<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <id type="integer">1786</id>
  <title>T3D1782</title>
  <common-name>Bromodeoxyuridine</common-name>
  <description>Bromodeoxyuridine is an organobromide compound and a synthetic nucleoside that is an analogue of thymidine.  It is brominated derivative of deoxyuridine that acts as an antimetabolite or base analog, substituting for thymidine in DNA. It can induce DNA mutations in the same way as 2-aminopurine It is used in the detection of proliferating cells in living tissues, as it can be incorporated into the newly synthesized DNA of replicating cells, then detected using antibodies.</description>
  <cas>59-14-3</cas>
  <pubchem-id>6035</pubchem-id>
  <chemical-formula>C9H11BrN2O5</chemical-formula>
  <weight>305.985130</weight>
  <appearance>White crystalline powder.</appearance>
  <melting-point>192.5°C</melting-point>
  <boiling-point></boiling-point>
  <density nil="true"/>
  <solubility></solubility>
  <specific-gravity nil="true"/>
  <flash-point nil="true"/>
  <vapour-pressure nil="true"/>
  <route-of-exposure>Oral (L626) ; inhalation (L626) ; dermal (L626)</route-of-exposure>
  <target nil="true"/>
  <mechanism-of-toxicity>5-bromodeoxyuridine acts on DNA. It induces a random DNA point mutation via base substitution. The base pair will change from an A-T to a G-C or from a G-C to an A-T after a number of replication cycles. As a thymine analog, 5-bromodeoxyuridine normally pairs with adenine. </mechanism-of-toxicity>
  <metabolism>5-bromodeoxyuridine is phosphorylated by thymidine kinase to produce 5-bromodeoxyuridine-phosphate. (L626)
</metabolism>
  <toxicity>LD50: 2500 mg/kg (Intravenous, Mouse) (T14)
LD50: 3500 mg/kg (Subcutaneous, Mouse) (T14)
LD50: 3050 mg/kg (Intraperitoneal, Mouse) (T14)
LD50: 9100 mg/kg (Oral, Mouse) (T14)</toxicity>
  <lethaldose></lethaldose>
  <carcinogenicity>Not listed by IARC. May cause heritable genetic damage.</carcinogenicity>
  <use-source>Laboratory chemical used as a mutagen in mutagenesis experiments. It is more commonly used in the detection of proliferating cells in living tissues.
</use-source>
  <min-risk-level></min-risk-level>
  <health-effects>5-bromodeoxyuridine is a mutagen (causes mutations), a cytotoxin, a teratogen and a weak carcinogen.  The primary harmful effects are genetic mutation, anemia, reproductive disorders (fetal death or abnormality), cataracts, and skin irritation. It can cause respiratory tract irritation if inhaled, skin irritation if it contacts the skin and eye irritation if it contacts the eyes.  As a reproductive toxin BrDU would be considered a “particularly hazardous substance” under the OSHA lab standard.</health-effects>
  <symptoms>5-bromodeoxyuridine can cause hypermotility, diarrhea, weight loss and possibly death if large amounts are repeatedly ingested.</symptoms>
  <treatment>EYES: irrigate opened eyes for several minutes under running water.
      
INGESTION: do not induce vomiting. Rinse mouth with water (never give anything by mouth to an unconscious person). Seek immediate medical advice.
      
SKIN: should be treated immediately by rinsing the affected parts in cold running water for at least 15 minutes, followed by thorough washing with soap and water. If necessary, the person should shower and change contaminated clothing and shoes, and then must seek medical attention.
      
INHALATION: supply fresh air. If required provide artificial respiration.</treatment>
  <created-at type="dateTime">2009-06-22T16:08:36Z</created-at>
  <updated-at type="dateTime">2014-12-24T20:24:37Z</updated-at>
  <interacting-proteins nil="true"/>
  <wikipedia></wikipedia>
  <uniprot-id></uniprot-id>
  <kegg-compound-id></kegg-compound-id>
  <omim-id></omim-id>
  <chebi-id>472552</chebi-id>
  <biocyc-id></biocyc-id>
  <ctd-id>D001973</ctd-id>
  <stitch-id>Bromodeoxyuridine</stitch-id>
  <drugbank-id></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>OCC1OC(CC1O)N1C=C(Br)C(=O)NC1=O</moldb-smiles>
  <moldb-formula>C9H11BrN2O5</moldb-formula>
  <moldb-inchi>InChI=1S/C9H11BrN2O5/c10-4-2-12(9(16)11-8(4)15)7-1-5(14)6(3-13)17-7/h2,5-7,13-14H,1,3H2,(H,11,15,16)</moldb-inchi>
  <moldb-inchikey>InChIKey=WOVKYSAHUYNSMH-UHFFFAOYSA-N</moldb-inchikey>
  <moldb-average-mass type="decimal">307.098</moldb-average-mass>
  <moldb-mono-mass type="decimal">305.985134119</moldb-mono-mass>
  <origin>Exogenous</origin>
  <state>Solid</state>
  <logp></logp>
  <hmdb-id></hmdb-id>
  <chembl-id></chembl-id>
  <chemspider-id></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>
