5-フルオロウラシル
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
識別子と物理属性
| CAS No. | 51-21-8 |
|---|---|
| 分子式 | C4H3FN2O2 |
| 平均分子量 | 130.08 g/mol |
| 単同位体質量 | 130.01785556 g/mol |
| SMILES | O=c1[nH]cc(F)c(=O)[nH]1 |
| InChIKey | GHASVSINZRGABV-UHFFFAOYSA-N |
| PubChem CID | 3385 |
| ChEMBL | CHEMBL185 |
| ChEBI | CHEBI:46345 |
| EC No. | 200-085-6 |
| DTXSID | DTXSID2020634 |
| 現地名 | 5-フルオロウラシル |
化学・物理的性質
| XLogP | -0.9 |
|---|---|
| 極性表面積 | 58.2 |
| 水素結合供与体数 | 2 |
| 水素結合受容体数 | 3 |
| 回転可能結合数 | 0 |
| 重原子数 | 9 |
| 形式電荷 | 0 |
| 複雑度 | 199 |
| 物質分類 | Teratogens |
| 医薬品 | PharmaceuticalsPharmaceuticals -> Antineoplastic and immunomodulating agents -> Antineoplastic agentsPharmaceuticals -> Listed in ZINC15Pharmaceuticals -> Used in SwitzerlandPharmaceuticals -> Metabolite of Capecitabine |
| SpringerMaterials Properties | 19F nuclear magnetic resonance spectrum |
| LogP（分配係数） | log Kow = -0.89 |
| 臭い | PRACTICALLY ODORLESS |
| Color/Form | White to practically white crystalline powderCrystals from water or methanol-ether |
| 溶解度 | less than 1 mg/mL at 66 °F (NTP, 1992)1 G IN 80 ML WATER, 170 ML ALCOHOL & 55 ML METHANOLPRACTICALLY INSOL IN CHLOROFORM, ETHER & BENZENESOLUBILITY IN AQ SOLN INCR WITH INCR PH OF SOLNSoluble in methanol-water mixturesSparingly soluble in water and slightly soluble in alcohol. 1 g is soluble in 100 ml of propylene glycol.In water, 1.11X10+4 mg/L at 22 °CH2O: 10 mg/mL、透明12.2g/L 20℃ |
| Human Drugs | Breast FeedingLactationMilk, HumanAntimetabolitesAntineoplastic AgentsAntimetabolites, AntineoplasticImmunosuppressive AgentsFDA approved drugs -> Active ingredientCytotoxic medicines |
| 沸点 | Decomposes at 282-283 °Csublimes (0.1 mm): 190-200 °C361 °C @760 [mm Hg]190-200°C/0.1mmHg |
| Decomposition | When heated to decomposition it emits very toxic fumes of /hydrogen fluoride and nitrogen oxides/. |
| 融点 | Decomposes at 540-541 °F (EPA, 1998)282-283282 °C (decomposes)280 - 282 °C282-286 °C (dec.) (lit.) |
| 蒸気圧 | 0.00001 [mm Hg] @25 °C |
| 密度 | 1.4593 (estimate) |
| 貯蔵条件 | 2-8°C |
| 外観・状態 | 粉 |
| pKa（酸解離定数） | 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℃) |
| Merck | 14,4181 |
| BRN | 127172 |
| ヘンリー定数 | 5.8×104 mol/(m3Pa) at 25℃, HSDB (2015) |
| 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。 |
| 主な用途 | 診断アッセイの製造血液学組織学 |
| InChI | 1S/C4H3FN2O2/c5-2-1-6-4(9)7-3(2)8/h1H,(H2,6,7,8,9) |
| InChIKey | GHASVSINZRGABV-UHFFFAOYSA-N |
| SMILES | FC1=CNC(=O)NC1=O |
| CAS データベース | 51-21-8(CAS DataBase Reference) |
| 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) |
化学的特性
White or almost white, crystalline powder
安全性と法規制
| GHS 分類 | This chemical does not meet GHS hazard criteria for 32.2% (55 of 171) of reports.DangerH301 (66.7%): Toxic if swallowed [Danger Acute toxicity, oral]P203, P261, P264, P264+P265, P270, P271, P273, P280, P301+P316, P302+P352, P304+P340, P305+P351+P338, P317, P318, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 171 reports by companies from 21 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| 規制情報 | Hazard Traits - Developmental ToxicityStatus: Active Update: 29-05-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/108555-Fluorouracil: Does not have an individual approval but may be used under an appropriate group standardThe New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.) |
| その他の安全情報 | IMAP assessments - 2,4(1H,3H)-Pyrimidinedione, 5-fluoro-: Human health tier I assessment |
| 火災危険 | Emits very toxic fumes of flourides and nitrogen oxides when heated to decomposition. Avoid decomposing heat. (EPA, 1998) |
| 健康有害性 | 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 fluorouracil. (EPA, 1998) |
| FDA 要件 | The Approved Drug Products with Therapeutic Equivalence Evaluations List identifies currently marketed prescription drug products, incl fluorouracil, approved on the basis of safety and effectiveness by FDA under sections 505 of the Federal Food, Drug, and Cosmetic Act. |
| 反応性グループ | Amides and Imides |
用途
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
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。
用途
抗癌剤研究用。
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.
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.
一般的な説明
White to nearly white crystalline powder; practically odorless. Used as an anti neoplastic drug, chemosterilant for insects.