Mitomycin C (Ametycine)

Alias: Ametycine; mitomycine C; mitomycinX. US trade names: Mitozytrex; Mutamycin. Foreign brand names: Ametycine; MitocinC; Mitolem; MitoMedac; Mutamycine. Abbreviations: MITC; MITO; MITOC; MTC; NCIC04706
Cat No.:V1426 Purity: =99.66%
Mitomycin C(Mitozytrex; Mutamycin; Ametycine) is an antineoplastic antibiotic drug that acts by inhibiting DNA synthesis, and has been approved to treat different cancers.
Mitomycin C (Ametycine) Chemical Structure CAS No.: 50-07-7
Product category: DNA(RNA) Synthesis
This product is for research use only, not for human use. We do not sell to patients.
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Purity & Quality Control Documentation

Purity: =99.66%

Purity: ≥98%

Product Description

Mitomycin C (Mitozytrex; Mutamycin; Ametycine) is an antineoplastic antibiotic drug that acts by inhibiting DNA synthesis, and has been approved to treat different cancers. Mitomycine C is an analog of methylazirinopyrroloindoledione that has been isolated from Streptomyces caespitosus and other Streptomyces type bacteria. By producing interstrand DNA cross-links, oxygen radicals, and alkylation of DNA, bioreduced mitomycin C inhibits the synthesis of new DNA.

Biological Activity I Assay Protocols (From Reference)
Targets
Traditional Cytotoxic Agents
ln Vitro

Mitomycin C physically prevents DNA replication, recombination, and RNA transcription by generating DNA interstrand crosslinks.[1] Through the JNK-independent upregulation of death receptors, mitomycin C sensitizes TRAIL-resistant colon cancer cells HT-29 to the cytokine and amplifies TRAIL-induced apoptosis in HCT116 (p53-/-) colon cancer cells.[2] Mitomycin C exhibits cytotoxic activity in various human cancer cell lines, including OVCAR-5 (ovary), HT-29 (colon), SK-N-MC (neuroblastoma), HEP-2 (liver), COLO-205 (colon), NIH-OVCAR-3 (ovary), and A-549 (lung) cells.[3]

ln Vivo
Mitomycin C (400 μM) is the clinical first choice for superficial bladder tumors because it significantly inhibits intravesical tumor growth in a rat bladder tumor model.[4]
Cell Assay
Human colon cancer cells, HT-29 and colon adenocarcinoma HCT116, are employed respectively. The number of viable cells present in the culture is indicated by the luminescent signal generated by the CellTiter-Glo Luminescent Cell Viability Assay, which measures ATP using a special, stable form of luciferase. After exposing the cells to varying concentrations of TRAIL for 12 hours, the cells are pretreated with 5 μM of mitomycin C for either 12 or 24 hours. After adding an equivalent volume (100 μL) of CellTiter-GloTM reagent, the mixture is carefully mixed on an orbital shaker for two minutes. After allowing the luminescent signal to stabilize for ten minutes at room temperature, the mixture is imaged using the Xenogen IVIS system to determine the viability of the cells.
Animal Protocol
Mice: Four- to six-week-old NCr nude mice receive a single intravenous dose of purified rhTRAIL (100 μg) after receiving intraperitoneal injections of mitomycin C (1 mg/kg) for 24 hours. In a subset of mice, saline (vehicle) is injected intraperitoneally and intravenously (IV) at the same treatment frequency as a negative control. Three weeks are spent treating the animals. Using caliper measurements of the tumor volume, the tumor size is tracked once a week.
Rats: Four groups of ten young adult female Wistar rats, each with a median weight of 217 g (range: 187 to 255) and a period of 13 weeks, are randomly assigned. These groups include the normal group, which receives no instillations, the NaCl 0.9% or placebo group, and the group that receives instillations with the solvent of the chemotherapeutic agent, Mitomycin C (1 mg/mL).
References

[1]. Mol Cell . 2009 Sep 11;35(5):704-15.

[2]. Cell Cycle . 2012 Sep 1;11(17):3312-23.

