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Mitomycin C

description Chemical properties Side effects Uses
Mitomycin C
Mitomycin C structure
CAS No.
50-07-7
Chemical Name:
Mitomycin C
Synonyms
MMC;Mitonco;MitoMyci;nsc26980;AMETYCIN;Mitoplus;ametycine;mytomycin;nsc-26980;MITOCIN C
CBNumber:
CB8456544
Molecular Formula:
C15H18N4O5
Formula Weight:
334.33
MOL File:
50-07-7.mol

Mitomycin C Properties

Melting point:
360 °C
Boiling point:
471.14°C (rough estimate)
Density 
1.2238 (rough estimate)
refractive index 
1.6800 (estimate)
storage temp. 
2-8°C
solubility 
H2O: 4 mL/vial Stock solutions should be filter sterilized and stored at 2-8 °C in the dark., clear to slightly hazy, blue to purple
form 
powder
pka
pKa 2.8(H2O,t =25,I=0.1) (Uncertain)
color 
blue-gray
PH
pH (0.5 g/l, 25℃ : )5.0~7.0
Water Solubility 
soluble
Merck 
14,6215
BRN 
7231816
Stability:
Stable. Incompatible with strong acids, strong bases, strong oxidizing agents.
CAS DataBase Reference
50-07-7(CAS DataBase Reference)
EPA Substance Registry System
Azirino[2', 3':3,4]pyrrolo[1,2-a] indole-4,7-dione, 6-amino-8-[[(aminocarbonyl) oxy]methyl]-1,1a,2,8,8a,8b- hexahydro-8a-methoxy-5-methyl-, (1aS,8S,8aR,8bS)-(50-07-7)
SAFETY
  • Risk and Safety Statements
  • Hazard and Precautionary Statements (GHS)
Hazard Codes  T,Xn,T+
Risk Statements  25-40-22-45-26/27/28
Safety Statements  36/37-45-28A-28-53-22
RIDADR  UN 3462 6.1/PG 2
WGK Germany  3
RTECS  CN0700000
8-10
TSCA  Yes
HazardClass  6.1(a)
PackingGroup  II
HS Code  29419090
Hazardous Substances Data 50-07-7(Hazardous Substances Data)
Toxicity LD50 i.v. in mice: 5 mg/kg (Wakaki); also reported as 9 mg/kg (Kinoshita)
Symbol(GHS):
Signal word: Warning
Hazard statements:
Code Hazard statements Hazard class Category Signal word Pictogram P-Codes
H300 Fatal if swallowed Acute toxicity,oral Category 1, 2 Danger P264, P270, P301+P310, P321, P330,P405, P501
H351 Suspected of causing cancer Carcinogenicity Category 2 Warning P201, P202, P281, P308+P313, P405,P501
Precautionary statements:
P201 Obtain special instructions before use.
P280 Wear protective gloves/protective clothing/eye protection/face protection.
P308+P313 IF exposed or concerned: Get medical advice/attention.
P405 Store locked up.

Mitomycin C price More Price(12)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich M0440 Mitomycin C from Streptomyces caespitosus ≥970 μg/mg (USP XXIV) 50-07-7 5mg $97.3 2018-11-23 Buy
Sigma-Aldrich M0440 Mitomycin C from Streptomyces caespitosus ≥970 μg/mg (USP XXIV) 50-07-7 25mg $381 2018-11-23 Buy
TCI Chemical M2320 Ametycin >98.0%(HPLC) 50-07-7 10mg $99 2018-11-22 Buy
TCI Chemical M2320 Ametycin >98.0%(HPLC) 50-07-7 50mg $297 2018-11-22 Buy
Alfa Aesar J67460 Mitomycin C, 5 mg/ml in DMSO, sterile-filtered 50-07-7 1ml $278 2018-11-13 Buy

Mitomycin C Chemical Properties,Uses,Production

description

Mitomycin C (MMC), an antineoplastic antibiotic derived from Streptomyces caespitosus or Streptomyces lavendulae, is a cell cycle-specific alkylating agent, inhibits DNA synthesis through covalent mitomycin C-DNA adduct with EC50 values of 0.14μM in PC3 cells. Therefore, it was served as a chemotherapeutic agent that has demonstrated its antitumor activity and has been used widely in treatment of various cancers.
Although it is active against a wide variety of tumors, newer agents have largely replaced MMC except in anal cancer; outside of the United States, MMC is infrequently used for treatment of advanced non-small cell lung cancer (NSCLC), and breast cancer.

