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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 of BLEOMYCIN A2

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
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

Curator's Comment: Bleomycin does not cross the blood-brain barrier.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
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
Primary
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
Primary
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
Primary
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
Primary
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
Primary
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
Primary
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
Primary
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
Primary
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
Primary
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
Primary
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
Primary
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
Primary
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
Primary
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

PubMed

TitleDatePubMed
Biochemical effects of bleomycin A2 on Novikoff hepatoma ascites cells.
1975
Ultrastructural study of the effect of bleomycin A2 on the nucleolus and its possibly related cytoplasmic constituents in Novikoff hepatoma cells.
1975 Feb
The effect of bleomycin A2(-Cu) on the proliferation of brain tumor cells and strained epithelial cells in vitro.
1976 Mar 20
Lack of metabolism as the biochemical basis of bleomycin-induced pulmonary toxicity.
1983 May
Hypomagnesemia, renal dysfunction, and Raynaud's phenomenon in patients treated with cisplatin, vinblastine, and bleomycin.
1985 Dec 15
[Raynaud's disease after treatment with bleomycin and vinblastine].
1986 Feb 17
Renovascular hypertension after combination chemotherapy for testicular cancer.
1988 Jan
Acute vascular toxicity after combination chemotherapy with cisplatin, vinblastine, and bleomycin for testicular cancer.
1988 May
Drug-induced encephalopathy after previous ifosfamide treatment.
1988 Nov 5
Pulmonary emboli in patients receiving chemotherapy for non-Hodgkin's lymphoma.
1988 Sep
Hemolytic uremic syndrome following cisplatin, bleomycin, and vincristine chemotherapy: a report of a case and a review of the literature.
1989
Raynaud's phenomenon in patients treated with cisplatin, vinblastine, and bleomycin for germ cell cancer: measurement of vasoconstrictor response to cold.
1989 Jul
Long-term neurotoxicity in patients treated with cisplatin, vinblastine, and bleomycin for metastatic germ cell cancer.
1989 Oct
Hemolytic-uremic syndrome associated with neoadjuvant chemotherapy in the treatment of advanced cervical cancer.
1990 Nov
Pharmacological inhibition of leukotrienes in an animal model of bleomycin-induced acute lung injury.
2006 Nov 21
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 Aug 10
Telomerase activity is required for bleomycin-induced pulmonary fibrosis in mice.
2007 Dec
Early lung injury contributes to lung fibrosis via AT1 receptor in rats.
2007 Feb
Are platinum-based chemotherapeutic drugs safe for patients with Charcot-Marie-Tooth disease?
2007 Jun
Characterization of DNA reactive and non-DNA reactive anticancer drugs by gene expression profiling.
2007 Jun 1
Effects of curcumin in treatment of experimental pulmonary fibrosis: a comparison with hydrocortisone.
2007 Jun 13
DNA methylation inhibitor 5-Aza-2'-deoxycytidine induces reversible genome-wide DNA damage that is distinctly influenced by DNA methyltransferases 1 and 3B.
2008 Jan
Cerebellar dysfunction caused by procarbazine and consumption of excessive amount of bananas.
2008 Jun
Simvastatin attenuates bleomycin-induced pulmonary fibrosis in mice.
2008 Sep 20
Radiation-induced cathepsin S is involved in radioresistance.
2009 Apr 15
Rosiglitazone abrogates bleomycin-induced scleroderma and blocks profibrotic responses through peroxisome proliferator-activated receptor-gamma.
2009 Feb
Protection of bleomycin-induced fibrosis and inflammation by taurine.
2009 Jul
