CAS Number3094-09-5
Synonyms5-Fluorodesoxyuridine; RO-21-9738; EINECS 221-440-1; doxifluridine; 5'DFURD; Flutron; Furtulon; 1-(5-Deoxy-β-D-ribofuranosyl)-5-fluorouracil; 5'-DFUR; doxyfluridine; 1-(b-D-5'-Deoxyribofuranosyl)-5-fluorouracil; 5-Fluoro-5'-deoxyuridine; 5'-Deoxy-5-fluorouridine; MFCD00866530; 5'-dFUrd; 5'-DEOXYFLUOROURIDINE; (+)-5-Fluoro-5'-deoxyuridine; Doxifluidine; DOXIFLUIRDINE
Molecular FormulaC9H11FN2O5
Molecular Weight246.19
Purity98%
Density1.6±0.1 g/cm3
Melting Point188-192 °C(lit.)
Appearancewhite solid
EINECS221-440-1
Symbol
Signal WordWarning
| Chemical & Physical Properties | |
|---|---|
| CAS Number | 3094-09-5 |
| Catalog No. | 2A-9006500 |
| Chinese Name | 去氧氟尿苷 |
| Synonyms | 5-Fluorodesoxyuridine; RO-21-9738; EINECS 221-440-1; doxifluridine; 5'DFURD; Flutron; Furtulon; 1-(5-Deoxy-β-D-ribofuranosyl)-5-fluorouracil; 5'-DFUR; doxyfluridine; 1-(b-D-5'-Deoxyribofuranosyl)-5-fluorouracil; 5-Fluoro-5'-deoxyuridine; 5'-Deoxy-5-fluorouridine; MFCD00866530; 5'-dFUrd; 5'-DEOXYFLUOROURIDINE; (+)-5-Fluoro-5'-deoxyuridine; Doxifluidine; DOXIFLUIRDINE |
| Molecular Formula | C9H11FN2O5 |
| Molecular Weight | 246.19 |
| Purity | 98 |
| Density | 1.6±0.1 g/cm3 |
| Melting Point | 188-192 °C(lit.) |
| Appearance | white solid |
| Storage Condition | Sealed in a cool, dry environment |
| Application | Doxifluridine is an activator of thymidine phosphorylase, with an IC50 of 0.62 μM on PC9-DPE2 cells. |
| EINECS | 221-440-1 |
| HTC | 2934999090 |
| PubChem ID | 24278444 |
| MDL Number | MFCD00866530 |
| SMILES | C[C@H]1O[C@H]([C@H](O)[C@@H]1O)N2C=C(F)C(=O)NC2=O |
| InChI | 1S/C9H11FN2O5/c1-3-5(13)6(14)8(17-3)12-2-4(10)7(15)11-9(12)16/h2-3,5-6,8,13-14H,1H3,(H,11,15,16)/t3-,5-,6-,8-/m1/s1 |
| InChI Key | ZWAOHEXOSAUJHY-ZIYNGMLESA-N |
| NACRES Code | NA.77 |
| UNSPSC | 12352200 |
| Hazard Symbols | Transport |
| MSDS | msds/6500_1_3094_09_5.pdf |
| Bioactivity | Doxifluridine(Ro 21-9738; 5'-DFUR) is a thymidine phosphorylase activator for PC9-DPE2 cells with IC50 of 0.62 μM. IC50 value: 0.62 μM(PC9-DPE2 cell).Target: Nucleoside antimetabolite/analogDoxifluridine is a fluoropyrimidine derivative and oral prodrug of the antineoplastic agent 5-fluorouracil (5-FU) with antitumor activity. Doxifluridine, designed to circumvent the rapid degradation of 5-FU by dihydropyrimidine dehydrogenase in the gut wall, is converted into 5-FU in the presence of pyrimidine nucleoside phosphorylase. 5-FU interferes with DNA synthesis and subsequent cell division by reducing normal thymidine production and interferes with RNA transcription by competing with uridine triphosphate for incorporation into the RNA strand.in vitro: 5'-DFUR's metabolic product(N3-Me-5'-dFUR) was found to be non-toxic in all the cell growth experiments performed. The absence of cytotoxicity could be explained by the observation that the metabolite was not recognized as a substrate by thymidine phosphorilase, the enzyme responsible for 5-fluorouracil (5-FU) release from doxifluridine, as ascertained by high-performance liquid chromatography/ultraviolet (HPLC-UV) analysis of the incubation mixture[1].in vivo: Administration of 200 mg of Furtulon to 23 beagle dogs, the plasma concentrations of doxifluridine, 5-FU, and 5-FUrd were measured simultaneously, using LC-MS/MS. The parent-metabolite compartment model with first-order absorption and Michaelis-Menten kinetics described the pharmacokinetics of doxifluridine, 