You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:52 UTC
Update Date2019-07-23 06:02:01 UTC
HMDB IDHMDB0015533
Secondary Accession Numbers
  • HMDB15533
Metabolite Identification
Common NameCinolazepam
DescriptionCinolazepam is only found in individuals that have used or taken this drug. It is a benzodiazepine derivative. It possesses anxiolytic, anticonvulsant, sedative and skeletal muscle relaxant properties. Cinolazepam is not approved for sale in the United States or Canada.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.
Structure
Data?1563861721
Synonyms
ValueSource
1-(2-Cyanoethyl)-7-chloro-3-hydroxy-5-(2'-fluorophenyl)-1,3-dihydro-2H-1,4-benzodiazepin-2-oneChEBI
7-chloro-5-(2-Fluorophenyl)-2,3-dihydro-3-hydroxy-2-oxo-1H-1,4-benzodiazepine-1-propanenitrileChEBI
7-chloro-5-(O-Fluorophenyl)-2,3-dihydro-3-hydroxy-2-oxo-1H-1,4-benzodiazepine-1-propionitrileChEBI
CinolazepamumChEBI
7-chloro-5-(2-Fluorophenyl)-2,3-dihydro-3-hydroxy-2-oxo-1H-1,4-benzodiazepine-1-propionitrileMeSH
Chemical FormulaC18H13ClFN3O2
Average Molecular Weight357.766
Monoisotopic Molecular Weight357.068032587
IUPAC Name3-[7-chloro-5-(2-fluorophenyl)-3-hydroxy-2-oxo-2,3-dihydro-1H-1,4-benzodiazepin-1-yl]propanenitrile
Traditional Namecinolazepam
CAS Registry Number75696-02-5
SMILES
OC1N=C(C2=CC=CC=C2F)C2=C(C=CC(Cl)=C2)N(CCC#N)C1=O
InChI Identifier
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
InChI KeyXAXMYHMKTCNRRZ-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis 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.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzodiazepines
Sub Class1,4-benzodiazepines
Direct Parent1,4-benzodiazepines
Alternative Parents
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
  • Carboxamide group
  • Ketimine
  • Lactam
  • Alkanolamine
  • Azacycle
  • Carboxylic acid derivative
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Carbonitrile
  • Nitrile
  • Imine
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Carbonyl group
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organohalogen compound
  • Organochloride
  • Organofluoride
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Biological location:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.012 g/LNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.012 g/LALOGPS
logP2.42ALOGPS
logP2.7ChemAxon
logS-4.5ALOGPS
pKa (Strongest Acidic)10.68ChemAxon
pKa (Strongest Basic)-2.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area76.69 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity90.99 m³·mol⁻¹ChemAxon
Polarizability34.12 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0iki-0397000000-6dc71c0e52cf323c4249JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0ir9-8139300000-76aa398fb739bbfd5ec5JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-1019000000-3fb8d424ad020ac2a56eJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-2019000000-7cfb2f9949767ef2eaf4JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-9110000000-981eb27764717ef665cdJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0009000000-2d5c6a3df2ed9be23c27JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0k92-0179000000-d07cdeed3541a874c6b4JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00dl-8191000000-920c5d9c75b7fbb9e1f5JSpectraViewer | MoNA
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB01594 details
UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB01594 details
Abnormal Concentrations
Not Available
Predicted Concentrations
BiospecimenValueOriginal ageOriginal sexOriginal conditionComments
Blood0.000 uMAdult (>18 years old)BothNormalPredicted based on drug qualities
Blood0.000 umol/mmol creatinineAdult (>18 years old)BothNormalPredicted based on drug qualities
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01594
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID2298251
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkCinolazepam
METLIN IDNot Available
PubChem Compound3033621
PDB IDNot Available
ChEBI ID59514
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Only showing the first 10 proteins. There are 16 proteins in total.

Enzymes

General function:
Involved in ion transport
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:
GABRG2
Uniprot ID:
P18507
Molecular weight:
54161.8
References
  1. 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 ]
General function:
Involved in ion transport
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:
GABRA1
Uniprot ID:
P14867
Molecular weight:
51801.4
References
  1. 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 ]
General function:
Involved in ion transport
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
Molecular weight:
51325.9
References
  1. 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 ]
General function:
Involved in ion transport
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
Molecular weight:
55164.1
References
  1. 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 ]
General function:
Involved in ion transport
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
Molecular weight:
52145.6
References
  1. 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 ]
General function:
Involved in ion transport
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:
GABRB1
Uniprot ID:
P18505
Molecular weight:
54234.1
References
  1. 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 ]
General function:
Involved in ion transport
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:
GABRB2
Uniprot ID:
P47870
Molecular weight:
59149.9
References
  1. 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 ]
General function:
Involved in ion transport
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:
GABRB3
Uniprot ID:
P28472
Molecular weight:
54115.0
References
  1. 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 ]
General function:
Involved in ion transport
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
Molecular weight:
50707.8
References
  1. 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 ]
General function:
Involved in ion transport
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
Molecular weight:
57971.2
References
  1. 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 ]

Only showing the first 10 proteins. There are 16 proteins in total.