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Details

Stereochemistry ABSOLUTE
Molecular Formula C55H83N17O21S3
Molecular Weight 1414.5493
Optical Activity UNSPECIFIED
Defined Stereocenters 19 / 19
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of BLEOMYCIN A2

SMILES

Cc1c(C(=N[C@@]([H])([C@]([H])(c2cnc[nH]2)O[C@@]3([H])[C@]([H])([C@]([H])([C@@]([H])([C@]([H])(CO)O3)O)O)O[C@]4([H])[C@]([H])([C@]([H])([C@@]([H])([C@@]([H])(CO)O4)O)OC(=N)[O-])O)C(=N[C@]([H])(C)[C@]([H])([C@]([H])(C)C(=N[C@@]([H])([C@@]([H])(C)O)C(=NCCc5nc(cs5)-c6nc(cs6)C(=NCCC[S+](C)C)O)O)O)O)O)O)nc([C@]([H])(CC(=N)O)NC[C@@]([H])(C(=N)O)N)[nH]c1=N

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 1414.5493
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
Drug-induced encephalopathy after previous ifosfamide treatment.
1988 Nov 5
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
Selective loss of optic nerve beta-tubulin in vincristine-induced blindness.
1992 Aug
Haemolytic uraemic syndrome following chemotherapy for an unusual germ-cell tumour.
1999 Jul
Expression and prognostic significance of IAP-family genes in human cancers and myeloid leukemias.
2000 May
Attenuation of bleomycin-induced pneumopathy in mice by monoclonal antibody to interleukin-12.
2001 Jun
Posterior leukoencephalopathy following cisplatin, bleomycin and vinblastine therapy for germ cell tumor of the ovary.
2002 Apr
An antisense oligonucleotide targeted to human Ku86 messenger RNA sensitizes M059K malignant glioma cells to ionizing radiation, bleomycin, and etoposide but not DNA cross-linking agents.
2002 Oct 15
Codon 64 of K-ras gene mutation pattern in hepatocellular carcinomas induced by bleomycin and 1-nitropyrene in A/J mice.
2003
CC-chemokine receptor 2 required for bleomycin-induced pulmonary fibrosis.
2003 Dec 21
Tetrathiomolybdate therapy protects against bleomycin-induced pulmonary fibrosis in mice.
2003 Mar
Effect of Feitai on bleomycin-induced pulmonary fibrosis in rats.
2005 Jan 15
[Effects of valsartan on bleomycin-induced pulmonary fibrosis in rats and the expression of hepatocyte growth factor in lung tissue].
2005 Jul
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
Dexrazoxane-associated risk for acute myeloid leukemia/myelodysplastic syndrome and other secondary malignancies in pediatric Hodgkin's disease.
2007 Feb 10
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
FDG-PET in bleomycin-induced pneumonitis following ABVD chemotherapy for Hodgkin's disease--a useful tool for monitoring pulmonary toxicity and disease activity.
2007 Nov
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
PPAR-gamma agonists inhibit profibrotic phenotypes in human lung fibroblasts and bleomycin-induced pulmonary fibrosis.
2008 May
Agents associated with lung inflammation induce similar responses in NCI-H292 lung epithelial cells.
2008 Oct
Bleomycin-induced nuclear factor-kappaB activation in human bronchial epithelial cells involves the phosphorylation of glycogen synthase kinase 3beta.
2009 Jun 22
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
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
Thymoquinone blocks lung injury and fibrosis by attenuating bleomycin-induced oxidative stress and activation of nuclear factor Kappa-B in rats.
2012 Dec 16
Assessment of Brd4 inhibition in idiopathic pulmonary fibrosis lung fibroblasts and in vivo models of lung fibrosis.
2013 Aug
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
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 Sat Jun 26 06:11:18 UTC 2021
Edited
by admin
on Sat Jun 26 06:11:18 UTC 2021
Record UNII
13M89UEA7W
Record Status Validated (UNII)
Record Version
  • Download
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 Sat Jun 26 06:11:18 UTC 2021 , Edited by admin on Sat Jun 26 06:11:18 UTC 2021
Code System Code Type Description
PUBCHEM
11672633
Created by admin on Sat Jun 26 06:11:18 UTC 2021 , Edited by admin on Sat Jun 26 06:11:18 UTC 2021
PRIMARY
CAS
11116-31-7
Created by admin on Sat Jun 26 06:11:18 UTC 2021 , Edited by admin on Sat Jun 26 06:11:18 UTC 2021
PRIMARY
EVMPD
SUB74829
Created by admin on Sat Jun 26 06:11:18 UTC 2021 , Edited by admin on Sat Jun 26 06:11:18 UTC 2021
PRIMARY
FDA UNII
13M89UEA7W
Created by admin on Sat Jun 26 06:11:18 UTC 2021 , Edited by admin on Sat Jun 26 06:11:18 UTC 2021
PRIMARY
EPA CompTox
11116-31-7
Created by admin on Sat Jun 26 06:11:18 UTC 2021 , Edited by admin on Sat Jun 26 06:11:18 UTC 2021
PRIMARY
ECHA (EC/EINECS)
234-356-5
Created by admin on Sat Jun 26 06:11:18 UTC 2021 , Edited by admin on Sat Jun 26 06:11:18 UTC 2021
PRIMARY
NCI_THESAURUS
C311
Created by admin on Sat Jun 26 06:11:18 UTC 2021 , Edited by admin on Sat Jun 26 06:11:18 UTC 2021
PRIMARY
MERCK INDEX
M2589
Created by admin on Sat Jun 26 06:11:18 UTC 2021 , Edited by admin on Sat Jun 26 06:11:18 UTC 2021
PRIMARY Merck Index
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SALT/SOLVATE -> PARENT
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ACTIVE MOIETY