Bleomycin

DCTPepD ID  DCTPepD0014

Active Ingredients   Bleomycin

Description  A mixture of glycopeptide antineoplastic antibiotics isolated from the bacterium Streptomyces verticillus. Bleomycin forms complexes with iron that reduce molecular oxygen to superoxide and hydroxyl radicals which cause single- and double-stranded breaks in DNA; these reactive oxygen species also induce lipid peroxidation, carbohydrate oxidation, and alterations in prostaglandin synthesis and degradation.

Synonyms  Bleo; BLM; Bleomycin

Disease  Various malignancies

Classification

  

Antibiotics Peptide and derivative

Structure Information


Molecular Formula  C55H84N17O21S3

Molecular Weight  1415.6

Active Sequence  Not available

Sequence Length  Not available

Modification  Not available

Structure

 

Show IUPAC/InChI/SMILES

IUPAC Name  (3-{[2-(2-{2-[(2S,3R)-2-[(2S,3S,4R)-4-[(2S,3R)-2-({6-amino-2-[(1S)-1-{[(2S)-2-amino-2-carbamoylethyl]amino}-2-carbamoylethyl]-5-methylpyrimidin-4-yl}formamido)-3-[(3-{[4-(carbamoyloxy)-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl)oxy]-3-(1H-imidazol-4-yl)propanamido]-3-hydroxy-2-methylpentanamido]-3-hydroxybutanamido]ethyl}-1,3-thiazol-4-yl)-1,3-thiazol-4-yl]formamido}propyl)dimethylsulfanium

InChI  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)/p+1/t21-,22+,23+,24-,25-,29-,30+,34-,35-,36-,37+,38+,39-,40-,41-,42-,43-,53+,54-/m0/s1

InChI_Key OYVAGSVQBOHSSS-UAPAGMARSA-O

SMILES  O=C(N[C@@](C)([H])[C@@H](O)[C@H](C)C(N[C@]([C@@](O)([H])C)([H])C(NCCC1=NC(C2=NC(C(NCCC[S+](C)C)=O)=CS2)=CS1)=O)=O)[C@](NC(C3=NC([C@H](CC(N)=O)NC[C@H](N)C(N)=O)=NC(N)=C3C)=O)([H])[C@@](C4=CNC=N4)([H])O[C@H](O[C@H]5CO)[C@H]([C@@H](O)[C@@H]5O)O[C@@H](O[C@@H]6CO)[C@@H](O)[C@@H](OC(N)=O)[C@@H]6O

External Codes


PubChem CID  5360373

DrugBank Accession Number  DB00290

NCI Thesaurus Code  C313  

UNII  40S1VHN69B   GSRS

CAS  11056-06-7



Drug approval


Drug indication
    For palliative treatment in the management malignant neoplasm (trachea, bronchus, lung), squamous cell carcinoma, and lymphomas.

Drug Name Strength Dosage Form/Route Company Marketing Status Drug ID Approval year
Bleomycin Sulfate eq 15 units base/vial Injectable; Injection Teva Parenteral Discontinued ANDA: 064084 1999
Bleomycin Sulfate eq 30 units base/vial Injectable; Injection Teva Parenteral Discontinued ANDA: 064084 1999
Bleomycin Sulfate eq 15 units base/vial Injectable; Injection Hospira Prescription ANDA: 065031 2015
Bleomycin Sulfate eq 30 units base/vial Injectable; Injection Hospira Prescription ANDA: 065031 2015
Bleomycin Sulfate eq 15 units base/vial Unknown Teva Pharms Usa Prescription ANDA: 065033 2013
Bleomycin Sulfate eq 30 units base/vial Unknown Teva Pharms Usa Prescription ANDA: 065033 2013
Bleomycin Sulfate eq 30 units base/vial Injectable; Injection Hikma Prescription ANDA: 065042 2011
Bleomycin Sulfate eq 15 units base/vial Injectable; Injection Hikma Prescription ANDA: 065042 2011
Bleomycin Sulfate eq 15 units base/vial Injectable; Injection Fresenius Kabi Usa Prescription ANDA: 065185 2011
Bleomycin Sulfate eq 30 units base/vial Injectable; Injection Fresenius Kabi Usa Prescription ANDA: 065185 2011
Bleomycin Sulfate eq 15 units base/vial Injectable; Injection Pharmachemie Bv Discontinued ANDA: 065201 2007
Bleomycin Sulfate eq 15 units base/vial Injectable; Injection Meitheal Prescription ANDA: 205030 2018
Bleomycin Sulfate eq 30 units base/vial Injectable; Injection Meitheal Prescription ANDA: 205030 2018
Bleomycin Sulfate eq 15 units base/vial Injectable; Injection Cipla Discontinued ANDA: 209439 2019

ClinicalTrials.gov Identifier Title Condition or disease Phase Purpose
NCT00198263 An Open-Label Study Using the Medpulser® Electroporation System to Treat Head and Neck Cancer Head and Neck Cancer Phase 4 Treatment
NCT03225781 A Clinical Trial Using Electrochemotherapy With Bleomycin for the Treatment of Non-metastatic Unresectable Pancreatic Cancer Pancreatic Cancer Not Applicable Treatment
NCT03628417 Fázis II, randomizált, kettős Vak vizsgálat a bőr metasztázisok kezelésére kálcium elektroporációval Cutaneous Melanoma Not Applicable Treatment
NCT01872923 Dose Escalating Study to Evaluate the Tolerability, Efficacy and Safety of Amphinex 0.125 mg/kg or Lower in Amphinex-based PCI of Bleomycin in Patients With Local Recurrence or Advanced/Metastatic, Cutaneous or Sub-cutaneous Malignancies. Cutaneous or Sub-cutaneous Malignancies Phase 1 Treatment
NCT05395962 Electrochemotherapy With Carboplatinum Plus Bleomycin Versus Bleomycin Alone in Vulvar Cancer: the ElechtraPlatinum Study. A Randomized Controlled Trial Vulvar Cancer Phase 2 Treatment

    More clinical information is obtained from ClinicalTrials.gov.





DCTPep is developed by Dr.Zheng's team.