<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <id type="integer">3011</id>
  <title>T3D2969</title>
  <common-name>Rifampin</common-name>
  <description>A semisynthetic antibiotic produced from Streptomyces mediterranei. It has a broad antibacterial spectrum, including activity against several forms of Mycobacterium. In susceptible organisms it inhibits DNA-dependent RNA polymerase activity by forming a stable complex with the enzyme. It thus suppresses the initiation of RNA synthesis. Rifampin is bactericidal, and acts on both intracellular and extracellular organisms. (From Gilman et al., Goodman and Gilman&amp;#39;s The Pharmacological Basis of Therapeutics, 9th ed, p1160)</description>
  <cas>13292-46-1</cas>
  <pubchem-id>5381226</pubchem-id>
  <chemical-formula>C43H58N4O12</chemical-formula>
  <weight>822.405120</weight>
  <appearance>White powder.</appearance>
  <melting-point>183°C</melting-point>
  <boiling-point nil="true"/>
  <density nil="true"/>
  <solubility>1400 mg/L (at 25°C)</solubility>
  <specific-gravity nil="true"/>
  <flash-point nil="true"/>
  <vapour-pressure nil="true"/>
  <route-of-exposure>Oral. Well absorbed from gastrointestinal tract.</route-of-exposure>
  <target nil="true"/>
  <mechanism-of-toxicity>Rifampin acts via the inhibition of DNA-dependent RNA polymerase, leading to a suppression of RNA synthesis and cell death.</mechanism-of-toxicity>
  <metabolism>Primarily hepatic, rapidly deacetylated.Route of Elimination: Less than 30% of the dose is excreted in the urine as rifampin or metabolites.Half Life: 3.35 (+/- 0.66) hours</metabolism>
  <toxicity>LD50: 1570 mg/kg (Rat) (A308)</toxicity>
  <lethaldose nil="true"/>
  <carcinogenicity>3, not classifiable as to its carcinogenicity to humans. (L135)</carcinogenicity>
  <use-source>For the treatment of Tuberculosis and Tuberculosis-related mycobacterial infections.</use-source>
  <min-risk-level nil="true"/>
  <health-effects>Antibiotic resistance</health-effects>
  <symptoms>Chronic exposure may cause nausea and vomiting and unconsciousness</symptoms>
  <treatment>Intensive support measures should be instituted and individual symptoms treated as they arise. Since nausea and vomiting are likely to be present, gastric lavage  is probably preferable to induction of emesis. Following evacuation of the gastric contents, the instillation of activated charcoal slurry into the stomach may help absorb any remaining drug from the gastrointestinal tract. Antiemetic medication may be required to control severe nausea and vomiting. Active diuresis (with measured intake and output) will help promote excretion of the drug. Hemodialysis  may be of value in some patients. (L1712)</treatment>
  <created-at type="dateTime">2009-07-21T20:28:15Z</created-at>
  <updated-at type="dateTime">2014-12-24T20:25:54Z</updated-at>
  <interacting-proteins nil="true"/>
  <wikipedia>Rifampin</wikipedia>
  <uniprot-id></uniprot-id>
  <kegg-compound-id>C06688</kegg-compound-id>
  <omim-id></omim-id>
  <chebi-id>28077</chebi-id>
  <biocyc-id></biocyc-id>
  <ctd-id nil="true"/>
  <stitch-id>Rifampin</stitch-id>
  <drugbank-id>DB01045</drugbank-id>
  <pdb-id>RFP</pdb-id>
  <actor-id nil="true"/>
  <organism nil="true"/>
  <export type="boolean">true</export>
  <metabolizing-proteins nil="true"/>
  <transporting-proteins nil="true"/>
  <moldb-smiles>[H]C(=NN1CCN(C)CC1)C1=C(O)C2=C3C(O)=C(C)C4=C2C(=O)[C@](C)(O4)O\C([H])=C([H])/[C@]([H])(OC)[C@@]([H])(C)[C@@]([H])(OC(C)=O)[C@]([H])(C)[C@]([H])(O)[C@]([H])(C)[C@@]([H])(O)[C@@]([H])(C)C([H])=C([H])\C([H])=C(C)/C(O)=NC1=C3O</moldb-smiles>
  <moldb-formula>C43H58N4O12</moldb-formula>
  <moldb-inchi>InChI=1S/C43H58N4O12/c1-21-12-11-13-22(2)42(55)45-33-28(20-44-47-17-15-46(9)16-18-47)37(52)30-31(38(33)53)36(51)26(6)40-32(30)41(54)43(8,59-40)57-19-14-29(56-10)23(3)39(58-27(7)48)25(5)35(50)24(4)34(21)49/h11-14,19-21,23-25,29,34-35,39,49-53H,15-18H2,1-10H3,(H,45,55)/b12-11+,19-14-,22-13-,44-20-/t21-,23+,24+,25+,29-,34-,35+,39+,43-/m0/s1</moldb-inchi>
  <moldb-inchikey>InChIKey=JQXXHWHPUNPDRT-XHVADFQNSA-N</moldb-inchikey>
  <moldb-average-mass type="decimal">822.9402</moldb-average-mass>
  <moldb-mono-mass type="decimal">822.40512334</moldb-mono-mass>
  <origin>Exogenous</origin>
  <state>Solid</state>
  <logp>2.7</logp>
  <hmdb-id>HMDB15179</hmdb-id>
  <chembl-id>CHEMBL374478</chembl-id>
  <chemspider-id>10468813</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;Klaus Jurgen, Joachim Seydel, &amp;#8220;Combination preparations containing rifampicin and thioacetazon.&amp;#8221; U.S. Patent US5104875, issued August, 1973.&lt;/p&gt;</synthesis-reference>
  <structure-image-caption nil="true"/>
</compound>
