Mitomycin

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Cat Number

API0231524

CAS Number

50-07-7

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Product Detail Description Scientific Support Customer Q&A

CAS Number

50-07-7

EINECS

200-008-6

Storage

Store at 2-8℃

Synonyms

Ametycine; Mutamycin; Mitomycin-C; Mitocin-C; Ametycin; Mitomycinum; 7-Amino-9alpha-methoxymitosane; [(4S,6S,7R,8S)-11-amino-7-methoxy-12-methyl-10,13-dioxo-2,5-diazatetracyclo[7.4.0.02,7.04,6]trideca-1(9),11-dien-8-yl]methyl carbamate

Molecular Formula

C15H18N4O5

Molecular Weight

334.33

Smiles

CC1=C(C(=O)C2=C(C1=O)N3C[C@H]4[C@@H]([C@@]3([C@@H]2COC(=O)N)OC)N4)N

Appearance

Blue-violet crystalline powder

Melting Point

360℃

Boiling Point

581.8℃

General Description

Mitomycin is an antitumor antibiotic isolated from Streptomyces caespitosus, functioning as a potent alkylating agent. It is a cell cycle non-specific agent available as a lyophilized powder for intravenous or intracavitary administration. This compound is distinguished by its unique quinone structure, which requires bioreductive activation to exert its cytotoxic effects.

Mechanism of Action

Following intracellular enzymatic reduction, mitomycin undergoes activation to form a bifunctional alkylating species that cross-links DNA at the N-6 position of guanine. This cross-linking inhibits DNA synthesis, transcription, and ultimately leads to cell death. The drug is particularly active in hypoxic conditions, as low oxygen tension enhances reductive activation, making it effective against poorly oxygenated tumor cells resistant to radiation and other chemotherapies.

Application

Systemic mitomycin is utilized in the treatment of disseminated adenocarcinoma of the stomach and pancreas, often in combination regimens. Its primary contemporary application is in the intravesical treatment of non-muscle invasive bladder cancer, where it reduces recurrence rates following transurethral resection. Additionally, it is employed as a sclerosing agent in the management of refractory esophageal strictures and as a topical adjunct in ophthalmic surgery to prevent scarring after trabeculectomy.

The mechanism by which mitomycin C reduces epidural scar adhesion after spinal decompression surgery was investigated in human epidural scar fibroblasts. Mitomycin C suppressed cell growth in a dose‑ and time‑dependent manner, increased pro‑apoptotic proteins (Fas, DR4/5, cleaved caspase‑8/9, Bax, Bim, cleaved caspase‑3), and decreased anti‑apoptotic Bcl‑2 and Bcl‑xL. It also induced endoplasmic reticulum stress via upregulation of GRP78, CHOP, and caspase‑4; the CHOP inhibitor salubrinal blocked apoptosis. The authors conclude that mitomycin C induces fibroblast apoptosis at least partly through the ER stress pathway.

Fig. 1 Effects of MMC on human epidural scar fibroblasts. (Sui T, et al., 2017)

References

Sui T, et al. Mitomycin C induces apoptosis in human epidural scar fibroblasts after surgical decompression for spinal cord injury. Neural Regen Res. 2017; 12(4):644-653.

Does Mitomycin require strict cold chain storage as an antitumor antibiotic?

Yes, it must be stored at 2-8°C. It is thermally labile and rapidly degrades at room temperature, leading to loss of potency and increased impurities.

Is Mitomycin sensitive to light during handling and storage?

Yes, it is highly photosensitive. Exposure to light causes photodegradation. It must be stored in light-resistant containers and handled under subdued light.

What is the stability of Mitomycin after reconstitution for intravesical or intravenous use?

Reconstituted solutions have limited stability. We provide detailed in-use stability data for various diluents and storage conditions.

How is the impurity profile of Mitomycin monitored during stability studies?

We use a stability-indicating HPLC method to monitor for degradation products, including mitomycin analogs and hydrolytic degradation products, ensuring levels remain within specifications.