<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <id type="integer">4006</id>
  <title>T3D3952</title>
  <common-name>Lymecycline</common-name>
  <description>Lymecycline is a tetracycline broad-spectrum antibiotic marketed by the pharmaceutical company Galderma. It is approximately 5,000 times more soluble than tetracycline base and is unique amongst tetracyclines in that it is absorbed by an active transport process across the intestinal wall, making use of the same fast and efficient mechanism by which carbohydrates are absorbed.</description>
  <cas>992-21-2</cas>
  <pubchem-id>24757945</pubchem-id>
  <chemical-formula>C29H38N4O10</chemical-formula>
  <weight nil="true"/>
  <appearance>White powder.</appearance>
  <melting-point></melting-point>
  <boiling-point></boiling-point>
  <density nil="true"/>
  <solubility>Soluble (at all physiological pH values)</solubility>
  <specific-gravity nil="true"/>
  <flash-point nil="true"/>
  <vapour-pressure nil="true"/>
  <route-of-exposure>Absorption is fast and efficient. Bioavailability is 100% 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>For the treatment of infections and to treat acne. It may also be used to treat urinary tract infections, gum disease, and other bacterial infections such as gonorrhea and chlamydia. Lymecycline is also used commonly as a prophylactic treatment for infection by &lt;i&gt;Bacillus anthracis&lt;/i&gt; (anthrax). It is also effective against &lt;i&gt;Yersinia pestis&lt;/i&gt; and malaria and is also prescribed for the treatment of Lyme disease.</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 include nausea, vomiting, diarrhoea, glossitis, enterocolitis, dysphagia, dermatitis, hypersensitivity reactions, proctitis, and vaginitis.</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">2014-08-28T19:48:07Z</created-at>
  <updated-at type="dateTime">2026-05-14T16:24:58Z</updated-at>
  <interacting-proteins nil="true"/>
  <wikipedia>Lymecycline</wikipedia>
  <uniprot-id></uniprot-id>
  <kegg-compound-id></kegg-compound-id>
  <omim-id></omim-id>
  <chebi-id>59040</chebi-id>
  <biocyc-id></biocyc-id>
  <ctd-id></ctd-id>
  <stitch-id></stitch-id>
  <drugbank-id>DB00256</drugbank-id>
  <pdb-id></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@@]12C[C@@]3([H])C(C(=O)C4=C(O)C=CC=C4[C@@]3(C)O)=C(O)[C@]1(O)C(=O)C(C(=O)NCNCCCC[C@H](N)C(O)=O)=C(O)[C@H]2N(C)C</moldb-smiles>
  <moldb-formula>C29H38N4O10</moldb-formula>
  <moldb-inchi>InChI=1S/C29H38N4O10/c1-28(42)13-7-6-9-17(34)18(13)22(35)19-14(28)11-15-21(33(2)3)23(36)20(25(38)29(15,43)24(19)37)26(39)32-12-31-10-5-4-8-16(30)27(40)41/h6-7,9,14-16,21,31,34,36-37,42-43H,4-5,8,10-12,30H2,1-3H3,(H,32,39)(H,40,41)/t14-,15-,16-,21-,28+,29-/m0/s1</moldb-inchi>
  <moldb-inchikey>AHEVKYYGXVEWNO-UEPZRUIBSA-N</moldb-inchikey>
  <moldb-average-mass type="decimal">602.6328</moldb-average-mass>
  <moldb-mono-mass type="decimal">602.258793456</moldb-mono-mass>
  <origin>Exogenous</origin>
  <state>Solid</state>
  <logp>0.3</logp>
  <hmdb-id>HMDB14401</hmdb-id>
  <chembl-id>CHEMBL2103929</chembl-id>
  <chemspider-id>23501197</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;Willis L. Winstrom, &amp;#8220;Process and apparatus for the preparation of chlortetracycline-containing animal feed compositions.&amp;#8221; U.S. Patent US06844006, issued January 18, 2005.&lt;/p&gt;</synthesis-reference>
  <structure-image-caption nil="true"/>
  <chemdb-id>CHEM002912</chemdb-id>
  <dsstox-id>DTXSID9045344</dsstox-id>
  <toxcast-id nil="true"/>
  <stoff-ident-origin nil="true"/>
  <stoff-ident-id nil="true"/>
  <susdat-id>NS00021415</susdat-id>
  <iupac>(2S)-6-[({[(4S,4aS,5aS,6S,12aS)-4-(dimethylamino)-3,6,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydrotetracen-2-yl]formamido}methyl)amino]-2-aminohexanoic acid</iupac>
  <moldb-polar-surface-area>242.98</moldb-polar-surface-area>
  <moldb-refractivity>154.50959999999998</moldb-refractivity>
  <moldb-polarizability>62.87541329559511</moldb-polarizability>
  <moldb-rotatable-bond-count>10</moldb-rotatable-bond-count>
  <moldb-acceptor-count>13</moldb-acceptor-count>
  <moldb-donor-count>9</moldb-donor-count>
  <moldb-pka-strongest-acidic>0.4019689064642926</moldb-pka-strongest-acidic>
  <moldb-pka-strongest-basic>9.498336165371285</moldb-pka-strongest-basic>
  <moldb-physiological-charge>0</moldb-physiological-charge>
  <moldb-number-of-rings>4</moldb-number-of-rings>
  <moldb-alogps-logp>-0.27</moldb-alogps-logp>
  <moldb-alogps-logs>-2.66</moldb-alogps-logs>
  <moldb-alogps-solubility>1.31e+00 g/l</moldb-alogps-solubility>
</compound>