Chemical properties

It is a crystalline powder or a powder with blue-purple shiny crystal. Its solid state is stable, while easily deactivated in acidic and alkaline solution. Mp> 360 ℃; the maximum absorption wavelength in methanol is 216nm, 360nm and 560nm.The maximum absorption wavelength in aqueous solution is 365nm ± 2nm. This product is soluble in water, methanol, acetone and ethyl acetate and other organic solvents, slightly soluble in benzene, ether and carbon tetrachloride, insoluble in petroleum ether. Highly toxic chemical, LD50 (rat, oral) 14mg/kg. Tests show that this product has potential carcinogenic effects on experimental animals.

Side effects

As with many other chemotherapeutic agents, most of the side effects of Mitomycin C (MMC)  are dose-related, including myelosuppression (which is typically delayed in onset), nausea, vomiting, diarrhea, stomatitis, dementia, and alopecia. Pulmonary toxicity associated with MMC is unpredictable, but more likely to occur at higher doses.
The following side effects are common (occurring in greater than 30%) for patients taking Mitomycin C:
Low blood counts.  Your white and red blood cells and platelets may temporarily decrease.  This can put you at increased risk for infection, anemia and/or bleeding.  The nadir counts are delayed with this drug.
Nadir: Meaning low point, nadir is the point in time between chemotherapy cycles in which you experience low blood counts.
Onset: 3 weeks
Nadir: 4-6 weeks
Recovery: 6-8 weeks
Mouth sores
Poor appetite
Fatigue
These side effects are less common side effects (occurring in about 10-29%) of patients receiving Mitomycin C:
Nausea and vomiting, usually mild
Diarrhea
Hair loss
Bladder inflammation (urinary frequency, burning, cramping, pain)-seen with intravesical (into the bladder) therapy.

Uses

(1) It is a cell division inhibitors, nucleic acid inhibitors and phage inducer; an anti-tumor drugs in clinical use.
(2) This drug has a broad anti-tumor spectrum, and effective for gastric cancer, breast cancer. It has a certain effect on lung cancer, liver cancer, malignant lymphoma, Hodgkin's disease, reticular cell sarcoma, uterine cancer, leukemia, intestinal cancer and pancreatic cancer, but with a short remission. Combination with urokinase can improve the efficacy. The goods exert its function quickly, but the number of operators is not high, and it has a high toxicity. The goods and bleomycin as well as its derivatives ——doxorubicin are anti-cancer drugs of antibiotic which can disrupt DNA. It can depolymerize DNA in the cell, inhibit DNA replication in proliferating cell. The LD50 of intravenous injection of mice is 5ml/kg. It acts as an anticancer drugs, commonly used in the treatment of digestive system cancers.

Chemical Properties

Blue-violet crystals or crystalline powder.

Chemical Properties

Mitomycin is a blue-violet crystalline solid.

Uses

An antitumor antibiotic. It is used as antineoplastic.

Uses

Mitomycin C is the most studied of a family of highly distinctive blue/purple metabolites produced by several Streptomyces species. Mitomyin C exhibits potent antibacterial and antitumour activity and inhibits DNA synthesis by intercalation, blocking nuclear division with the induction of apoptosis in cancer cells.

