Mitomycin C | CAS#50-07-7 | MedKoo Biosciences

MedKoo Cat#: 100630 | Name: Mitomycin C

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Mitomycine C is a methylazirinopyrroloindoledione antineoplastic antibiotic isolated from the bacterium Streptomyces caespitosus and other Streptomyces bacterial species. Bioreduced mitomycin C generates oxygen radicals, alkylates DNA, and produces interstrand DNA cross-links, thereby inhibiting DNA synthesis. Preferentially toxic to hypoxic cells, mitomycin C also inhibits RNA and protein synthesis at high concentrations.

Chemical Structure

Mitomycin C

CAS#50-07-7

Theoretical Analysis

MedKoo Cat#: 100630

Name: Mitomycin C

CAS#: 50-07-7

Chemical Formula: C15H18N4O5

Exact Mass: 334.1277

Molecular Weight: 334.33

Elemental Analysis: C, 53.89; H, 5.43; N, 16.76; O, 23.93

Price and Availability

Size	Price	Availability
10mg	USD 90.00	Ready to ship
25mg	USD 150.00	Ready to ship
50mg	USD 250.00	Ready to ship
100mg	USD 450.00	Ready to ship
200mg	USD 750.00	Ready to ship
500mg	USD 1,650.00	Ready to ship
1g	USD 2,950.00	Ready to ship
2g	USD 5,250.00	Ready to ship

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Synonym

mitomycine C; mitomycinX. US brand names: Mitozytrex; Mutamycin. Foreign brand names: Ametycine; MitocinC; Mitolem; MitoMedac; Mutamycine. Abbreviations: MITC; MITO; MITOC; MTC. Code name: NCIC04706

IUPAC/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](CN@6C[16]()=C@5C(C(N)=C(C@16=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

Appearance

Black solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO, not in water

Shelf Life

>2 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

MUTAMYCINÂ® (mitomycin for injection, USP) (also known as mitomycin and/or mitomycin-C) is an antibiotic isolated from the broth of Streptomyces caespitosus which has been shown to have antitumor activity. The compound is heat stable, has a high melting point, and is freely soluble in organic solvents. The mitomycins are a family of aziridine-containing natural products isolated from Streptomyces caespitosus or 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), anal cancers, 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. Mitomycin C has also been used topically rather than intravenously in several areas. The first is cancers, particularly bladder cancers and intraperitoneal tumours. It is now well known that a single instillation of this agent within 6 hours of bladder tumor resection can prevent recurrence. The second is in eye surgery where mitomycin c 0.02% is applied topically for 20 seconds to prevent haze after PRK or superlasik. The third is in esophageal and tracheal stenosis where application of mitomycin C onto the mucosa immediately following dilatation will decrease re-stenosis by decreasing the production of fibroblasts and scar tissue. (the information was directly from http://en.wikipedia.org/wiki/Mitomycin_C). CLINICAL PHARMACOLOGY MUTAMYCIN selectively inhibits the synthesis of deoxyribonucleic acid (DNA). The guanine and cytosine content correlates with the degree of MUTAMYCIN-induced cross-linking. At high concentrations of the drug, cellular RNA and protein synthesis are also suppressed. In humans, MUTAMYCIN is rapidly cleared from the serum after intravenous administration. Time required to reduce the serum concentration by 50% after a 30 mg bolus injection is 17 minutes. After injection of 30 mg, 20 mg, or 10 mg I.V., the maximal serum concentrations were 2.4 Âµg/mL, 1.7 Âµg/mL, and 0.52 Âµg/mL, respectively. Clearance is effected primarily by metabolism in the liver, but metabolism occurs in other tissues as well. The rate of clearance is inversely proportional to the maximal serum concentration because, it is thought, of saturation of the degradative pathways. Approximately 10% of a dose of MUTAMYCIN is excreted unchanged in the urine. Since metabolic pathways are saturated at relatively low doses, the percent of a dose excreted in urine increases with increasing dose. In children, excretion of intravenously administered MUTAMYCIN is similar.

Product Data

Product Data

Certificate of Analysis

View CoA: current batch, Lot#EOS50316

QC Data

View QC data: current batch, Lot#EOS50316

Safety Data Sheet (SDS)

View Safety Data Sheet (SDS)

Instruction

View handling instruction

Biological target:

Mitomycin C is an antineoplastic antibiotic by inhibiting DNA synthesis and inducing apoptosis in a caspases-dependent and Fas/CD95-independent manner.

