5-Chlorouracil , 98% , 1820-81-1

Synonym(s):
5-Chloro-2,4-dihydroxypyrimidine;5-Chloropyrimidine-2,4(1H,3H)-dione;5-Chlorouracil;Fluorouracil Impurity E (PhEur)

CAS NO.：1820-81-1

Empirical Formula: C4H3ClN2O2

Molecular Weight: 146.53

MDL number: MFCD00006019

EINECS: 217-339-7

PRODUCT Properties

• Melting point: >300 °C (lit.)
• Density: 1.6838 (rough estimate)
• refractive index: 1.6550 (estimate)
• storage temp.: 2-8°C
• solubility: 1 M NH4OH: soluble50mg/mL
• pka: 6.77±0.10(Predicted)
• form: Solid
• color: White to Off-White
• Water Solubility: 2.501g/L(25 ºC)
• BRN: 127173
• InChI: InChI=1S/C4H3ClN2O2/c5-2-1-6-4(9)7-3(2)8/h1H,(H2,6,7,8,9)
• InChIKey: ZFTBZKVVGZNMJR-UHFFFAOYSA-N
• SMILES: C1(=O)NC=C(Cl)C(=O)N1
• CAS DataBase Reference: 1820-81-1(CAS DataBase Reference)
• EPA Substance Registry System: 5-Chlorouracil (1820-81-1)

Description and Uses

5-Chlorouracil (5-CU) may have advantages for the inhibition of undesired fibroblast proliferation taking place after surgery for glaucoma and results in filtration failure. A comparison of 5-CU and 5-fluorouracil (5-FU) cytotoxicity shows that 5-CU is approximately 1000 times less toxic to nonproliferative cells while maintaining good antimitotic activity. In addition, 5-CU induces apoptotic-controlled cell death, whereas the influence of 5-FU is by apoptonecrosis. The 5-CU apoptotic mechanism is driven mainly by the nuclear translocation of AIF and activation of the LEI/L-DNase II pathways, which are caspase-independent. In conclusion, even though 5-CU is a weaker antiproliferating agent than 5-FU, its reduced toxic side effects on the epithelium and sclera allow for its enhanced efficacy and extended reduction of IOP after filtering surgery for glaucoma. 5-CU is an effective mutagen, clastogen and toxicant, and an effective inducer of sister-chromatid exchange, and is not as sensitive to ionizing radiation as other thymine analogues[1].

5-Chlorouracil was used as a control in resazurin-based cytotoxicity assay for screening of cytotoxicity in hepatocytes and liver cell lines.

Safety

• Symbol(GHS): GHS06,GHS08
• Signal word: Danger
• Hazard statements: H301-H341
• Precautionary statements: P201-P202-P264-P270-P280-P301+P310
• Hazard Codes: Xi
• Risk Statements: 36/37/38
• Safety Statements: 22-24/25-36-26
• WGK Germany: 3
• RTECS: YQ9410000
• HS Code: 29335995