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9041-93-4 (Bleomycin (sulfate))

1

Identification

Bleomycin (sulfate) Bleomycin (sulfate)
Name Bleomycin (sulfate)
Formula C110H168N34O46S7
MW 2927.17
CAS No. 9041-93-4
EINECS 232-925-2
Smiles O=C(N[[email protected]](C)[[email protected]@H](O)[[email protected]](C)C(N[[email protected]]([[email protected]](O)C)C(NCCC1=NC(C2=NC=C(C(NCCC[S+](C)C)=O)S2)=CS1)=O)=O)[[email protected]](NC(C3=C(C)C(N)=NC([[email protected]](CC(N)=O)NC[[email protected]](N)C(N)=O)=N3)=O)[[email protected]](C4=CNC=N4)O[[email protected]](O[[email protected]]5CO)[[email protected]]([[email protected]@H](O)[[email protected]@H]5O)O[[email protected]]6[[email protected]@H](O)[[email protected]](OC(N)=O)[[email protected]](O)[[email protected]@H](CO)O6.O=C(N[[email protected]](C)[[email protected]@H](O)[[email protected]](C)C(N[[email protected]]([[email protected]](O)C)C(NCCC7=NC(C8=NC=C(C(NCCC[S+](C)C)=O)S8)=CS7)=O)=O)[[email protected]](NC(C9=C(C)C(N)=NC([[email protected]](CC(N)=O)NC[[email protected]](N)C(N)=O)=N9)=O)[[email protected]](C%10=CNC=N%10)O[[email protected]](O[[email protected]]%11CO)[[email protected]]([[email protected]@H](O)[[email protected]@H]%11O)O[[email protected]]%12[[email protected]@H](O)[[email protected]](OC(N)=O)[[email protected]](O)[[email protected]@H](CO)O%12.O=S([O-])([O-])=O
Synonyms 3-[[2-[2-[2-[2-[4-[2-[6-Amino-2-[1-(2-amino-2-carbamoyl-ethyl)amino-2-carbamoyl-ethyl]-5-methyl-pyrimidin-4-yl]carbonylamino-3-[3-[4-carbamoyloxy-3,5-dihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]ox; (3-(2'-((3R,6R,7S,8S,11R)-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-(((2S,3S,4R,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)-[2,4'-bithiazole]-5-carboxamido)propyl)dimethylsulfonium sulfate
InChI InChI=1S/2C55H83N17O21S3.H2O4S/c2*1-20-33(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)63-10-8-32-68-27(18-94-32)52-65-15-30(95-52)48(84)62-9-7-11-96(5)6;1-5(2,3)4/h2*14-15,18-19,21-25,28-29,34-43,53-54,64,73-75,77-81H,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)/t2*21-,22+,23+,24-,25-,28-,29+,34+,35+,36-,37+,38+,39-,40-,41-,42+,43-,53-,54-;/m00./s1
2

Introduction

Bleomycin (Blenoxane) is a glycopeptide antibiotic; used as an anticancer agent; Bleomycin acts by induction of DNA strand breaks.

