Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C55H83N17O21S3 |
| Molecular Weight | 1414.544 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 19 / 19 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
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=NC(=NC(N)=C1C)[C@H](CC(N)=O)NC[C@H](N)C(N)=O)[C@@H](O[C@@H]2O[C@@H](CO)[C@@H](O)[C@H](O)[C@@H]2O[C@H]3O[C@H](CO)[C@@H](O)[C@H](OC(N)=O)[C@@H]3O)C4=CN=C[N-]4)C(=O)NCCC5=NC(=CS5)C6=NC(=CS6)C(=O)NCCC[S+](C)C
InChI
InChIKey=OYVAGSVQBOHSSS-UAPAGMARSA-N
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)/t21-,22+,23+,24-,25-,29-,30+,34-,35-,36-,37+,38+,39-,40-,41-,42-,43-,53+,54-/m0/s1
| Molecular Formula | C55H83N17O21S3 |
| Molecular Weight | 1414.544 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 19 / 19 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
DescriptionSources: http://www.drugbank.ca/drugs/DB00290#targetshttp://news.cancerconnect.com/wp-content/uploads/2010/06/bleomycin.pdf | https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/050443s036lbl.pdfCurator's Comment: description was created based on several sources, including, http://www.accessdata.fda.gov/drugsatfda_docs/label/2010/050443s036lbl.pdf
Sources: http://www.drugbank.ca/drugs/DB00290#targetshttp://news.cancerconnect.com/wp-content/uploads/2010/06/bleomycin.pdf | https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/050443s036lbl.pdf
Curator's Comment: description was created based on several sources, including, http://www.accessdata.fda.gov/drugsatfda_docs/label/2010/050443s036lbl.pdf
Bleomycin sulfate is an antineoplastic antibiotic isolated
from Streptomyces verticillus. It is a mixture of
glycopeptide antibiotics containing primarily Bleomycin
A2 (~70%) and B2 (~30%). Bleomycin binds to DNA, inhibits DNA
synthesis, and causes single strand scission of DNA in
vivo and in vitro at specific base sequences.
Originator
Sources: http://onlinelibrary.wiley.com/doi/10.1002/1097-0142(1967)20:5%3C891::AID-CNCR2820200550%3E3.0.CO;2-V/pdfhttps://www.ncbi.nlm.nih.gov/pubmed/5953301 | https://www.ncbi.nlm.nih.gov/pubmed/23060708
Curator's Comment: Bleomycin was discovered by Umezawa et al. (1966)
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL2311221 |
20.0 µM [Kd] | ||
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | BLEOMYCIN SULFATE Approved UseBleomycin for Injection, USP should be considered a palliative treatment. It has been shown to be useful in the management of the following neoplasms either as a single agent or in proven combinations with other approved chemotherapeutic agents:
Squamous Cell Carcinoma: Head and neck (including mouth, tongue, tonsil, nasopharynx, oropharynx, sinus, palate, lip, buccal mucosa, gingivae, epiglottis, skin, larynx), penis, cervix, and vulva. The response to Bleomycin for Injection is poorer in patients with previously irradiated head and neck cancer.
Lymphomas: Hodgkin’s disease, non-Hodgkin’s lymphoma.
Testicular Carcinoma: Embryonal cell, choriocarcinoma, and teratocarcinoma.
Bleomycin for Injection, USP has also been shown to be useful in the management of:
Malignant Pleural Effusion: Bleomycin for Injection is effective as a sclerosing agent for the treatment of malignant pleural effusion and prevention of recurrent pleural effusions. Launch Date1973 |
|||
| Primary | BLEOMYCIN SULFATE Approved UseBleomycin for Injection, USP should be considered a palliative treatment. It has been shown to be useful in the management of the following neoplasms either as a single agent or in proven combinations with other approved chemotherapeutic agents:
Squamous Cell Carcinoma: Head and neck (including mouth, tongue, tonsil, nasopharynx, oropharynx, sinus, palate, lip, buccal mucosa, gingivae, epiglottis, skin, larynx), penis, cervix, and vulva. The response to Bleomycin for Injection is poorer in patients with previously irradiated head and neck cancer.
