5-フルオロウラシル

5-フルオロウラシル 化学構造式
51-21-8
CAS番号.
51-21-8
化学名:
5-フルオロウラシル
别名:
5-フルオロウラシル;ルナコールDS;5-フルオロピリミジン-2,4-ジオール;フルラシル;5-フルオロ-1,2,3,4-テトラヒドロピリミジン-2,4-ジオン;フルオロプレックス;フルリル;ルナポン;カルゾナール;フラシル;フルオロプレクス;フルオロウラシル;アドルシル;エフデックス;5-フルオロピリミジン-2,4(1H,3H)-ジオン;5-フルオロ-2,4(1H,3H)-ピリミジンジオン;5-フルロウラシル;5フルオロウラシル;5-フルオルウラシル;5‐フルオロウラシル
英語名:
5-Fluorouracil
英語别名:
51-21-8;5-FU;FLUOROURACIL;5-FLUOROPYRIMIDINE-2,4(1H,3H)-DIONE;FU;Efudex;Efudix;Adrucil;Fluracil;Fluoracil
CBNumber:
CB8162744
化学式:
C4H3FN2O2
分子量:
130.08
MOL File:
51-21-8.mol
MSDS File:
SDS

5-フルオロウラシル 物理性質

融点 :
282-286 °C (dec.) (lit.)
沸点 :
190-200°C/0.1mmHg
比重(密度) :
1.4593 (estimate)
貯蔵温度 :
2-8°C
溶解性:
H2O: 10 mg/mL、透明
外見 :
酸解離定数(Pka):
pKa 8.0±0.1 (H2O) (Uncertain);3.0±0.1(H2O) (Uncertain)
色:
白い
PH:
4.3-5.3 (10g/l, H2O, 20℃)
水溶解度 :
12.2g/L 20℃
Sensitive :
Air Sensitive
Merck :
14,4181
BRN :
127172
安定性::
安定。光に敏感。可燃性。強酸化剤、強塩基とは相容れない。
InChIKey:
GHASVSINZRGABV-UHFFFAOYSA-N
CAS データベース:
51-21-8(CAS DataBase Reference)
IARC:
3 (Vol. 26, Sup 7) 1987
NISTの化学物質情報:
2,4-Pyrimidinedione, 5-fluoro-(51-21-8)
EPAの化学物質情報:
5-Fluorouracil (51-21-8)
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  Xn,T,C,Xi
Rフレーズ  22-20/21/22-52-25
Sフレーズ  36-36/37-36/37/39-22-45-26
RIDADR  UN 2811 6.1/PG 3
WGK Germany  3
RTECS 番号 YR0350000
10-23
Hazard Note  Irritant/Highly Toxic
TSCA  T
国連危険物分類  6.1
容器等級  III
HSコード  29335995
有毒物質データの 51-21-8(Hazardous Substances Data)
毒性 LD50 orally in Rabbit: 230 mg/kg
化審法 (9)-1180
絵表示(GHS) GHS hazard pictogramsGHS hazard pictograms
注意喚起語 危険
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
H301 飲み込むと有毒 急性毒性、経口 3 危険 GHS hazard pictograms 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。
P202 全ての安全注意を読み理解するまで取り扱わないこ と。
P264 取扱い後は皮膚をよく洗うこと。
P264 取扱い後は手や顔をよく洗うこと。
P270 この製品を使用する時に、飲食または喫煙をしないこ と。
P280 保護手袋/保護衣/保護眼鏡/保護面を着用するこ と。
P301+P310 飲み込んだ場合:直ちに医師に連絡すること。

5-フルオロウラシル 価格 もっと(31)

