Tegafur

Base Information

• Chemical Name: Tegafur
• CAS No.: 17902-23-7
• Deprecated CAS: 35959-67-2,37308-51-3,56767-38-5,65732-47-0,73120-84-0,79107-97-4
• Molecular Formula: C8H9FN2O3
• Molecular Weight: 200.169
• Hs Code.: 29349990
• European Community (EC) Number: 241-846-2
• UNII: 1548R74NSZ
• DSSTox Substance ID: DTXSID001009966
• Nikkaji Number: J4.543H
• Wikipedia: Tegafur
• Wikidata: Q413370
• NCI Thesaurus Code: C513
• Metabolomics Workbench ID: 67501
• ChEMBL ID: CHEMBL20883
• Mol file: 17902-23-7.mol

Synonyms:1-(2-Tetrahydrofuryl)-5-fluorouracil;1-(Tetrahydro-2-furanyl)-5-fluorouracil;5-Fluoro-1-(tetrahydro-2-furanyl)-2,4-pyrimidinedione;Florafur;Fluorofur;FT 207;FT-207;FT207;Ftorafur;Futraful;N1-(2'-Tetrahydrofuryl)-5-fluorouracil;Sunfural S;Tegafur;Uftoral;Utefos

Chemical Property of Tegafur

Chemical Property:

• Appearance/Colour: white crystalline powder
• Melting Point: 171-173 °C(lit.)
• Refractive Index: 1.557
• PKA: 7.63±0.10(Predicted)
• PSA: 64.09000
• Density: 1.45 g/cm³
• LogP: -0.01530
• Storage Temp.: 2-8°C
• Solubility.: DMSO: >50mg/mL
• XLogP3: -0.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 200.05972032
• Heavy Atom Count: 14
• Complexity: 316

Purity/Quality:

99% ^*data from raw suppliers

Tegafur ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T
• Hazard Codes: T
• Statements: 23/24/25
• Safety Statements: 22-36/37/39-45

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1CC(OC1)N2C=C(C(=O)NC2=O)F
• Recent ClinicalTrials: Toripalimab Plus Radiotherapy for Elderly Esophageal Cancer Patients Treated With Non-chemotherapy Strategy
• Recent EU Clinical Trials: A randomized phase II study of gemcitabine versus reduced-dose combination chemotherapy in fragile patients with non-resectable pancreatic cancer.
• Recent NIPH Clinical Trials: HiSCO 03 study
• Uses: this product is a derivative of 5-fluorouracil, the role and application of the product is the same as 5-fluorouracil, but it has less toxicity and its chemotherapy index is high. After the activion by the liver in vivo ,it becomes 5-fluorouracil to play a role in cancer. It is effective on Gastric cancer, colon cancer, colorectal cancer, pancreatic cancer and breast cancer, lung cancer. Isotope labelled Tegafur (T013900), used as an antineoplastic. Used as an antineoplastic
• Description: Tegafur is an orally bioavailable prodrug form of 5-fluorouracil (5-FU; ). It is converted to 5-FU in vivo enzymatically or by cytochrome P450 oxidation. Tegafur inhibits proliferation of HT-29, BxPC-3, and Panc02 cells (IC50s = 201, 172, and 179 μM, respectively). It also reduces tumor growth in an HT-27 colon carcinoma mouse xenograft model when administered at a dose of 50 mg/kg and in a 4-1ST gastric carcinoma mouse xenograft model when used in combination with uracil. Formulations containing tegafur, in combination with uracil, have been used in the treatment of cancer.
• Therapeutic Function: Antineoplastic

Technology Process of Tegafur

There total 34 articles about Tegafur which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.8%

5-fluorouracil (51-21-8) + Succinic semialdehyde (692-29-5) → tegafur (17902-23-7,65732-47-0,79107-97-4)

Guidance literature:

With indium(III) bromide; 1,1,3,3-Tetramethyldisiloxane; In tetrahydrofuran; at 15 - 20 ℃; for 12h; Solvent; Reagent/catalyst; Temperature;

Reference yield: 98.7%

2,3-dihydro-2H-furan (1191-99-7,75454-45-4) + 5-fluorouracil (51-21-8) → tegafur (17902-23-7,65732-47-0,79107-97-4)

Guidance literature:

With bis(acetylacetonate)nickel(II); tris(2,2′-bipyridine)ruthenium(II) bis(tetrafluoroborate); In tetrahydrofuran; at 25 - 30 ℃; Temperature; Solvent; Wavelength; Reagent/catalyst; Irradiation;

Reference yield: 95.2%

5-fluorouracil (51-21-8) + tetrahydrofuran-2-yl benzoate (3333-44-6) → tegafur (17902-23-7,65732-47-0,79107-97-4)

Guidance literature:

With sodium acetate; tetra-(n-butyl)ammonium iodide; In dichloromethane; water; at 35 ℃; for 2h; Solvent; Temperature; Reagent/catalyst;

upstream raw materials:

2-chlorotetrahydrofuran

5-fluorouracil

2,3-dihydro-2H-furan

5-fluoro-2,4-bis(trimethylsilyloxy)pyrimidine

Downstream raw materials:

3-[3-(2-acetoxy-5-chloro-4-pyridyloxycarbonyl)-benzoyl]-5-fluoro-1-(2-tetrahydrofuranyl)uracil

5-(α-tegafur-m-nitro-p-tolyl)-10,15,20-triphenylporphyrin

1-(tetrahydrofuran-2-yl)-3-(m-nitrobenzyl)-5-fluorouracil

5-fluoro-3-(4-nitrobenzyl)-1-(tetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione

Refernces

• 1、 Iwasaki,Nishitani,Horikawa,Inoue. "A novel synthesis of 5-fluorouracil derivatives having oxacycloalkane moieties". . p. 1029 - 1032. Retrieved 1981.
• 2、 -. "Preparation method of tegafur". Paragraph 0030-0055. . Retrieved 2021/04/21.
• 3、 -. "Preparation method of tegafur". Paragraph 0035-0056. . Retrieved 2020/01/25.