<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <id type="integer">3537</id>
  <title>T3D3495</title>
  <common-name>Ciprofloxacin</common-name>
  <description>Ciprofloxacin is only found in individuals that have used or taken this drug. It is a broad-spectrum antimicrobial carboxyfluoroquinoline. The bactericidal action of ciprofloxacin results from inhibition of the enzymes topoisomerase II (DNA gyrase) and topoisomerase IV, which are required for bacterial DNA replication, transcription, repair, strand supercoiling repair, and recombination.</description>
  <cas>85721-33-1</cas>
  <pubchem-id>2764</pubchem-id>
  <chemical-formula>C17H18FN3O3</chemical-formula>
  <weight>331.133220</weight>
  <appearance>White powder.</appearance>
  <melting-point>255-257°C</melting-point>
  <boiling-point nil="true"/>
  <density nil="true"/>
  <solubility>3E+004 mg/L (at 20°C)</solubility>
  <specific-gravity nil="true"/>
  <flash-point nil="true"/>
  <vapour-pressure nil="true"/>
  <route-of-exposure>Eye contact; parenteral (intravenous injection); oral. Rapidly and well absorbed from the gastrointestinal tract after oral administration. The absolute bioavailability is approximately 70% with no substantial loss by first pass metabolism.</route-of-exposure>
  <target nil="true"/>
  <mechanism-of-toxicity>The bactericidal action of ciprofloxacin results from inhibition of the enzymes topoisomerase II (DNA gyrase) and topoisomerase IV, which are required for bacterial DNA replication, transcription, repair, strand supercoiling repair, and recombination.</mechanism-of-toxicity>
  <metabolism>Hepatic. Four metabolites have been identified in human urine which together account for approximately 15% of an oral dose. The metabolites have antimicrobial activity, but are less active than unchanged ciprofloxacin.Route of Elimination: Approximately 40 to 50% of an orally administered dose is excreted in the urine as unchanged drug.Half Life: 4 hours</metabolism>
  <toxicity nil="true"/>
  <lethaldose nil="true"/>
  <carcinogenicity>No indication of carcinogenicity to humans (not listed by IARC).</carcinogenicity>
  <use-source>For the treatment of the following infections caused by susceptible organisms: urinary tract infections, acute uncomplicated cystitis, chronic bacterial prostatitis, lower respiratory tract infections, acute sinusitis, skin and skin structure infections, bone and joint infections, complicated intra-abdominal infections (used in combination with metronidazole), infectious diarrhea, typhoid fever (enteric fever), uncomplicated cervical and urethral gonorrhea, and inhalational anthrax (post-exposure).</use-source>
  <min-risk-level nil="true"/>
  <health-effects>Inflammation of the skin (exfoliative dermatitis) </health-effects>
  <symptoms>The major adverse effect seen with use of is gastrointestinal irritation, common with many antibiotics.</symptoms>
  <treatment nil="true"/>
  <created-at type="dateTime">2009-07-30T17:58:47Z</created-at>
  <updated-at type="dateTime">2014-12-24T20:26:07Z</updated-at>
  <interacting-proteins nil="true"/>
  <wikipedia>Ciprofloxacin</wikipedia>
  <uniprot-id></uniprot-id>
  <kegg-compound-id>C05349</kegg-compound-id>
  <omim-id></omim-id>
  <chebi-id>100241</chebi-id>
  <biocyc-id></biocyc-id>
  <ctd-id nil="true"/>
  <stitch-id>Ciprofloxacin  </stitch-id>
  <drugbank-id>DB00537</drugbank-id>
  <pdb-id>CPF</pdb-id>
  <actor-id nil="true"/>
  <organism nil="true"/>
  <export type="boolean">true</export>
  <metabolizing-proteins nil="true"/>
  <transporting-proteins nil="true"/>
  <moldb-smiles>OC(=O)C1=CN(C2CC2)C2=CC(N3CCNCC3)=C(F)C=C2C1=O</moldb-smiles>
  <moldb-formula>C17H18FN3O3</moldb-formula>
  <moldb-inchi>InChI=1S/C17H18FN3O3/c18-13-7-11-14(8-15(13)20-5-3-19-4-6-20)21(10-1-2-10)9-12(16(11)22)17(23)24/h7-10,19H,1-6H2,(H,23,24)</moldb-inchi>
  <moldb-inchikey>InChIKey=MYSWGUAQZAJSOK-UHFFFAOYSA-N</moldb-inchikey>
  <moldb-average-mass type="decimal">331.3415</moldb-average-mass>
  <moldb-mono-mass type="decimal">331.133219662</moldb-mono-mass>
  <origin>Exogenous</origin>
  <state>Solid</state>
  <logp>0.28</logp>
  <hmdb-id>HMDB14677</hmdb-id>
  <chembl-id>CHEMBL8</chembl-id>
  <chemspider-id>2662</chemspider-id>
  <structure-image-file-name nil="true"/>
  <structure-image-content-type nil="true"/>
  <structure-image-file-size type="integer" nil="true"/>
  <structure-image-updated-at type="dateTime" nil="true"/>
  <biodb-id nil="true"/>
  <synthesis-reference>&lt;p&gt;&lt;a href="http://www.drugsyn.org/Ciprofloxacin.htm"&gt;DrugSyn.org&lt;/a&gt;&lt;/p&gt;</synthesis-reference>
  <structure-image-caption nil="true"/>
</compound>
