Bleomycin sulfate
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MedKoo CAT#: 100090

CAS#: 9041-93-4 (sulfate)

Description: Bleomycin sulfate is a mixture of the sulfate salts of basic glycopeptide antineoplastic antibiotics isolated from Streptomyces verticillus. Bleomycin sulfate 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.


Chemical Structure

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Bleomycin sulfate
CAS# 9041-93-4 (sulfate)

Theoretical Analysis

MedKoo Cat#: 100090
Name: Bleomycin sulfate
CAS#: 9041-93-4 (sulfate)
Chemical Formula: C55H85N17O25S4
Exact Mass:
Molecular Weight: 1512.62
Elemental Analysis: C, 43.67; H, 5.66; N, 15.74; O, 26.44; S, 8.48

Price and Availability

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10.0mg USD 150.0 Same day
25.0mg USD 250.0 Same day
50.0mg USD 450.0 Same day
100.0mg USD 750.0 Same day
200.0mg USD 1250.0 Same day
500.0mg USD 2250.0 Same day
1.0g USD 3650.0 Same day
2.0g USD 5850.0 2 weeks
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Related CAS #: 9041-93-4 (sulfate)   1056-06-7 (free base)  

Synonym: BLEO; BLM; BLEO cell; BLEO-cell; BLEOcell; Bleolem; Bleomycin sulfate; US brand name: Blenoxane. Blanoxan.

IUPAC/Chemical Name: (3-(2'-((3S,6R,7S,8S,11S)-1-(6-amino-2-((S)-3-amino-1-(((S)-2,3-diamino-3-oxopropyl)amino)-3-oxopropyl)-5-methylpyrimidin-4-yl)-3-((R)-(((2R,3S,4S,5S,6S)-3-(((2R,3S,4S,5R,6R)-4-(carbamoyloxy)-3,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-4,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)(1H-imidazol-4-yl)methyl)-7-hydroxy-11-((R)-1-hydroxyethyl)-6,8-dimethyl-1,4,9,12-tetraoxo-2,5,10,13-tetraazapentadecan-15-yl)-[2,5'-bithiazole]-4-carboxamido)propyl)dimethylsulfonium hydrogensulfate

InChi Key: BRDAHBLYMDUECM-QIMPUPMHSA-N

InChi Code: InChI=1S/C55H83N17O21S3.H2O4S/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(26-14-61-19-66-26)91-54-43(39(80)37(78)28(16-73)90-54)92-53-40(81)42(93-55(60)88)38(79)29(17-74)89-53)51(87)67-22(3)36(77)21(2)47(83)70-34(23(4)75)49(85)63-10-8-32-65-15-30(95-32)52-68-27(18-94-52)48(84)62-9-7-11-96(5)6;1-5(2,3)4/h14-15,18-19,21-25,28-29,34-43,53-54,64,73-75,77-81H,7-13,16-17,56H2,1-6H3,(H13-,57,58,59,60,61,62,63,66,67,69,70,71,72,76,82,83,84,85,86,87,88);(H2,1,2,3,4)/t21-,22+,23+,24-,25-,28-,29+,34-,35-,36-,37+,38+,39-,40-,41-,42-,43-,53+,54-;/m0./s1

SMILES Code: C[S+](CCCNC(C1=CSC(C2=CN=C(CCNC([C@H]([C@H](O)C)NC([C@@H](C)[C@H](O)[C@@H](C)NC([C@H]([C@@H](O[C@H]3[C@@H](O[C@@H]4[C@@H](O)[C@@H](OC(N)=O)[C@H](O)[C@@H](CO)O4)[C@@H](O)[C@H](O)[C@H](CO)O3)C5=CNC=N5)NC(C6=NC([C@@H](NC[C@H](N)C(N)=O)CC(N)=O)=NC(N)=C6C)=O)=O)=O)=O)S2)=N1)=O)C.O=S(O)([O-])=O

Appearance: Solid powder

Purity: >90% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO, not in water

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

Preparing Stock Solutions

The following data is based on the product molecular weight 1512.62 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL

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1: Hay AE, Meyer RM. Balancing risks and benefits of therapy for patients with favorable-risk limited-stage Hodgkin lymphoma: the role of doxorubicin, bleomycin, vinblastine, and dacarbazine chemotherapy alone. Hematol Oncol Clin North Am. 2014 Feb;28(1):49-63. doi: 10.1016/j.hoc.2013.10.001. Review. PubMed PMID: 24287067; PubMed Central PMCID: PMC3859248.

