Mitomycin C

Modify Date: 2024-01-02 15:55:06

Mitomycin C Structure
Mitomycin C structure
Common Name Mitomycin C
CAS Number 50-07-7 Molecular Weight 334.327
Density 1.9±0.1 g/cm3 Boiling Point 532.0±60.0 °C at 760 mmHg
Molecular Formula C15H18N4O5 Melting Point 360 °C
MSDS Chinese USA Flash Point 275.5±32.9 °C
Symbol GHS06 GHS08
GHS06, GHS08
Signal Word Danger

 Use of Mitomycin C


Mitomycin C is an antitumor drug and antibiotic that shows extraordinary ability to inhibit DNA synthesis.

 Names

Name mitomycin C
Synonym More Synonyms

 Mitomycin C Biological Activity

Description Mitomycin C is an antitumor drug and antibiotic that shows extraordinary ability to inhibit DNA synthesis.
Related Catalog
Target

DNA synthesis[1]

In Vitro The HCT116 (p53-/-) cells are minimally sensitive to either Mitomycin C or TRAIL alone. However, surprisingly, combination treatment with MMC and TRAIL decreases cell viability significantly. Although Mitomycin C and TRAIL alone are moderately effective, Mitomycin C substantially enhances the effect of TRAIL on suppression of the cell proliferation. Mitomycin C and TRAIL treatment alone induces 9.5% and 35.0% apoptosis, respectively. However, combination treatment with Mitomycin C and TRAIL enhances apoptosis to 66.6%[1]. Mitomycin C is a cytotoxic chemotherapeutic agent that causes DNA damage in the form of DNA cross-links as well as a variety of DNA monoadducts and is known to induce p53[2].
In Vivo Mice bearing xenografted HCT116 (p53-/-) colon tumors and HT-29 colon tumors are treated with Mitomycin C (i.p., 1 mg/kg) and TRAIL (i.v., 100 μg) every other day. Animals are treated with 10 consecutive cycles of the combination therapy regimen. The combination therapy suppresses tumor growth significantly and does not impact the weight of the mice, indicating that the therapeutic combination of Mitomycin C and TRAIL is well-tolerated and has anti-tumor activity in vivo[1]. Intravesical Mitomycin C instillations has an effect on body weight that is not observed in normal, NaCl instilled or Epirubicin instilled rats. After 3 consecutive weekly instillations of 1 mg/mL Mitomycin C there is almost no weight gain, whereas rats in the other 3 groups has a statistically significant weight gain compared with MMC treated rats[3].
Cell Assay Colon adenocarcinoma HCT116 and HT-29 human colon cancer cells are used. The CellTiter-Glo Luminescent Cell Viability Assay is used to measure cell viability, which use a unique, stable form of luciferase to measure ATP as an indicator of viable cells, and the luminescent signal produced is proportional to the number of viable cells present in culture. Cells are pretreated with Mitomycin C (5 μM) for 12 h or 24 h, and then exposed to different concentrations of TRAIL for 12 h. An equal volume (100 μL) of CellTiter-GloTM reagent is added and the solution is mixed gently for 2 min on an orbital shaker. Mixture is incubated at room temperature for 10 min to allow luminescent signal to stabilize, and then imaging is performed using the Xenogen IVIS system to quantify the cell viability[1].
Animal Admin Mice[1] Four- to 6-wk-old NCr nude mice are treated with Mitomycin C (1 mg/kg) by intraperitoneal injection for 24 h, followed by one intravenous dose of purified rhTRAIL (100 μg). As a negative control, a subset of the mice are injected (i.p. and i.v.) with saline (vehicle) at the same frequency of treatment. Animals are treated for 3 consecutive weeks. The tumor size is monitored every week using caliper measurements of the tumor volume. Rats[3] Young adult female Wistar rats at age 13 weeks with a median weight of 217 g (range 187 to 255) are randomized into 4 groups of 10 each, namely a normal group with no instillations, an NaCl 0.9% or placebo group that received instillations with the solvent of the chemotherapeutic agents, an Mitomycin C (1 mg/mL) group and an Epirubicin (1 mg/mL) group.
References

[1]. Cheng H, et al. Mitomycin C potentiates TRAIL-induced apoptosis through p53-independent upregulation of death receptors: Evidence for the role of c-Jun N-terminal kinase activation. Cell Cycle. 2012 Sep 1;11(17): 3312-23.

[2]. Abbas T, et al. Differential activation of p53 by the various adducts of mitomycin C. J Biol Chem. 2002 Oct 25;277(43):40513-9.

[3]. Michielsen D, et al. Mitomycin C and epirubicin: functional bladder damage in rats after repeat intravesical instillations. J Urol. 2005 Jun;173(6):2166-70.