Lymphomas: Hodgkin’s disease, non-Hodgkin’s lymphoma.
Testicular Carcinoma: Embryonal cell, choriocarcinoma, and teratocarcinoma.
Bleomycin for Injection, USP has also been shown to be useful in the management of:
Malignant Pleural Effusion: Bleomycin for Injection is effective as a sclerosing agent for the treatment of malignant pleural effusion and prevention of recurrent pleural effusions. Launch Date1973 |
|||
| Primary | BLEOMYCIN SULFATE Approved UseBleomycin for Injection, USP should be considered a palliative treatment. It has been shown to be useful in the management of the following neoplasms either as a single agent or in proven combinations with other approved chemotherapeutic agents:
Squamous Cell Carcinoma: Head and neck (including mouth, tongue, tonsil, nasopharynx, oropharynx, sinus, palate, lip, buccal mucosa, gingivae, epiglottis, skin, larynx), penis, cervix, and vulva. The response to Bleomycin for Injection is poorer in patients with previously irradiated head and neck cancer.
Lymphomas: Hodgkin’s disease, non-Hodgkin’s lymphoma.
Testicular Carcinoma: Embryonal cell, choriocarcinoma, and teratocarcinoma.
Bleomycin for Injection, USP has also been shown to be useful in the management of:
Malignant Pleural Effusion: Bleomycin for Injection is effective as a sclerosing agent for the treatment of malignant pleural effusion and prevention of recurrent pleural effusions. Launch Date1973 |
|||
| Primary | BLEOMYCIN SULFATE Approved UseBleomycin for Injection, USP should be considered a palliative treatment. It has been shown to be useful in the management of the following neoplasms either as a single agent or in proven combinations with other approved chemotherapeutic agents:
Squamous Cell Carcinoma: Head and neck (including mouth, tongue, tonsil, nasopharynx, oropharynx, sinus, palate, lip, buccal mucosa, gingivae, epiglottis, skin, larynx), penis, cervix, and vulva. The response to Bleomycin for Injection is poorer in patients with previously irradiated head and neck cancer.
Lymphomas: Hodgkin’s disease, non-Hodgkin’s lymphoma.
Testicular Carcinoma: Embryonal cell, choriocarcinoma, and teratocarcinoma.
Bleomycin for Injection, USP has also been shown to be useful in the management of:
Malignant Pleural Effusion: Bleomycin for Injection is effective as a sclerosing agent for the treatment of malignant pleural effusion and prevention of recurrent pleural effusions. Launch Date1973 |
|||
| Primary | BLEOMYCIN SULFATE Approved UseBleomycin for Injection, USP should be considered a palliative treatment. It has been shown to be useful in the management of the following neoplasms either as a single agent or in proven combinations with other approved chemotherapeutic agents:
Squamous Cell Carcinoma: Head and neck (including mouth, tongue, tonsil, nasopharynx, oropharynx, sinus, palate, lip, buccal mucosa, gingivae, epiglottis, skin, larynx), penis, cervix, and vulva. The response to Bleomycin for Injection is poorer in patients with previously irradiated head and neck cancer.
Lymphomas: Hodgkin’s disease, non-Hodgkin’s lymphoma.
Testicular Carcinoma: Embryonal cell, choriocarcinoma, and teratocarcinoma.
