BLEOMYCIN A2

First approved in 1973

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

Structure Search

SMILES

[H][C@]6(O[C@@H]1[C@H](O[C@H]([C@H](NC(=O)C2=NC(=NC(N)=C2C)[C@H](CC(N)=O)NC[C@H](N)C(N)=O)C(=O)N[C@H](C)[C@@H](O)[C@H](C)C(=O)N[C@@H]([C@@H](C)O)C(=O)NCCC3=NC(=CS3)C4=NC(=CS4)C(=O)NCCC[S+](C)C)C5=CN=C[N-]5)O[C@@H](CO)[C@@H](O)[C@@H]1O)O[C@H](CO)[C@@H](O)[C@H](OC(N)=O)[C@@H]6O

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

HIDE SMILES / InChI

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

Description
Sources: http://news.cancerconnect.com/wp-content/uploads/2010/06/bleomycin.pdf | https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/050443s036lbl.pdfhttp://www.drugbank.ca/drugs/DB00290#targets
Curator's Comment: description was created based on several sources, including, http://www.accessdata.fda.gov/drugsatfda_docs/label/2010/050443s036lbl.pdf

Bleomycin is a mixture of cytotoxic glycopeptide antibiotics isolated from a strain of Streptomyces verticillus. Bleomycin has 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).

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
DNA 241 Target ID: CHEMBL2311221 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2010/050443s036lbl.pdf	Inhibitor 8146		20.0 µM [Kd]
DNA 241 Target ID: CHEMBL2311221 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18597467 \| https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/050443s036lbl.pdf \| https://www.ncbi.nlm.nih.gov/pubmed/50602	Inhibitor 8146

Conditions

Condition	Modality	Highest Phase	Product
Squamous cell carcinoma 7 Sources: http://news.cancerconnect.com/wp-content/uploads/2010/06/bleomycin.pdf	Primary	Approved 8307	BLEOMYCIN SULFATE Approved Use Bleomycin 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 Date 1.12924803E11
Hodgkin's lymphoma 34 Sources: http://news.cancerconnect.com/wp-content/uploads/2010/06/bleomycin.pdf	Primary	Approved 8307	BLEOMYCIN SULFATE Approved Use Bleomycin 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 Date 1.12924803E11
Non-Hodgkin's lymphoma 79 Sources: http://news.cancerconnect.com/wp-content/uploads/2010/06/bleomycin.pdf	Primary	Approved 8307	BLEOMYCIN SULFATE Approved Use Bleomycin 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 Date 1.12924803E11
Testicular cancer 7 Sources: https://dailymed.nlm.nih.gov/dailymed/fda/fdaDrugXsl.cfm?setid=b5806c40-12ce-48e3-8abd-9f8997ef4428&type=display	Primary	Approved 8307	BLEOMYCIN SULFATE Approved Use Bleomycin 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 Date 1.12924803E11
Malignant pleural effusion 6 Sources: https://dailymed.nlm.nih.gov/dailymed/fda/fdaDrugXsl.cfm?setid=b5806c40-12ce-48e3-8abd-9f8997ef4428&type=display	Primary	Approved 8307	BLEOMYCIN SULFATE Approved Use Bleomycin 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 Date 1.12924803E11
Head and neck squamous cell carcinoma 31 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2010/050443s036lbl.pdf	Primary	Approved 8307	BLENOXANE Approved Use BLENOXANE 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 Date 1.74355202E11
Malignant pleural effusion 6 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2010/050443s036lbl.pdf	Primary	Approved 8307	BLENOXANE Approved Use BLENOXANE 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 Date 1.74355202E11
Embryonal cell, choriocarcinoma 5 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2010/050443s036lbl.pdf	Primary	Approved 8307	BLENOXANE Approved Use BLENOXANE 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 Date 1.74355202E11
Teratocarcinoma 5 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2010/050443s036lbl.pdf	Primary	Approved 8307	BLENOXANE Approved Use BLENOXANE 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 Date 1.74355202E11
Hodgkin's lymphoma 34 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2010/050443s036lbl.pdf	Primary	Approved 8307	BLENOXANE Approved Use BLENOXANE 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 Date 1.74355202E11
Non-Hodgkin's lymphoma 79 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2010/050443s036lbl.pdf	Primary	Approved 8307	BLENOXANE Approved Use BLENOXANE 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 Date 1.74355202E11
Squamous cell carcinoma, penis 5 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2010/050443s036lbl.pdf	Primary	Approved 8307	BLENOXANE Approved Use BLENOXANE 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 Date 1.74355202E11
Squamous cell carcinoma, cervix 5 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2010/050443s036lbl.pdf	Primary	Approved 8307	BLENOXANE Approved Use BLENOXANE 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 Date 1.74355202E11
Squamous cell carcinoma, vulva 5 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2010/050443s036lbl.pdf	Primary	Approved 8307	BLENOXANE Approved Use BLENOXANE 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 Date 1.74355202E11