2: Froudarakis M, Hatzimichael E, Kyriazopoulou L, Lagos K, Pappas P, Tzakos AG, Karavasilis V, Daliani D, Papandreou C, Briasoulis E. Revisiting bleomycin from pathophysiology to safe clinical use. Crit Rev Oncol Hematol. 2013 Jul;87(1):90-100. doi: 10.1016/j.critrevonc.2012.12.003. Epub 2013 Jan 9. Review. PubMed PMID: 23312772.

3: Liu W, Fang Y, Cai B, Xu J, You C, Zhang H. Intracystic bleomycin for cystic craniopharyngiomas in children (abridged republication of cochrane systematic review). Neurosurgery. 2012 Nov;71(5):909-15. doi: 10.1227/NEU.0b013e31826d5c31. Review. PubMed PMID: 22902333.

4: Fang Y, Cai BW, Zhang H, Liu W, Wu B, Xu JG, You C. Intracystic bleomycin for cystic craniopharyngiomas in children. Cochrane Database Syst Rev. 2012 Apr 18;4:CD008890. doi: 10.1002/14651858.CD008890.pub2. Review. Update in: Cochrane Database Syst Rev. 2014;9:CD008890. PubMed PMID: 22513968.

5: Inaoki M, Kawabata C, Nishijima C, Yoshio N, Kita T. Case of bleomycin-induced scleroderma. J Dermatol. 2012 May;39(5):482-4. doi: 10.1111/j.1346-8138.2011.01301.x. Epub 2011 Sep 28. Review. PubMed PMID: 21955042.

6: Mouratis MA, Aidinis V. Modeling pulmonary fibrosis with bleomycin. Curr Opin Pulm Med. 2011 Sep;17(5):355-61. doi: 10.1097/MCP.0b013e328349ac2b. Review. PubMed PMID: 21832918.

7: Gobbi PG, Federico M. What has happened to VBM (vinblastine, bleomycin, and methotrexate) chemotherapy for early-stage Hodgkin lymphoma? Crit Rev Oncol Hematol. 2012 Apr;82(1):18-24. doi: 10.1016/j.critrevonc.2011.04.003. Epub 2011 May 17. Review. PubMed PMID: 21592816.

8: Galm U, Wendt-Pienkowski E, Wang L, Huang SX, Unsin C, Tao M, Coughlin JM, Shen B. Comparative analysis of the biosynthetic gene clusters and pathways for three structurally related antitumor antibiotics: bleomycin, tallysomycin, and zorbamycin. J Nat Prod. 2011 Mar 25;74(3):526-36. doi: 10.1021/np1008152. Epub 2011 Jan 6. Review. PubMed PMID: 21210656; PubMed Central PMCID: PMC3064724.

9: Fyfe AJ, McKay P. Toxicities associated with bleomycin. J R Coll Physicians Edinb. 2010 Sep;40(3):213-5. doi: 10.4997/JRCPE.2010.306. Review. PubMed PMID: 21127762.

10: Aouida M, Ramotar D. A new twist in cellular resistance to the anticancer drug bleomycin-A5. Curr Drug Metab. 2010 Sep;11(7):595-602. Review. PubMed PMID: 20812903.



Additional Information

Bleomycin is a glycopeptide antibiotic produced by the bacterium Streptomyces verticillus. Bleomycin refers to a family of structurally related compounds. When used as an anticancer agent, the chemotherapeutical forms are primarily bleomycin A2 and B2. The drug is used in the treatment of Hodgkin's lymphoma (as a component of the ABVD and BEACOPP regimen), squamous cell carcinomas, and testicular cancer, as well as in the treatment of plantar warts  and as a means of effecting pleurodesis.  The mechanism of action involves breaking DNA. Bleomycin is on the World Health Organization's List of Essential Medicines that are needed for a basic health system.
 
Mechanism of Action
Although the exact mechanism of action of BLENOXANE is unknown, available evidence indicates that the main mode of action is the inhibition of DNA synthesis with some evidence of lesser inhibition of RNA and protein synthesis. Bleomycin is known to cause single, and to a lesser extent, double-stranded breaks in DNA. In in vitro and in vivo experiments, bleomycin has been shown to cause cell cycle arrest in G2 and in mitosis. When administered into the pleural cavity in the treatment of malignant pleural effusion, BLENOXANE acts as a sclerosing agent.

Bleomycin sulfate
Chemical Formula: C55H85N17O25S4
Molecular Weight: 1512.62
Elemental Analysis: C, 43.67; H, 5.66; N, 15.74; O, 26.44; S, 8.48

Bleomycin
Chemical Formula: C55H84N17O21S3+
Exact Mass: 1414.5184
Molecular Weight: 1415.55
Elemental Analysis: C, 46.67; H, 5.98; N, 16.82; O, 23.73; S, 6.79