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Identification
- Summary
Bleomycin is a chemotherapy agent used to treat various malignancies, including head and neck malignancy, lymphoma, and testicular tumors, among others.
- Generic Name
- Bleomycin
- DrugBank Accession Number
- DB00290
- Background
A complex of related glycopeptide antibiotics from Streptomyces verticillus 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.
- Type
- Small Molecule
- Groups
- Approved, Investigational
- Structure
Structure for Bleomycin (DB00290)
- Weight
- Average: 1415.552
Monoisotopic: 1414.518979905 - Chemical Formula
- C55H84N17O21S3
- Synonyms
- Bleocin
- Bleomicin
- Bleomicina
- Bleomycin
- Bleomycine
- Bleomycinum
Pharmacology
- Indication
For palliative treatment in the management malignant neoplasm (trachea, bronchus, lung), squamous cell carcinoma, and lymphomas.
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Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Management of Hodgkin's lymphoma •••••••••••• Management of Malignant pleural effusion •••••••••••• Management of Non-hodgkin's lymphoma •••••••••••• Management of Squamous cell carcinoma (scc) •••••••••••• Management of Teratocarcinoma •••••••••••• - Associated Therapies
- Contraindications & Blackbox Warnings
Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- Pharmacodynamics
Bleomycin is an antibiotic which has been shown to have antitumor activity. Bleomycin selectively inhibits the synthesis of deoxyribonucleic acid (DNA). The guanine and cytosine content correlates with the degree of mitomycin-induced cross-linking. At high concentrations of the drug, cellular RNA and protein synthesis are also suppressed. Bleomycin has been shown in vitro to inhibit B cell, T cell, and macrophage proliferation and impair antigen presentation, as well as the secretion of interferon gamma, TNFa, and IL-2. The antibiotic antitumor drugs are cell cycle-nonspecific except for Bleomycin (which has major effects in G2 and M phases).
- Mechanism of action
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. As evident in in vitro studies, the DNA-cleaving actions of bleomycin is dependent on oxygen and metal ions. It is believed that bleomycin chelates metal ions (primarily iron) producing a pseudoenzyme that reacts with oxygen to produce superoxide and hydroxide free radicals that cleave DNA.
Target Actions Organism ADNA cleavageHumans UDNA ligase 1 inhibitorHumans UDNA ligase 3 inhibitorHumans - Absorption
Systemic absorption is approximately 45%.
- Volume of distribution
Not Available
- Protein binding
1%
- 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
- Clearance
Not Available
- Adverse Effects
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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.
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
Interacting Gene/Enzyme Allele name Genotype(s) Defining Change(s) Type(s) Description Details Bleomycin hydrolase --- (G;G) G Allele Effect Directly Studied Patients with this genotype have reduced survival time and increased frequency of early relapse when using bleomycin to treat testicular cancer. Details
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your softwareAbacavir Bleomycin may decrease the excretion rate of Abacavir which could result in a higher serum level. Abatacept The risk or severity of adverse effects can be increased when Bleomycin is combined with Abatacept. Aceclofenac Aceclofenac may decrease the excretion rate of Bleomycin which could result in a higher serum level. Acemetacin Acemetacin may decrease the excretion rate of Bleomycin which could result in a higher serum level. Acetaminophen Bleomycin may decrease the excretion rate of Acetaminophen which could result in a higher serum level. - Food Interactions
- No interactions found.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Product Ingredients
