ContaminantDB: Bleomycin

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (4)XML

Record Information

Version

1.0

Creation Date

2009-07-21 20:26:29 UTC

Update Date

2026-05-14 16:25:13 UTC

Accession Number

CHEM002161

Identification

Common Name

Bleomycin

Class

Small Molecule

Description

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.

Contaminant Sources

HMDB Contaminants - Urine
IARC Carcinogens Group 1
IARC Carcinogens Group 2B
STOFF IDENT Compounds
T3DB toxins

Contaminant Type

Amide
Amine
Antibiotic, Antineoplastic
Antimetabolite
Drug
Ester
Lachrymator
Metabolite
Organic Compound
Synthetic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Bleocin	HMDB
Bleomicin	HMDB
Bleomycin a2	HMDB
Bleomycin sulfate	HMDB
Bleomycin sulphate	HMDB
BLM	HMDB
Almirall brand OF bleomycin sulfate	HMDB
Bleo cell	HMDB
Bleo-cell	HMDB
BLEOcell	HMDB
Bellon brand OF bleomycin sulfate	HMDB
Bellon, bléomycine	HMDB
Blanoxan	HMDB
Blenoxane	HMDB
Bleolem	HMDB
Bleomicina	HMDB
Bleomycin a(2)	HMDB
Bleomycin b(2)	HMDB
Bleomycin b2	HMDB
Bleomycins	HMDB
Bleomycinum mack	HMDB
Bléomycine bellon	HMDB
Bristol myers squibb brand OF bleomycin sulfate	HMDB
Bristol-myers squibb brand OF bleomycin sulfate	HMDB
Bull brand OF bleomycin sulfate	HMDB
Lemery brand OF bleomycin sulfate	HMDB
Lundbeck brand OF bleomycin sulfate	HMDB
Mack brand OF bleomycin sulfate	HMDB
Mack, bleomycinum	HMDB
Sulfate, bleomycin	HMDB
Cell pharm brand OF bleomycin sulfate	HMDB
Bleomycin	MeSH

Chemical Formula

C₅₅H₈₄N₁₇O₂₁S₃

Average Molecular Mass

1415.552 g/mol

Monoisotopic Mass

1414.519 g/mol

CAS Registry Number

11056-06-7

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

Traditional Name

bleomycin

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

InChI Identifier

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

InChI Key

OYVAGSVQBOHSSS-WXFSZRTFSA-O

Chemical Taxonomy

Description

belongs to the class of organic compounds known as hybrid glycopeptides. Hybrid glycopeptides 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

Substituents

Hybrid glycopeptide
Histidine or derivatives
Fatty acyl glycoside of mono- or disaccharide
Fatty acyl glycoside
N-acyl-alpha amino acid or derivatives
Gamma amino acid or derivatives
Alpha-amino acid amide
Beta amino acid or derivatives
O-glycosyl compound
Glycosyl compound
Disaccharide
N-substituted-alpha-amino acid
Alpha-amino acid or derivatives
Pyrimidine-6-carboxylic acid or derivatives
2-heteroaryl carboxamide
Thiazolecarboxamide
Thiazolecarboxylic acid or derivatives
Aralkylamine
2,4-disubstituted 1,3-thiazole
Aminopyrimidine
Fatty amide
Fatty acyl
N-acyl-amine
Imidolactam
Oxane
Pyrimidine
Azole
Carbamic acid ester
Heteroaromatic compound
Thiazole
Imidazole
Secondary alcohol
Carboxamide group
Carbonic acid derivative
Amino acid or derivatives
Secondary carboxylic acid amide
Primary carboxylic acid amide
Organoheterocyclic compound
Secondary aliphatic amine
Oxacycle
Acetal
Carboxylic acid derivative
Azacycle
Secondary amine
Organic nitrogen compound
Organic oxygen compound
Primary aliphatic amine
Organonitrogen compound
Organooxygen compound
Carbonyl group
Organosulfur compound
Primary alcohol
Primary amine
Amine
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Alcohol
Organic cation
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Non-ribosomal peptide/polyketide hybrids (LMPK14000006 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Cytoplasm
Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

antineoplastic agent

Biological Roles

metabolite

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	71°C
Boiling Point	Not Available
Solubility	Soluble

Predicted Properties

Property	Value	Source
Water Solubility	0.028 g/L	ALOGPS
logP	-0.52	ALOGPS
logP	-9.7	ChemAxon
logS	-4.7	ALOGPS
pKa (Strongest Acidic)	11.34	ChemAxon
pKa (Strongest Basic)	7.67	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	344.16 m³·mol⁻¹	ChemAxon
Polarizability	142.03 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

Spectra

Spectrum Type	Description	Splash Key	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0002-5519000000-a9e7e590fae8c464ce36	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-05fr-5918000000-5ca154887c83cf983142	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-05fr-5925010000-dfb06a8f5285854a7878	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-052b-2009100001-5547a667899fb11dad81	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0bt9-0009400042-5683bd6165401e99baa9	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0cdl-2129410101-b208548fe3870fadd6fe	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum

Toxicity Profile

Route of Exposure

Intravenous; systemic absorption is approximately 45%.

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 (2). 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. (3).

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

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

2B, possibly carcinogenic to humans. (5)

Uses/Sources

For palliative treatment in the management malignant neoplasm (trachea, bronchus, lung), squamous cell carcinoma, and lymphomas.

Minimum Risk Level

Not Available

Health Effects

The most serious complication of bleomycin is pulmonary fibrosis and impaired lung function. (Wikipedia) Bleomycin can also induce scleroderma (4, 2).

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.

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

DB00290

HMDB ID

HMDB0014435

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Chemspider ID

ChEBI ID

PubChem Compound ID

Kegg Compound ID

YMDB ID

Not Available

ECMDB ID

Not Available

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.

MSDS

Link

General References

1. Claussen CA, Long EC: Nucleic Acid recognition by metal complexes of bleomycin. Chem Rev. 1999 Sep 8;99(9):2797-816.

Bleomycin (CHEM002161)

Structure for CHEM002161: Bleomycin