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) W01W0106-0140 5-フルオロウラシル 98.5+% (HPLC)
5-Fluorouracil 98.5+% (HPLC)
51-21-8 5g ¥5300 2024-03-01 購入
富士フイルム和光純薬株式会社(wako) W01LKTF4480 5-フルオロウラシル
5-Fluorouracil
51-21-8 5g ¥22100 2024-03-01 購入
東京化成工業 F0151 5-フルオロウラシル >99.0%(HPLC)(T)
5-Fluorouracil >99.0%(HPLC)(T)
51-21-8 5g ¥3500 2024-03-01 購入
東京化成工業 F0151 5-フルオロウラシル >99.0%(HPLC)(T)
5-Fluorouracil >99.0%(HPLC)(T)
51-21-8 25g ¥10400 2024-03-01 購入
関東化学株式会社(KANTO) 22844-2A 5‐フルロウラシル 99%
5‐Fluorouracil 99%
51-21-8 5g ¥11300 2024-03-01 購入

5-フルオロウラシル MSDS


5-Fluoropyrimidine-2,4-dione

5-フルオロウラシル 化学特性,用途語,生産方法

外観

白色, 結晶~粉末

溶解性

ジメチルホルムアミドに溶けやすく、水にやや溶けにくく、エタノールに溶けにくく、アセトンにほとんど溶けない。

解説

フルオロウラシル,化学式はC4II3FN2O2,核酸塩基ウラシルの5位の水素をフッ素原子で置換した誘導体で,代表的な抗癌剤の一つ。ウラシルをフッ素化すると得られる.白色の結晶.分解点280~282 ℃.λmax 265~266 nm(ε 7070,pH 1.0).水に難溶,DMFに易溶.抗悪性腫瘍剤で,消化器がん,乳がん治療薬として使用される.LD50 226 mg/kg(マウス,経口).融点約280℃。水に微溶,エタノールに難溶。腫瘍細胞内でDNA合成を妨げて増殖を阻止,またRNAに取り込まれて異常タンパク質を合成させ,細胞を死亡させる。乳癌や消化器癌などに用いられる。

用途

抗癌剤研究用。

用途

人間と動物医療域の抗腫瘍剤(乳房と消化管)

用途

チミジル酸シンターゼを阻害 することにより DNA 合成阻害作用を示しま す

用途

チミジル酸シンターゼを阻害 することにより DNA 合成阻害作用を示しま す。

効能

抗悪性腫瘍薬, 代謝拮抗薬

商品名

5−FU (協和発酵キリン); 5−FU (協和発酵キリン); 5−FU (協和発酵キリン)

説明

5-Fluorouracil (5-FU) is a prodrug form of the thymidylate synthase inhibitor fluorodeoxyuridylate (FdUMP). It is also converted to the active metabolites FUTP and FdUTP, which induce RNA and DNA damage, respectively. In vivo, 5-FU (15 mg/kg) when administered in combination with docetaxel reduces tumor growth in B88 and CAL 27 oral squamous cell carcinoma (OSCC) mouse xenograft models. Formulations containing 5-FU have been used in the treatment of colorectal, breast, gastric, and pancreatic cancers.

化学的特性

White or almost white, crystalline powder

使用

5-Fluorouracil is used as an antitumor agent in the treatment of anal, breast, colorectal, oesophageal, stomach, pancreatic and skin cancers. It finds application as a suicide inhibitor due to its irreversible inhibition of thymidylate synthase. It is also used in the treatment of actinic keratoses and bowen's disease. Further, it serves as a potent antineoplastic agent in clinical use. In addition to this, it acts as a DNA synthesis inhibitor.

適応症

Fluorouracil (5-fluorouracil, 5-fluorouracil, Efudex, Adrucil) is a halogenated pyrimidine analogue that must be activated metabolically. The active metabolite that inhibits DNA synthesis is the deoxyribonucleotide 5-fluoro-2'deoxyuridine-S'-phosphate (FdUMP). 5- Fluorouracil is selectively toxic to proliferating rather than non-proliferating cells and is active in both the G1- and S-phases. The target enzyme inhibited by 5-fluorouracilfluorouracil is thymidylate synthetase.
methylenetetrahydrofolate dihydrofolate The carbon-donating cofactor for this reaction is N5,N10 methylenetetrahydrofolate, which is converted to dihydrofolate. The reduced folate cofactor occupies an allosteric site on thymidylate synthetase, which allows for the covalent binding of 5-FdUMP to the active site of the enzyme.