Ingredient UNII CAS InChI Key Bleomycin hydrochloride 7Z9O46JA4A 67763-87-5 BEQASIAARPDOGM-GKQFXSEVSA-O Bleomycin sulfate 7DP3NTV15T 9041-93-4 WUIABRMSWOKTOF-OCBSMOPSSA-N - Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Blenoxane Injection, powder, for solution 15 [USP'U]/1 Intramuscular; Intrapleural; Intravenous; Subcutaneous E.R. Squibb & Sons, L.L.C. 2009-06-01 2010-01-31 US 
Blenoxane Injection, powder, for solution 30 [USP'U]/1 Intramuscular; Intrapleural; Intravenous; Subcutaneous E.R. Squibb & Sons, L.L.C. 2009-06-01 2010-02-28 US Blenoxane Pws 15unit Powder, for solution 15 unit / amp Intramuscular; Intravenous Bristol Labs Division Of Bristol Myers Squibb 1973-12-31 2011-10-19 Canada 
Bleomycin Injection, powder, lyophilized, for solution 15000 [iU]/1 Intra-arterial; Intramuscular; Intravenous Amneal Pharmaceuticals LLC 2016-06-20 Not applicable US Bleomycin for Injection Powder, for solution 15 unit / vial Intramuscular; Intrapleural; Intravenous; Subcutaneous Fresenius Kabi 2009-03-20 Not applicable Canada - Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Bleomycin Injection, powder, lyophilized, for solution 15 [USP'U]/1 Intramuscular; Intrapleural; Intravenous; Subcutaneous Hikma Pharmaceuticals USA Inc. 2018-01-09 Not applicable US Bleomycin Injection, powder, lyophilized, for solution 15 [USP'U]/1 Intramuscular; Intrapleural; Intravenous; Subcutaneous Bedford Pharmaceuticals 2003-03-10 2009-02-28 US Bleomycin Injection 15 [USP'U]/1 Intramuscular; Intrapleural; Intravenous; Subcutaneous Cipla USA Inc. 2019-03-11 Not applicable US Bleomycin Injection, powder, lyophilized, for solution 15 [USP'U]/1 Intramuscular; Intrapleural; Intravenous; Subcutaneous Hospira, Inc. 2000-04-11 Not applicable US Bleomycin Powder, for solution 15 [USP'U]/1 Intramuscular; Intrapleural; Intravenous; Subcutaneous Meitheal Pharmaceuticals Inc. 2018-08-31 Not applicable US - Unapproved/Other Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Bleomycin Bleomycin sulfate (15000 [iU]/1) Injection, powder, lyophilized, for solution Intra-arterial; Intramuscular; Intravenous Amneal Pharmaceuticals LLC 2016-06-20 Not applicable US
Categories
- ATC Codes
- L01DC01 — Bleomycin
- Drug Categories
- Amino Acids, Peptides, and Proteins
- Antibiotics, Antineoplastic
- Antineoplastic Agents
- Antineoplastic and Immunomodulating Agents
- Carbohydrates
- Cardiotoxic antineoplastic agents
- Cytoprotective Agent
- Cytotoxic Antibiotics and Related Substances
- Drugs that are Mainly Renally Excreted
- Glycoconjugates
- Glycopeptides
- Immunosuppressive Agents
- Narrow Therapeutic Index Drugs
- Peptides
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as hybrid glycopeptides. These are compounds containing a carbohydrate component linked to a hybrid peptide component.
- Kingdom
- Organic compounds
- Super Class
- Organic acids and derivatives
- Class
- Peptidomimetics
- Sub Class
- Hybrid peptides
- Direct Parent
- Hybrid glycopeptides
- Alternative Parents
- Histidine and derivatives / Fatty acyl glycosides of mono- and disaccharides / N-acyl-alpha amino acids and derivatives / Gamma amino acids and derivatives / Alpha amino acid amides / Beta amino acids and derivatives / Disaccharides / O-glycosyl compounds / Pyrimidinecarboxylic acids and derivatives / 2-heteroaryl carboxamides show 26 more
- Substituents
- 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 show 50 more
- Molecular Framework
- Aromatic heteromonocyclic compounds
- External Descriptors
- Non-ribosomal peptide/polyketide hybrids (LMPK14000006)
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- 40S1VHN69B
- CAS number
- 11056-06-7
- InChI Key
- OYVAGSVQBOHSSS-WXFSZRTFSA-O
- 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
- IUPAC Name
- (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
- SMILES
- [H][C@](C)(NC(=O)[C@@]([H])(NC(=O)C1=NC(=NC(N)=C1C)[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=CNC=N1)[C@@H](O)[C@H](C)C(=O)N[C@]([H])(C(=O)NCCC1=NC(=CS1)C1=NC(=CS1)C(=O)NCCC[S+](C)C)[C@@]([H])(C)O
References
- Synthesis Reference
Hamao Umezawa, Kenji Maeda, Tomohisa Takita, Yuya Nakayama, Akio Fujii, Nobuyoshi Shimada, Hideo Chimura, "Novel process for producing antibiotics bleomycin." U.S. Patent USRE0304514, issued October, 1970.
