<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <id type="integer">2780</id>
  <title>T3D2738</title>
  <common-name>Bleomycin</common-name>
  <description>A complex of related glycopeptide antibiotics from &lt;i&gt;Streptomyces verticillus&lt;/i&gt; consisting of bleomycin A2 and B2 (B2 CAS # 9060-10-0). It inhibits DNA metabolism and is used as an antineoplastic, especially for solid tumors. Bleomycin A2 is used as the representative structure for Bleomycin.</description>
  <cas>11056-06-7</cas>
  <pubchem-id>5360373</pubchem-id>
  <chemical-formula>C55H84N17O21S3</chemical-formula>
  <weight></weight>
  <appearance>White powder.</appearance>
  <melting-point>71°C</melting-point>
  <boiling-point></boiling-point>
  <density nil="true"/>
  <solubility>Soluble</solubility>
  <specific-gravity nil="true"/>
  <flash-point nil="true"/>
  <vapour-pressure nil="true"/>
  <route-of-exposure>Intravenous; systemic absorption is approximately 45%.</route-of-exposure>
  <target nil="true"/>
  <mechanism-of-toxicity>It has been suggested that bleomycin induces sensitivity to oxygen toxicity and recent studies support the role of the proinflammatory cytokines IL-18 and IL-1beta in the mechanism of bleomycin-induced lung injury. (Wikipedia) In primary pulmonary endothelial cells, bleomycin initiates apoptosis via the extrinsic pathway (A15408). In relation to bleomycin-induced scleroderma, bleomycin exerts various effects on skin-constituted cells such as fibroblasts, keratinocytes, and endothelial cells, as well as immunocytes. Bleomycin upregulates gene expression of ECM proteins as well as fibrogenic cytokines such as TGF-β and CTGF in cultured human skin fibroblasts. Also, in vitro studies showed a dose-dependent stimulation of endothelial cell secretion of collagen synthesis by bleomycin, which was inhibited by the anti-TGF-β antibody. (A15409).</mechanism-of-toxicity>
  <metabolism>Hepatic
Route of Elimination: It was reported that patients with moderately severe renal failure excreted less than 20% of the dose in the urine.
Half Life: 115 minutes</metabolism>
  <toxicity></toxicity>
  <lethaldose></lethaldose>
  <carcinogenicity>2B, possibly carcinogenic to humans. (L135)</carcinogenicity>
  <use-source>For palliative treatment in the management malignant neoplasm (trachea, bronchus, lung), squamous cell carcinoma, and lymphomas.</use-source>
  <min-risk-level></min-risk-level>
  <health-effects>The most serious complication of bleomycin is pulmonary fibrosis and impaired lung function. (Wikipedia) Bleomycin can also induce scleroderma (A15410, A15408).</health-effects>
  <symptoms>Excessive exposure may cause fever, chills, nausea, vomiting, mental, confusion, and wheezing. Bleomycin may cause irritation to eyes, skin and respiratory tract. It may also cause a darkening or thickening of the skin. It may cause an allergic reaction.</symptoms>
  <treatment></treatment>
  <created-at type="dateTime">2009-07-21T20:26:29Z</created-at>
  <updated-at type="dateTime">2026-05-14T16:25:13Z</updated-at>
  <interacting-proteins nil="true"/>
  <wikipedia>Bleomycin</wikipedia>
  <uniprot-id></uniprot-id>
  <kegg-compound-id>C06854</kegg-compound-id>
  <omim-id></omim-id>
  <chebi-id>22907</chebi-id>
  <biocyc-id></biocyc-id>
  <ctd-id></ctd-id>