 Chemical & Physical Properties

Density 1.9±0.1 g/cm3
Boiling Point 532.0±60.0 °C at 760 mmHg
Melting Point 360 °C
Molecular Formula C15H18N4O5
Molecular Weight 334.327
Flash Point 275.5±32.9 °C
Exact Mass 334.127716
PSA 146.89000
LogP -0.27
Vapour Pressure 0.0±3.2 mmHg at 25°C
Index of Refraction 1.828
Stability Stable. Incompatible with strong acids, strong bases, strong oxidizing agents.
Water Solubility soluble

 MSDS

Name: Mitomycin C (Contains 2mg Mitomycin C and 48mg Sodium Chloride) Material Safety Data Sheet
Synonym: Ametycine
CAS: 50-07-7
Section 1 - Chemical Product MSDS Name:Mitomycin C (Contains 2mg Mitomycin C and 48mg Sodium Chloride) Material Safety Data Sheet
Synonym:Ametycine

Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS
CAS# Chemical Name content EINECS#
50-07-7 Mitomycin C 4 200-008-6
Hazard Symbols: T
Risk Phrases: 25 33

Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Toxic if swallowed. Danger of cumulative effects.
Potential Health Effects
Eye:
May cause eye irritation.
Skin:
May cause skin irritation.
Ingestion:
Harmful if swallowed. May cause liver damage. May cause digestive tract disturbances. May cause bone marrow depression.
Inhalation:
May cause respiratory tract irritation. May cause effects similar to those described for ingestion. May cause pulmonary fibrosis and permanent damage.
Chronic:
May cause cancer according to animal studies. Chronic exposure may cause liver damage. Adverse reproductive effects have been reported in animals. Potential cancer hazard.

Section 4 - FIRST AID MEASURES
Eyes: Flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Get medical aid.
Skin:
Get medical aid. Flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes. Wash clothing before reuse.
Ingestion:
Do not induce vomiting. If victim is conscious and alert, give 2-4 cupfuls of milk or water. Never give anything by mouth to an unconscious person. Get medical aid.
Inhalation:
Remove from exposure and move to fresh air immediately. If not breathing, give artificial respiration. If breathing is difficult, give oxygen. Get medical aid. Do NOT use mouth-to-mouth resuscitation.
Notes to Physician:

Section 5 - FIRE FIGHTING MEASURES
General Information:
As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear. During a fire, irritating and highly toxic gases may be generated by thermal decomposition or combustion.
Non-combustible, substance itself does not burn but may decompose upon heating to produce irritating, corrosive and/or toxic fumes.
Extinguishing Media:
In case of fire, use water, dry chemical, chemical foam, or alcohol-resistant foam. Substance is noncombustible; use agent most appropriate to extinguish surrounding fire.

Section 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Clean up spills immediately, observing precautions in the Protective Equipment section. Sweep up, then place into a suitable container for disposal. Avoid generating dusty conditions. Provide ventilation.

Section 7 - HANDLING and STORAGE
Handling:
Wash thoroughly after handling. Remove contaminated clothing and wash before reuse. Use only in a well-ventilated area. Minimize dust generation and accumulation. Do not get in eyes, on skin, or on clothing. Keep container tightly closed. Do not ingest or inhale.
Storage:
Do not store in direct sunlight. Keep container closed when not in use. Store in a cool, dry, well-ventilated area away from incompatible substances. Hormones and antibiotics room. Store below 40C.

Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Facilities storing or utilizing this material should be equipped with an eyewash facility and a safety shower. Use adequate general or local exhaust ventilation to keep airborne concentrations below the permissible exposure limits.
Exposure Limits CAS# 50-07-7: CAS# 7647-14-5: Russia: 5 mg/m3 TWA Personal Protective Equipment Eyes: Wear safety glasses and chemical goggles if splashing is possible.
Skin:
Wear appropriate protective gloves and clothing to prevent skin exposure.
Clothing:
Wear appropriate protective clothing to minimize contact with skin.
Respirators:
A respiratory protection program that meets OSHA's 29 CFR 1910.134 and ANSI Z88.2 requirements or European Standard EN 149 must be followed whenever workplace conditions warrant respirator use.

Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Crystalline powder
Color: blue-violet
Odor: None reported.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: > 360 deg C
Autoignition Temperature: Not applicable.
Flash Point: Not applicable.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water: soluble
Specific Gravity/Density:
Molecular Formula: C15H18N4O5
Molecular Weight: 334.32

Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable under normal temperatures and pressures.
Conditions to Avoid:
Incompatible materials, light, dust generation, excess heat, temperatures above 40C.
Incompatibilities with Other Materials:
Strong oxidizing agents - strong acids - strong bases.
Hazardous Decomposition Products:
Nitrogen oxides, carbon monoxide, carbon dioxide, nitrogen.
Hazardous Polymerization: Has not been reported.

Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 50-07-7: CN0700000 CAS# 7647-14-5: VZ4725000 LD50/LC50:
CAS# 50-07-7: Oral, mouse: LD50 = 23 mg/kg; Oral, rat: LD50 = 30 mg/kg.
CAS# 7647-14-5: Draize test, rabbit, eye: 100 mg Mild; Draize test, rabbit, eye: 100 mg/24H Moderate; Draize test, rabbit, eye: 10 mg Moderate; Draize test, rabbit, skin: 50 mg/24H Mild; Draize test, rabbit, skin: 500 mg/24H Mild; Inhalation, rat: LC50 = >42 gm/m3/1H; Oral, mouse: LD50 = 4 gm/kg; Oral, rat: LD50 = 3000 mg/kg; Skin, rabbit: LD50 = >10 gm/kg.
Carcinogenicity:
Mitomycin C - California: carcinogen, initial date 4/1/88 IARC: Group 2B carcinogen Sodium chloride - Not listed by ACGIH, IARC, or NTP.
Other:
See actual entry in RTECS for complete information.