USRE0304514- General References
- Claussen CA, Long EC: Nucleic Acid recognition by metal complexes of bleomycin. Chem Rev. 1999 Sep 8;99(9):2797-816. [Article]
- External Links
- Human Metabolome Database
- HMDB0014435
- KEGG Compound
- C06854
- PubChem Compound
- 5360373
- PubChem Substance
- 46509116
- ChemSpider
- 4514492
- BindingDB
- 50122169
- 1622
- ChEBI
- 22907
- ChEMBL
- CHEMBL403664
- Therapeutic Targets Database
- DAP000531
- PharmGKB
- PA448645
- PDBe Ligand
- BLM
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Bleomycin
- FDA label
- Download (46.3 KB)
- MSDS
- Download (34.4 KB)
Clinical Trials
- Clinical Trials
Clinical Trial & Rare Diseases Add-on Data Package
Explore 4,000+ rare diseases, orphan drugs & condition pairs, clinical trial why stopped data, & more. Preview package Phase Status Purpose Conditions Count Start Date Why Stopped 100+ additional columns Unlock 175K+ rows when you subscribe.View sample dataNot Available Completed Not Available AIDS-related Kaposi's Sarcoma / Human Immunodeficiency Virus 1 Positive 1 somestatus stop reason just information to hide Not Available Completed Treatment Comparison of Efficacy of Sclerotherapy in Infantile Hemangioma 1 somestatus stop reason just information to hide Not Available Completed Treatment Extragonadal Germ Cell Tumor / Pediatric Germ Cell Tumor 1 somestatus stop reason just information to hide Not Available Completed Treatment Hemangiomas / Propranolol 1 somestatus stop reason just information to hide Not Available Completed Treatment Hodgkin's Lymphoma 1 somestatus stop reason just information to hide
Pharmacoeconomics
- Manufacturers
- Bristol myers squibb co pharmaceutical research institute
- App pharmaceuticals llc
- Bedford laboratories div ben venue laboratories inc
- Hospira inc
- Pharmachemie bv
- Teva parenteral medicines inc
- Packagers
- APP Pharmaceuticals
- Bedford Labs
- Bristol-Myers Squibb Co.
- Hospira Inc.
- Mead Johnson and Co.
- Nippon Kayaku Co. Ltd.
- Sicor Pharmaceuticals
- Teva Pharmaceutical Industries Ltd.