  <stitch-id>Bleomycin</stitch-id>
  <drugbank-id>DB00290</drugbank-id>
  <pdb-id>BLM</pdb-id>
  <actor-id></actor-id>
  <organism nil="true"/>
  <export type="boolean">true</export>
  <metabolizing-proteins nil="true"/>
  <transporting-proteins nil="true"/>
  <moldb-smiles>C[C@@H](O)[C@H](NC(=O)[C@@H](C)[C@H](O)[C@@H](C)NC(=O)[C@@H](NC(=O)C1=C(C)C(N)=NC(=N1)[C@H](CC(N)=O)NC[C@H](N)C(N)=O)[C@@H](OC1OC(CO)C(O)C(O)C1OC1OC(CO)C(O)C(OC(N)=O)C1O)C1=CN=CN1)C(=O)NCCC1=NC(=CS1)C1=NC(=CS1)C(=O)NCCC[S+](C)C</moldb-smiles>
  <moldb-formula>C55H84N17O21S3</moldb-formula>
  <moldb-inchi>InChI=1S/C55H83N17O21S3/c1-20-33(69-46(72-44(20)58)25(12-31(57)76)64-13-24(56)45(59)82)50(86)71-35(41(26-14-61-19-65-26)91-54-43(39(80)37(78)29(15-73)90-54)92-53-40(81)42(93-55(60)88)38(79)30(16-74)89-53)51(87)66-22(3)36(77)21(2)47(83)70-34(23(4)75)49(85)63-10-8-32-67-28(18-94-32)52-68-27(17-95-52)48(84)62-9-7-11-96(5)6/h14,17-19,21-25,29-30,34-43,53-54,64,73-75,77-81H,7-13,15-16,56H2,1-6H3,(H13-,57,58,59,60,61,62,63,65,66,69,70,71,72,76,82,83,84,85,86,87,88)/p+1/t21-,22+,23+,24-,25-,29?,30?,34-,35-,36-,37?,38?,39?,40?,41-,42?,43?,53?,54?/m0/s1</moldb-inchi>
  <moldb-inchikey>OYVAGSVQBOHSSS-WXFSZRTFSA-O</moldb-inchikey>
  <moldb-average-mass type="decimal">1415.552</moldb-average-mass>
  <moldb-mono-mass type="decimal">1414.518979905</moldb-mono-mass>
  <origin>Exogenous</origin>
  <state>Solid</state>
  <logp></logp>
  <hmdb-id>HMDB14435</hmdb-id>
  <chembl-id>CHEMBL403664</chembl-id>
  <chemspider-id>4514492</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;Hamao Umezawa, Kenji Maeda, Tomohisa Takita, Yuya Nakayama, Akio Fujii, Nobuyoshi Shimada, Hideo Chimura, &amp;#8220;Novel process for producing antibiotics bleomycin.&amp;#8221; U.S. Patent USRE0304514, issued October, 1970.&lt;/p&gt;</synthesis-reference>
  <structure-image-caption nil="true"/>
  <chemdb-id>CHEM002161</chemdb-id>
  <dsstox-id>DTXSID1030862</dsstox-id>
  <toxcast-id nil="true"/>
  <stoff-ident-origin nil="true"/>
  <stoff-ident-id nil="true"/>
  <susdat-id>NS00006983</susdat-id>
  <iupac>(3-{[2-(2-{2-[(2S,3R)-2-[(2S,3S,4R)-4-[(2S,3R)-2-({6-amino-2-[(1S)-1-{[(2S)-2-amino-2-carbamoylethyl]amino}-2-carbamoylethyl]-5-methylpyrimidin-4-yl}formamido)-3-[(3-{[4-(carbamoyloxy)-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl)oxy]-3-(1H-imidazol-4-yl)propanamido]-3-hydroxy-2-methylpentanamido]-3-hydroxybutanamido]ethyl}-1,3-thiazol-4-yl)-1,3-thiazol-4-yl]formamido}propyl)dimethylsulfanium</iupac>
  <moldb-polar-surface-area>627.0699999999997</moldb-polar-surface-area>
  <moldb-refractivity>344.15939999999995</moldb-refractivity>
  <moldb-polarizability>142.03063073159115</moldb-polarizability>
  <moldb-rotatable-bond-count>36</moldb-rotatable-bond-count>
  <moldb-acceptor-count>28</moldb-acceptor-count>
  <moldb-donor-count>20</moldb-donor-count>
  <moldb-pka-strongest-acidic>11.343569780146002</moldb-pka-strongest-acidic>
  <moldb-pka-strongest-basic>7.668791734854689</moldb-pka-strongest-basic>
  <moldb-physiological-charge>2</moldb-physiological-charge>
  <moldb-number-of-rings>6</moldb-number-of-rings>
  <moldb-alogps-logp>-0.52</moldb-alogps-logp>
  <moldb-alogps-logs>-4.71</moldb-alogps-logs>
  <moldb-alogps-solubility>2.82e-02 g/l</moldb-alogps-solubility>
</compound>
