5-フルオロシトシン
5-フルオロシトシン · 4-アミノ-5-フルオロ-1,2-ジヒドロピリミジン-2-オン · 4-アミノ-5-フルオロピリミジン-2(1H)-オン · フルオシトシン · 4-アミノ-5-フルオロ-2-ヒドロキシピリミジン · フルシトシン · 5-フルシトシン · アンコチル

識別子と物理属性
| CAS No. | 2022-85-7 |
|---|---|
| 分子式 | C4H4FN3O |
| 平均分子量 | 129.09 g/mol |
| 単同位体質量 | 129.03383997 g/mol |
| SMILES | Nc1[nH]c(=O)ncc1F |
| InChIKey | XRECTZIEBJDKEO-UHFFFAOYSA-N |
| PubChem CID | 3366 |
| ChEMBL | CHEMBL1463 |
| ChEBI | CHEBI:5100 |
| EC No. | 217-968-7 |
| DTXSID | DTXSID3023059 |
| 現地名 | 5-フルオロシトシン |
化学・物理的性質
| XLogP | -0.9 |
|---|---|
| 極性表面積 | 67.5 |
| 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 | 208 |
| 医薬品 | PharmaceuticalsPharmaceuticals -> Listed in ZINC15Pharmaceuticals -> Metabolite of Capecitabine, EmtricitabinePharmaceuticals -> AntibioticsPharmaceuticals -> Anti infectives for systemic use -> Antibacterials for systemic use |
| LogP(分配係数) | -1.1 |
| 臭い | Odorless |
| Color/Form | White crystalline solid |
| 溶解度 | In water, 1.5 g/100 mL at 25 °CSlightly soluble in alcoholpractically insoluble in chloroform, ether1 g in about 12 mL 0.1 N HCL1.92e+00 g/L>19.4 [ug/mL] (The mean of the results at pH 7.4)水に溶けにくく、エタノールに溶けにくい(96%)1.5g/100mL(25℃) |
| Human Drugs | FDA approved drugs -> Active ingredientAntifungal medicines |
| Decomposition | When heated to decomposition it emits very toxic fumes of /floride ions and nitrogen oxides/. |
| 融点 | 295-297 °C (dec)296 °C298-300 °C (dec.) (lit.) |
| Physical Description | Solid |
| Stability/Shelf Life | Stable under recommended storage conditions. |
| Dissociation Constants | 3.26pKa1 = 3.26pKa2 = 10.71 |
| Collision Cross Section | 118.4 Ų [M+H]+ [CCS Type: TWMethod: calibrated with polyalanine and drug standards] |
| 密度 | 1.3990 (estimate) |
| 蒸気圧 | 0Pa at 25℃ |
| 貯蔵条件 | 2-8°C |
| 外観・状態 | 結晶性粉末 |
| pKa(酸解離定数) | 3.26(at 25℃) |
| 色 | 白~ほぼ白 |
| Merck | 14,4125 |
| BRN | 127285 |
| BCS Class | 1 |
| 安定性 | 光に敏感 |
| InChI | 1S/C4H4FN3O/c5-2-1-7-4(9)8-3(2)6/h1H,(H3,6,7,8,9) |
| InChIKey | XRECTZIEBJDKEO-UHFFFAOYSA-N |
| SMILES | NC1=NC(=O)NC=C1F |
| LogP(分配係数) | -1.36 at 22.1℃ and pH6.4-6.9 |
| CAS データベース | 2022-85-7(CAS DataBase Reference) |
化学的特性
White Crystalline Solid
安全性と法規制
| GHS 分類 | This chemical does not meet GHS hazard criteria for 5.9% (4 of 68) of reports.WarningH361 (83.8%): Suspected of damaging fertility or the unborn child [Warning Reproductive toxicity]P203, P280, P318, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 68 reports by companies from 12 notifications to the ECHA C&L Inventory. |
|---|---|
| 規制情報 | Status: Active Update: 08-04-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/19073 |
| FDA 要件 | The Approved Drug Products with Therapeutic Equivalence Evaluations identifies currently marketed prescription drug products, including flucytosine, approved on the basis of safety and effectiveness by FDA under sections 505 of the Federal Food, Drug, and Cosmetic Act. |
| Toxic Combustion Products | Special hazards arising from the substance or mixture: Carbon oxides, nitrogen oxides (NOx), Hydrogen fluoride. |
| Hazard Classes and Categories | Repr. 2 (83.8%) |
| Hazardous Reactivities and Incompatibilities | Incompatible materials: Strong oxidizing agents. |
| 消火手順 | Suitable extinguishing media: Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.Advice for firefighters: Wear self contained breathing apparatus for fire fighting if necessary. |
| 保管条件 | Keep container tightly closed in a dry and well-ventilated place. Light sensitive. Keep in a dry place.Store at 25 °C (77 °F)excursions permitted between 15 deg - 30 °C (59 deg - 86 °F). |
| 清掃方法 | ACCIDENTAL RELEASE MEASURES: Personal precautions, protective equipment and emergency procedures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapors, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. Environmental precautions: Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Methods and materials for containment and cleaning up: Pick up and arrange disposal without creating dust. Sweep up and shovel. Keep in suitable, closed containers for disposal. |
用途
用途
フルシトシンは5-フルオロシトシン(5-FC)とも知られる抗真菌薬である。具体的にはアムホテリシンBと併用され、重度のカンジダ 感染症とクリプトコッカス症の治療に用いられる。単体またはその他の抗真菌薬と併用し黒色分芽菌症の治療に使用されることもある。フルシトシンの投与法は経口または静脈点滴である。 フルシトシンはフッ素化ピリミジンアナログに属する医薬品である。その作用は真菌細胞内でフルオロウラシルとなり、真菌のタンパク質合成を阻害することにより効果がある。
用途
フルシトシンは5-フルオロシトシン(5-FC)とも知られる抗真菌薬である。具体的にはアムホテリシンBと併用され、重度のカンジダ 感染症とクリプトコッカス症の治療に用いられる[1]。単体またはその他の抗真菌薬と併用し黒色分芽菌症の治療に使用されることもある。 フルシトシンはフッ素化ピリミジンアナログに属する医薬品である。その作用は真菌細胞内でフルオロウラシルとなり、真菌のタンパク質合成を阻害することにより効果がある。
説明
5-Fluorocytosine (5-FC), a fluorinated pyrimidine analog, is a synthetic antimycotic prodrug that is converted by cytosine deaminase to 5-fluorouracil. 5-Fluorouracil, a widely used cytotoxic drug, is further metabolized to fluorinated ribo- and deoxyribonucleotides, resulting in the inhibition of DNA and protein synthesis, which has multiple effects including inhibition of Candida species and C. neoformans infections and cytotoxicity towards cancer cells. In combination with a retroviral replicating vector carrying a cytosine deaminase prodrug-activating gene, 5-FC has been shown to selectively eliminate CT26 and Tu-2449 tumor cells in vitro (IC50s = 4.2 and 1.5 μM, respectively) and to significantly improve survival and reduce tumor size (at a dose of 500 mg/kg) in two different syngeneic mouse glioma models.
使用
5-Fluorocytosine acts as an antidiabetic, antifungal and antimicrobial agent. It is useful for the treatment of serious infections arises due to susceptible strains of Candida or Cryptococcus neoformans and chromomycosis. Further, it is employed in studies on TMP biosynthesis.