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マイトマイシンC

マイトマイシンC 化学構造式
50-07-7
CAS番号.
50-07-7
化学名:
マイトマイシンC
别名:
ミトシンC;ムタマイシン;ミトマイシンC;マイトマイシンC;マイトマイシン;(1aS,8S,8aR,8bS)-6-アミノ-8-[[(アミノカルボニル)オキシ]メチル]-1,1a,2,8,8a,8b-ヘキサヒドロ-8a-メトキシ-5-メチルアジリノ[2',3':3,4]ピロロ[1,2-a]インドール-4,7-ジオン;アメチシン;(1aS)-6-アミノ-8β-(アミノカルボニルオキシメチル)-1,1aα,2,8,8aα,8bα-ヘキサヒドロ-8a-メトキシ-5-メチルアジリノ[2',3':3,4]ピロロ[1,2-a]インドール-4,7-ジオン;マイトマイシン C;マイトマイシンC, ストレプトマイセス由来;マイトマイシンC STREPTOMYCES CAESPITOSUS由来;マイトマイシンC (JP17)
英語化学名:
Mitomycin C
英語别名:
MMC;0/7/50;Mitonco;nsc26980;AMETYCIN;Mitoplus;MitoMyci;ametycine;mytomycin;nsc-26980
CBNumber:
CB8456544
化学式:
C15H18N4O5
分子量:
334.33
MOL File:
50-07-7.mol

マイトマイシンC 物理性質

融点 :
360 °C
沸点 :
471.14°C (rough estimate)
比重(密度) :
1.2238 (rough estimate)
屈折率 :
1.6800 (estimate)
貯蔵温度 :
2-8°C
溶解性:
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
外見 :
powder
酸解離定数(Pka):
pKa 2.8(H2O,t =25,I=0.1) (Uncertain)
色:
blue-gray
PH:
pH (0.5 g/l, 25℃ : )5.0~7.0
水溶解度 :
soluble
Merck :
14,6215
BRN :
7231816
安定性::
Stable. Incompatible with strong acids, strong bases, strong oxidizing agents.
CAS データベース:
50-07-7(CAS DataBase Reference)
IARC:
2B (Vol. 10, Sup 7) 1987
EPAの化学物質情報:
Mitomycin C (50-07-7)
安全性情報
  • リスクと安全性に関する声明
  • 危険有害性情報のコード(GHS)
主な危険性  T,Xn,T+
Rフレーズ  25-40-22-45-26/27/28
Sフレーズ  36/37-45-28A-28-53-22
RIDADR  UN 3462 6.1/PG 2
WGK Germany  3
RTECS 番号 CN0700000
8-10
TSCA  Yes
国連危険物分類  6.1(a)
容器等級  II
HSコード  29419090
有毒物質データの 50-07-7(Hazardous Substances Data)
毒性 LD50 i.v. in mice: 5 mg/kg (Wakaki); also reported as 9 mg/kg (Kinoshita)
絵表示(GHS)
注意喚起語 Warning
危険有害性情報
コード 危険有害性情報 危険有害性クラス 区分 注意喚起語 シンボル P コード
H300 飲み込むと生命に危険 急性毒性、経口 1, 2 危険 P264, P270, P301+P310, P321, P330,P405, P501
H351 発がんのおそれの疑い 発がん性 2 警告 P201, P202, P281, P308+P313, P405,P501
注意書き
P201 使用前に取扱説明書を入手すること。
P280 保護手袋/保護衣/保護眼鏡/保護面を着用するこ と。
P308+P313 暴露または暴露の懸念がある場合:医師の診断/手当てを 受けること。
P405 施錠して保管すること。

マイトマイシンC 価格 もっと(20)

メーカー 製品番号 製品説明 CAS番号 包装 価格 更新時間 購入
富士フイルム和光純薬株式会社(wako) W01LKTM3377 マイトマイシンC
Mitomycin C
50-07-7 1mg ¥8700 2021-03-23 購入
富士フイルム和光純薬株式会社(wako) W01LKTM3377 マイトマイシンC
Mitomycin C
50-07-7 5mg ¥18200 2021-03-23 購入
東京化成工業 M2320 アメチシン >98.0%(HPLC)
Ametycin >98.0%(HPLC)
50-07-7 10mg ¥9500 2021-03-23 購入
東京化成工業 M2320 アメチシン >98.0%(HPLC)
Ametycin >98.0%(HPLC)
50-07-7 50mg ¥32700 2021-03-23 購入
関東化学株式会社(KANTO) 22694-1A マイトマイシンC
Mitomycin C
50-07-7 2mg ¥14800 2021-03-23 購入

