6-Amino-8-(((aminocarbonyl)oxy)-methyl)-1,1a,2,8,8a,8b-hexahydro-8a-methoxy-5-methylazirino-(2',3': 3,4)pyrrolo(1,2-a)indol-4,7-dion,(1aS-(1a alpha, 8 beta, 8a alpha,8b alpha))-

Gefahreninformationscode (GHS)

• Bildanzeige (GHS)

  

• Alarmwort

  Achtung

• Gefahrenhinweise

  H300：Lebensgefahr bei Verschlucken.

  H351：Kann vermutlich Krebs verursachen.

• Sicherheit

  P201：Vor Gebrauch besondere Anweisungen einholen.

  P202：Vor Gebrauch alle Sicherheitshinweise lesen und verstehen.

  P264：Nach Gebrauch gründlich waschen.

  P264：Nach Gebrauch gründlich waschen.

  P270：Bei Gebrauch nicht essen, trinken oder rauchen.

  P280：Schutzhandschuhe/Schutzkleidung/Augenschutz tragen.

  P301+P310：BEI VERSCHLUCKEN: Sofort GIFTINFORMATIONSZENTRUM/Arzt/... (geeignete Stelle für medizinische Notfallversorgung vom Hersteller/Lieferanten anzugeben) anrufen.

Mitomycin C Chemische Eigenschaften,Einsatz,Produktion Methoden

• R-Sätze Betriebsanweisung:

  R25:Giftig beim Verschlucken.
  R40:Verdacht auf krebserzeugende Wirkung.
  R22:Gesundheitsschädlich beim Verschlucken.
  R45:Kann Krebs erzeugen.
  R26/27/28:Sehr giftig beim Einatmen, Verschlucken und Berührung mit der Haut.

• S-Sätze Betriebsanweisung:

  S36/37:Bei der Arbeit geeignete Schutzhandschuhe und Schutzkleidung tragen.
  S45:Bei Unfall oder Unwohlsein sofort Arzt zuziehen (wenn möglich, dieses Etikett vorzeigen).
  S28:Bei Berührung mit der Haut sofort abwaschen mit viel . . . (vom Hersteller anzugeben).
  S53:Exposition vermeiden - vor Gebrauch besondere Anweisungen einholen.
  S22:Staub nicht einatmen.

• Beschreibung

  Mitomycin C is naturally produced by Streptomyces caespitosus, an Actinobacteria found in soil. Mitomycin C has antibiotic and antitumor activities and has been studied extensively since the 1950s. A unique feature of this drug is strong bioreductive alkylation under hypoxic conditions. Oxygen-poor cells internal to solid tumors provide an environment in which this drug is highly activated. As an antitumor agent, it has shown efficacy in a wide variety of cancers, including gastric cancer, pancreatic cancer, breast cancer, non-small-cell lung cancer, cervical cancer, prostate cancer, and bladder cancer. The sideeffect profile is large, which prohibits its widespread use. Mitomycin C is antibacterial to gram-positive, gram-negative, and acid-fast bacilli.

• Chemische Eigenschaften

  Mitomycin is a blue-violet crystalline solid.

• Chemische Eigenschaften

  Blue-violet crystals or crystalline powder.

• Originator

  Mitomycin,Medac,W. Germany,1960

• Verwenden

  Mitomycin C USP (Mutamycin) is used to treat chronic myelogenous leukemia; reticulum cell sarcoma; Hodgkin.s disease; non-Hodgkin.s lymphomas; cancer of stomach, pancreas, lung; epithelial tumors.

• Verwenden

  An antitumor antibiotic. It is used as antineoplastic.

• Verwenden

  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.

• Definition

  Antibiotic derivedfrom Streptomyces, stated to be effective againsttumors.

• 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.

