Doxifluridine
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MedKoo CAT#: 100274

CAS#: 3094-09-5

Description: Doxifluridine, also known as 5'-Deoxy-5-fluorouridine, 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.


Chemical Structure

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Doxifluridine
CAS# 3094-09-5

Theoretical Analysis

MedKoo Cat#: 100274
Name: Doxifluridine
CAS#: 3094-09-5
Chemical Formula: C9H11FN2O5
Exact Mass: 246.0652
Molecular Weight: 246.19
Elemental Analysis: C, 43.91; H, 4.50; F, 7.72; N, 11.38; O, 32.49

Price and Availability

Size Price Availability Quantity
100.0mg USD 95.0 2 weeks
200.0mg USD 150.0 2 weeks
500.0mg USD 250.0 2 weeks
1.0g USD 350.0 2 weeks
2.0g USD 450.0 2 weeks
5.0g USD 650.0 2 weeks
10.0g USD 850.0 2 weeks
20.0g USD 1250.0 2 weeks
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Synonym: doxifluridine; Furtulon; Flutron; doxyfluridine; 5'-Deoxy-5-fluorouridine.

IUPAC/Chemical Name: 1-((2R,3R,4S,5R)-3,4-dihydroxy-5-methyltetrahydrofuran-2-yl)-5-fluoropyrimidine-2,4(1H,3H)-dione

InChi Key: ZWAOHEXOSAUJHY-ZIYNGMLESA-N

InChi Code: 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

SMILES Code: O=C1NC(C(F)=CN1[C@@H]2O[C@H](C)[C@@H](O)[C@H]2O)=O

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO, not in water

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

Preparing Stock Solutions

The following data is based on the product molecular weight 246.19 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL

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1: Baek IH, Lee BY, Kim MS, Kwon KI. 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. [Epub ahead of print] PubMed PMID: 23564503.

2: Kang YK, Chang HM, Yook JH, Ryu MH, Park I, Min YJ, Zang DY, Kim GY, Yang DH, Jang SJ, Park YS, Lee JL, Kim TW, Oh ST, Park BK, Jung HY, Kim BS. Adjuvant chemotherapy for gastric cancer: a randomised phase 3 trial of mitomycin-C plus either short-term doxifluridine or long-term doxifluridine plus cisplatin after curative D2 gastrectomy (AMC0201). Br J Cancer. 2013 Apr 2;108(6):1245-51. doi: 10.1038/bjc.2013.86. Epub 2013 Feb 28. PubMed PMID: 23449357; PubMed Central PMCID: PMC3619263.

3: Kusama M. [Doxifluridine, medroxyprogesterone acetate and cyclophosphamide(DMpC)combination therapy found effective for case of chest wall recurrent breast cancer with bone and pleural metastases]. Gan To Kagaku Ryoho. 2012 Aug;39(8):1239-41. Japanese. PubMed PMID: 22902449.

4: Takeyoshi I, Makita F, Iwazaki S, Ishikawa H, Kakinuma S, Sato Y, Ohya T, Nakagami K, Tomizawa N, Izumi M, Kobayashi I, Tanahashi Y, Kobayashi J, Kamoshita N, Kawate S, Sunose Y, Sakamoto I, Yoshinari D, Yamada T, Okabe T. Weekly paclitaxel in combination with doxifluridine for peritoneally disseminated gastric cancer with malignant ascites. Anticancer Res. 2011 Dec;31(12):4625-30. PubMed PMID: 22199340.

5: Jiang J, Zheng X, Xu X, Zhou Q, Yan H, Zhang X, Lu B, Wu C, Ju J. Prognostic significance of miR-181b and miR-21 in gastric cancer patients treated with S-1/Oxaliplatin or Doxifluridine/Oxaliplatin. PLoS One. 2011;6(8):e23271. doi: 10.1371/journal.pone.0023271. Epub 2011 Aug 18. PubMed PMID: 21876743; PubMed Central PMCID: PMC3158077.

6: Yakabe T, Noshiro H, Ikeda O, Miyoshi A, Kitajima Y, Satoh S. Second-line chemotherapy with paclitaxel and doxifluridine after failure of S-1 in elderly patients with unresectable advanced or recurrent gastric cancer. J Cancer Res Clin Oncol. 2011 Oct;137(10):1499-504. doi: 10.1007/s00432-011-1025-x. Epub 2011 Aug 10. PubMed PMID: 21830159.

7: Naganuma Y, Choijamts B, Shirota K, Nakajima K, Ogata S, Miyamoto S, Kawarabayashi T, Emoto M. Metronomic doxifluridine chemotherapy combined with the anti-angiogenic agent TNP-470 inhibits the growth of human uterine carcinosarcoma xenografts. Cancer Sci. 2011 Aug;102(8):1545-52. doi: 10.1111/j.1349-7006.2011.01998.x. Epub 2011 Jul 3. PubMed PMID: 21631643.

8: Takeyoshi I, Makita F, Tanahashi Y, Iwazaki S, Ogawa T, Tomizawa N, Nakamura S, Ishikawa H, Ohya T, Kakinuma S, Nakagami K, Sato Y, Koyano T, Roppongi T, Izumi M, Kobayashi J, Kawate S, Sunose Y, Kobayashi M, Yamada T, Sakamoto I. A phase II study of weekly paclitaxel and doxifluridine combination chemotherapy for advanced/recurrent gastric cancer. Anticancer Res. 2011 Jan;31(1):287-91. PubMed PMID: 21273612.

9: Watanabe T, Matsuda K, Ishihara S, Nozawa K, Hayama T, Yamada H, Iinuma H. Significance of microsatellite instability (MSI) for colorectal cancer following adjuvant therapy with doxifluridine. Med Oncol. 2012 Mar;29(1):133. doi: 10.1007/s12032-010-9799-2. Epub 2011 Jan 15. PubMed PMID: 21234714.

10: Kang BW, Kim JG, Lee SJ, Chae YS, Moon JH, Sohn SK, Jeon SW, Jung MK, Lim KH, Jang YS, Park JS, Jun SH, Choi GS. Clinical significance of microsatellite instability for stage II or III colorectal cancer following adjuvant therapy with doxifluridine. Med Oncol. 2011 Dec;28 Suppl 1:S214-8. doi: 10.1007/s12032-010-9701-2. Epub 2010 Oct 16. PubMed PMID: 20953739.



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