da
References
- Walash MI, Belal F, Metwally ME, Hefnawy MM: A selective fluorimetric method for the determination of some 1,4-benzodiazepine drugs containing a hydroxyl group at C-3. J Pharm Biomed Anal. 1994 Nov;12(11):1417-23. [PubMed:7849137]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Potentiator
- General Function
- Inhibitory extracellular ligand-gated ion channel activity
- Specific Function
- GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel.
- Gene Name
- GABRE
- Uniprot ID
- P78334
- Uniprot Name
- Gamma-aminobutyric acid receptor subunit epsilon
- Molecular Weight
- 57971.175 Da
References
- Walash MI, Belal F, Metwally ME, Hefnawy MM: A selective fluorimetric method for the determination of some 1,4-benzodiazepine drugs containing a hydroxyl group at C-3. J Pharm Biomed Anal. 1994 Nov;12(11):1417-23. [PubMed:7849137]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Potentiator
- General Function
- Gaba-a receptor activity
- Specific Function
- GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel. In the ute...
- Gene Name
- GABRP
- Uniprot ID
- O00591
- Uniprot Name
- Gamma-aminobutyric acid receptor subunit pi
- Molecular Weight
- 50639.735 Da
References
- Walash MI, Belal F, Metwally ME, Hefnawy MM: A selective fluorimetric method for the determination of some 1,4-benzodiazepine drugs containing a hydroxyl group at C-3. J Pharm Biomed Anal. 1994 Nov;12(11):1417-23. [PubMed:7849137]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Potentiator
- General Function
- Gaba-a receptor activity
- Specific Function
- GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel. Rho-1 GABA...
- Gene Name
- GABRR1
- Uniprot ID
- P24046
- Uniprot Name
- Gamma-aminobutyric acid receptor subunit rho-1
- Molecular Weight
- 55882.91 Da
References
- Walash MI, Belal F, Metwally ME, Hefnawy MM: A selective fluorimetric method for the determination of some 1,4-benzodiazepine drugs containing a hydroxyl group at C-3. J Pharm Biomed Anal. 1994 Nov;12(11):1417-23. [PubMed:7849137]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Potentiator
- General Function
- Gaba-a receptor activity
- Specific Function
- GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel. Rho-2 GABA...
- Gene Name
- GABRR2
- Uniprot ID
- P28476
- Uniprot Name
- Gamma-aminobutyric acid receptor subunit rho-2
- Molecular Weight
- 54150.41 Da
References
- Walash MI, Belal F, Metwally ME, Hefnawy MM: A selective fluorimetric method for the determination of some 1,4-benzodiazepine drugs containing a hydroxyl group at C-3. J Pharm Biomed Anal. 1994 Nov;12(11):1417-23. [PubMed:7849137]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Potentiator
- General Function
- Gaba-a receptor activity
- Specific Function
- GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel.
- Gene Name
- GABRR3
- Uniprot ID
- A8MPY1
- Uniprot Name
- Gamma-aminobutyric acid receptor subunit rho-3
- Molecular Weight
- 54271.1 Da
References
- Walash MI, Belal F, Metwally ME, Hefnawy MM: A selective fluorimetric method for the determination of some 1,4-benzodiazepine drugs containing a hydroxyl group at C-3. J Pharm Biomed Anal. 1994 Nov;12(11):1417-23. [PubMed:7849137]
Drug created on August 29, 2007 11:43 / Updated on March 01, 2020 18:43
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