1.0 2009-07-21 20:26:29 UTC 2026-05-14 16:25:13 UTC T3D2738 Bleomycin SmallMolecule Bleomycin belongs to the hybrid peptides, a subclass of peptidomimetics within the organic compounds. With an average molecular weight of 1,416 g/mol, Bleomycin is a heavy molecule. This exogenous solid has the chemical formula C55H84N17O21S3 and is classified as an organic acid and derivative. It functions as a metabolite and is utilized as an antineoplastic agent. Bleomycin is used in the treatment of cancer (PMC6375222, PMC6395624) and Kaposi's sarcoma (PMC1492602). The compound is found in healthcare, pharmaceuticals, and veterinary products. Recorded exposure routes include intra-arterial, intracavitary, intramuscular, intrapleural, intravenous, and subcutaneous administration, with literature support for inhalation (PMC13296829, PMC5137940). Its protein targets include DNA ligase 3 (LIG3), Transient receptor potential cation channel subfamily A member 1 (TRPA1), and DNA ligase 1 (LIG1). Regarding the latter, available evidence indicates the main mode of action is the inhibition of DNA synthesis, with some evidence of lesser inhibition of RNA and protein synthesis. Bleomycin is associated with several health effects. It is linked to an increase in inflammation (PMC2787721) and pneumonitis (PMC2787721), as well as scleroderma (PMC2995912) and melanoma (PMC10137892). Additionally, it is associated with a decrease in pulmonary fibrosis (PMC2787721, PMC5677010, PMC6536957, PMC6537011). Drug Synthetic Toxin Organic Compound Amine Amide Ester Drug Antimetabolite Antibiotic, Antineoplastic Metabolite Lachrymator Synthetic Compound Blenoxane Bleo Bleocin Bleomicin Bleomicina Bleomycin A2 Bleomycin sulfate Bleomycin sulphate Bleomycine Bleomycins Bleomycinum BLM Etoposide in combination with cisplatin and bleomycin C55H84N17O21S3 1415.552 1414.518979905 (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-5-yl)propanamido]-3-hydroxy-2-methylpentanamido]-3-hydroxybutanamido]ethyl}-1,3-thiazol-4-yl)-1,3-thiazol-4-yl]formamido}propyl)dimethylsulfanium bleomycin 11056-06-7 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 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 OYVAGSVQBOHSSS-WXFSZRTFSA-O Organic compounds Organic acids and derivatives Peptidomimetics Hybrid peptides Hybrid glycopeptides 2,4-disubstituted thiazoles 2-heteroaryl carboxamides Acetals Alpha amino acid amides Aminopyrimidines and derivatives Aralkylamines Azacyclic compounds Beta amino acids and derivatives Carbamate esters Carbonyl compounds Dialkylamines Disaccharides Fatty acyl glycosides of mono- and disaccharides Gamma amino acids and derivatives Heteroaromatic compounds Histidine and derivatives Hydrocarbon derivatives Imidazoles Imidolactams Monoalkylamines N-acyl amines N-acyl-alpha amino acids and derivatives O-glycosyl compounds Organic carbonic acids and derivatives Organic cations Organic oxides Organopnictogen compounds Organosulfur compounds Oxacyclic compounds Oxanes Primary alcohols Primary carboxylic acid amides Pyrimidinecarboxylic acids and derivatives Secondary alcohols Secondary carboxylic acid amides Thiazolecarboxamides 2,4-disubstituted 1,3-thiazole 2-heteroaryl carboxamide Acetal Alcohol Alpha-amino acid amide Alpha-amino acid or derivatives Amine Amino acid or derivatives Aminopyrimidine Aralkylamine Aromatic heteromonocyclic compound Azacycle Azole Beta amino acid or derivatives Carbamic acid ester Carbonic acid derivative Carbonyl group Carboxamide group Carboxylic acid derivative Disaccharide Fatty acyl Fatty acyl glycoside Fatty acyl glycoside of mono- or disaccharide Fatty amide Gamma amino acid or derivatives Glycosyl compound Heteroaromatic compound Histidine or derivatives Hybrid glycopeptide Hydrocarbon derivative Imidazole Imidolactam N-acyl-alpha amino acid or derivatives N-acyl-amine N-substituted-alpha-amino acid O-glycosyl compound Organic cation Organic nitrogen compound Organic oxide Organic oxygen compound Organoheterocyclic compound Organonitrogen compound Organooxygen compound Organopnictogen compound Organosulfur compound Oxacycle Oxane Primary alcohol Primary aliphatic amine Primary amine Primary carboxylic acid amide Pyrimidine Pyrimidine-6-carboxylic acid or derivatives Secondary alcohol Secondary aliphatic amine Secondary amine Secondary carboxylic acid amide Thiazole Thiazolecarboxamide Thiazolecarboxylic acid or derivatives Aromatic heteromonocyclic compounds Non-ribosomal peptide/polyketide hybrids Detected and Not Quantified Exogenous Cytoplasm Membrane Bleomycin Drug Metabolism Action Pathway SMP0142750 Solid White powder. melting_point 71°C solubility Soluble logp -0.52 ALOGPS logs -4.71 ALOGPS solubility 2.82e-02 g/l ALOGPS logp -9.7 ChemAxon pka_strongest_acidic 11.34 ChemAxon pka_strongest_basic 7.67 ChemAxon 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-5-yl)propanamido]-3-hydroxy-2-methylpentanamido]-3-hydroxybutanamido]ethyl}-1,3-thiazol-4-yl)-1,3-thiazol-4-yl]formamido}propyl)dimethylsulfanium ChemAxon average_mass 1415.552 ChemAxon mono_mass 1414.518979905 ChemAxon 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 ChemAxon formula C55H84N17O21S3 ChemAxon 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 ChemAxon inchikey OYVAGSVQBOHSSS-WXFSZRTFSA-O ChemAxon polar_surface_area 627.07 ChemAxon refractivity 344.16 ChemAxon polarizability 142.03 ChemAxon rotatable_bond_count 36 ChemAxon acceptor_count 28 ChemAxon donor_count 20 ChemAxon physiological_charge 2 ChemAxon formal_charge 1 ChemAxon Intravenous; systemic absorption is approximately 45%. 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). 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 2B, possibly carcinogenic to humans. (L135) For palliative treatment in the management malignant neoplasm (trachea, bronchus, lung), squamous cell carcinoma, and lymphomas. #<HealthEffect::ActiveRecord_Associations_CollectionProxy:0x00007f7225b15c80> 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. DB00290 HMDB14435 5360373 CHEMBL403664 4514492 C06854 22907 Bleomycin BLM Bleomycin 11749501 20154224 22028717 6160247 Drugs.com: http://www.drugs.com/cons/Bleomycin.html International Agency for Research on Cancer (2014). IARC Monographs on the Evaluation of Carcinogenic Risks to Humans. : http://monographs.iarc.fr/index.php BE0004796 BE0000199 Although the exact mechanism of action of bleomycin is unknown, available evidence would seem to indicate that the main mode of action is the inhibition of DNA synthesis with some evidence of lesser inhibition of RNA and protein synthesis. BE0000167 Although the exact mechanism of action of bleomycin is unknown, available evidence would seem to indicate that the main mode of action is the inhibition of DNA synthesis with some evidence of lesser inhibition of RNA and protein synthesis. BE0001122