Bleomycin for Injection, USP has also been shown to be useful in the management of:
Malignant Pleural Effusion: Bleomycin for Injection is effective as a sclerosing agent for the treatment of malignant pleural effusion and prevention of recurrent pleural effusions. Launch Date1973 |
|||
| Primary | BLENOXANE Approved UseBLENOXANE should be considered a palliative treatment. It has been shown to be useful in the management of the following neoplasms either as a single agent or in proven combinations with other approved chemotherapeutic agent:Squamous Cell Carcinoma, Lymphomas, Testicular Carcinoma, Malignant Pleural Effusion. Launch Date1975 |
|||
| Primary | BLENOXANE Approved UseBLENOXANE should be considered a palliative treatment. It has been shown to be useful in the management of the following neoplasms either as a single agent or in proven combinations with other approved chemotherapeutic agent:Squamous Cell Carcinoma, Lymphomas, Testicular Carcinoma, Malignant Pleural Effusion. Launch Date1975 |
|||
| Primary | BLENOXANE Approved UseBLENOXANE should be considered a palliative treatment. It has been shown to be useful in the management of the following neoplasms either as a single agent or in proven combinations with other approved chemotherapeutic agent:Squamous Cell Carcinoma, Lymphomas, Testicular Carcinoma, Malignant Pleural Effusion. Launch Date1975 |
|||
| Primary | BLENOXANE Approved UseBLENOXANE should be considered a palliative treatment. It has been shown to be useful in the management of the following neoplasms either as a single agent or in proven combinations with other approved chemotherapeutic agent:Squamous Cell Carcinoma, Lymphomas, Testicular Carcinoma, Malignant Pleural Effusion. Launch Date1975 |
|||
| Primary | BLENOXANE Approved UseBLENOXANE should be considered a palliative treatment. It has been shown to be useful in the management of the following neoplasms either as a single agent or in proven combinations with other approved chemotherapeutic agent:Squamous Cell Carcinoma, Lymphomas, Testicular Carcinoma, Malignant Pleural Effusion. Launch Date1975 |
|||
| Primary | BLENOXANE Approved UseBLENOXANE should be considered a palliative treatment. It has been shown to be useful in the management of the following neoplasms either as a single agent or in proven combinations with other approved chemotherapeutic agent:Squamous Cell Carcinoma, Lymphomas, Testicular Carcinoma, Malignant Pleural Effusion. Launch Date1975 |
|||
| Primary | BLENOXANE Approved UseBLENOXANE should be considered a palliative treatment. It has been shown to be useful in the management of the following neoplasms either as a single agent or in proven combinations with other approved chemotherapeutic agent:Squamous Cell Carcinoma, Lymphomas, Testicular Carcinoma, Malignant Pleural Effusion. Launch Date1975 |
|||
| Primary | BLENOXANE Approved UseBLENOXANE should be considered a palliative treatment. It has been shown to be useful in the management of the following neoplasms either as a single agent or in proven combinations with other approved chemotherapeutic agent:Squamous Cell Carcinoma, Lymphomas, Testicular Carcinoma, Malignant Pleural Effusion. Launch Date1975 |
|||
| Primary | BLENOXANE Approved UseBLENOXANE should be considered a palliative treatment. It has been shown to be useful in the management of the following neoplasms either as a single agent or in proven combinations with other approved chemotherapeutic agent:Squamous Cell Carcinoma, Lymphomas, Testicular Carcinoma, Malignant Pleural Effusion. Launch Date1975 |
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
80 μU/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2412684/ |
150 unit single, intraperitoneal dose: 150 unit route of administration: Intraperitoneal experiment type: SINGLE co-administered: |
BLEOMYCIN serum | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
318 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6203661/ |
15 mg single, intramuscular dose: 15 mg route of administration: Intramuscular experiment type: SINGLE co-administered: |
BLEOMYCIN serum | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
AUC
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
1192 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6203661/ |