In vitro activity:

In the current study, short-term MMC (Mitomycin C) treatment increased LN332 deposition by HCLE cells and attenuated the ability of vitamin C and TGFβ1 to enhance collagen deposition by HCFs. Also, epithelial-derived CMM blocked vitamin C and TGFβ1 mediated collagen deposition in HCFs, but fibroblast-derived CMM did not. These results indicate for the first time that the ability of MMC to reduce fibrosis is due to its ability to both enhance epithelial basement membrane protein deposition by corneal epithelial cells and to reduce expression of αSMA and FN by corneal fibroblasts. Reference: Sci Rep. 2019; 9: 13905. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6761181/

In vivo activity:

The surgery was well tolerated by all animals without any sign of wound infection, neurological deficit and cerebrospinal leak. The recovery of all rats was uneventful after the operations. Six rats in each group were selected for the histological analysis (Figure 5). The results showed that extensive and dense epidural scar tissue that adhered to the dura matter was found in the laminectomy defects in control group. In 0.1 mg/ml MMC (Mitomycin C) group or 0.2 mg/ml MMC group, moderate epidural scar tissue with a decreased density of fibroblasts were found in the laminectomy defects compared with those of control group. However, loose or little epidural scar tissue without significant adhesion was observed in the laminectomy defects in 0.5 mg/ml MMC group. These results demonstrated that MMC could reduce epidural fibrosis and showed in a concentration manner. Reference: Int J Clin Exp Pathol. 2017; 10(12): 11779–11788. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6966039/

	Solvent	mg/mL	mM
Solubility
	DMSO	39.8	119.07
	DMF	20.0	59.82
	Ethanol	0.1	0.30
	PBS (pH 7.2)	0.5	1.50
	Water	1.7	5.00

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 334.33 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

1. Pal-Ghosh S, Tadvalkar G, Lieberman VR, Guo X, Zieske JD, Hutcheon A, Stepp MA. Transient Mitomycin C-treatment of human corneal epithelial cells and fibroblasts alters cell migration, cytokine secretion, and matrix accumulation. Sci Rep. 2019 Sep 25;9(1):13905. doi: 10.1038/s41598-019-50307-9. PMID: 31554858; PMCID: PMC6761181. 2. Sato N, Haga J, Anazawa T, Kenjo A, Kimura T, Wada I, Mori T, Marubashi S, Gotoh M. Ex vivo Pretreatment of Islets with Mitomycin C: Reduction in Immunogenic Potential of Islets by Suppressing Secretion of Multiple Chemotactic Factors. Cell Transplant. 2017 Aug;26(8):1392-1404. doi: 10.1177/0963689717721233. PMID: 28901184; PMCID: PMC5680981. 3. Hiller BM, Marmion DJ, Gross RM, Thompson CA, Chavez CA, Brundin P, Wakeman DR, McMahon CW, Kordower JH. Mitomycin-C treatment during differentiation of induced pluripotent stem cell-derived dopamine neurons reduces proliferation without compromising survival or function in vivo. Stem Cells Transl Med. 2021 Feb;10(2):278-290. doi: 10.1002/sctm.20-0014. Epub 2020 Sep 30. PMID: 32997443; PMCID: PMC7848297. 4. Wang S, Li X, Yan L, Chen H, Wang J, Sun Y. Upregulation of P27Kip1 by mitomycin C induces fibroblast apoptosis and reduces epidural fibrosis. Int J Clin Exp Pathol. 2017 Dec 1;10(12):11779-11788. PMID: 31966541; PMCID: PMC6966039.

In vitro protocol:

In vivo protocol:

1. Hiller BM, Marmion DJ, Gross RM, Thompson CA, Chavez CA, Brundin P, Wakeman DR, McMahon CW, Kordower JH. Mitomycin-C treatment during differentiation of induced pluripotent stem cell-derived dopamine neurons reduces proliferation without compromising survival or function in vivo. Stem Cells Transl Med. 2021 Feb;10(2):278-290. doi: 10.1002/sctm.20-0014. Epub 2020 Sep 30. PMID: 32997443; PMCID: PMC7848297. 2. Wang S, Li X, Yan L, Chen H, Wang J, Sun Y. Upregulation of P27Kip1 by mitomycin C induces fibroblast apoptosis and reduces epidural fibrosis. Int J Clin Exp Pathol. 2017 Dec 1;10(12):11779-11788. PMID: 31966541; PMCID: PMC6966039.

