Doxifluridine

For research use only. Not for therapeutic Use.

  • CAT Number: A000465
  • CAS Number: 3094-09-5
  • Molecular Formula: C9H11FN2O5
  • Molecular Weight: 246.2
  • Purity: ≥95%
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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.


Catalog Number A000465
CAS Number 3094-09-5
Synonyms

5/’-Deoxy-5-fluorouridine; 3094-09-5; 5-fluoro-5/’-deoxyuridine; Furtulon; 5/’-Dfur

Molecular Formula C9H11FN2O5
Purity ≥95%
Target Thymidylate Synthase
Solubility >10mg/mL in DMSO
Storage -20°C
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
InChIKey ZWAOHEXOSAUJHY-MMRIIKACSA-N
SMILES CC1C(C(C(O1)N2C=C(C(=O)NC2=O)F)O)O
Reference

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. PubMed PMID: 27364610.
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2: Kang MH, Lee WS, Go SI, Kim MJ, Lee US, Choi HJ, Kim DC, Lee JH, Kim HG, Bae
KS, Cho JM. Can thymidine phosphorylase be a predictive marker for gemcitabine
and doxifluridine combination chemotherapy in cholangiocarcinoma?: case series.
Medicine (Baltimore). 2014 Dec;93(28):e305. doi: 10.1097/MD.0000000000000305.
PubMed PMID: 25526478; PubMed Central PMCID: PMC4603134.
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3: 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
Dec;38(4):295-9. doi: 10.1007/s13318-013-0130-4. Epub 2013 Apr 7. PubMed PMID:
23564503.
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4: 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.
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5: 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.

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6: 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.
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7: 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.
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8: 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.
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9: 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.
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10: 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.

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