• Manufacturing Process

  The commercial production of mitomycin involves the preparation of mitomycin-containing broths by culturing a mitomycin-producing organism, e.g. Streptomyces caespitosus, in suitable media as described at length in the literature. At the end of the fermentation cycle the whole broth is usually centrifuged, filtered or otherwise treated to separate the solids (mycelia) from the supernatant which contains substantially all of the antibiotic activity.
  In commercial processes there is usually a period of time intervening between the end of the fermentation cycle and the time at which the mycelia is actually removed from the broth; such a period may range from several minutes to several hours in length and may be due to a number of factors, e.g., the time necessary to conduct the actual centrifugation or filtration of large quantities of broth, or the time involved in waiting for equipment to become available for use. In the commercial preparation of mitomycin, the mitomycin-containing whole broths decrease rapidly in potency during the time following the completion of the fermentation cycle and prior to the removal of the mycelia. It has been observed that a whole broth will lose substantially all of its mitomycin activity within about 6 hours at room temperature and within about 24 hours at 10°C. It has, however, been discovered, as described in US Patent 3,042,582, that in the process for the recovery of mitomycin C from mitomycin C-containing whole broth, the step of adding about 0.1 wt % with whole broth of sodium lauryl sulfate to the whole broth at the completion of the fermentation cycle substantially eliminates such destruction of mitomycin C by mitase.

• Trademarks

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

• Therapeutic Function

  Cancer chemotherapy

• Allgemeine Beschreibung

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

• Allgemeine Beschreibung

  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.

• Allgemeine Beschreibung

  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,.

• Air & Water Reaktionen

  Water soluble.

• Reaktivität anzeigen

  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.

• Brandgefahr

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

• Biologische Aktivität

  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.

• Nebenwirkungen

  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.

• mögliche Exposition

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

• Arzneimittelwechselwirkung

  Potentially hazardous interactions with other drugs
  Antipsychotics: avoid with clozapine (increased risk of agranulocytosis).
  Live vaccines: risk of generalised infections - avoid.

• Erste Hilfe

  If this chemical gets into the eyes, remove anycontact lenses at once and irrigate immediately for at least15 min, occasionally lifting upper and lower lids. Seek medical attention immediately. If this chemical contacts theskin, remove contaminated clothing and wash immediatelywith soap and water. Seek medical attention immediately. Ifthis chemical has been inhaled, remove from exposure,begin rescue breathing (using universal precautions, including resuscitation mask) if breathing has stopped and CPR ifheart action has stopped. Transfer promptly to a medicalfacility. When this chemical has been swallowed, get medical attention. Give large quantities of water and inducevomiting. Do not make an unconscious person vomit. Keepvictim quiet and maintain normal body temperature.

• Environmental Fate

  Mitomycin C is naturally produced by S. caespitosus, a microorganism found in soil and decaying vegetation. As a compound potentially released in commercial solid waste or in spill or container residue, mitomycin C is not thought to persist in soil and water. Calculations based on its hydrolysis rate in water at 25 ℃ show a half-life of 12.9 days. It is readily soluble in water, so mobility in groundwater is high. Mitomycin persistence in air is low and bioaccumulation is low.

• Stoffwechsel

  Mitomycin is administered IV in the treatment of disseminated adenocarcinoma of the stomach or pancreas, and it has been used intravesically in superficial bladder cancer. Biotransformation pathways are saturable, and approximately 10% of an administered dose is eliminated unchanged via the kidneys.

• Lager

  +4°C

• Versand/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.

• läuterung methode

  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.]

• Toxicity evaluation

  Mitomycin C inhibits DNA synthesis and cross-links DNA at the N6 position of adenine and at the O6 and N2 positions of guanine. In addition, single-strand breakage of DNA is caused by reduced mitomycin C (this can be prevented by free radical scavengers). Its action is most prominent during the late G1 and early S phases of the cell cycle. Mitomycin C can inhibit RNA and protein synthesis at high concentrations. Mytomycin C is an aneuploidy-inducing agent. Oxygen and radiation therapy have been shown to enhance the development of toxicity.

• Inkompatibilitäten

  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.

• Einzelnachweise

  1) Tee and Proud (2000), DNA-damaging agents cause inactivation of translational regulators linked to mTOR signaling; Oncogene, 30 21 2) Park et al. (2000), Mitomycin C induces apoptosis in a caspases-dependent and Fas/CD95- independent manner in human gastric adenocarcinoma cells; Cancer Lett., 158 125 3) Merck Index 14:6215

Mitomycin C Upstream-Materialien And Downstream Produkte

6-Amino-8-(((aminocarbonyl)oxy)-methyl)-1,1a,2,8,8a,8b-hexahydro-8a-methoxy-5-methylazirino-(2',3': 3,4)pyrrolo(1,2-a)indol-4,7-dion,(1aS-(1a alpha, 8 beta, 8a alpha,8b alpha))- Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

Global(186)Suppliers

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