Bleomycin

Synopsis, Chemistry

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Also known as: Bleomycin sulfate, 9041-93-4, Blexane, Bleomycin sulphate, Bleomycin, sulfate (salt), Bleomycin, sulfate

Molecular Formula

C₅₅H₈₅N₁₇O₂₅S₄

Molecular Weight

1512.6 g/mol

InChI Key

WUIABRMSWOKTOF-OCBSMOPSSA-N

A complex of related glycopeptide antibiotics from Streptomyces verticillus consisting of bleomycin A2 and B2. It inhibits DNA metabolism and is used as an antineoplastic, especially for solid tumors.

1 2D Structure

Bleomycin

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

3-[[2-[2-[2-[[2-[[4-[[2-[[6-amino-2-[3-amino-1-[(2,3-diamino-3-oxopropyl)amino]-3-oxopropyl]-5-methylpyrimidine-4-carbonyl]amino]-3-[(2R,3S,4S,5S,6S)-3-[(2R,3S,4S,5R,6R)-4-carbamoyloxy-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3-(1H-imidazol-5-yl)propanoyl]amino]-3-hydroxy-2-methylpentanoyl]amino]-3-hydroxybutanoyl]amino]ethyl]-1,3-thiazol-4-yl]-1,3-thiazole-4-carbonyl]amino]propyl-dimethylsulfanium;hydrogen sulfate

2.1.2 InChI

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(26-14-61-19-65-26)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;1-5(2,3)4/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);(H2,1,2,3,4)/t21?,22?,23?,24?,25?,29-,30+,34?,35?,36?,37+,38+,39-,40-,41?,42-,43-,53+,54-;/m0./s1

2.1.3 InChI Key

WUIABRMSWOKTOF-OCBSMOPSSA-N

2.1.4 Canonical SMILES

CC1=C(N=C(N=C1N)C(CC(=O)N)NCC(C(=O)N)N)C(=O)NC(C(C2=CN=CN2)OC3C(C(C(C(O3)CO)O)O)OC4C(C(C(C(O4)CO)O)OC(=O)N)O)C(=O)NC(C)C(C(C)C(=O)NC(C(C)O)C(=O)NCCC5=NC(=CS5)C6=NC(=CS6)C(=O)NCCC[S+](C)C)O.OS(=O)(=O)[O-]

2.1.5 Isomeric SMILES

CC1=C(N=C(N=C1N)C(CC(=O)N)NCC(C(=O)N)N)C(=O)NC(C(C2=CN=CN2)O[C@H]3[C@H]([C@H]([C@@H]([C@@H](O3)CO)O)O)O[C@@H]4[C@H]([C@H]([C@@H]([C@H](O4)CO)O)OC(=O)N)O)C(=O)NC(C)C(C(C)C(=O)NC(C(C)O)C(=O)NCCC5=NC(=CS5)C6=NC(=CS6)C(=O)NCCC[S+](C)C)O.OS(=O)(=O)[O-]

2.2 Synonyms

2.2.1 MeSH Synonyms

1. Bellon, Blomycine

2. Blomycine Bellon

3. Blanoxan

4. Bleo Cell

5. Bleo-cell

6. Bleocell

7. Bleolem

8. Bleomicina

9. Bleomycin

10. Bleomycin A(2)

11. Bleomycin A2

12. Bleomycin B(2)

13. Bleomycin B2

14. Bleomycin Sulfate

15. Bleomycins

16. Bleomycinum Mack

17. Mack, Bleomycinum

18. Sulfate, Bleomycin

2.2.2 Depositor-Supplied Synonyms

1. Bleomycin Sulfate

2. 9041-93-4

3. Blexane

4. Bleomycin Sulphate

5. Bleomycin, Sulfate (salt)

6. Bleomycin, Sulfate

7. Bleomycin Sulfate [bleomycins]

8. Ccris 2470

9. Bleomycin Sulfate (salt)

10. Einecs 232-925-2

11. Unii-7dp3ntv15t

12. Bleomycin Sulfate [usan:usp:jan]

13. Bleomycin Sulfate Salt

14. 7dp3ntv15t

15. Schembl1648595

16. Mfcd00070310

17. Akos015896273

18. Akos022190415

19. Sr-01000941586

20. Sr-01000941586-2

2.3 Create Date

2005-08-08

3 Chemical and Physical Properties

Molecular Formula	C₅₅H₈₅N₁₇O₂₅S₄
Molecular Weight	1512.6 g/mol
Hydrogen Bond Donor Count	21
Hydrogen Bond Acceptor Count	35
Rotatable Bond Count	36
Exact Mass	1511.4785360 g/mol
Monoisotopic Mass	1511.4785360 g/mol
Topological Polar Surface Area	770 Å²
Heavy Atom Count	101
Formal Charge	0
Complexity	2660
Isotope Atom Count	0
Defined Atom Stereocenter Count	10
Undefined Atom Stereocenter Count	9
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	2

4 Drug and Medication Information

4.1 Drug Information

1 of 2
Drug Name	Bleomycin sulfate
Drug Label	Bleomycin for Injection, USP is a mixture of cytotoxic glycopeptide antibiotics isolated from a strain of Streptomyces verticillus. It is freely soluble in water.It is available as a lyophilized powder for intramuscular, intravenous or subcutaneous i...
Active Ingredient	Bleomycin sulfate
Dosage Form	Injectable
Route	Injection
Strength	eq 15 units base/vial; eq 30 units base/vial
Market Status	Prescription
Company	Fresenius Kabi Usa; Hospira; Teva Pharms Usa; Eurohlth Intl

2 of 2
Drug Name	Bleomycin sulfate
Drug Label	Bleomycin for Injection, USP is a mixture of cytotoxic glycopeptide antibiotics isolated from a strain of Streptomyces verticillus. It is freely soluble in water.It is available as a lyophilized powder for intramuscular, intravenous or subcutaneous i...
Active Ingredient	Bleomycin sulfate
Dosage Form	Injectable
Route	Injection
Strength	eq 15 units base/vial; eq 30 units base/vial
Market Status	Prescription
Company	Fresenius Kabi Usa; Hospira; Teva Pharms Usa; Eurohlth Intl

5 Pharmacology and Biochemistry

5.1 MeSH Pharmacological Classification

Antibiotics, Antineoplastic

Chemical substances, produced by microorganisms, inhibiting or preventing the proliferation of neoplasms. (See all compounds classified as Antibiotics, Antineoplastic.)

5.2 FDA Pharmacological Classification

5.2.1 Pharmacological Classes

Cytoprotective Agent [EPC]