Tìm theo
Bleomycin
Các tên gọi khác (7 ) :
  • Bleocin
  • Bleomicin
  • Bleomicina
  • Bleomycin A2
  • Bleomycine
  • Bleomycinum
  • BLM
Thuốc chống ung thư và tác động vào hệ thống miễn dịch
Thuốc Gốc
Small Molecule
CAS: 11056-06-7
ATC: L01DC01
ĐG : APP Pharmaceuticals , http://www.apppharma.com
CTHH: C55H84N17O21S3
PTK: 1415.552
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.
Nhận Dạng Quốc Tế & Đặc Tính Hóa Học
Công thức hóa học
C55H84N17O21S3
Phân tử khối
1415.552
Monoisotopic mass
1414.518979905
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
InChIKey=OYVAGSVQBOHSSS-WXFSZRTFSA-O
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
Traditional 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-(3H-imidazol-4-yl)propanamido]-3-hydroxy-2-methylpentanamido]-3-hydroxybutanamido]ethyl}-1,3-thiazol-4-yl)-1,3-thiazol-4-yl]formamido}propyl)dimethylsulfanium
SMILES
C[C@@H](O)[C@H](NC(=O)[C@@H](C)[C@H](O)[C@@H](C)NC(=O)[C@@H](NC(=O)C1=C(C)C(N)=NC(=N1)[C@H](CC(N)=O)NC[C@H](N)C(N)=O)[C@@H](OC1OC(CO)C(O)C(O)C1OC1OC(CO)C(O)C(OC(N)=O)C1O)C1=CN=CN1)C(=O)NCCC1=NC(=CS1)C1=NC(=CS1)C(=O)NCCC[S+](C)C
Độ tan chảy
71 °C
Độ hòa tan
Soluble
logP
-9.7
logS
-4.7
pKa (strongest acidic)
11.34
pKa (Strongest Basic)
7.67
PSA
627.07 Å2
Refractivity
344.16 m3·mol-1
Polarizability
142.03 Å3
Rotatable Bond Count
36
H Bond Acceptor Count
28
H Bond Donor Count
20
Physiological Charge
2
Number of Rings
6
Bioavailability
0
MDDR-Like Rule
true
Dược Lực Học : 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).
Cơ Chế Tác Dụng : 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. Although the exact mechanism of action of bleomycin is unknown, available evidence would seem to indicate that the main mode of action is the inhibition of DNA synthesis with some evidence of lesser inhibition of RNA and protein synthesis. DNA cleavage by bleomycin depends on oxygen and metal ions, at least in vitro. It is believed that bleomycin chelates metal ions (primarily iron) producing a pseudoenzyme that reacts with oxygen to produce superoxide and hydroxide free radicals that cleave DNA.
Dược Động Học :
▧ Absorption :
Systemic absorption is approximately 45%.
▧ Protein binding :
1%
▧ Metabolism :
Hepatic
▧ Route of Elimination :
It was reported that patients with moderately severe renal failure excreted less than 20% of the dose in the urine.
▧ Half Life :
115 minutes
Độc Tính : 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.
Chỉ Định : For palliative treatment in the management malignant neoplasm (trachea, bronchus, lung), squamous cell carcinoma, and lymphomas.
Tương Tác Thuốc :
  • Brentuximab vedotin Pulmonary toxicity of bleomycin may be increased. Avoid combination.
  • Digoxin The antineoplasic agent decreases the effect of digoxin
  • Filgrastim Monitor therapy due to enhanced adverse effects of bleomycin especially pulmonary toxicity.
  • Fosphenytoin The antineoplasic agent decreases the effect of hydantoin
  • Leflunomide Immunosuppressants like bleomycin may enhance the adverse/toxic effect of Leflunomide. Specifically, the risk for hematologic toxicity such as pancytopenia, agranulocytosis, and/or thrombocytopenia may be increased. Consider eliminating the use of a leflunomide loading dose in patients who are receiving other immunosuppressants in order to reduce the risk for serious adverse events such as hematologic toxicity.
  • Natalizumab Immunosuppressants like bleomycin may enhance the adverse/toxic effect of Natalizumab. Specifically, the risk of concurrent infection may be increased. Patients receiving natalizumab should not use concurrent immunosuppressants.
  • Phenytoin The antineoplasic agent decreases the effect of hydantoin
  • Pimecrolimus Pimecrolimus may enhance the adverse/toxic effect of immunosuppressants like bleomycin. This combination is contraindicated
  • Roflumilast Roflumilast may enhance the immunosuppressive effect of Immunosuppressants.The Canadian product monograph (Daxas brand) recommends avoiding concurrent use with immunosuppressants. U.S. prescribing information (Daliresp brand) does not include such a warning.
  • Tacrolimus Tacrolimus (Topical) may enhance the adverse/toxic effect of Immunosuppressants. Avoid use of tacrolimus ointment in patients receiving immunosuppressants.
  • Trastuzumab Trastuzumab may increase the risk of neutropenia and anemia. Monitor closely for signs and symptoms of adverse events.
Liều Lượng & Cách Dùng : Powder, for solution - Intravenous
Dữ Kiện Thương Mại
Giá thị trường
Nhà Sản Xuất
  • Công ty :
    Sản phẩm biệt dược : Blenoxane
  • Công ty :
    Sản phẩm biệt dược : Bleo
Đóng gói
Tài Liệu Tham Khảo Thêm
drugbank
http://www.drugbank.ca/drugs/DB00290
PubChem Compound
http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=5360373
PubChem Substance
http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=46509116
KEGG Compound
http://www.genome.jp/dbget-bin/www_bget?cpd:C06854
ChemSpider
http://www.chemspider.com/Chemical-Structure.4514492.html
BindingDB
http://www.bindingdb.org/bind/chemsearch/marvin/MolStructure.jsp?monomerid=50122169
National Drug Code Directory
http://www.hipaaspace.com/Medical_Billing/Coding/National.Drug.Codes/PDF/0703-3154-01
PharmGKB
http://www.pharmgkb.org/drug/PA448645
Wikipedia
http://en.wikipedia.org/wiki/Bleomycin
RxList
http://www.rxlist.com/cgi/generic3/bleomycin.htm
Drugs.com
http://www.drugs.com/cdi/bleomycin.html
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