Bleomycin
DRACPC ID DRACPC0014
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
Type Small Molecule
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
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.