Indications

Mitomycin (mitomycin C, Mitocin-C, Mutamycin) is an antibiotic that is derived from a species of Streptomyces. It is sometimes classified as an alkylating agent because it can covalently bind to and cross-link DNA. Mitomycin is thought to inhibit DNA synthesis through its ability to alkylate double-strand DNA and bring about interstrand cross-linking. There is evidence that enzymatic reduction by a reduced nicotinamide– adenine dinucleotide phosphate (NADPH) dependent reductase is necessary to activate the drug.
The drug is rapidly cleared from serum after intravenous injection but is not distributed to the brain.

Definition

Antibiotic derivedfrom Streptomyces, stated to be effective againsttumors.

brand name

Mutamycin (Bristol-Myers Squibb);Mytozytrex (SuperGen).

General Description

Blue-violet crystals. Used as an anti-tumor antibiotic complex.

General Description

administration in the treatment of cancers of the stomachand pancreas when other treatments have failed. Other useshave included breast, NSCLC, cervical, bladder, and headand neck cancers. Mechanisms of resistance include increasedsynthesis of nucleophilic detoxifying compoundssuch as glutathione, decreased expression of activating enzymessuch as DT-diaphorase, and increased efflux by Pgp.The drug is rapidly cleared from the plasma after administrationand widely distributed but does not cross the bloodbrainbarrier. The parent and metabolites are excretedmainly in the feces with an elimination half-life of 50 minutes.Adverse effects include dose-limiting myelosuppression,mild nausea and vomiting,.

General Description

Mitomycin C was isolated from Streptomyces caespitosus in 1958 by Japanese workers and is considered the prototype of the bioreductive alkylating agents. Mitomycin is sometimes included as an alkylating agent but is included here because. It was reasoned that selective activation could be achieved in a reductive environment such as that found in an area of low oxygen content. This is known to occur in tumors where the fast-growing cells often grow beyond the blood supply that would normally provide oxygen. Mitomycin C is capable of being activated and alkylating DNA in an anaerobic environment. The drug contains what would appear to be reactive functionalities, including the quinone and aziridine functionalities, both or which would be thought to be susceptible to nucleophilic attack; however, the reactivity of these functionalities is reduced because of steric and electronic effects in the parent molecule. It was reasoned that selective activation could be achieved in a reductive environment such as that found in an area of low oxygen content. This is known to occur in tumors where the fast-growing cells often grow beyond the blood supply that would normally provide oxygen.A normal cell would undergo apoptosis under these conditions, but because cancer cells often have their apoptotic mechanisms inhibited they continue to survive with little or no oxygen available. Mitomycin C is capable of being activated and alkylating DNA in an anaerobic environment, but there is actually little selectivity for hypoxic cells. Activation can occur enzymatically by both one- and twoelectron processes. Reductive enzymes such as NADPHCYP reductase and DT-diaphorase have been implicated in these processes.Involvement of one-electron processes such as those seen for the anthracylines result in redox cycling and the production of ROS that may result in DNA damage, but the cytotoxicity of mitomycin C is primarily associated with its ability to alkylate DNA.

Air & Water Reactions

Water soluble.

Reactivity Profile

Mitomycin C is sensitive to prolonged exposure to light. Mitomycin C may be sensitive to prolonged exposure to air. Mitomycin C is incompatible with strong oxidizing agents, strong acids and strong bases. Calcium salts may cause decomposition.

Hazard

Possible carcinogen.

Health Hazard

Toxic doses as low as 750 mg/kg have been reported in humans. The major toxic effect is myelosuppression, characterized by marked leukopenia and thrombocytopenia; this may be delayed and cumulative. Interstitial pneumonia and glomerular damage resulting in kidney failure are unusual but well documented complications. Lung conditions -- administration of mitomycin has been recognized as causing pneumonitis, alveolitis and pulmonary fibrosis. Kidney conditions -- administration of Mitomycin Can cause kidney damage. Kidney toxicity was observed in 1-5 percent of patients. Depressed immune conditions.

Fire Hazard

Flash point data for Mitomycin C are not available; however, Mitomycin C is probably combustible.

Biological Activity

Antibiotic and antitumor agent. Covalently binds DNA forming intra- and interstrand crosslinks. Inhibits DNA synthesis.