マイトマイシンC 化学特性,用途語,生産方法

外観

暗紫色、結晶~粉末

溶解性

水, エタノール及びアセトンに難溶。水, メタノール及びアセトンにやや溶けやすく、ジエチルエーテルにやや溶けにくい。

解説

C15H18N4O5(334.33).Streptomyces caespitosusが産生する抗腫瘍抗生物質."青紫色の結晶.融点360 ℃.UV(メタノール)λmax 216,360,560 nm(ε 24800,24800,2).水,エタノールに難溶,ジエチルエーテルに不溶.グラム陽性菌,グラム陰性菌,結核菌などに強い抗菌力をもつ.内服または注射で,慢性リンパ性白血病,慢性骨髄性白血病,胃がん,肝がん,結腸·直腸がん,肺がん,子宮頸がん,子宮体がん,乳がんなどのがんの治療に単独あるいは併用で用いられる.作用機序は,がん細胞内で還元された活性化体が,二本鎖DNAのグアニン残基に結合して架橋し,DNAの複製を阻害することである.LD50 4 mg/kg(マウス,静注).[CAS 50-07-7]
森北出版「化学辞典(第2版)

用途

DNA のグアニンと結合して架 橋切断を起し、DNA 生合成阻害作用を示しま す。

用途

制癌作用研究用。

効能

抗悪性腫瘍薬

商品名

マイトマイシン (協和発酵キリン); マイトマイシン (協和発酵キリン)

説明

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.

化学的特性

Mitomycin is a blue-violet crystalline solid.

化学的特性

Blue-violet crystals or crystalline powder.

Originator

Mitomycin,Medac,W. Germany,1960

使用

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.

使用

An antitumor antibiotic. It is used as antineoplastic.

使用

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.

適応症

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.

定義

Antibiotic derivedfrom Streptomyces, stated to be effective againsttumors.

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.

brand name

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

Therapeutic Function

Cancer chemotherapy

一般的な説明

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,.

一般的な説明

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.

一般的な説明

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

空気と水の反応

Water soluble.

反応プロフィール

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.

危険性

Possible carcinogen.

健康ハザード

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.

火災危険

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

生物活性

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

臨床応用

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

副作用

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.

職業ばく露

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

環境運命予測

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.

代謝

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.

輸送方法

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.

純化方法

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.

不和合性

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.

廃棄物の処理

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.

マイトマイシンC 上流と下流の製品情報

原材料

準備製品


マイトマイシンC 生産企業

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50-07-7(マイトマイシンC)キーワード:

(1aS)-6-メトキシ-8aα-ヒドロキシ-1,5-ジメチル-8β-[(カルバモイルオキシ)メチル]-1,1aα,2,8,8a,8bα-ヘキサヒドロアジリノ[2',3':3,4]ピロロ[1,2-a]インドール-4,7-ジオン (1aS)-6-アミノ-8aα-ヒドロキシ-1,5-ジメチル-8β-[(カルバモイルオキシ)メチル]-1,1aα,2,8,8a,8bα-ヘキサヒドロアジリノ[2',3':3,4]ピロロ[1,2-a]インドール-4,7-ジオン (1aS,8R,8aR,8bS)-8-[[(アミノカルボニル)オキシ]メチル]-1,1a,2,8,8a,8b-ヘキサヒドロ-6,8a-ジメトキシ-1,5-ジメチルアジリノ[2',3':3,4]ピロロ[1,2-a]インドール-4,7-ジオン マイトマイシンC, STREPTOMYCES CAESPITOTUS, キャリアフリー (1aR)-8α-[[(アミノカルボニル)オキシ]メチル]-1,1aβ,2,8,8aβ,8bβ-ヘキサヒドロ-6,8a-ジメトキシ-1,5-ジメチルアジリノ[2',3':3,4]ピロロ[1,2-a]インドール-4,7-ジオン (1aS)-6-アミノ-8-メチレン-1,1aα,2,8,8a,8bα-ヘキサヒドロ-8aα-メトキシ-1,5-ジメチルアジリノ[2',3':3,4]ピロロ[1,2-a]インドール-4,7-ジオン (1aS)-8α-[[(アミノカルボニル)オキシ]メチル]-1,1aα,2,8,8aα,8bα-ヘキサヒドロ-1,5-ジメチル-8a-ヒドロキシ-6-メトキシアジリノ[2',3':3,4]ピロロ[1,2-a]インドール-4,7-ジオン (1aS,8R,8aR,8bS)-6-アミノ-8-[[(アミノカルボニル)オキシ]メチル]-1,1a,2,8,8a,8b-ヘキサヒドロ-8a-ヒドロキシ-1,5-ジメチルアジリノ[2',3':3,4]ピロロ[1,2-a]インドール-4,7-ジオン チオりん酸ジメチル=4-ニトロフェニル 2-チオフェンカルボン酸 メチル アジスロマイシン 5-(4,6-ジメトキシ-2-ピリミジニルアミノカルボニルスルファモイル)-1-メチル-1H-ピラゾール-4-カルボン酸エチル クリンダマイシン 2-エチルアジリジン (2S,3E)-2-アミノ-4-(2-アミノエトキシ)-3-ブテン酸·塩酸塩 ポルフィロマイシン 2,5-ジアミノ-p-ベンゾキノン ゲンタミシン

