(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-5-yl)propanamido]-3-hydroxy-2-methylpentanamido]-3-hydroxybutanamido]ethyl}-1,3-thiazol-4-yl)-1,3-thiazol-4-yl]formamido}propyl)dimethylsulfanium

• ChemBase ID: 175
• Molecular Formular: C55H84N17O21S3+
• Molecular Mass: 1415.55176
• Monoisotopic Mass: 1414.51898079
• SMILES: s1c(nc(c1)c1scc(n1)C(=O)NCCC[S+](C)C)CCNC(=O)[C@@H](NC(=O)[C@H]([C@H](O)[C@H](NC(=O)[C@@H](NC(=O)c1nc(nc(N)c1C)[C@@H](NC[C@H](N)C(=O)N)CC(=O)N)[C@@H](OC1OC(C(O)C(O)C1OC1OC(C(O)C(OC(=O)N)C1O)CO)CO)c1[nH]cnc1)C)C)[C@H](O)C
• Canonical SMILES: OCC1OC(O[C@H]([C@@H](C(=O)N[C@@H]([C@H]([C@@H](C(=O)N[C@H](C(=O)NCCc2scc(n2)c2scc(n2)C(=O)NCCC[S+](C)C)[C@H](O)C)C)O)C)NC(=O)c2nc(nc(c2C)N)[C@H](CC(=O)N)NC[C@@H](C(=O)N)N)c2[nH]cnc2)C(C(C1O)O)OC1OC(CO)C(C(C1O)OC(=O)N)O
• 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
• InChIKey: OYVAGSVQBOHSSS-WXFSZRTFSA-O

NAMES AND DATABASE IDS

Names

• 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-5-yl)propanamido]-3-hydroxy-2-methylpentanamido]-3-hydroxybutanamido]ethyl}-1,3-thiazol-4-yl)-1,3-thiazol-4-yl]formamido}propyl)dimethylsulfanium
• IUPAC Traditional name: bleomycin
• Brand Name: Blenoxane; Bleo
• Synonyms: BLM; Bleomycin sulfate; Bleomicin; Bleomicina [INN-Spanish]; Bleomycine [INN-French]; Bleomycinum [INN-Latin]; Bleocin; Bleomycin A2; Bleomycin B2; Bleomycin

Database IDs

• CAS Number: 11056-06-7
• PubChem SID: 46509116; 160963638
• PubChem CID: 5360373

CALCULATED PROPERTIES

JChem

• Acid pKa: 11.34357
• H Acceptors: 28
• H Donor: 20
• LogD (pH = 5.5): -9.303759
• LogD (pH = 7.4): -8.932185
• Log P: -9.710223
• Molar Refractivity: 344.1594 cm^3
• Polarizability: 132.3702 Å^3
• Polar Surface Area: 627.07 Å^2
• Rotatable Bonds: 36
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: -0.52
• LOG S: -4.71
• Solubility (Water): 2.82e-02 g/l

PROPERTIES

Physical Property

• Solubility: Soluble

DETAILS

DrugBank - DB00290

• Drug Groups: approved
• Description: A complex of related glycopeptide antibiotics from Streptomyces verticillus consisting of bleomycin A2 and B2 (B2 CAS # 9060-10-0). It inhibits DNA metabolism and is used as an antineoplastic, especially for solid tumors. Bleomycin A2 is used as the representative structure for Bleomycin.
• Indication: For palliative treatment in the management malignant neoplasm (trachea, bronchus, lung), squamous cell carcinoma, and lymphomas.
• Pharmacology: Bleomycin is an antibiotic which has been shown to have antitumor activity. Bleomycin selectively inhibits the synthesis of deoxyribonucleic acid (DNA). The guanine and cytosine content correlates with the degree of mitomycin-induced cross-linking. At high concentrations of the drug, cellular RNA and protein synthesis are also suppressed. Bleomycin has been shown in vitro to inhibit B cell, T cell, and macrophage proliferation and impair antigen presentation, as well as the secretion of interferon gamma, TNFa, and IL-2. The antibiotic antitumor drugs are cell cycle-nonspecific except for Bleomycin (which has major effects in G2 and M phases).
• Toxicity: Excessive exposure may cause fever, chills, nausea, vomiting, mental, confusion, and wheezing. Bleomycin may cause irritation to eyes, skin and respiratory tract. It may also cause a darkening or thickening of the skin. It may cause an allergic reaction.
• Affected Organisms: Humans and other mammals
• Biotransformation: Hepatic
• Absorption: Systemic absorption is approximately 45%.
• Half Life: 115 minutes
• Protein Binding: 1%
• Elimination: It was reported that patients with moderately severe renal failure excreted less than 20% of the dose in the urine.
• References: Claussen CA, Long EC: Nucleic Acid recognition by metal complexes of bleomycin. Chem Rev. 1999 Sep 8;99(9):2797-816. [Pubmed]
• External Links: Wikipedia; RxList; Drugs.com

REFERENCES

• Claussen CA, Long EC: Nucleic Acid recognition by metal complexes of bleomycin. Chem Rev. 1999 Sep 8;99(9):2797-816. Pubmed