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://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.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
DNA 278 Target ID: CHEMBL2311221 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2010/050443s036lbl.pdf	Inhibitor 8297		20.0 µM [Kd]
DNA 278 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 8297

Conditions

Condition	Modality	Highest Phase	Product
Squamous cell carcinoma 7 Sources: http://news.cancerconnect.com/wp-content/uploads/2010/06/bleomycin.pdf	Primary	Approved 8429	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 1973
Hodgkin's lymphoma 34 Sources: http://news.cancerconnect.com/wp-content/uploads/2010/06/bleomycin.pdf	Primary	Approved 8429	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 1973
Non-Hodgkin's lymphoma 79 Sources: http://news.cancerconnect.com/wp-content/uploads/2010/06/bleomycin.pdf	Primary	Approved 8429	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 1973
Testicular cancer 7 Sources: https://dailymed.nlm.nih.gov/dailymed/fda/fdaDrugXsl.cfm?setid=b5806c40-12ce-48e3-8abd-9f8997ef4428&type=display	Primary	Approved 8429	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 1973
Malignant pleural effusion 6 Sources: https://dailymed.nlm.nih.gov/dailymed/fda/fdaDrugXsl.cfm?setid=b5806c40-12ce-48e3-8abd-9f8997ef4428&type=display	Primary	Approved 8429	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 1973
Head and neck squamous cell carcinoma 32 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2010/050443s036lbl.pdf	Primary	Approved 8429	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 1975
Malignant pleural effusion 6 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2010/050443s036lbl.pdf	Primary	Approved 8429	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 1975
Embryonal cell, choriocarcinoma 5 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2010/050443s036lbl.pdf	Primary	Approved 8429	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 1975
Teratocarcinoma 5 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2010/050443s036lbl.pdf	Primary	Approved 8429	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 1975
Hodgkin's lymphoma 34 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2010/050443s036lbl.pdf	Primary	Approved 8429	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 1975
Non-Hodgkin's lymphoma 79 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2010/050443s036lbl.pdf	Primary	Approved 8429	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 1975
Squamous cell carcinoma, penis 5 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2010/050443s036lbl.pdf	Primary	Approved 8429	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 1975
Squamous cell carcinoma, cervix 5 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2010/050443s036lbl.pdf	Primary	Approved 8429	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 1975
Squamous cell carcinoma, vulva 5 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2010/050443s036lbl.pdf	Primary	Approved 8429	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 1975

PubMed

Title	Date	PubMed
[Raynaud's disease after treatment with bleomycin and vinblastine].	1986 Feb 17	2423995
Acute vascular toxicity after combination chemotherapy with cisplatin, vinblastine, and bleomycin for testicular cancer.	1988 May	2456930
Pulmonary emboli in patients receiving chemotherapy for non-Hodgkin's lymphoma.	1988 Sep	2457470
Hemolytic uremic syndrome following cisplatin, bleomycin, and vincristine chemotherapy: a report of a case and a review of the literature.	1989	2482985
Raynaud's phenomenon in patients treated with cisplatin, vinblastine, and bleomycin for germ cell cancer: measurement of vasoconstrictor response to cold.	1989 Jul	2472472
Long-term neurotoxicity in patients treated with cisplatin, vinblastine, and bleomycin for metastatic germ cell cancer.	1989 Oct	2476531
Autonomic neuropathy after treatment with cisplatin, vinblastine, and bleomycin for germ cell cancer.	1990 Feb 24	1690581
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
Nucleic Acid recognition by metal complexes of bleomycin.	1999 Sep 8	11749501
Expression and prognostic significance of IAP-family genes in human cancers and myeloid leukemias.	2000 May	10815900
Posterior leukoencephalopathy following cisplatin, bleomycin and vinblastine therapy for germ cell tumor of the ovary.	2002 Apr	12078977
Dual roles of IL-4 in lung injury and fibrosis.	2003 Feb 15	12574379
Inhibition of key cytokines by tetrathiomolybdate in the bleomycin model of pulmonary fibrosis.	2004 Dec	15541506
The influence of dexamethasone on the proliferation and apoptosis of pulmonary inflammatory cells in bleomycin-induced pulmonary fibrosis in rats.	2004 Mar	14982598
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
Feitai, a Chinese herbal medicine, reduces transforming growth factor-beta1 and monocyte chemoattractant protein-1 expression in bleomycin-induced lung fibrosis in mice.	2005 Dec	16445573
ROLE OF ENDOGENOUS AND EXOGENOUS LIGANDS FOR THE PEROXISOME PROLIFERATOR-ACTIVATED RECEPTOR alpha IN THE DEVELOPMENT OF BLEOMYCIN-INDUCED LUNG INJURY.	2005 Dec	16317386
Role of Eotaxin-1 (CCL11) and CC chemokine receptor 3 (CCR3) in bleomycin-induced lung injury and fibrosis.	2005 Dec	16314464
Secondary transitional cell carcinoma and nitrogen mustard treatment.	2005 Jun	15922437
Pharmacological inhibition of leukotrienes in an animal model of bleomycin-induced acute lung injury.	2006 Nov 21	17118201
Resveratrol alleviates bleomycin-induced lung injury in rats.	2007	17035056
Dexrazoxane-associated risk for acute myeloid leukemia/myelodysplastic syndrome and other secondary malignancies in pediatric Hodgkin's disease.	2007 Feb 10	17290056
Are platinum-based chemotherapeutic drugs safe for patients with Charcot-Marie-Tooth disease?	2007 Jun	17565539
Simvastatin attenuates bleomycin-induced pulmonary fibrosis in mice.	2008 Sep 20	19080365
Protection of bleomycin-induced fibrosis and inflammation by taurine.	2009 Jul	19362168
Epigallocatechin-3-gallate exhibits anti-fibrotic effect by attenuating bleomycin-induced glycoconjugates, lysosomal hydrolases and ultrastructural changes in rat model pulmonary fibrosis.	2009 Jul 15	19497426
Bleomycin-induced nuclear factor-kappaB activation in human bronchial epithelial cells involves the phosphorylation of glycogen synthase kinase 3beta.	2009 Jun 22	19429264
Effects of erlotinib on lung injury induced by intratracheal administration of bleomycin (BLM) in rats.	2010 Aug	20686337
XRCC1 deficiency sensitizes human lung epithelial cells to genotoxicity by crocidolite asbestos and Libby amphibole.	2010 Dec	20705543
Influence of p53 expression on sensitivity of cancer cells to bleomycin.	2010 Jul-Aug	20135637
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 Nov	20719937
Anti-inflammatory and antifibrotic effects of methyl palmitate.	2011 Aug 1	21575650
Protocatechuic aldehyde ameliorates experimental pulmonary fibrosis by modulating HMGB1/RAGE pathway.	2015 Feb 15	25582705

Patents

Sample Use Guides

In Vivo Use Guide

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

In Vitro Use Guide

1-200 ug/ml

Substance Class	Chemical Created by `admin` on `Fri Dec 15 16:36:54 GMT 2023` Edited by `admin` on `Fri Dec 15 16:36:54 GMT 2023`
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