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Mitomycin
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| Systematic (IUPAC) name |
| 6-Amino-1,1a,2,8,8a,8b-hexahydro-8- (hydroxymethyl)- 8a-methoxy-5-methyl-azirino[2', 3':3,4] pyrrolo[1,2-a]indole-4,7-dione carbamate (ester) |
| Identifiers |
| CAS number |
50-07-7 |
| ATC code |
L01DC03 |
| PubChem |
5746 |
| DrugBank |
APRD00284 |
| Chemical data |
| Formula |
C15H18N4O5 |
| Mol. mass |
334.327 g/mol |
| Pharmacokinetic data |
| Bioavailability |
? |
| Metabolism |
Hepatic |
| Half life |
8-48 min |
| Excretion |
? |
| Therapeutic considerations |
| Pregnancy cat. |
D (Au, U.S.)
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| Legal status |
℞-only (U.S.), POM (UK)
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| Routes |
Exclusively intravenous |
The mitomycins are a family of aziridine-containing natural products isolated from Streptomyces lavendulae. One of these compounds, mitomycin C, finds use as a chemotherapeutic agent by virtue of its antitumour antibiotic activity. It is given intravenously to treat upper gastro-intestinal (e.g. esophageal carcinoma) and breast cancers, as well as by bladder instillation for superficial bladder tumours. It causes delayed bone marrow toxicity and therefore it is usually administered at 6-weekly intervals. Prolonged use may result in permanent bone-marrow damage. It may also cause lung fibrosis and renal damage.
[edit] References
- Hata, T.; Sano, Y.; Sugawara, R.; Matsumae, A.; Kanamori, K.; Shima, T.; Hoshi, T. J. Antibiot. Ser. A 1956, 9, 141-146.
- Fukuyama, T.; Yang, L. "Total Synthesis of (±)-Mitomycins via Isomitomycin A." J. Am. Chem. Soc. 1987, 109, 7881-7882.
- Mao, Y.; Varoglu, M.; Sherman, D.H. "Molecular characterization and analysis of the biosynthetic cluster for the antitumor antibiotic mitomycin C from Streptomyces lavendulae NRRL 2564." Chemistry & Biology 1999, 6, 251-263.
- Varoglu, M.; Mao, Y.; Sherman, D.H. "Mapping the Biosynthetic Pathway by Functional Analysis of the MitM Aziridine N-Methyltransferase." J. Am. Chem. Soc. 2001, 123, 6712-6713 and references therein.
[edit] External links
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Chemotherapeutic agents/Antineoplastic agents (L01) |
| Alkylating agents |
Nitrogen mustards: (Chlorambucil, Chlormethine, Cyclophosphamide, Ifosfamide, Melphalan). Nitrosoureas:(Carmustine, Fotemustine, Lomustine, Streptozocin). Platinum: (Carboplatin, Cisplatin, Oxaliplatin, BBR3464). Busulfan, Dacarbazine, Mechlorethamine, Procarbazine, Temozolomide, ThioTEPA, Uramustine |
| Antimetabolites |
Folic acid: (Aminopterin, Methotrexate, Pemetrexed, Raltitrexed). Purine:(Cladribine, Clofarabine, Fludarabine, Mercaptopurine, Pentostatin, Thioguanine). Pyrimidine:(Capecitabine, Cytarabine, Fluorouracil, Floxuridine, Gemcitabine) |
| Spindle poison plant alkaloids |
Taxane: (Docetaxel, Paclitaxel). Vinca: (Vinblastine, Vincristine, Vindesine, Vinorelbine). |
| Cytotoxic/antitumor antibiotics |
Anthracycline family: (Daunorubicin, Doxorubicin, Epirubicin, Idarubicin, Mitoxantrone, Valrubicin). Bleomycin, Hydroxyurea, Mitomycin, Actinomycin |
| Topoisomerase inhibitors |
Camptotheca: (Camptothecin, Topotecan, Irinotecan), Podophyllum:(Etoposide, Teniposide). |
| CI monoclonal antibodies |
Alemtuzumab, Bevacizumab, Cetuximab, Gemtuzumab, Panitumumab, Rituximab, Tositumomab, Trastuzumab |
| Photosensitizers |
Aminolevulinic acid, Methyl aminolevulinate, Porfimer sodium, Verteporfin |
| Kinase inhibitors |
Dasatinib, Erlotinib, Gefitinib, Imatinib, Lapatinib, Nilotinib, Sorafenib, Sunitinib, Vandetanib (ZD6474) |
| Other |
Alitretinoin, Altretamine, Amsacrine, Anagrelide, Arsenic trioxide, Asparaginase, Bexarotene, Bortezomib, Denileukin diftitox, Estramustine, Hydroxycarbamide, Masoprocol, Mitotane, Pegaspargase, Tretinoin |