15 mg single, intramuscular dose: 15 mg route of administration: Intramuscular experiment type: SINGLE co-administered: |
BLEOMYCIN serum | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
T1/2
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
5 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2412684/ |
150 unit single, intraperitoneal dose: 150 unit route of administration: Intraperitoneal experiment type: SINGLE co-administered: |
BLEOMYCIN serum | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
2.5 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6203661/ |
15 mg single, intramuscular dose: 15 mg route of administration: Intramuscular experiment type: SINGLE co-administered: |
BLEOMYCIN serum | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Protocatechuic aldehyde ameliorates experimental pulmonary fibrosis by modulating HMGB1/RAGE pathway. | 2015-02-15 |
|
| Distinct mechanisms of cell-kill by triapine and its terminally dimethylated derivative Dp44mT due to a loss or gain of activity of their copper(II) complexes. | 2014-10-01 |
|
| Direct activation of ATM by resveratrol under oxidizing conditions. | 2014 |
|
| Diallylsulfide attenuates excessive collagen production and apoptosis in a rat model of bleomycin induced pulmonary fibrosis through the involvement of protease activated receptor-2. | 2013-09-01 |
|
| Assessment of Brd4 inhibition in idiopathic pulmonary fibrosis lung fibroblasts and in vivo models of lung fibrosis. | 2013-08 |
|
| Suppression of nuclear factor erythroid 2-related factor 2 via extracellular signal-regulated kinase contributes to bleomycin-induced oxidative stress and fibrogenesis. | 2013-06-20 |
|
| Berberine attenuates bleomycin induced pulmonary toxicity and fibrosis via suppressing NF-κB dependant TGF-β activation: a biphasic experimental study. | 2013-05-23 |
|
| Matrix metalloproteinase Mmp-1a is dispensable for normal growth and fertility in mice and promotes lung cancer progression by modulating inflammatory responses. | 2013-05-17 |
|
| Comparison of bleomycin-induced pulmonary apoptosis between NMRI mice and C57BL/6 mice. | 2013-01 |
|
| Thymoquinone blocks lung injury and fibrosis by attenuating bleomycin-induced oxidative stress and activation of nuclear factor Kappa-B in rats. | 2012-12-16 |
|
| Preventing cleavage of Mer promotes efferocytosis and suppresses acute lung injury in bleomycin treated mice. | 2012-08-15 |
|
| The ToxTracker assay: novel GFP reporter systems that provide mechanistic insight into the genotoxic properties of chemicals. | 2012-01 |
|
| Testing chemical agents with the cytokinesis-block micronucleus cytome assay. | 2012 |
|
| Removal of reactive oxygen species-induced 3'-blocked ends by XPF-ERCC1. | 2011-11-21 |
|
| Anti-inflammatory and antifibrotic effects of methyl palmitate. | 2011-08-01 |
|
| Essential role of MeCP2 in the regulation of myofibroblast differentiation during pulmonary fibrosis. | 2011-04 |
|
| Links between DNA polymerase beta expression and sensitivity to bleomycin. | 2011-03-15 |
|
| Pulmonary fibrosis inducer, bleomycin, causes redox-sensitive activation of phospholipase D and cytotoxicity through formation of bioactive lipid signal mediator, phosphatidic acid, in lung microvascular endothelial cells. | 2011-02 |
|
| C/EBPβ-Thr217 phosphorylation signaling contributes to the development of lung injury and fibrosis in mice. | 2011 |
|
| XRCC1 deficiency sensitizes human lung epithelial cells to genotoxicity by crocidolite asbestos and Libby amphibole. | 2010-12 |
|
| The D prostanoid receptor agonist BW245C [(4S)-(3-[(3R,S)-3-cyclohexyl-3-hydroxypropyl]-2,5-dioxo)-4-imidazolidineheptanoic acid] inhibits fibroblast proliferation and bleomycin-induced lung fibrosis in mice. | 2010-11 |
|
| Effects of erlotinib on lung injury induced by intratracheal administration of bleomycin (BLM) in rats. | 2010-08 |
|
| Influence of p53 expression on sensitivity of cancer cells to bleomycin. | 2010-02-06 |
|
| Epigallocatechin-3-gallate exhibits anti-fibrotic effect by attenuating bleomycin-induced glycoconjugates, lysosomal hydrolases and ultrastructural changes in rat model pulmonary fibrosis. | 2009-07-15 |
|
| Protection of bleomycin-induced fibrosis and inflammation by taurine. | 2009-07 |
|
| Bleomycin-induced nuclear factor-kappaB activation in human bronchial epithelial cells involves the phosphorylation of glycogen synthase kinase 3beta. | 2009-06-22 |
