Mitomycin C
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MedKoo CAT#: 100630

CAS#: 50-07-7

Description: 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

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Mitomycin C
CAS# 50-07-7

Theoretical Analysis

MedKoo Cat#: 100630
Name: Mitomycin C
CAS#: 50-07-7
Chemical Formula: C15H18N4O5
Exact Mass: 334.12772
Molecular Weight: 334.33
Elemental Analysis: C, 53.89; H, 5.43; N, 16.76; O, 23.93

Price and Availability

Size Price Availability Quantity
50.0mg USD 150.0 Same day
100.0mg USD 250.0 Same day
200.0mg USD 450.0 Same day
500.0mg USD 750.0 Same day
1.0g USD 1250.0 Same day
2.0g USD 2250.0 Same day
10.0g USD 6950.0 2 Weeks
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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

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.

Recalculate based on batch purity %
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

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 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, Niederdräing 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-Guérin 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.



Additional Information

 
MUTAMYCIN® (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 µg/mL, 1.7 µg/mL, and 0.52 µg/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.