5-FU, and 5-FUrd. Michaelis-Menten kinetics sufficiently explained the generation and elimination processes of 5-FU and 5-FUrd[2].Clinical trial: A phase II study of doxifluridine and docetaxel combination chemotherapy for advanced or recurrent gastric cancer was reported in 2009[3]. Related Catalog Signaling Pathways >> Cell Cycle/DNA Damage >> Nucleoside Antimetabolite/Analog Research Areas >> Cancer References [1]. Dipartimento di Chimica, Università degli Studi della Basilicata, Potenza, In vitro toxicity of N3-methyl-5'-deoxy-5-fluorouridine, a novel metabolite of doxifluridine: a bioanalytical investigation. J Pharm Biomed Anal. 1998 May;17(1):11-6. [2]. Baek IH, Lee BY, Kim MS, Pharmacokinetic analysis of doxifluridine and its metabolites, 5-fluorouracil and 5-fluorouridine, after oral administration in beagle dogs. Eur J Drug Metab Pharmacokinet. 2013 Apr 7. [3]. Yoshikawa T, Tsuburaya A, Shimada K, A phase II study of doxifluridine and docetaxel combination chemotherapy for advanced or recurrent gastric cancer. Gastric Cancer. 2009;12(4):212-8. Chemical & Physical Properties Density 1.6±0.1 g/cm3 Melting Point 188-192 °C(lit.) Molecular Formula C9H11FN2O5 Molecular Weight 246.192 Exact Mass 246.065201 PSA 104.55000 LogP -0.96 Index of Refraction 1.605 InChIKey ZWAOHEXOSAUJHY-SAAKZLLZSA-N SMILES CC1OC(n2cc(F)c(=O)[nH]c2=O)C(O)C1O Storage condition -20°C Freezer |
| Use of | Properties Articles33 Name doxifluridine Synonym More Synonyms Doxifluridine Biological Activity Related Catalog Signaling Pathways >> Cell Cycle/DNA Damage >> Nucleoside Antimetabolite/Analog Research Areas >> Cancer References [1]. Dipartimento di Chimica, Università degli Studi della Basilicata, Potenza, In vitro toxicity of N3-methyl-5'-deoxy-5-fluorouridine, a novel metabolite of doxifluridine: a bioanalytical investigation. J Pharm Biomed Anal. 1998 May;17(1):11-6. [2]. Baek IH, Lee BY, Kim MS, Pharmacokinetic analysis of doxifluridine and its metabolites, 5-fluorouracil and 5-fluorouridine, after oral administration in beagle dogs. Eur J Drug Metab Pharmacokinet. 2013 Apr 7. [3]. Yoshikawa T, Tsuburaya A, Shimada K, A phase II study of doxifluridine and docetaxel combination chemotherapy for advanced or recurrent gastric cancer. Gastric Cancer. 2009;12(4):212-8. Chemical & Physical Properties Molecular Formula C9H11FN2O5 Exact Mass 246.065201 PSA 104.55000 LogP -0.96 Index of Refraction 1.605 InChIKey ZWAOHEXOSAUJHY-SAAKZLLZSA-N |
| Tax Rebate | 13.0% |
| Supervision | None. MFN tariff: 6.5%. Ordinary tariff: 20.0% |
| Transport Info | Product name: Purity: 98.0% |
| MSDS Transport Info | Module 14. Shipping information 14.1 UN dangerous goods number European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.2 Names specified by the United Nations (UN) European Land Transport Dangerous Regulations: Non-dangerous goods IMDG Code: Non-dangerous goods International air transport dangerous goods regulations: non-dangerous goods 14.3 Transport hazard categories European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.4 Package group European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.5 Environmental hazards European Land Transport Dangerous Regulations: No International Maritime Transport Dangerous Regulations Maritime Pollutants: No International Air Transport Risk Regulations: No 14.6 Special reminder to users No data available |
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