<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <id type="integer">2880</id>
  <title>T3D2838</title>
  <common-name>Rifabutin</common-name>
  <description>Rifabutin is only found in individuals that have used or taken this drug. It is a broad-spectrum antibiotic that is being used as prophylaxis against disseminated Mycobacterium avium complex infection in HIV-positive patients. [PubChem]Rifabutin acts via the inhibition of DNA-dependent RNA polymerase in gram-positive and some gram-negative bacteria, leading to a suppression of RNA synthesis and cell death.</description>
  <cas>72559-06-9</cas>
  <pubchem-id>6323490</pubchem-id>
  <chemical-formula>C46H62N4O11</chemical-formula>
  <weight>846.441510</weight>
  <appearance>White powder.</appearance>
  <melting-point></melting-point>
  <boiling-point nil="true"/>
  <density nil="true"/>
  <solubility>Minimally soluble (0.19 mg/mL)</solubility>
  <specific-gravity nil="true"/>
  <flash-point nil="true"/>
  <vapour-pressure nil="true"/>
  <route-of-exposure>Rifabutin is readily absorbed from the gastrointestinal tract, with an absolute bioavailability averaging 20%.</route-of-exposure>
  <target nil="true"/>
  <mechanism-of-toxicity>Rifabutin acts via the inhibition of DNA-dependent RNA polymerase in gram-positive and some gram-negative bacteria, leading to a suppression of RNA synthesis and cell death.</mechanism-of-toxicity>
  <metabolism>Hepatic. Of the five metabolites that have been identified, 25-O-desacetyl and 31-hydroxy are the most predominant. The former metabolite has an activity equal to the parent drug and contributes up to 10% to the total antimicrobial activity.Route of Elimination: A mass-balance study in three healthy adult volunteers with 14C-labeled rifabutin showed that 53% of the oral dose was excreted in the urine, primarily as metabolites. About 30% of the dose is excreted in the feces.Half Life: 45 (&amp;plusmn; 17) hours</metabolism>
  <toxicity>LD50: 4.8 g/kg (male mouse)</toxicity>
  <lethaldose nil="true"/>
  <carcinogenicity>No indication of carcinogenicity to humans (not listed by IARC).</carcinogenicity>
  <use-source>For the prevention of disseminated &lt;i&gt;Mycobacterium avium&lt;/i&gt; complex (MAC) disease in patients with advanced HIV infection. Used in the treatment of tuberculosis. It has also found to be useful in the treatment of (Chlamydia) Chlamydophila pneumoniae (Cpn) Infection.[Wikipedia]</use-source>
  <min-risk-level nil="true"/>
  <health-effects nil="true"/>
  <symptoms>Symptoms include diarrhea, eructation, abdominal pain, vomitting, nausea, and  insomnia.</symptoms>
  <treatment>Clinical experience with rifamycins suggests that gastric lavage to evacuate gastric contents (within a few hours of overdose), followed by instillation of an activated charcoal slurry into the stomach, may help absorb any remaining drug from the gastrointestinal tract. (L1712)</treatment>
  <created-at type="dateTime">2009-07-21T20:27:15Z</created-at>
  <updated-at type="dateTime">2014-12-24T20:25:52Z</updated-at>
  <interacting-proteins nil="true"/>
  <wikipedia>Rifabutin</wikipedia>
  <uniprot-id></uniprot-id>
  <kegg-compound-id>C07235</kegg-compound-id>
  <omim-id></omim-id>
  <chebi-id>8857</chebi-id>
  <biocyc-id></biocyc-id>
  <ctd-id nil="true"/>
  <stitch-id>Rifabutin</stitch-id>
  <drugbank-id>DB00615</drugbank-id>
  <pdb-id>RBT</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]\C1=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)=NC2=C3NC4(CCN(CC(C)C)CC4)N=C3C3=C(C(O)=C(C)C4=C3C(=O)[C@](C)(O4)O1)C2=O</moldb-smiles>
  <moldb-formula>C46H62N4O11</moldb-formula>
  <moldb-inchi>InChI=1S/C46H62N4O11/c1-22(2)21-50-18-16-46(17-19-50)48-34-31-32-39(54)28(8)42-33(31)43(56)45(10,61-42)59-20-15-30(58-11)25(5)41(60-29(9)51)27(7)38(53)26(6)37(52)23(3)13-12-14-24(4)44(57)47-36(40(32)55)35(34)49-46/h12-15,20,22-23,25-27,30,37-38,41,49,52-54H,16-19,21H2,1-11H3,(H,47,57)/b13-12-,20-15-,24-14-/t23-,25+,26+,27+,30-,37-,38+,41+,45-/m0/s1</moldb-inchi>
  <moldb-inchikey>InChIKey=ATEBXHFBFRCZMA-DVAZEERGSA-N</moldb-inchikey>
  <moldb-average-mass type="decimal">847.0047</moldb-average-mass>
  <moldb-mono-mass type="decimal">846.441508846</moldb-mono-mass>
  <origin>Exogenous</origin>
  <state>Solid</state>
  <logp>4.1</logp>
  <hmdb-id>HMDB14753</hmdb-id>
  <chembl-id>CHEMBL444633</chembl-id>
  <chemspider-id>4883445</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></synthesis-reference>
  <structure-image-caption nil="true"/>
</compound>