- Dosage Forms
Form Route Strength Injection Intramuscular; Intrapleural; Intravenous; Subcutaneous Injection, powder, lyophilized, for solution 15 mg Injection, powder, lyophilized, for solution Injection, powder, for solution Intramuscular; Intrapleural; Intravenous; Subcutaneous 15 [USP'U]/1 Injection, powder, for solution Intramuscular; Intrapleural; Intravenous; Subcutaneous 30 [USP'U]/1 Powder, for solution Intramuscular; Intravenous 15 unit / amp Injection, powder, for solution 15 mg Injection, solution Intramuscular; Intrapleural; Intravenous; Subcutaneous 15 mg Solution Parenteral 15 UI Injection, powder, for solution Injection, powder, lyophilized, for solution Intramuscular; Intravenous 15 U Powder Intravenous 15 IU Injection, powder, lyophilized, for solution Parenteral 15 IU Injection, powder, lyophilized, for solution Intramuscular; Intravenous 15 IU Injection Intramuscular; Intrapleural; Intravenous; Subcutaneous 15 [USP'U]/1 Injection, powder, lyophilized, for solution Intra-arterial; Intramuscular; Intravenous 15000 [iU]/1 Injection, powder, lyophilized, for solution Intramuscular; Intrapleural; Intravenous; Subcutaneous 15 [USP'U]/1 Injection, powder, lyophilized, for solution Intramuscular; Intrapleural; Intravenous; Subcutaneous 30 [USP'U]/1 Powder, for solution Intramuscular; Intrapleural; Intravenous; Subcutaneous 15 [USP'U]/1 Powder, for solution Intramuscular; Intrapleural; Intravenous; Subcutaneous 30 [USP'U]/1 Injection, powder, for solution Parenteral 15000 IU/mg Injection, powder, for solution Parenteral 15000 IE Powder, for solution Intra-arterial; Intracavitary; Intramuscular; Intravenous; Subcutaneous 15 unit / vial Powder, for solution Intramuscular; Intrapleural; Intravenous; Subcutaneous 15 unit / vial Injection, powder, for solution Parenteral 15 MG Injection, powder, for solution 15 unit/1vial Solution Parenteral 15.000 UI Injection, powder, for solution Intramuscular; Intravenous; Subcutaneous 15000 iu/vial Injection Intramuscular; Intrapleural; Intravenous; Subcutaneous 1 U/ml Solution Intravenous 9.900 mg Injection, powder, lyophilized, for solution Intramuscular; Intravenous; Subcutaneous 15 IU Powder Intravenous 15 unit/1vial - Prices
Unit description Cost Unit Blenoxane 30 unit vial 584.83USD vial Blenoxane 15 unit vial 292.42USD vial Bleomycin sulfate 30 unit vial 120.0USD vial Bleomycin sulfate 15 unit vial 81.6USD vial DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 71 °C Not Available water solubility Soluble Not Available - Predicted Properties
Property Value Source Water Solubility 0.0277 mg/mL ALOGPS logP -0.41 ALOGPS logP -9.3 Chemaxon logS -4.7 ALOGPS pKa (Strongest Acidic) 11.39 Chemaxon pKa (Strongest Basic) 7.65 Chemaxon Physiological Charge 2 Chemaxon Hydrogen Acceptor Count 28 Chemaxon Hydrogen Donor Count 20 Chemaxon Polar Surface Area 627.07 Å2 Chemaxon Rotatable Bond Count 36 Chemaxon Refractivity 343.83 m3·mol-1 Chemaxon Polarizability 139.19 Å3 Chemaxon Number of Rings 6 Chemaxon Bioavailability 0 Chemaxon Rule of Five No Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule Yes Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption - 0.8877 Blood Brain Barrier - 0.9732 Caco-2 permeable - 0.6551 P-glycoprotein substrate Substrate 0.853 P-glycoprotein inhibitor I Non-inhibitor 0.8781 P-glycoprotein inhibitor II Non-inhibitor 0.8454 Renal organic cation transporter Non-inhibitor 0.9331 CYP450 2C9 substrate Non-substrate 0.7773 CYP450 2D6 substrate Non-substrate 0.7966 CYP450 3A4 substrate Substrate 0.6154 CYP450 1A2 substrate Non-inhibitor 0.7423 CYP450 2C9 inhibitor Non-inhibitor 0.7035 CYP450 2D6 inhibitor Non-inhibitor 0.8678 CYP450 2C19 inhibitor Non-inhibitor 0.6794 CYP450 3A4 inhibitor Non-inhibitor 0.67 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.8609 Ames test AMES toxic 0.772 Carcinogenicity Non-carcinogens 0.8957 Biodegradation Not ready biodegradable 0.8863 Rat acute toxicity 2.6132 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.991 hERG inhibition (predictor II) Inhibitor 0.6172
