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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:50 UTC
Update Date2022-03-07 02:51:48 UTC
HMDB IDHMDB0014965
Secondary Accession Numbers
  • HMDB14965
Metabolite Identification
Common NameCinoxacin
DescriptionCinoxacin, also known as CINX or cinobac, belongs to the class of organic compounds known as cinnolines. These are organic aromatic compounds containing a benzene fused to a pyridazine ring. Within the most recent package insert (circa 1999) Cinobac is listed as being contraindicated in patients with a history of hypersensitivity to cinoxacin or other quinolones. Cinoxacin is a drug which is used for the treatment of initial and recurrent urinary tract infections in adults caused by the following susceptible microorganisms: escherichia coli, proteus mirabilis, proteus vulgaris, klebsiella species (including k. pneumoniae), and enterobacter species. There are reports that cinoxacin had also been used to treat initial and recurrent urinary tract infections and bacterial prostatitis in dogs. Cinoxacin is an extremely weak basic (essentially neutral) compound (based on its pKa). Relative to nalidixic acid, cinoxacin was found to have a slightly greater inhibitory and bactericidal activity.
Structure
Data?1582753242
Synonyms
ValueSource
1-Ethyl-6,7-methylenedioxy-4(1H)-oxocinnoline-3-carboxylic acidChEBI
5-Ethyl-8-oxo-5,8-dihydro-1,3-dioxa-5,6-diaza-cyclopenta[b]naphthalene-7-carboxylic acidChEBI
CinoxacineChEBI
CinoxacinoChEBI
CinoxacinumChEBI
CINXKegg
CinobacKegg
1-Ethyl-6,7-methylenedioxy-4(1H)-oxocinnoline-3-carboxylateGenerator
5-Ethyl-8-oxo-5,8-dihydro-1,3-dioxa-5,6-diaza-cyclopenta[b]naphthalene-7-carboxylateGenerator
64716, CompoundHMDB
Azolinic acidHMDB
Acid, azolinicHMDB
Compound 64716HMDB
ClinoxacinHMDB
Chemical FormulaC12H10N2O5
Average Molecular Weight262.2182
Monoisotopic Molecular Weight262.05897144
IUPAC Name1-ethyl-4-oxo-1H,4H,7H-[1,3]dioxolo[4,5-g]cinnoline-3-carboxylic acid
Traditional Namecinoxacin
CAS Registry Number28657-80-9
SMILES
CCN1N=C(C(O)=O)C(=O)C2=CC3=C(OCO3)C=C12
InChI Identifier
InChI=1S/C12H10N2O5/c1-2-14-7-4-9-8(18-5-19-9)3-6(7)11(15)10(13-14)12(16)17/h3-4H,2,5H2,1H3,(H,16,17)
InChI KeyVDUWPHTZYNWKRN-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as cinnolines. These are organic aromatic compounds containing a benzene fused to a pyridazine ring.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassDiazanaphthalenes
Sub ClassBenzodiazines
Direct ParentCinnolines
Alternative Parents
Substituents
  • Cinnoline
  • Benzodioxole
  • Pyridazine
  • Benzenoid
  • Heteroaromatic compound
  • Vinylogous amide
  • Oxacycle
  • Azacycle
  • Acetal
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Organic oxide
  • Organopnictogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point261 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.96 g/LNot Available
LogP1.5Not Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+Not Available148.476http://allccs.zhulab.cn/database/detail?ID=AllCCS00000973
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.96 g/LALOGPS
logP1.25ALOGPS
logP1.72ChemAxon
logS-2.4ALOGPS
pKa (Strongest Acidic)4.93ChemAxon
pKa (Strongest Basic)-4.6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area88.43 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity73.6 m³·mol⁻¹ChemAxon
Polarizability24.72 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+159.81631661259
DarkChem[M-H]-157.52431661259
DeepCCS[M-2H]-188.1430932474
DeepCCS[M+Na]+163.68830932474
AllCCS[M+H]+156.132859911
AllCCS[M+H-H2O]+152.332859911
AllCCS[M+NH4]+159.732859911
AllCCS[M+Na]+160.732859911
AllCCS[M-H]-158.532859911
AllCCS[M+Na-2H]-157.932859911
AllCCS[M+HCOO]-157.432859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
CinoxacinCCN1N=C(C(O)=O)C(=O)C2=CC3=C(OCO3)C=C123070.0Standard polar33892256
CinoxacinCCN1N=C(C(O)=O)C(=O)C2=CC3=C(OCO3)C=C122281.8Standard non polar33892256
CinoxacinCCN1N=C(C(O)=O)C(=O)C2=CC3=C(OCO3)C=C122614.6Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Cinoxacin,1TMS,isomer #1CCN1N=C(C(=O)O[Si](C)(C)C)C(=O)C2=CC3=C(C=C21)OCO32503.2Semi standard non polar33892256