一般的な説明

White to nearly white crystalline powder; practically odorless. Used as an anti neoplastic drug, chemosterilant for insects.

空気と水の反応

Insoluble in water.

反応プロフィール

5-Fluorouracil may be sensitive to prolonged exposure to light. Solutions discolor on storage. 5-Fluorouracil can react with oxidizing agents and strong bases. Incompatible with methotrexate sodium.

危険性

Questionable carcinogen.

健康ハザード

Minimum toxic dose in humans is approximately 450 mg/kg (total dose) over 30 days for the ingested drug. Intravenous minimum toxic dose in humans is a total dose of 6 mg/kg over three days. Depression of white blood cells occurred after intravenous administrative of a total dose of 480 mg/kg over 32 days. Occasional neuropathy and cardiac toxicity have been reported. Do not use during pregnancy. Patients with impaired hepatic or renal function, with a history of high-dose pelvic irradiation or previous use of alkylating agents should be treated with extreme caution. Patients with nutritional deficiencies and protein depletion have a reduced tolerance to 5-Fluorouracil.

火災危険

Emits very toxic fumes of flourides and nitrogen oxides when heated to decomposition. Avoid decomposing heat.

生物活性

Anticancer agent. Metabolized to form fluorodeoxyuridine monophosphate (FdUMP), fluorodeoxyuridine triphosphate (FdUTP) and fluorouridine (FUTP). FdUMP inhibits thymidylate reductase causing a reduction in dTMP synthesis. FUTP and FdUTP are misincorporated into RNA and DNA respectively.

作用機序

Another action proposed for 5-fluorouracil may involve the incorporation of the nucleotide 5-fluorouridine triphosphate (5-FUTP) into RNA. The cytotoxic role of these “fraudulent” 5-fluorouracil-containing RNAs is not well understood.
Several possible mechanisms of resistance to 5-fluorouracil have been identified, including increased synthesis of the target enzyme, altered affinity of thymidylate synthetase for FdUMP, depletion of enzymes (especially uridine kinase) that activate 5-fluorouracil to nucleotides, an increase in the pool of the normal metabolite deoxyuridylic acid (dUMP), and an increase in the rate of catabolism of 5-fluorouracil.
The drug has been administered orally, but absorption by this route is erratic. The plasma half-life of 5- fluorouracil after intravenous injection is 10 to 20 minutes. It readily enters CSF. Less than 20% of the parent compound is excreted into the urine, the rest being largely metabolized in the liver.

薬理学

Local inflammatory reactions characterized by erythema, edema, crusting, burning, and pain are common (and, some would argue, desirable) but may be minimized by reduced frequency of application or use in combination with a topical corticosteroid.

臨床応用

5-Fluorouracil (FU) is widely used in the treatment of a range of cancers including breast and cancers of the aerodigestive tract, but has had the greatest impact in colorectal cancer. 5-FU-based chemotherapy improves overall and disease-free survival of patients with resected stage III colorectal cancer. Nonetheless, response rates for 5-FU-based chemotherapy as a first-line treatment for advanced colorectal cancer are only between 10 and 15%. Combination of 5-FU with newer chemotherapies, such as irinotecan and oxaliplatin, has improved the response rates for advanced colorectal cancer to between 40 and 50%.

副作用

Patients who are genetically deficient in this enzyme will experience a more pronounced effect from this drug and are at significant risk for use-limiting toxicity. In general, women clear fluorouracil faster than men do. Dosage adjustments usually are not required in hepatic or renal dysfunction. Major toxicities are related to bone marrow depression, stomatitis/esophagopharyngitis, and potential GI ulceration. Nausea and vomiting are common. Solutions of fluorouracil are light sensitive, but discolored products that have been properly stored and protected from light are still safe to use.