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Not Available
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 359.93567 predictedDeepCCS 1.0 (2019) [M+H]+ 361.65942 predictedDeepCCS 1.0 (2019) [M+Na]+ 367.8209 predictedDeepCCS 1.0 (2019)
Targets
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Yes
Cleavage
References
- Ma Q, Akiyama Y, Xu Z, Konishi K, Hecht SM: Identification and cleavage site analysis of DNA sequences bound strongly by bleomycin. J Am Chem Soc. 2009 Feb 11;131(5):2013-22. doi: 10.1021/ja808629s. [Article]
- Chow MS, Liu LV, Solomon EI: Further insights into the mechanism of the reaction of activated bleomycin with DNA. Proc Natl Acad Sci U S A. 2008 Sep 9;105(36):13241-5. doi: 10.1073/pnas.0806378105. Epub 2008 Aug 29. [Article]
- Akiyama Y, Ma Q, Edgar E, Laikhter A, Hecht SM: Identification of strong DNA binding motifs for bleomycin. J Am Chem Soc. 2008 Jul 30;130(30):9650-1. doi: 10.1021/ja802905g. Epub 2008 Jul 3. [Article]
- Mirabelli CK, Ting A, Huang CH, Mong S, Crooke ST: Bleomycin and talisomycin sequence-specific strand scission of DNA: a mechanism of double-strand cleavage. Cancer Res. 1982 Jul;42(7):2779-85. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- DNA ligase that seals nicks in double-stranded during DNA repair (PubMed:30395541). Also involved in DNA replication and DNA recombination
- Specific Function
- ATP binding
- Gene Name
- LIG1
- Uniprot ID
- P18858
- Uniprot Name
- DNA ligase 1
- Molecular Weight
- 101735.11 Da
References
- Rose JL, Reeves KC, Likhotvorik RI, Hoyt DG: Base excision repair proteins are required for integrin-mediated suppression of bleomycin-induced DNA breakage in murine lung endothelial cells. J Pharmacol Exp Ther. 2007 Apr;321(1):318-26. Epub 2007 Jan 3. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Isoform 3 functions as a heterodimer with DNA-repair protein XRCC1 in the nucleus and can correct defective DNA strand-break repair and sister chromatid exchange following treatment with ionizing radiation and alkylating agents. Isoform 1 is targeted to mitochondria, where it functions as a DNA ligase in mitochondrial base-excision DNA repair (PubMed:10207110, PubMed:24674627)
- Specific Function
- ATP binding
- Gene Name
- LIG3
- Uniprot ID
- P49916
- Uniprot Name
- DNA ligase 3
- Molecular Weight
- 112905.96 Da
References
- Rose JL, Reeves KC, Likhotvorik RI, Hoyt DG: Base excision repair proteins are required for integrin-mediated suppression of bleomycin-induced DNA breakage in murine lung endothelial cells. J Pharmacol Exp Ther. 2007 Apr;321(1):318-26. Epub 2007 Jan 3. [Article]
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- The normal physiological role of BLM hydrolase is unknown, but it catalyzes the inactivation of the antitumor drug BLM (a glycopeptide) by hydrolyzing the carboxamide bond of its B-aminoalaninamide moiety thus protecting normal and malignant cells from BLM toxicity
- Specific Function
- aminopeptidase activity
- Gene Name
- BLMH
- Uniprot ID
- Q13867
- Uniprot Name
- Bleomycin hydrolase
- Molecular Weight
- 52561.93 Da
References
- Lazo JS, Boland CJ, Schwartz PE: Bleomycin hydrolase activity and cytotoxicity in human tumors. Cancer Res. 1982 Oct;42(10):4026-31. [Article]
- Lefterov IM, Koldamova RP, King J, Lazo JS: The C-terminus of human bleomycin hydrolase is required for protection against bleomycin-induced chromosomal damage. Mutat Res. 1998 Oct 12;421(1):1-7. [Article]
Drug created at June 13, 2005 13:24 / Updated at October 07, 2024 13:57