Cinoxacin,1TBDMS,isomer #1CCN1N=C(C(=O)O[Si](C)(C)C(C)(C)C)C(=O)C2=CC3=C(C=C21)OCO32706.8Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Cinoxacin GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-0970000000-d6e7abdaf83ac6915d9c2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Cinoxacin GC-MS (1 TMS) - 70eV, Positivesplash10-0006-4934000000-f98fd908e7ab28b030cf2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Cinoxacin GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Cinoxacin LC-ESI-qTof , Positive-QTOFsplash10-00kr-2930000000-d8548621f53001ee222d2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Cinoxacin , positive-QTOFsplash10-00kr-2930000000-d8548621f53001ee222d2017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cinoxacin 10V, Positive-QTOFsplash10-03di-0090000000-334244d6a89f0ca6b5462016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cinoxacin 20V, Positive-QTOFsplash10-02ta-0190000000-4212f062c3b83386b0412016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cinoxacin 40V, Positive-QTOFsplash10-0gi0-0890000000-25eee1869a982bf913fc2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cinoxacin 10V, Negative-QTOFsplash10-02t9-0290000000-79e8373fadc1994621022016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cinoxacin 20V, Negative-QTOFsplash10-014i-0790000000-7942d2310d6730a23c272016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cinoxacin 40V, Negative-QTOFsplash10-03dl-1900000000-05b7716167bca8f2dd582016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cinoxacin 10V, Positive-QTOFsplash10-03di-0090000000-4fd0af9aad9b9655f4312021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cinoxacin 20V, Positive-QTOFsplash10-0002-0090000000-4e532ea6a8a7a3dfc2f72021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cinoxacin 40V, Positive-QTOFsplash10-03xr-1950000000-5d613602c0ff21ac9ab52021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cinoxacin 10V, Negative-QTOFsplash10-03xr-0090000000-4920e9eef443d07b78d72021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cinoxacin 20V, Negative-QTOFsplash10-000i-0920000000-9e4a8c05b0c3ecae8d012021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cinoxacin 40V, Negative-QTOFsplash10-0909-0980000000-b400ebb127f6687745bf2021-10-11Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00827 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00827 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00827
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID2660
KEGG Compound IDC08052
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkCinoxacin
METLIN IDNot Available
PubChem Compound2762
PDB IDNot Available
ChEBI ID3716
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Transporters

General function:
Involved in ion transmembrane transporter activity
Specific function:
Involved in the renal elimination of endogenous and exogenous organic anions. Functions as organic anion exchanger when the uptake of one molecule of organic anion is coupled with an efflux of one molecule of endogenous dicarboxylic acid (glutarate, ketoglutarate, etc). Mediates the sodium-independent uptake of 2,3-dimercapto-1-propanesulfonic acid (DMPS). Mediates the sodium-independent uptake of p- aminohippurate (PAH), ochratoxin (OTA), acyclovir (ACV), 3'-azido- 3-'deoxythymidine (AZT), cimetidine (CMD), 2,4-dichloro- phenoxyacetate (2,4-D), hippurate (HA), indoleacetate (IA), indoxyl sulfate (IS) and 3-carboxy-4-methyl-5-propyl-2- furanpropionate (CMPF), cidofovir, adefovir, 9-(2- phosphonylmethoxyethyl) guanine (PMEG), 9-(2- phosphonylmethoxyethyl) diaminopurine (PMEDAP) and edaravone sulfate. PAH uptake is inhibited by p- chloromercuribenzenesulphonate (PCMBS), diethyl pyrocarbonate (DEPC), sulindac, diclofenac, carprofen, glutarate and okadaic acid. PAH uptake is inhibited by benzothiazolylcysteine (BTC), S-chlorotrifluoroethylcysteine (CTFC), cysteine S-conjugates S-dichlorovinylcysteine (DCVC), furosemide, steviol, phorbol 12-myristate 13-acetate (PMA), calcium ionophore A23187, benzylpenicillin, furosemide, indomethacin, bumetamide, losartan, probenecid, phenol red, urate, and alpha-ketoglutarate
Gene Name:
SLC22A6
Uniprot ID:
Q4U2R8
Molecular weight:
61815.8
References
  1. Jariyawat S, Sekine T, Takeda M, Apiwattanakul N, Kanai Y, Sophasan S, Endou H: The interaction and transport of beta-lactam antibiotics with the cloned rat renal organic anion transporter 1. J Pharmacol Exp Ther. 1999 Aug;290(2):672-7. [PubMed:10411577 ]