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MedKoo Cat#: 100274 | Name: Doxifluridine
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

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

Doxifluridine
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
1g USD 350.00 2 Weeks
5g USD 550.00 2 Weeks
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Related CAS #
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Synonym
Doxifluridine; Furtulon; Flutron; Doxyfluridine; 5'-Deoxy-5-fluorouridine; 5'-dFUrd; 5-DFUR; 5DFUR; 5 DFUR; AMC 0101; AMC0101; AMC-0101; Ro 21-9738; Ro21-9738; Ro-21-9738;
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
More Info
     
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Doxifluridine (Ro 21-9738; 5'-DFUR) is a thymidine phosphorylase activator for PC9-DPE2 cells with IC50 of 0.62 μM.
In vitro activity:
The doxifluridine-conjugated 8-methyladenosine-substituted 2-5A analog was significantly more effective as an activator of RNase L than the parent 5'-monophophorylated 2-5A tetramer and showed a tumor suppressive effect against human cervical cancer cells. Reference: Bioorg Med Chem. 2016 Aug 15;24(16):3870-4. https://pubmed.ncbi.nlm.nih.gov/27364610/
In vivo activity:
The antitumor and anti-angiogenic effects of metronomic doxifluridine (delivered via oral gavage) in combination with TNP-470 were evaluated in vivo in mice. Metronomic doxifluridine alone significantly suppressed tumor growth compared with the untreated (control) group, while metronomic doxifluridine in combination with TNP-470 significantly inhibited tumor growth compared with each treatment alone. Reference: Cancer Sci. 2011 Aug;102(8):1545-52. https://pubmed.ncbi.nlm.nih.gov/21631643/
Solvent mg/mL mM
Solubility
DMF 58.0 235.59
DMSO 53.0 215.28
PBS (pH 7.2) 5.0 0.81
Water 34.5 140.13
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

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
Formulation protocol:
1. Kitamura Y, Kito S, Nakashima R, Tanaka K, Nagaoka K, Kitade Y. Doxifluridine-conjugated 2-5A analog shows strong RNase L activation ability and tumor suppressive effect. Bioorg Med Chem. 2016 Aug 15;24(16):3870-4. doi: 10.1016/j.bmc.2016.06.033. Epub 2016 Jun 16. PMID: 27364610. 2. 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. PMID: 21631643. 3. Konishi H, Yoshimoto T, Morita K, Minouchi T, Sato T, Yamaji A. Depression of phenytoin metabolic capacity by 5-fluorouracil and doxifluridine in rats. J Pharm Pharmacol. 2003 Jan;55(1):143-9. doi: 10.1211/002235702298. PMID: 12625878.
In vitro protocol:
1. Kitamura Y, Kito S, Nakashima R, Tanaka K, Nagaoka K, Kitade Y. Doxifluridine-conjugated 2-5A analog shows strong RNase L activation ability and tumor suppressive effect. Bioorg Med Chem. 2016 Aug 15;24(16):3870-4. doi: 10.1016/j.bmc.2016.06.033. Epub 2016 Jun 16. PMID: 27364610.
In vivo protocol:
1. 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. PMID: 21631643. 2. Konishi H, Yoshimoto T, Morita K, Minouchi T, Sato T, Yamaji A. Depression of phenytoin metabolic capacity by 5-fluorouracil and doxifluridine in rats. J Pharm Pharmacol. 2003 Jan;55(1):143-9. doi: 10.1211/002235702298. PMID: 12625878.
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.