Effects of erlotinib on lung injury induced by intratracheal administration of bleomycin (BLM) in rats.
2010 Aug
XRCC1 deficiency sensitizes human lung epithelial cells to genotoxicity by crocidolite asbestos and Libby amphibole.
2010 Dec
Influence of p53 expression on sensitivity of cancer cells to bleomycin.
2010 Jul-Aug
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
C/EBPβ-Thr217 phosphorylation signaling contributes to the development of lung injury and fibrosis in mice.
2011
Essential role of MeCP2 in the regulation of myofibroblast differentiation during pulmonary fibrosis.
2011 Apr
Anti-inflammatory and antifibrotic effects of methyl palmitate.
2011 Aug 1
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 Feb
Links between DNA polymerase beta expression and sensitivity to bleomycin.
2011 Mar 15
Removal of reactive oxygen species-induced 3'-blocked ends by XPF-ERCC1.
2011 Nov 21
Testing chemical agents with the cytokinesis-block micronucleus cytome assay.
2012
Preventing cleavage of Mer promotes efferocytosis and suppresses acute lung injury in bleomycin treated mice.
2012 Aug 15
Thymoquinone blocks lung injury and fibrosis by attenuating bleomycin-induced oxidative stress and activation of nuclear factor Kappa-B in rats.
2012 Dec 16
The ToxTracker assay: novel GFP reporter systems that provide mechanistic insight into the genotoxic properties of chemicals.
2012 Jan
Assessment of Brd4 inhibition in idiopathic pulmonary fibrosis lung fibroblasts and in vivo models of lung fibrosis.
2013 Aug
Comparison of bleomycin-induced pulmonary apoptosis between NMRI mice and C57BL/6 mice.
2013 Jan
Suppression of nuclear factor erythroid 2-related factor 2 via extracellular signal-regulated kinase contributes to bleomycin-induced oxidative stress and fibrogenesis.
2013 Jun 20
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
Berberine attenuates bleomycin induced pulmonary toxicity and fibrosis via suppressing NF-κB dependant TGF-β activation: a biphasic experimental study.
2013 May 23
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 Sep 1
Direct activation of ATM by resveratrol under oxidizing conditions.
2014
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 Oct 1
Protocatechuic aldehyde ameliorates experimental pulmonary fibrosis by modulating HMGB1/RAGE pathway.
2015 Feb 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.
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 Thu Jul 06 00:02:12 UTC 2023
Edited
by admin
on Thu Jul 06 00:02:12 UTC 2023
Record UNII
13M89UEA7W
Record Status Validated (UNII)
Record Version
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Name Type Language
BLEOMYCIN A2
MI  
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
Created by admin on Thu Jul 06 00:02:12 UTC 2023 , Edited by admin on Thu Jul 06 00:02:12 UTC 2023
Code System Code Type Description
PUBCHEM
11672633
Created by admin on Thu Jul 06 00:02:12 UTC 2023 , Edited by admin on Thu Jul 06 00:02:12 UTC 2023
PRIMARY
CAS
11116-31-7
Created by admin on Thu Jul 06 00:02:12 UTC 2023 , Edited by admin on Thu Jul 06 00:02:12 UTC 2023
PRIMARY
SMS_ID
100000136583
Created by admin on Thu Jul 06 00:02:12 UTC 2023 , Edited by admin on Thu Jul 06 00:02:12 UTC 2023
PRIMARY
EVMPD
SUB74829
Created by admin on Thu Jul 06 00:02:12 UTC 2023 , Edited by admin on Thu Jul 06 00:02:12 UTC 2023
PRIMARY
FDA UNII
13M89UEA7W
Created by admin on Thu Jul 06 00:02:12 UTC 2023 , Edited by admin on Thu Jul 06 00:02:12 UTC 2023
PRIMARY
EPA CompTox
DTXSID20872327
Created by admin on Thu Jul 06 00:02:12 UTC 2023 , Edited by admin on Thu Jul 06 00:02:12 UTC 2023
PRIMARY
ECHA (EC/EINECS)
234-356-5
Created by admin on Thu Jul 06 00:02:12 UTC 2023 , Edited by admin on Thu Jul 06 00:02:12 UTC 2023
PRIMARY
CHEBI
3139
Created by admin on Thu Jul 06 00:02:12 UTC 2023 , Edited by admin on Thu Jul 06 00:02:12 UTC 2023
PRIMARY
NCI_THESAURUS
C311
Created by admin on Thu Jul 06 00:02:12 UTC 2023 , Edited by admin on Thu Jul 06 00:02:12 UTC 2023
PRIMARY
MERCK INDEX
M2589
Created by admin on Thu Jul 06 00:02:12 UTC 2023 , Edited by admin on Thu Jul 06 00:02:12 UTC 2023
PRIMARY Merck Index
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ACTIVE MOIETY