Tegafur - CAS 17902-23-7

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Category
APIs
Product Name
Tegafur
Catalog Number
17902-23-7
CAS Number
17902-23-7
Molecular Weight
200.17
Molecular Formula
C8H9FN2O3
Quality Standard
JP
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Structure
CAS 17902-23-7 Tegafur
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Reference Reading
1. Solvent-mediated phase transformation between two tegafur polymorphs in several solvents
Raitis Bobrovs,* Linda Setonb, Andris Actiņš. CrystEngComm.,2014, 16,10581–10591
Here we study SMPT of the metastable α tegafur to the the rmodynamically stable β tegafur in several popular solvents from different solvent classes: aprotic polar, aliphatic aprotic apolar, hydrogen bond donor and aromatic apolar. Both polymorphs of tegafur are produced commercially; therefore, knowledge of the SMPT of these polymorphic systems might be relevant for the pharmaceutical industry. The pharmaceutically active compound used in this research, tegafur (5-fluoro-1-IJtetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione), is an antitumor agent, which is widely used in the treatment of various malignancies, particularly gastrointestinal and breast cancers. Over many years, the α, β, δ, γ and ε forms of tegafur have been reported in the pharmaceutical literature, but only the α and β modifications are used for therapeutic purposes.
2. A continuous perfusion microplate for cell culture
Vasiliy N. Goral, Chunfeng Zhou, Fang Lai, Po Ki Yuen*. Lab Chip, 2013, 13, 1039–1043
In the absence of primary human hepatocytes, tegafur had little effect on the growth of HCT 116 colon cancer cells (y20% drop in cell viability) after 3 days of perfusion cell culture in the 96-well perfusion microplate while the hepatocyte metabolite 5-FU was toxic to HCT 116 colon cancer cells (y95% drop in cell viability). On the other hand, when primary human hepatocytes were cultured in the source well with tegafur, HCT 116 colon cancer cells were exposed to the perfusate containing the cytotoxic metabolite 5-FU. We observed that a significant number of HCT 116 colon cancer cells died and detached from the surface after 3 days of perfusion cell culture (y70% drop in cell viability).When primary human hepatocytes were cultured in the source well in the absence of tegafur, HCT 116 colon cancer cells readily proliferated.
3. Transmembrane delivery of anticancer drugs through self-assembly of cyclic peptide nanotubes
Jian Chen, Bei Zhang, Fei Xia, Yunchang Xie, Sifan Jiang, Rui Su, Yi Lu, Wei Wu*. Nanoscale,2016, 8,7127–7136
The transmembrane transport of 5-FU, tegafur, cisplatin and cytarabine was studied by monitoring their release from liposomes by dynamic dialysis (Mw cutoff 3.5 kDa). Aliquots of 1 mL liposome suspension were instilled into dialysis bags, followed by 25 μL of CP DMF solution. After gentle mixing, the liposome suspension was sealed and dialyzed against pH 7.3 PBS for either 5-FU or tegafur or cytarabine, and 0.2% NaCl for cisplatin (30 mL, 37 °C, 100 rpm) within a period of 90 min. The CP concentrations were 0, 1, 2 and 4 mg mL−1, corresponding to CP/total lipid molar ratios of 0, 1/1200, 1/600 and 1/300, respectively. At predetermined time intervals, 40 μL of the release media of 5-FU, tegafur and cytarabine, or 500 μL of cisplatin was removed and replaced with an equal volume of pre-heated corresponding release medium. Drug content was determined as described above. All release tests were performed six times in duplicate.
4. A micro cell culture analog (mCCA) with 3-D hydrogel culture of multiple cell lines to assess metabolism-dependent cytotoxicity of anti-cancer drugs
Jong Hwan Sung and Michael L. Shuler*. Lab Chip, 2009, 9, 1385–1394
5-FU is an anti-cancer drug that has been widely used to treat colon cancer for several decades. However, 5-FU has an unpredictable bioavailability when taken orally, and is subject to a rapid degradation by the enzyme dihydropyrimidine dehydrogenase (DPD), resulting in a low response rate when administered alone. Tegafur is an oral prodrug of 5-FU, and has a better oral bioavailability. It is not cytotoxic to tumor cells, but becomes cytotoxic after conversion to 5-FU by P450 enzymes in the liver. It was developed to provide a better pharmacokinetic profile than 5-FU since the conversion of Tegafur to 5-FU in the liver by P450 enzymes provides a more consistent supply of 5-FU into the body over a longer period of time than a sharp peak observed with bolus 5-FU injection. In addition, uracil is often added to Tegafur to inhibit the degradation of 5-FU by DPD enzyme, which is a major catabolizing enzyme for 5-FU. Uracil is a natural substrate of DPD, and competes with 5-FU for the enzyme.
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