Background Information

Bleomycin sulfate (Blenoxane) is an anticancer agent for squamous cell carcinomas with IC50 of 4 nM in UT-SCC-19A cells. Bleomycin sulfate inhibits DNA synthesis and causes DNA scissions at specific base sequences. Bleomycin sulfate also inhibits tumor angiogenesis. Bleomycin sulfate causes single and double-strand DNA breaks in tumor cells, which interrupts the cell cycle. Bleomycin is thought to achieve this by chelating metal ions, producing a pseudoenzyme that reacts with oxygen to produce superoxide and hydroxide free radicals that cleave DNA. Bleomycin sulfate-induced telomere instability in mammalian cells persists for several generations after exposure. Moreover, the appearance of telomere fusions in Bleomycin sulfate-exposed cells 10 days after treatment suggests that Bleomycin sulfate can induce delayed telomere instability. Bleomycin has been used for the treatment of Hodgkin’s lymphoma in combination with doxorubicin, squamous cell carcinomas, testicular cancer, as well as in animal models of pulmonary fibrosis. Bleomycin sulfate plus Rituximab, Doxorubicin, Vinblastine or Dacarbazine has entered phase II clinical trial hodgkin lymphoma. ......by AbMole BioScience
Bleomycin sulfate is a mixture of the sulfate salts of basic glycopeptide antineoplastic antibiotics isolated from Streptomyces verticillus. ......by AdooQ BioScience, LLC
Description ......by Apexbio Technology LLC
A complex of 11 glycopeptide antitumour antibiotics originally isolated from streptomyces verticillus; the dominant components of the complex are bleomycin A2 and B2, which typically represent >90% of the total weight; with clinical application in the tre ......by BOC Sciences
An antitumor antibiotic isolated from Streptomyces verticillus. Radiomimetic DNA-cleaving agent that produces double and single DNA strand breaks through an oxygen-radical-dependent mechanism. Inhibits intracellular DNA replication. DNA alkylating agent. Inducer and regulator of apoptosis in a variety of cells. Inhibits tumor angiogenesis. ......by BioVision, Inc.,
Bleomycin sulfate is a potent DNA damaging agent, as the best-studied micronucleus (MN) inducer. Bleomycin also is a natural antibiotic, toxic to dividing cells (G2/M-phase), also proven effective in squamous cell carcinomas (SCC). ......by MedChemexpress Co., Ltd.
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. ......by MedKoo Biosciences, Inc.
An anticancer agent that acts by induction of DNA strand breaks; also inhibits incorporation of thymidine into DNA strands; a hybrid peptide-polyketide natural product.Pancreatic CancerPhase 3 Clinical ......by ProbeChem
Bleomycin Sulfate is a glycopeptide antibiotic and an anticancer agent for squamous cell carcinomas (SCC) with IC50 of 4 nM in UT-SCC-19A cells. ......by Selleck Chemicals LLC
Bleomycin Sulfate is a glycopeptide antibiotic and an anticancer agent for squamous cell carcinomas (SCC) with IC50 of 4 nM in UT-SCC-19A cells. ......by Target Molecule Corp.
3

Protocol(Only for Reference)

Cell Experiment

Animal Experiment

4

Physical and Chemical Properties

Appearance:Light yellow to yellow Solid EBNumber:EB000011662

Storage condition

Solubility

DMSO by MedChemexpress Co., Ltd.
DMSO 100 mg/mL (66 mM) ; Water 100 mg/mL (66 mM) ; Ethanol <1 mg/mL (<1 mM) by Selleck Chemicals LLC
5

Mechanism and Indication

6

Clinical Information

Product Name Sponsor & Collaborators Indications Start Date End Date Phase
Bleomycin (sulfate) Gynecologic Oncology Group Malignant Ovarian Surface Epithelial-Stromal Tumor 2010/1/1 2014/12/1 Phase 2 Clinical
Bleomycin (sulfate) Case Comprehensive Cancer Center Lymphoma 1999/11/1 2010/6/1 Phase 2 Clinical
Bleomycin (sulfate) Nexstar Pharmaceuticals Sarcoma, Kaposi HIV Infections 1999/11/2 2005/6/1 Phase 3 Clinical
Bleomycin (sulfate) - Launched
7

Safety Data of Bleomycin (sulfate)

Hazard Symbols : T,Xi
Risk Statements : 46-40-36/37/38-63
Safety Statements : 53-36/37-45-36-26
RTECS : EC5991990
WGKGermany : 3
8

