CAS 18209-14-8

Mitomycin F

Description:

Mitomycin F is a naturally occurring antibiotic and antitumor agent derived from the bacterium *Streptomyces caespitosus*. It belongs to the mitomycin family, which is known for its ability to intercalate DNA and inhibit DNA synthesis, making it effective in cancer treatment. Mitomycin F exhibits a unique structure characterized by a quinone moiety, which contributes to its reactivity and biological activity. It is typically used in chemotherapy regimens for various cancers, including bladder and breast cancer. The compound is known for its cytotoxic properties, which arise from its ability to form cross-links in DNA, ultimately leading to cell death. Mitomycin F is less commonly used than its analogs, such as Mitomycin C, but it shares similar mechanisms of action. Due to its potent effects, handling Mitomycin F requires caution, as it can pose risks of toxicity and adverse effects. Its use in clinical settings is often accompanied by monitoring for potential side effects, including myelosuppression and gastrointestinal disturbances.

Formula: C₁₇H₂₁N₃O₆

InChI: InChI=1S/C17H21N3O6/c1-7-12(21)11-10(13(22)14(7)24-3)8(6-26-16(18)23)17(25-4)15-9(19(15)2)5-20(11)17/h8-9,15H,5-6H2,1-4H3,(H2,18,23)/t8-,9+,15+,17-,19?/m1/s1

InChI key: InChIKey=FMMDHGNWABITNT-JZWICRQDSA-N

SMILES: O(C)[C@]12N(C3=C([C@H]1COC(N)=O)C(=O)C(OC)=C(C)C3=O)C[C@]4([C@@]2(N4C)[H])[H]

Synonyms:

• (1aS,8S,8aR,8bS)-8-[[(Aminocarbonyl)oxy]methyl]-1,1a,2,8,8a,8b-hexahydro-6,8a-dimethoxy-1,5-dimethylazirino[2′,3′:3,4]pyrrolo[1,2-a]indole-4,7-dione
• Azirino(2',3':3,4)pyrrolo(1,2-a)indole-4,7-dione, 1,1a,2,8,8a,8b-hexahydro-6,8a-alpha-dimethoxy-1,5-dimethyl-8-(hydroxymethyl)-, carbamate (ester)
• Azirino(2',3':3,4)pyrrolo(1,2-a)indole-4,7-dione, 8-(((aminocarbonyl)oxy)methyl)-1,1a,2,8,8a,8b-hexahydro-6,8a-dimethoxy-1,5-dimethyl-, (1aS-(1aalpha,8beta,8aalpha,8balpha))-
• Azirino[2′,3′:3,4]pyrrolo[1,2-a]indole-4,7-dione, 1,1a,2,8,8a,8b-hexahydro-8-(hydroxymethyl)-6,8aα-dimethoxy-1,5-dimethyl-, carbamate (ester)
• Azirino[2′,3′:3,4]pyrrolo[1,2-a]indole-4,7-dione, 8-[[(aminocarbonyl)oxy]methyl]-1,1a,2,8,8a,8b-hexahydro-6,8a-dimethoxy-1,5-dimethyl-, (1aS,8S,8aR,8bS)-
• Azirino[2′,3′:3,4]pyrrolo[1,2-a]indole-4,7-dione, 8-[[(aminocarbonyl)oxy]methyl]-1,1a,2,8,8a,8b-hexahydro-6,8a-dimethoxy-1,5-dimethyl-, [1aS-(1aα,8β,8aα,8bα)]-
• Mitomycin F
• [(1aS,8S,8aR,8bS)-6,8a-dimethoxy-1,5-dimethyl-4,7-dioxo-1,1a,2,4,7,8,8a,8b-octahydroazireno[2',3':3,4]pyrrolo[1,2-a]indol-8-yl]methyl carbamate
• N-Methylmitomycin A

Azirino[2',3':3,4]pyrrolo[1,2-a]indole-4,7-dione, 8-[[(aminocarbonyl)oxy]methyl]-1,1a,2,8,8a,8b-hexahydro-6,8a-dimethoxy-1,5-dimethyl-, (1aS,8S,8aR,8bS)-

CAS: 18209-14-8

Formula: C₁₇H₂₁N₃O₆

Color and Shape: Solid

Molecular weight: 363.3651

Ref: IN-DA0023D0

N-Methyl Mitomycin A

Controlled Product

CAS: 18209-14-8

Applications Used as an intermediate in the formation of mitomycin B (M371895), an antitumor antibiotic that is also used as an antineoplastic.
References Kinoshita, S., et al.: J. Med. Chem., 14, 13 (1971); Beijnen, J.H., et al.: Anal. Profiles Drug Subs., 16, 361 (1986),

Formula: C₁₇H₂₁N₃O₆

Color and Shape: Neat

Molecular weight: 363.37

Ref: TR-M323080

N-Methyl mitomycin A

CAS: 18209-14-8

N-Methyl mitomycin A is an aziridine compound that is used as a cytotoxic agent to treat inflammatory diseases, such as cavity. It is also used to treat cancer and autoimmune diseases. N-Methyl mitomycin A inhibits the growth of tumor cells by cross-linking DNA in the target tissue, which prevents replication of the cell. This drug has been shown to induce lymphocytic leukemia in some animals by binding with DNA sequences and preventing RNA synthesis. N-Methyl mitomycin A also inhibits protein synthesis, leading to the death of the cell.

Formula: C₁₇H₂₁N₃O₆

Purity: Min. 95%

Molecular weight: 363.4 g/mol

Ref: 3D-TAA20914