PubMed

Title	Date	PubMed
Biochemical effects of bleomycin A2 on Novikoff hepatoma ascites cells.	1975	50602
Ultrastructural study of the effect of bleomycin A2 on the nucleolus and its possibly related cytoplasmic constituents in Novikoff hepatoma cells.	1975 Feb	45894
Hypomagnesemia, renal dysfunction, and Raynaud's phenomenon in patients treated with cisplatin, vinblastine, and bleomycin.	1985 Dec 15	2413982
[Raynaud's disease after treatment with bleomycin and vinblastine].	1986 Feb 17	2423995
Hemolytic uremic syndrome following cisplatin, bleomycin, and vincristine chemotherapy: a report of a case and a review of the literature.	1989	2482985
Vascular toxicity and the mechanism underlying Raynaud's phenomenon in patients treated with cisplatin, vinblastine and bleomycin.	1990 Jul	1702313
Hemolytic-uremic syndrome associated with neoadjuvant chemotherapy in the treatment of advanced cervical cancer.	1990 Nov	1699855
Dysregulation of apoptosis by c-myc in transgenic hepatocytes and effects of growth factors and nongenotoxic carcinogens.	1999 Aug	10449034
Long-term results of an intensive regimen: VEBEP plus involved-field radiotherapy in advanced Hodgkin's disease.	1999 Sep-Oct	10526668
Lung interleukin-4 gene expression in a murine model of bleomycin-induced pulmonary fibrosis.	2001 Aug 7	11554783
The Chinese hamster FANCG/XRCC9 mutant NM3 fails to express the monoubiquitinated form of the FANCD2 protein, is hypersensitive to a range of DNA damaging agents and exhibits a normal level of spontaneous sister chromatid exchange.	2001 Dec	11751423
Lethal ischemic stroke after cisplatin-based chemotherapy for testicular carcinoma and cannabis inhalation.	2002	12373036
ChlVPP/ABVVP, a first line 'hybrid' combination chemotherapy for advanced Hodgkin's lymphoma: a retrospective analysis.	2004 Jun	15147373
Feitai attenuates bleomycin-induced pulmonary fibrosis in rats.	2004 May	15133236
Regulation of found in inflammatory zone 1 expression in bleomycin-induced lung fibrosis: role of IL-4/IL-13 and mediation via STAT-6.	2004 Sep 1	15322207
Time-dependent apoptosis of alveolar macrophages from rats exposed to bleomycin: involvement of tnf receptor 2.	2004 Sep 10	15371238
[Rat alveolar type II injured by bleomycin].	2005 Feb	15782499
Effect of rosiglitazone and 15-deoxy-Delta12,14-prostaglandin J2 on bleomycin-induced lung injury.	2005 Feb	15684285
Pharmacological inhibition of leukotrienes in an animal model of bleomycin-induced acute lung injury.	2006 Nov 21	17118201
ABVD for Hodgkin's lymphoma: full-dose chemotherapy without dose reductions or growth factors.	2007 Feb	17071938
Agents associated with lung inflammation induce similar responses in NCI-H292 lung epithelial cells.	2008 Oct	18684396
Simvastatin attenuates bleomycin-induced pulmonary fibrosis in mice.	2008 Sep 20	19080365
Effects of erlotinib on lung injury induced by intratracheal administration of bleomycin (BLM) in rats.	2010 Aug	20686337
Influence of p53 expression on sensitivity of cancer cells to bleomycin.	2010 Jul-Aug	20135637
Matrix metalloproteinase Mmp-1a is dispensable for normal growth and fertility in mice and promotes lung cancer progression by modulating inflammatory responses.	2013 May 17	23548910
Berberine attenuates bleomycin induced pulmonary toxicity and fibrosis via suppressing NF-κB dependant TGF-β activation: a biphasic experimental study.	2013 May 23	23523906
Direct activation of ATM by resveratrol under oxidizing conditions.	2014	24933654

Patents

Sample Use Guides

In Vivo Use Guide

The main components of Bleomycin for Injection are bleomycins A2 and B2. Squamous cell carcinoma, non-Hodgkin’s lymphoma, testicular carcinoma - 0.25 to 0.50 units/kg (10 to 20 units/m2) given intravenously, intramuscularly, or subcutaneously weekly or twice weekly.

Route of Administration: Other

In Vitro Use Guide

Purified nucleolar DNA was markedly degraded at a concentration of 13 ug/ml by bleomycin A2; bleomycin concentrations 20-30 times greater were required to degrade nucleoplasmic DNA. Whole nuclear DNA was degraded to only a small extent at 13 ug/ml but was markedly degraded at higher bleomycin concentrations.

Substance Class	Chemical Created by `admin` on `Fri Dec 16 20:36:50 UTC 2022` Edited by `admin` on `Fri Dec 16 20:36:50 UTC 2022`
Record UNII	13M89UEA7W
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

BLEOMYCIN A2

Common Name

English

BLEOGIN

Common Name

English

ZHENGGUANGMYCIN A2

Common Name

English

BLEOMYCIN A2 [MI]

Common Name

English

BLEOMYCINAMIDE, N1-(3-(DIMETHYLSULFONIO)PROPYL)-

Common Name

English

PINGYANGMYCIN A2

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C2311