Section 12 - ECOLOGICAL INFORMATION


Section 13 - DISPOSAL CONSIDERATIONS
Dispose of in a manner consistent with federal, state, and local regulations.

Section 14 - TRANSPORT INFORMATION

IATA
Shipping Name: TOXIC SOLID, ORGANIC, N.O.S.*
Hazard Class: 6.1
UN Number: 2811
Packing Group: II
IMO
Shipping Name: TOXIC SOLID, ORGANIC, N.O.S.
Hazard Class: 6.1
UN Number: 2811
Packing Group: II
RID/ADR
Shipping Name: TOXIC SOLID, ORGANIC, N.O.S.
Hazard Class: 6.1
UN Number: 2811
Packing group: II
USA RQ: CAS# 50-07-7: 10 lb final RQ; 4.54 kg final RQ

Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: T
Risk Phrases:
R 25 Toxic if swallowed.
R 33 Danger of cumulative effects.
Safety Phrases:
S 45 In case of accident or if you feel unwell, seek
medical advice immediately (show the label where
possible).
WGK (Water Danger/Protection)
CAS# 50-07-7: 3
CAS# 7647-14-5: 0
Canada
CAS# 50-07-7 is listed on Canada's NDSL List.
CAS# 7647-14-5 is listed on Canada's DSL List.
CAS# 50-07-7 is not listed on Canada's Ingredient Disclosure List.
CAS# 7647-14-5 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 50-07-7 is listed on the TSCA inventory.
CAS# 7647-14-5 is listed on the TSCA inventory.


SECTION 16 - ADDITIONAL INFORMATION
N/A

 Safety Information

Symbol GHS06 GHS08
GHS06, GHS08
Signal Word Danger
Hazard Statements H300-H351
Precautionary Statements P201-P202-P280-P301 + P310 + P330-P308 + P313-P501
Personal Protective Equipment Eyeshields;Faceshields;full-face particle respirator type N100 (US);Gloves;respirator cartridge type N100 (US);type P1 (EN143) respirator filter;type P3 (EN 143) respirator cartridges
Hazard Codes T:Toxic
Risk Phrases R25;R40
Safety Phrases S36/37-S45-S28A-S28
RIDADR UN 3462 6.1/PG 2
WGK Germany 3
RTECS CN0700000
Packaging Group II
Hazard Class 6.1(a)

 Synthetic Route

~10%

Mitomycin C Structure

Mitomycin C

CAS#:50-07-7

Literature: Kasai; Kono; Ikeda; Yoda; Hirayama Journal of Organic Chemistry, 1992 , vol. 57, # 26 p. 7296 - 7299

~81%

Mitomycin C Structure

Mitomycin C

CAS#:50-07-7

Literature: Arai, Hitoshi; Kasai, Masaji Journal of Organic Chemistry, 1993 , vol. 58, # 15 p. 4151 - 4152

~73%

Mitomycin C Structure

Mitomycin C

CAS#:50-07-7

Literature: Kasai; Kono; Ikeda; Yoda; Hirayama Journal of Organic Chemistry, 1992 , vol. 57, # 26 p. 7296 - 7299

~%

Mitomycin C Structure

Mitomycin C

CAS#:50-07-7

Literature: Kasai; Kono; Ikeda; Yoda; Hirayama Journal of Organic Chemistry, 1992 , vol. 57, # 26 p. 7296 - 7299

~79%

Mitomycin C Structure

Mitomycin C

CAS#:50-07-7

Literature: Furuhata; Komiyama; Takeda; Takayanagi; Torii; Mishima; Ogura; Hata Chemical and Pharmaceutical Bulletin, 1989 , vol. 37, # 10 p. 2651 - 2654

~20%

Mitomycin C Structure

Mitomycin C

CAS#:50-07-7

Detail
Literature: Vyas, D. M.; Chiang, Y.; Benigni, D.; Doyle, T. W. Journal of Organic Chemistry, 1987 , vol. 52, # 25 p. 5601 - 5605

~%

Mitomycin C Structure

Mitomycin C

CAS#:50-07-7

Literature: Senter; Pearce; Greenfield Journal of Organic Chemistry, 1990 , vol. 55, # 9 p. 2975 - 2978

~%

Mitomycin C Structure

Mitomycin C

CAS#:50-07-7

Literature: Chen; Coppola; Johns; Bogardus; Lipper Journal of Pharmaceutical Sciences, 1986 , vol. 75, # 2 p. 208 - 210

~%

Mitomycin C Structure

Mitomycin C

CAS#:50-07-7

Literature: Danishefsky; Ciufolini Journal of the American Chemical Society, 1984 , vol. 106, # 21 p. 6424 - 6425

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 Synonyms

MFCD00078109
Mitomycin C(Ametycine)
EINECS 200-008-6
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