Spectral Information

9

Suppliers List

Company Price and Availability Country/Region
AbMole BioScience 10mg/USD130(Out of stock) USA
Abcam 50mg/USD966() USA
AdooQ BioScience, LLC USA
Apexbio Technology LLC USA
BOC Sciences
BioVision, Inc., 50mg/USD895() USA
Biochempartner Co., Ltd China
CHEMSCENE, LLC 10mg/USD168();50mg/USD672() USA
Carbosynth Limited 10mg/USD55()
Cayman Chemical Company 1mg/USD40() USA
Dimysh ( ShangHai ) Trading Co., Ltd. China
EMD Millipore 10mg/USD379() USA
Matrix Scientific 250mg/USD1418() USA
MedChemexpress Co., Ltd. 10mg/USD168();50mg/USD672() USA
MedKoo Biosciences, Inc. USA
ProbeChem
Santa Cruz Biotechnology, Inc. 10mg/USD200();50mg/USD700() USA
Selleck Chemicals LLC 10mg/USD170(In stock);10mM/1mLIn DMSO/USD357(In stock);10mM(in 1mL DMSO) /USD357(in 1mL DMSO);50mg/USD670(In stock) USA
Shanghai Haoyuan Chemexpress Co., Ltd. 10mg/USD168();50mg/USD672() China
Shanghai Yingxuan Chempharm Co., Ltd. China
Sigma-Aldrich, Inc. 15mg/USD622(USP) USA
Spectrum Chemical Mfg. Corp. 5mg/USD209() USA
Target Molecule Corp. 10mg/USD156();25mg/USD209();50mg/USD392() USA
Tokyo Chemical Industry Co., Ltd. 10mg/USD99() Japan
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Related Products

Other Forms of 9041-93-4

Name CAS No Formula MW

Recommended Compounds in Bacterial DNA/RNA Synthesis

Name CAS No Formula MW
Fidaxomicin 873857-62-6 C52H74Cl2O18 1058.04
AVX 13616 900814-48-4 C50H73Cl2N7O7 955.06
Bedaquiline (fumarate) 845533-86-0 C36H35BrN2O6 671.58
Mafenide (Acetate) 13009-99-9 C9H14N2O4S 246.28
Cefozopran 113359-04-9 C19H17N9O5S2 515.53
Azithromycin 83905-01-5 C38H72N2O12 748.9845
Pazufloxacin 127045-41-4 C16H15FN2O4 318.3
Pazufloxacin (mesylate) 163680-77-1 C17H19FN2O7S 414.4054
Capreomycin (sulfate) 1405-37-4 C24H44N14O12S 752.76
G-418 (disulfate) 108321-42-2 C20H44N4O18S2 692.71
Demeclocycline (hydrochloride) 64-73-3 C21H22Cl2N2O8 501.31
Apramycin 37321-09-8 C21H41N5O11 539.58
Ceftriaxone 73384-59-5 C18H18N8O7S3 554.58
Ceftibuten 97519-39-6 C15H14N4O6S2 410.42
Dapsone 80-08-0 C12H12N2O2S 248.3
Vancomycin 1404-90-6 C66H76Cl3N9O24 1485.72
Lomefloxacin 98079-51-7 C17H19F2N3O3 351.35
Dirithromycin 62013-04-1 C42H78N2O14 835.07
Cefepime (Dihydrochloride Monohydrate) 123171-59-5 C19H28Cl2N6O6S2 571.5
Mafenide 138-39-6 C7H10N2O2S 186.23

Recommended Compounds in Same Indication

Name CAS No Formula MW
KX2-391 897016-82-9 C26H29N3O3 431.53
SNX-2112 908112-43-6 C23H27F3N4O3 464.48
PM00104 308359-57-1 C37H38F3N3O8 709.71
Plinabulin 714272-27-2 C19H20N4O2 336.39
Alvespimycin 467214-20-6 C32H48N4O8 616.75
CUDC-907 1339928-25-4 C23H24N8O4S 508.55
AZD1208 1204144-28-4 C21H21N3O2S 379.48
Perifosine 157716-52-4 C25H52NO4P 461.66
KX2-391 (dihydrochloride) 1038395-65-1 C26H31Cl2N3O3 504.45
MLN2238 1072833-77-2 C14H19BCl2N2O4 361.03
CPI-203 1446144-04-2 C19H18ClN5OS 399.9
Nelarabine 121032-29-9 C11H15N5O5 297.27
MLN4924 (hydrochloride) 1160295-21-5 C21H26ClN5O4S 479.98
AR-42 935881-37-1 C18H20N2O3 312.36
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Route of Synthesis

12

References

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More Information

Bleomycin (sulfate)

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