安全性プロファイル

Poison by ingestion, intraperitoneal, subcutaneous, and intravenous routes. Moderately toxic by parented and rectal routes. Experimental teratogenic and reproductive effects. Human systemic effects: EKG changes, bone marrow changes, cardiac, pulmonary, and gastrointestinal effects. Human mutation data reported. A human skin irritant. Questionable carcinogen. When heated to decomposition it emits very toxic fumes of Fand NOx.

職業ばく露

This material is used as an antineo plastic drug for cancer treatment and as a chemosterilant for insects.

輸送方法

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

不和合性

Incompatible with oxidizers (chlorates, nitrates, peroxides, permanganates, perchlorates, chlorine, bromine, fluorine, etc.); contact may cause fires or explo sions. Keep away from alkaline materials, strong bases, strong acids, oxoacids, epoxides, methotrexrate sodium, sources of heat.

5-フルオロウラシル 上流と下流の製品情報

原材料

準備製品


5-フルオロウラシル 生産企業

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51-21-8(5-フルオロウラシル)キーワード:


  • 51-21-8
  • 2,4(1H,3H)-Pyrimidinedione, 5-fluoro-
  • 2,4-dioxo-5-fluoropyrimidine
  • 3h)-pyrimidinedione,5-fluoro-4(1h
  • 5-faracil
  • fluoro-uracile
  • fluoro-uracilo
  • fluorouracilum
  • Fluracilum
  • Fluri
  • Fluril
  • fluroblastin
  • flurouracil
  • Ftoruracil
  • Kecimeton
  • NSC 19893
  • nsc19893
  • 1-FLUORO-1H-PYRIMIDINE-2,4-DIONE
  • 2,4-DIHYDROXY-5-FLUOROPYRIMIDINE
  • 5-Fluoro-2,4-(1H,3H)-pyrimidindion
  • Fluorouracil ,5-FU
  • FLUOROURACIL USP
  • 5-Fluorouracilgmpusp27
  • 5-FluorouracilGmp
  • 5-FluoroUracilExtraPure
  • 2,4(1H,3H)-Pyrimidinedione, 5-fluoro- (9CI)
  • 5-Fluorouracil,99%
  • 5-Fluorouracil (technical)
  • 5-FLUOROURACIL(FDA)
  • 5-Fluoropyrimidine-2,4(1H,3H)-dione, 2,4-Dioxo-5-fluoro-1,2,3,4-tetrahydropyrimidine
  • 5-Fluorouracil (2,4-dioxo-5-FluoropyriMidine)(5-FU)
  • 5-フルオロウラシル
  • ルナコールDS
  • 5-フルオロピリミジン-2,4-ジオール
  • フルラシル
  • 5-フルオロ-1,2,3,4-テトラヒドロピリミジン-2,4-ジオン
  • フルオロプレックス
  • フルリル
  • ルナポン
  • カルゾナール
  • フラシル
  • フルオロプレクス
  • フルオロウラシル
  • アドルシル
  • エフデックス
  • 5-フルオロピリミジン-2,4(1H,3H)-ジオン
  • 5-フルオロ-2,4(1H,3H)-ピリミジンジオン
  • 5-フルロウラシル
  • 5フルオロウラシル
  • 5-フルオルウラシル
  • 5‐フルオロウラシル
  • 5‐フルロウラシル
  • 2,4-ジヒドロキシ-5-フルオロピリミジン
  • 5-フルオロウラシル
  • フルオロウラシル (JP17)
  • ヌクレオシド,ヌクレオチド&関連試薬
  • フッ素化剤,含フッ素ビルディングブロック&含フッ素生理活性化合物
  • 含フッ素生理活性化合物
  • 核酸塩基と類似体
  • 生化学
  • 試験研究用抗腫瘍剤
  • 薬理研究用試薬
  • 有機合成化学
  • ピリミジン塩基
  • 抗腫瘍代謝拮抗物質
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