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5-Fluor-2'-desoxyuridin
FUDR · FDUR · 5-FLUORODEOXYURIDINE · 5-FUDR · 5-Fluoro-1-((2R,4S,5R)-4-hydroxy-5-(hydroxyMethyl)tetrahydrofuran-2-yl)pyriMidine-2,4(1H,3H)-dione · 5-FLUORO-2-DEOXYURIDINE · 2'-Deoxy-5-fluorouridine · FUD
Identifikatoren & physikalische Daten
| CAS No. | 50-91-9 |
|---|---|
| Summenformel | C9H11FN2O5 |
| Durchschnittliche Molmasse | 246,19 g/mol |
| Monoisotopische Masse | 246,06519967 g/mol |
| SMILES | O=c1[nH]c(=O)n([C@H]2C[C@H](O)[C@@H](CO)O2)cc1F |
| InChIKey | ODKNJVUHOIMIIZ-RRKCRQDMSA-N |
| PubChem CID | 5790 |
| ChEMBL | CHEMBL917 |
| ChEBI | CHEBI:60761 |
| EC No. | 200-072-5 |
| DTXSID | DTXSID3023057 |
| Lokaler Name | 5-Fluor-2'-desoxyuridin |
Chemische & physikalische Eigenschaften
| XLogP | -1,2 |
|---|---|
| Polarare Oberfläche (TPSA) | 99,1 |
| H-Brücken-Donoren | 3 |
| H-Brücken-Akzeptoren | 6 |
| Frei drehbare Bindungen | 2 |
| Schwere Atome | 17 |
| Formalladung | 0 |
| Komplexität | 386 |
| Arzneimittel | Pharmaceuticals -> Anti infectives for systemic use -> Antivirals for systemic usePharmaceuticals -> Listed in ZINC15 |
| LogP (Verteilungskoeffizient) | log Kow = -1.16-1.4 |
| Geruch | ODORLESS |
| Color/Form | Crystals from butyl acetateWHITE TO OFF-WHITE SOLID |
| Löslichkeit | 1 g in about 4.5 ml isopropanol, about 7.5 ml methanol, about 12 ml alcohol, about 27 ml acetoneinsol in chloroform, ether, and benzene4.08e+01 g/LSoluble to 100 mM in water and to 100 mM in DMSO |
| Human Drugs | FDA approved drugs -> Active ingredient |
| Decomposition | When heated to decomposition it emits very toxic fumes of /hydrogen fluoride and nitrogen oxides/. |
| Schmelzpunkt | 302 to 304 °F (NTP, 1992)150-151 °C150.5 °C148 °C(lit.) |
| Optical Rotation | Crystals from butyl acetate, mp 150-151 °C. Specific optical rotation at 25 °C for D (sodium) line = -21 deg (c = 2 in water) /alpha-Anomer/Specific optical rotation for D (sodium) line = +37 deg (water)+48.6 deg (DMF) |
| Physical Description | Inhibits DNA synthesis. (NTP, 1992)Solid |
| Dissociation Constants | 7.44pKa = 7.44 (imide nitrogen) |
| Siedepunkt | 150 °C |
| Dichte | 1.3751 (estimate) |
| Lagerbedingungen | room temp |
| pKa (Säurekonstante) | pKa 7.44 (Uncertain) |
| Aggregatzustand | Powder |
| Farbe | White to almost white |
| Biologische Quelle | synthetic (organic) |
| Merck | 14,4112 |
| BRN | 2645818 |
| Stabilität | Stable. Incompatible with strong oxidizing agents. |
| Hauptanwendungen | pharmaceutical small molecule |
| InChI | 1S/C9H11FN2O5/c10-4-2-12(9(16)11-8(4)15)7-1-5(14)6(3-13)17-7/h2,5-7,13-14H,1,3H2,(H,11,15,16)/t5-,6+,7+/m0/s1 |
| InChIKey | ODKNJVUHOIMIIZ-GFCOJPQKSA-N |
| SMILES | OC[C@H]1O[C@H](C[C@@H]1O)N2C=C(F)C(=O)NC2=O |
| CAS Datenbank | 50-91-9(CAS DataBase Reference) |
| NIST chemische Informationen | Uridine, 2'-deoxy-5-fluoro-(50-91-9) |
| EPA chemische Informationen | Floxuridine (50-91-9) |
Sicherheit & Vorschriften
| GHS-Einstufung | DangerH301 (96.1%): Toxic if swallowed [Danger Acute toxicity, oral]P203, P264, P270, P280, P301+P316, P318, P321, P330, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 51 reports by companies from 7 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| Regulatorische Informationen | Floxuridine: Does not have an individual approval but may be used under an appropriate group standard |
| DOT-Kennzeichnung | Corrosive |
| Brandgefahren | Flash point data for this chemical are not available, but it is probably combustible. (NTP, 1992) |
| Gesundheitsgefahren | ACUTE/CHRONIC HAZARDS: This material is highly toxic by ingestion. (NTP, 1992) |
| FDA-Anforderungen | The Approved Drug Products with Therapeutic Equivalence Evaluations List identifies currently marketed prescription drug products, incl floxuridine, approved on the basis of safety and effectiveness by FDA under sections 505 of the Federal Food, Drug, and Cosmetic Act. |
| Reaktive Gruppe | Alcohols and Polyols |
| Air and Water Reactions | No rapid reaction with air. No rapid reaction with water. |
| Hazard Classes and Categories | Acute Tox. 3 (96.1%) |
| Brandbekämpfung | Fires involving this compound should be controlled with a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992) |
| Erste Hilfe | EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop. |
| Lagerbedingungen | Floxuridine sterile powder should be protected from light and stored at 15-30 °C. In the dry state, floxuridine has an expiration date of 3 years following the date of manufacture. Reconstituted floxuridine injection should be stored at 2-8 °C and used within 2 weeks. |
Anwendungen & Verwendung
Verwenden
Floxuridine USP is used in Palliative treatment of gastrointestinal adenocarcinoma with liver metastases.