<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <id type="integer">4007</id>
  <title>T3D3953</title>
  <common-name>Oxytetracycline</common-name>
  <description>A tetracycline analog isolated from the actinomycete streptomyces rimosus and used in a wide variety of clinical conditions. [PubChem]</description>
  <cas>79-57-2</cas>
  <pubchem-id>5280972</pubchem-id>
  <chemical-formula>C22H24N2O9</chemical-formula>
  <weight nil="true"/>
  <appearance>White powder.</appearance>
  <melting-point>184.5°C</melting-point>
  <boiling-point></boiling-point>
  <density nil="true"/>
  <solubility>313 mg/L (at 25°C)</solubility>
  <specific-gravity nil="true"/>
  <flash-point nil="true"/>
  <vapour-pressure nil="true"/>
  <route-of-exposure>Readily absorbed following oral administration.</route-of-exposure>
  <target nil="true"/>
  <mechanism-of-toxicity>Tetracyclines target the 28S small subunit of the mitochondrial ribosome thereby deactivation mitochondrial protein synthesis. As a result tetracyclines are cytotoxic to the most metabolically active cells or tissues including the heart, liver, thymus and bone-marrow. (A7823).  The likely target of most tetracyclines is the 12S rRNA molecule in the mitochondrial ribosome, which is analogous to the 16S rRNA in bacterial ribosomes.</mechanism-of-toxicity>
  <metabolism></metabolism>
  <toxicity></toxicity>
  <lethaldose></lethaldose>
  <carcinogenicity>No indication of carcinogenicity to humans (not listed by IARC).</carcinogenicity>
  <use-source>Oxytetracycline is indicated for treatment of infections caused by a variety of Gram positive and Gram negative microorganisms including &lt;i&gt;Mycoplasma pneumoniae, Pasteurella pestis, Escherichia coli, Haemophilus influenzae&lt;/i&gt; (respiratory infections), and &lt;i&gt;Diplococcus pneumoniae&lt;/i&gt;.</use-source>
  <min-risk-level></min-risk-level>
  <health-effects>Side effects from normal doses of tetracyclines are relatively minimal, but of particular note is phototoxicity. Tetracylclines increase the risk of sunburn under exposure to light from the sun or other sources. Tetracyclines may also cause stomach or bowel upsets, and, on rare occasions, allergic reactions. Very rarely, severe headache and vision problems may be signs of dangerous secondary intracranial hypertension, also known as pseudotumor cerebri. Tetracyclines are teratogens and cause tooth discolouration and poor tooth mineralization in the fetus as they develop in infancy. Symptoms of tetracycline overdose include anorexia, nausea, diarrhea, glossitis, dysphagia, enterocolitis and inflammatory lesions, skin reactions such as maculopapular and erythematous rashes, exfoliative dermatitis, photosensitivity, hypersensitivity reactions such as urticaria, angioneurotic oedema, anaphylaxis, anaphyl-actoid purpura, pericarditis, and exacerbation of systemic lupus erythematosus, benign intracranial hypertension in adults disappearing on discontinuation of the medicine, haematologic abnormalities such as haemolytic anaemia, thrombocytopenia, neutropenia, and eosinophilia.</health-effects>
  <symptoms>Symptoms may include stomach or bowel upsets and rarely allergic reactions. Very rarely severe headache and vision problems may be signs of dangerous intracranial hypertenion.</symptoms>
  <treatment>Drug therapy is discontinued immediately; exchange transfusion may be required to remove the drug. Sometimes, phenobarbital (UGT induction) is used.</treatment>
  <created-at type="dateTime">2014-08-28T20:09:03Z</created-at>
  <updated-at type="dateTime">2014-12-24T20:26:34Z</updated-at>
  <interacting-proteins nil="true"/>
  <wikipedia>Oxytetracycline</wikipedia>
  <uniprot-id></uniprot-id>
  <kegg-compound-id>C06624</kegg-compound-id>
  <omim-id></omim-id>
  <chebi-id>27701</chebi-id>
  <biocyc-id></biocyc-id>
  <ctd-id></ctd-id>
  <stitch-id></stitch-id>
  <drugbank-id>DB00595</drugbank-id>
  <pdb-id>OAQ</pdb-id>
  <actor-id></actor-id>
  <organism nil="true"/>
  <export type="boolean">true</export>
  <metabolizing-proteins nil="true"/>
  <transporting-proteins nil="true"/>
  <moldb-smiles>[H][C@]1(O)[C@@]2([H])C(=C(O)[C@]3(O)C(=O)C(C(O)=N)=C(O)[C@@]([H])(N(C)C)[C@]13[H])C(=O)C1=C(C=CC=C1O)[C@@]2(C)O</moldb-smiles>
  <moldb-formula>C22H24N2O9</moldb-formula>
  <moldb-inchi>InChI=1S/C22H24N2O9/c1-21(32)7-5-4-6-8(25)9(7)15(26)10-12(21)17(28)13-14(24(2)3)16(27)11(20(23)31)19(30)22(13,33)18(10)29/h4-6,12-14,17,25,27-29,32-33H,1-3H3,(H2,23,31)/t12-,13-,14+,17+,21-,22+/m1/s1</moldb-inchi>
  <moldb-inchikey>InChIKey=IWVCMVBTMGNXQD-PXOLEDIWSA-N</moldb-inchikey>
  <moldb-average-mass type="decimal">460.434</moldb-average-mass>
  <moldb-mono-mass type="decimal">460.148180376</moldb-mono-mass>
  <origin>Exogenous</origin>
  <state>Solid</state>
  <logp>-0.9</logp>
  <hmdb-id>HMDB14733</hmdb-id>
  <chembl-id>CHEMBL1517</chembl-id>
  <chemspider-id>4444458</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;Janos Balint, Laszlo Cseke, Ferenc Fabian, Lajos Kun, Miklos Szarvas, &amp;#8220;Process for the preparation of an oxytetracycline-calcium silicate complex salt from fermentation broth.&amp;#8221; U.S. Patent US4584135, issued April, 1951.&lt;/p&gt;</synthesis-reference>
  <structure-image-caption nil="true"/>
</compound>
