F6627
Sigma

5-Fluorouracil

≥99% (TLC), powder

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Synonym

2,4-Dihydroxy-5-fluoropyrimidine

5-Fluoro-2,4(1H,3H)-pyrimidinedione

5-FU

Molecular Formula

C₄H₃FN₂O₂

Molecular Weight

130.08

CAS Number

51-21-8

Beilstein Registry Number

127172

MDL number

MFCD00006018

PubChem Substance ID

24278439

EG/EC Number

200-085-6

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Descriptions

Frequently Asked Questions

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Biochem/physiol Actions

A potent antitumor agent that affects pyrimidine synthesis by inhibiting thymidylate synthetase thus depleting intracellular dTTP pools. It is metabolized to ribonucleotides and deoxyribonucleotides, which can be incorporated into RNA and DNA. Treatment of cells with 5-FU leads to an accumulation of cells in S-phase and has been shown to induce p53 dependent apoptosis.

Properties

assay

≥99% (TLC)

form

powder

color

white

282-286 °C (dec.)(lit.)

solubility

1 M NH₄OH: soluble

DMSO/DMF: soluble

methanol: soluble

Gene Information

human ... TYMS(7298)

References

Reference

Wadler, S., et al., Effects of perturbations of pools of deoxyribonucleoside triphosphates on expression of ribonucleotide reductase, a G1/S transition state enzyme, in p53-mutated cells. Biochem. Pharmacol. 55, 1353-1360, (1998) abstract

Elstein, K.H., et al., Nucleoside-mediated mitigation of 5-fluorouracil-induced toxicity in synchronized murine erythroleukemic cells. Toxicol. Appl. Pharmacol. 146, 29-39, (1997) abstract

Takeda, H., et al., Effect of 5-fluorouracil on cell cycle regulatory proteins in human colon cancer cell line. Jpn. J. Cancer Res. 90, 677-684, (1999) abstract

Pritchard, D.M., et al., Chemically-induced apoptosis: p21 and p53 as determinants of enterotoxin activity. Toxicol. Lett. 102-103, 19-27, (1998) abstract

Inada, T., et al., 5-FU-induced apoptosis correlates with efficacy against human gastric and colon cancer xenografts in nude mice. Anticancer Res. 17, 1965-1971, (1997) abstract

Merck

Merck 13,4208

Beilstein

Beil. 24,IV,1229

reference

Aldrich MSDS 1, 978:A / Corp MSDS 1 (1), 1731:B / FT-IR 2 (3), 3829:C / FT-IR 1 (2), 809:D / FT-NMR 1 (3), 362:C / IR-Spectra (3), 1353:H / IR-Spectra (2), 1179:B / NMR-Reference 2 (2), 690:D / RegBook 1 (2), 2565:C / Sax 6, 1449 / Sigma FT-IR 1 (1), 996:C / Structure Index 1, 405:D:4

Safety

Hazard Codes

Risk Statements

RIDADR

UN 2811 6.1/PG 3

WGK Germany

RTECS

YR0350000

10-23