  • 50-07-7
  • Mitomycin C(Ametycine)
  • 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-
  • Mytomycin C
  • [1aR-(1aα,8β,8aα,8bα)]-6-Amino-8-[[(aminocarbonyl)oxy]methyl]-1,1a,2,8,8a,8b-hexahydro-8a-methoxy-5-methylazirino[2',3':3,4]pyrrolo[1,2-α]indole-4,7-dione
  • 6-Amino-1,1a,2,8,8a,8b-hexahydro-8-(hydroxymethyl)-8a-methox-5-methylazirino[2',3':3,4]pyrrolo[1,2-
  • MitonyycinC
  • [1aS-(1aα,8β,8aα,8bα)]-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]indole-4,7-dione
  • 8balpha)]-8aalph
  • ametycine
  • azirino(2’,3’:3,4)pyrrolo(1,2-a)indole-4,7-dione,6-amino-1,1a,2,8,8a,8b-hexahy
  • azirino(2’,3’:3,4)pyrrolo(1,2-a)indole-4,7-dione,6-amino-8-(((aminocarbonyl)oxy
  • azirino[2’,3’:3,4]pyrrolo[1,2-a]indole-4,7-dione,6-amino-8-[[(aminocarbonyl)ox
  • mitomycinum
  • mitomycynac
  • mitomycynac(polish)
  • mytomycin
  • nci-c04706
  • nsc26980
  • nsc-26980
  • rcrawastenumberu010
  • y]methyl]-1,1a,2,8,8a,8b-hexahydro-8a-methoxy-5-methyl-,[1as-(1aalpha,8beta,
  • 6-amino-1,1a,2,8,8a,8b-hexahydro-8-(hydroxymethyl)-8a-methoxy-5-methylazirino[2',3':3,4]pyrrolo[1,2-a]indole-4,7-dione carbamate (ester)
  • AMETYCIN
  • MITOCIN C
  • MITOMYCIN
  • MITOMYCIN C
  • MITOMYCIN C, STREPTOMYCES CAESPITOSUS
  • MMC
  • MUTAMYCIN
  • mitomycin C from streptomyces*caespitosus
  • ミトシンC
  • ムタマイシン
  • ミトマイシンC
  • マイトマイシンC
  • マイトマイシン
  • (1aS,8S,8aR,8bS)-6-アミノ-8-[[(アミノカルボニル)オキシ]メチル]-1,1a,2,8,8a,8b-ヘキサヒドロ-8a-メトキシ-5-メチルアジリノ[2',3':3,4]ピロロ[1,2-a]インドール-4,7-ジオン
  • アメチシン
  • (1aS)-6-アミノ-8β-(アミノカルボニルオキシメチル)-1,1aα,2,8,8aα,8bα-ヘキサヒドロ-8a-メトキシ-5-メチルアジリノ[2',3':3,4]ピロロ[1,2-a]インドール-4,7-ジオン
  • マイトマイシン C
  • マイトマイシンC, ストレプトマイセス由来
  • マイトマイシンC STREPTOMYCES CAESPITOSUS由来
  • マイトマイシンC (JP17)
  • 抗腫瘍抗生物質
  • 昆虫不妊剤
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