[3]. Indian J Biochem Biophys . 2014 Feb;51(1):46-51.

[4]. Int J Oncol . 2014 Jan;44(1):147-52.

These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C15H18N4O5
Molecular Weight
334.37
Exact Mass
334.13
Elemental Analysis
C, 53.89; H, 5.43; N, 16.76; O, 23.93
CAS #
50-07-7
Appearance
Black solid powder
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
InChi Key
NWIBSHFKIJFRCO-WUDYKRTCSA-N
InChi Code
InChI=1S/C15H18N4O5/c1-5-9(16)12(21)8-6(4-24-14(17)22)15(23-2)13-7(18-13)3-19(15)10(8)11(5)20/h6-7,13,18H,3-4,16H2,1-2H3,(H2,17,22)/t6-,7+,13+,15-/m1/s1
Chemical Name
[(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
Synonyms
Ametycine; mitomycine C; mitomycinX. US trade names: Mitozytrex; Mutamycin. Foreign brand names: Ametycine; MitocinC; Mitolem; MitoMedac; Mutamycine. Abbreviations: MITC; MITO; MITOC; MTC; NCIC04706
HS Tariff Code
2934.99.9001
Storage

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Shipping Condition
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
Solubility Data
Solubility (In Vitro)
DMSO: 50~67 mg/mL (149.6~200.4 mM)
Water: <1 mg/mL
Ethanol: <1 mg/mL
Solubility (In Vivo)

Chemical Name:((1aS,8S,8aR,8bS)-6-amino-8a-methoxy-5-methyl-4,7-dioxo-1,1a,2,4,7,8,8a,8b-octahydroazirino[2',3':3,4]pyrrolo[1,2-a]indol-8-yl)methyl carbamate

InChi Key:NWIBSHFKIJFRCO-WUDYKRTCSA-N

InChi Code:NC(OCC[4:S=I]H()C[5:S=N]()(OC)C[6:S=N]()(H)NC[S=N](C@H[16]()C@H(C(N)=C(C@H=O)C)=O)@7-H)=O

SMILES Code:NC(OC[C@H]1[C@]([C@](N2)([H])[C@]2([H])C3)(OC)N3C4=C1C(C(N)=C(C)C4=O)=O)=O

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 2.9907 mL 14.9535 mL 29.9070 mL
5 mM 0.5981 mL 2.9907 mL 5.9814 mL
10 mM 0.2991 mL 1.4953 mL 2.9907 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.

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Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
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In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
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Working concentration mg/mL;

Method for preparing DMSO stock solution mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.

Method for preparing in vivo formulation:Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O,mix and clarify.

(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
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Clinical Trial Information
NCT Number Recruitment interventions Conditions Sponsor/Collaborators Start Date Phases
NCT05243550 Active
Recruiting
Drug: UGN-102 Bladder Cancer
Urothelial Carcinoma
UroGen Pharma Ltd. March 1, 2022 Phase 3
NCT03018418 Active
Recruiting
Radiation: Proton therapy
Drug: Chemotherapy
Anus Neoplasms Jordan Kharofa January 4, 2017 Phase 2
NCT04230759 Active
Recruiting
Drug: Chemotherapy
Radiation: Radiation
Anal Cancer
Anal Carcinoma
Goethe University January 7, 2020 Phase 2
NCT03348969 Active
Recruiting
Drug: Mitomycin c Bladder Cancer Jørgen Bjerggaard Jensen November 1, 2017 Phase 4
NCT03658304 Active
Recruiting
Drug: Mitomycin c Urothelial Carcinoma University of Florida December 5, 2018 Phase 2
Biological Data
  • Mitomycin C

    MMC (Mitomycin C) potentiates TRAIL-induced apoptosis of HCT116 (p53−/−) cells. Cell Cycle. 2012 Sep 1;11(17):3312-23.
  • Mitomycin C

    Cell Cycle. 2012 Sep 1;11(17):3312-23.
  • Mitomycin C

    Effects of MMC on JNK kinase expression, which mediates DR4 and DR5 expression. Cell Cycle. 2012 Sep 1;11(17):3312-23.
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