Clinical Use

Mitomycin has limited palliative effects in carcinomas of the stomach, pancreas, colon, breast, and cervix.

Side effects

The major toxicity associated with mitomycin therapy is unpredictably long and cumulative myelosuppression that affects both white blood cells and platelets. A syndrome of microangiopathic hemolytic anemia, thrombocytopenia, and renal failure also has been described. Renal, hepatic, and pulmonary toxicity may occur. The drug is teratogenic and carcinogenic, and it can cause local blistering.

Potential Exposure

This compound is an antitumor antibiotic complex. This drug is usually injected intravenously.

First aid

Move victim to fresh air. Call 911 or emergency medical service. Give artificial respiration if victim is not breathing. Do not use mouth-to-mouth method if victim ingested or inhaled the substance; give artificial respiration with the aid of a pocket mask equipped with a one-way valve or other proper respiratory medical device. Administer oxygen if breathing is difficult. Remove and isolate contaminated clothing and shoes. In case of contact with substance, immediately flush skin or eyes with running water for at least 20 minutes. For minor skin contact, avoid spreading material on unaffected skin. Keep victim warm and quiet. Effects of exposure (inhalation, ingestion, or skin contact) to substance may be delayed. Ensure that medical personnel are aware of the material(s) involved and take precautions to protect themselves. Medical observation is recommended for 24 to 48 hours after breathing overexposure, as pulmonary edema may be delayed. As first aid for pulmonary edema, a doctor or authorized paramedic may consider administering a drug or other inhalation therapy.

Shipping

UN2811 Toxic solids, organic, n.o.s., Hazard Class: 6.1; Labels: 6.1-Poisonous materials, Technical Name Required. UN3249 Medicine, solid, toxic, n.o.s., Hazard Class: 6.1; Labels: 6.1-Poisonous materials.

Purification Methods

Mitomycin C forms blue-violet crystals from *C6H6/pet ether. It is soluble in Me2CO, MeOH and H2O, moderately soluble in *C6H6, CCl4 and Et2O but insoluble in pet ether. It has UV max at 216, 360 and a weak peak at 560nm in MeOH. [Stevens et al. J Med Chem 8 1 1965, Shirahata & Hirayama J Am Chem Soc 105 7199 1983, Beilstein 25 III/IV 516.]

Incompatibilities

Incompatible with oxidizers (chlorates, nitrates, peroxides, permanganates, perchlorates, chlorine, bromine, fluorine, etc.); contact may cause fires or explosions. Keep away from alkaline materials, strong bases, strong acids, oxoacids, epoxides, heat, strong light, calcium salts.

Waste Disposal

Consult with environmental regulatory agencies for guidance on acceptable disposal practices. Generators of waste containing this contaminant (≥100 kg/mo) must conform to EPA regulations governing storage, transportation, treatment, and waste disposal. It is inappropriate and possibly dangerous to the environment to dispose of expired or waste drugs and pharmaceuticals by flushing them down the toilet or discarding them to the trash. Household quantities of expired or waste pharmaceuticals may be mixed with wet cat litter or coffee grounds, double-bagged in plastic, discard in trash. Larger quantities shall carefully take into consideration applicable DEA, EPA, and FDA regulations. If possible return the pharmaceutical to the manufacturer for proper disposal being careful to properly label and securely package the material. Alternatively, the waste pharmaceutical shall be labeled, securely packaged, and transported by a state licensed medical waste contractor to dispose by burial in a licensed hazardous or toxic waste landfill or incinerator.

Mitomycin C Preparation Products And Raw materials

Raw materials

Preparation Products


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View Lastest Price from Mitomycin C manufacturers

Image Release date Product Price Min. Order Purity Supply Ability Manufacturer
2018-08-20 Mitomycin C
50-07-7
US $1.00 / KG 1G 98% 100KG career henan chemical co
2018-03-29 Mitomycin C Powder CAS NO 50-07-7
50-07-7
US $10.00 / KG 10G 99% 10MT Hubei XinRunde Chemical Co., Ltd.

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