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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:49 UTC
Update Date2020-02-26 21:40:01 UTC
HMDB IDHMDB0014630
Secondary Accession Numbers
  • HMDB14630
Metabolite Identification
Common NamePefloxacin
DescriptionPefloxacin is only found in individuals that have used or taken this drug. It is a synthetic broad-spectrum fluoroquinolone antibacterial agent active against most gram-negative and gram-positive bacteria. [PubChem]The bactericidal action of pefloxacin results from interference with the activity of the bacterial enzymes DNA gyrase and topoisomerase IV, which are needed for the transcription and replication of bacterial DNA. DNA gyrase appears to be the primary quinolone target for gram-negative bacteria. Topoisomerase IV appears to be the preferential target in gram-positive organisms. Interference with these two topoisomerases results in strand breakage of the bacterial chromosome, supercoiling, and resealing. As a result DNA replication and transcription is inhibited.
Structure
Data?1582753201
Synonyms
ValueSource
LaboctonChEBI
PefloxacineChEBI
PefloxacinoChEBI
PefloxacinumChEBI
PerfloxacinChEBI
PFLXChEBI
2589 R.B.HMDB
Dihydrate, pefloxacin mesylateHMDB
Mesylate dihydrate, pefloxacinHMDB
Mesylate, pefloxacinHMDB
Pefloxacin, silverHMDB
R.B., 2589HMDB
Silver pefloxacinHMDB
AbactalHMDB
PeflacineHMDB
Pefloxacin mesylate dihydrateHMDB
Pefloxacin mesylateHMDB
Chemical FormulaC17H20FN3O3
Average Molecular Weight333.3574
Monoisotopic Molecular Weight333.148869726
IUPAC Name1-ethyl-6-fluoro-7-(4-methylpiperazin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid
Traditional Namepefloxacin
CAS Registry Number70458-92-3
SMILES
CCN1C=C(C(O)=O)C(=O)C2=CC(F)=C(C=C12)N1CCN(C)CC1
InChI Identifier
InChI=1S/C17H20FN3O3/c1-3-20-10-12(17(23)24)16(22)11-8-13(18)15(9-14(11)20)21-6-4-19(2)5-7-21/h8-10H,3-7H2,1-2H3,(H,23,24)
InChI KeyFHFYDNQZQSQIAI-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as quinoline carboxylic acids. These are quinolines in which the quinoline ring system is substituted by a carboxyl group at one or more positions.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassQuinolines and derivatives
Sub ClassQuinoline carboxylic acids
Direct ParentQuinoline carboxylic acids
Alternative Parents
Substituents
  • Quinoline-3-carboxylic acid
  • Fluoroquinolone
  • N-arylpiperazine
  • Aminoquinoline
  • Haloquinoline
  • Dihydroquinolone
  • Dihydroquinoline
  • Pyridine carboxylic acid
  • Pyridine carboxylic acid or derivatives
  • Tertiary aliphatic/aromatic amine
  • Dialkylarylamine
  • N-alkylpiperazine
  • N-methylpiperazine
  • Benzenoid
  • Pyridine
  • Aryl fluoride
  • Piperazine
  • Aryl halide
  • 1,4-diazinane
  • Vinylogous amide
  • Heteroaromatic compound
  • Amino acid or derivatives
  • Tertiary aliphatic amine
  • Tertiary amine
  • Amino acid
  • Azacycle
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organopnictogen compound
  • Organic oxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Amine
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organohalogen compound
  • Organofluoride
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point271 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility1.23 g/LNot Available
LogP2.4Not Available
Experimental Spectral PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility1.23 g/LALOGPS
logP10(0.2) g/LALOGPS
logP10(0.88) g/LChemAxon
logS10(-2.4) g/LALOGPS
pKa (Strongest Acidic)5.66ChemAxon
pKa (Strongest Basic)6.47ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area64.09 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity90.77 m³·mol⁻¹ChemAxon
Polarizability34.42 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Spectral Properties

Predicted Kovats Retention Indices

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Pefloxacin,1TMS,#1CCN1C=C(C(=O)O[Si](C)(C)C)C(=O)C2=CC(F)=C(N3CCN(C)CC3)C=C212816.4Semi standard non polarhttps://arxiv.org/abs/1905.12712
Pefloxacin,1TBDMS,#1CCN1C=C(C(=O)O[Si](C)(C)C(C)(C)C)C(=O)C2=CC(F)=C(N3CCN(C)CC3)C=C213028.7Semi standard non polarhttps://arxiv.org/abs/1905.12712
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00487 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00487 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00487
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID46291
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkPefloxacin
METLIN IDNot Available
PubChem Compound51081
PDB IDNot Available
ChEBI ID50199
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

Enzymes

General function:
Involved in monooxygenase 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 unrelated compounds, including steroids, fatty acids, and xenobiotics. Most active in catalyzing 2-hydroxylation. Caffeine is metabolized primarily by cytochrome CYP1A2 in the liver through an initial N3-demethylation. Also acts in the metabolism of aflatoxin B1 and acetaminophen. Participates in the bioactivation of carcinogenic aromatic and heterocyclic amines. Catalizes the N-hydroxylation of heterocyclic amines and the O-deethylation of phenacetin.
Gene Name:
CYP1A2
Uniprot ID:
P05177
Molecular weight:
58406.915
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
General function:
Involved in sequence-specific DNA binding transcription factor activity
Specific function:
Control of topological states of DNA by transient breakage and subsequent rejoining of DNA strands. Topoisomerase II makes double-strand breaks
Gene Name:
TOP2A
Uniprot ID:
P11388
Molecular weight:
174383.9
References
  1. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]