|
| Radiation-induced cathepsin S is involved in radioresistance. | 2009-04-15 |
|
| Rosiglitazone abrogates bleomycin-induced scleroderma and blocks profibrotic responses through peroxisome proliferator-activated receptor-gamma. | 2009-02 |
|
| Agents associated with lung inflammation induce similar responses in NCI-H292 lung epithelial cells. | 2008-10 |
|
| Simvastatin attenuates bleomycin-induced pulmonary fibrosis in mice. | 2008-09-20 |
|
| Cerebellar dysfunction caused by procarbazine and consumption of excessive amount of bananas. | 2008-06 |
|
| PPAR-gamma agonists inhibit profibrotic phenotypes in human lung fibroblasts and bleomycin-induced pulmonary fibrosis. | 2008-05 |
|
| Hodgkin lymphoma presenting with various immunologic abnormalities, including autoimmune hepatitis, Hashimoto's thyroiditis, autoimmune hemolytic anemia, and immune thrombocytopenia. | 2008-02 |
|
| DNA methylation inhibitor 5-Aza-2'-deoxycytidine induces reversible genome-wide DNA damage that is distinctly influenced by DNA methyltransferases 1 and 3B. | 2008-01 |
|
| BMP-7 does not protect against bleomycin-induced lung or skin fibrosis. | 2008 |
|
| Telomerase activity is required for bleomycin-induced pulmonary fibrosis in mice. | 2007-12 |
|
| FDG-PET in bleomycin-induced pneumonitis following ABVD chemotherapy for Hodgkin's disease--a useful tool for monitoring pulmonary toxicity and disease activity. | 2007-11 |
|
| Two cycles of doxorubicin, bleomycin, vinblastine, and dacarbazine plus extended-field radiotherapy is superior to radiotherapy alone in early favorable Hodgkin's lymphoma: final results of the GHSG HD7 trial. | 2007-08-10 |
|
| Effects of curcumin in treatment of experimental pulmonary fibrosis: a comparison with hydrocortisone. | 2007-06-13 |
|
| Characterization of DNA reactive and non-DNA reactive anticancer drugs by gene expression profiling. | 2007-06-01 |
|
| Are platinum-based chemotherapeutic drugs safe for patients with Charcot-Marie-Tooth disease? | 2007-06 |
|
| Long-term neurotoxicity in patients treated with cisplatin, vinblastine, and bleomycin for metastatic germ cell cancer. | 1989-10 |
|
| Raynaud's phenomenon in patients treated with cisplatin, vinblastine, and bleomycin for germ cell cancer: measurement of vasoconstrictor response to cold. | 1989-07 |
|
| Hemolytic uremic syndrome following cisplatin, bleomycin, and vincristine chemotherapy: a report of a case and a review of the literature. | 1989 |
|
| Drug-induced encephalopathy after previous ifosfamide treatment. | 1988-11-05 |
|
| Pulmonary emboli in patients receiving chemotherapy for non-Hodgkin's lymphoma. | 1988-09 |
|
| Acute vascular toxicity after combination chemotherapy with cisplatin, vinblastine, and bleomycin for testicular cancer. | 1988-05 |
|
| Renovascular hypertension after combination chemotherapy for testicular cancer. | 1988-01 |
|
| [Raynaud's disease after treatment with bleomycin and vinblastine]. | 1986-02-17 |
|
| Hypomagnesemia, renal dysfunction, and Raynaud's phenomenon in patients treated with cisplatin, vinblastine, and bleomycin. | 1985-12-15 |
Patents
Sample Use Guides
In Vivo Use Guide
Curator's Comment: Bleomycin can be given intramuscularly, or subcutaneously in Squamous cell carcinoma, non-Hodgkin’s lymphoma, testicular carcinoma, Hodgkin’s disease and as a single dose bolus intrapleural injection (60 units) in Malignant Pleural Effusion.
0.25 to 0.50 units/kg weekly or twice weekly (Squamous cell carcinoma, non-Hodgkin’s lymphoma, testicular carcinoma, Hodgkin’s disease)
Route of Administration:
Intravenous
| Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 18:32:37 GMT 2025
by
admin
on
Mon Mar 31 18:32:37 GMT 2025
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| Record UNII |
13M89UEA7W
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| Record Status |
Validated (UNII)
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| Record Version |
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NCI_THESAURUS |
C2311
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3139
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m2589
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SALT/SOLVATE -> PARENT |
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ACTIVE MOIETY |