1: Steehler MK, Groblewski JC, Milmoe GJ, Harley EH. Management of subglottic cysts with Mitomycin-C-A case series and literature review. Int J Pediatr Otorhinolaryngol. 2011 Mar;75(3):360-3. doi: 10.1016/j.ijporl.2010.12.005. Epub 2011 Jan 15. Review. PubMed PMID: 21239066. 2: Kahmann L, Beyer U, Mehlhorn G, Thiel FC, Strnad V, Fasching PA, Lux MP. Mitomycin C in patients with gynecological malignancies. Onkologie. 2010;33(10):547-57. doi: 10.1159/000319742. Epub 2010 Sep 6. Review. PubMed PMID: 20926904. 3: Caso J, Qin D, Sexton WJ. Eosinophilic cystitis following immediate post-resection intravesical instillation of mitomycin-C. Can J Urol. 2010 Jun;17(3):5223-5. Review. PubMed PMID: 20566021. 4: Volpe A, Racioppi M, D'Agostino D, Cappa E, Filianoti A, Bassi PF. Mitomycin C for the treatment of bladder cancer. Minerva Urol Nefrol. 2010 Jun;62(2):133-44. Review. PubMed PMID: 20562793. 5: Gupta A, Muecke J. Treatment of ocular surface squamous neoplasia with Mitomycin C. Br J Ophthalmol. 2010 May;94(5):555-8. doi: 10.1136/bjo.2009.168294. Review. PubMed PMID: 20447963. 6: Dimou A, Syrigos KN, Saif MW. Is there a role for mitomycin C in metastatic colorectal cancer? Expert Opin Investig Drugs. 2010 Jun;19(6):723-35. doi: 10.1517/13543784.2010.485191. Review. PubMed PMID: 20433364. 7: Di Stasi SM, Liberati E, Dutto L, Verri C. Intravesical electromotive drug administration of mitomycin-C for non-muscle invasive bladder cancer. Arch Ital Urol Androl. 2008 Dec;80(4):157-61. Review. PubMed PMID: 19235432. 8: Schallenberg M, NiederdrÃ¤ing N, Steuhl KP, Meller D. [Topical Mitomycin C as a therapy of conjunctival tumours]. Ophthalmologe. 2008 Aug;105(8):777-84. doi: 10.1007/s00347-008-1800-5. Review. German. PubMed PMID: 18618124. 9: Hofheinz RD, Beyer U, Al-Batran SE, Hartmann JT. Mitomycin C in the treatment of gastrointestinal tumours: recent data and perspectives. Onkologie. 2008 May;31(5):271-81. doi: 10.1159/000122590. Epub 2008 Apr 10. Review. PubMed PMID: 18497518. 10: Kalsi J, Harland SJ, Feneley MR. Electromotive drug administration with mitomycin C for intravesical treatment of non-muscle invasive transitional cell carcinoma. Expert Opin Drug Deliv. 2008 Jan;5(1):137-45. Review. PubMed PMID: 18095933. 11: Volpato M, Phillips RM. Tailoring targeted therapy to individual patients: lessons to be learnt from the development of mitomycin C. Cancer Genomics Proteomics. 2007 May-Jun;4(3):175-86. Review. PubMed PMID: 17878521. 12: Shapiro O, Jones K, Wang C, Landas S, Haas GP. Risk of post-operative intravesical mitomycin C instillation following transurethral bladder tumor resection. Can J Urol. 2006 Dec;13(6):3317-20. Review. PubMed PMID: 17187694. 13: Oosterlinck W. Repeat transurethral resection lowers recurrence rates in T1 bladder tumors, even after intravesical mitomycin C. Nat Clin Pract Urol. 2006 Nov;3(11):582-3. Review. PubMed PMID: 17088923. 14: Bolenz C, Cao Y, Arancibia MF, Trojan L, Alken P, Michel MS. Intravesical mitomycin C for superficial transitional cell carcinoma. Expert Rev Anticancer Ther. 2006 Aug;6(8):1273-82. Review. PubMed PMID: 16925493. 15: Meyer F, Ridwelski K, Gebauer T, Grote R, Martens-Lobenhoffer J, Lippert H. Pharmacokinetics of the antineoplastic drug mitomycin C in regional chemotherapy using the aortic stop flow technique in advanced pancreatic carcinoma. Chemotherapy. 2005 Mar;51(1):1-8. Epub 2005 Feb 17. Review. PubMed PMID: 15722626. 16: Hara K, Iwasaka T. [Chemotherapy with mitomycin C, etoposide and cisplatin for adenocarcinoma of the uterine cervix]. Nihon Rinsho. 2004 Oct;62 Suppl 10:201-4. Review. Japanese. PubMed PMID: 15535234. 17: Seow HA, Penketh PG, Baumann RP, Sartorelli AC. Bioactivation and resistance to mitomycin C. Methods Enzymol. 2004;382:221-33. Review. PubMed PMID: 15047104. 18: Shelley MD, Wilt TJ, Court J, Coles B, Kynaston H, Mason MD. Intravesical bacillus Calmette-GuÃ©rin is superior to mitomycin C in reducing tumour recurrence in high-risk superficial bladder cancer: a meta-analysis of randomized trials. BJU Int. 2004 Mar;93(4):485-90. Review. PubMed PMID: 15008714. 19: van Ruth S, Verwaal VJ, Zoetmulder FA. Pharmacokinetics of intraperitoneal mitomycin C. Surg Oncol Clin N Am. 2003 Jul;12(3):771-80. Review. PubMed PMID: 14567030. 20: Shelley MD, Court JB, Kynaston H, Wilt TJ, Coles B, Mason M. Intravesical bacillus Calmette-Guerin versus mitomycin C for Ta and T1 bladder cancer. Cochrane Database Syst Rev. 2003;(3):CD003231. Review. PubMed PMID: 12917955.