5-Chlorouracil Chemical 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)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

22-24/25-36-26

WGK Germany 

3

RTECS 

YQ9410000

HS Code 

29335995

MSDS

• Language:English Provider:5-Chlorouracil
• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

5-Chlorouracil Usage And Synthesis

Description

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].

Chemical Properties

white to light beige crystalline powder

Uses

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

Uses

5-Chlorouracil can be used for the experimental and clinical treatment of neoplastic and viral diseases.

Definition

ChEBI: An organochlorine compound consisting of uracil having an chloro substituent at the 5-position. It is functionally related to a uracil.

General Description

The shape resonance spectra of 5-chlorouracil, obtained from fixed-nuclei elastic scattering calculations by the Schwinger multichannel method with pseudopotentials, was studied.

Purification Methods

It recrystallises from hot H2O (4g/500mL) using charcoal. [McOmie et al. J Chem Soc 3478 1955, West & Barrett J Am Chem Soc 76 3146 1954, Beilstein 24 III/IV 1231.]

References

[1] Marianne Berdugo Polak. “Controlled delivery of 5-chlorouracil using poly(ortho esters) in filtering surgery for glaucoma.” Investigative ophthalmology & visual science (2008): 2993–3003.

5-Chlorouracil(1820-81-1)Related Product Information

• Uracil
• Difluorochloromethane
• 5-Chlorouridine
• Terbacil
• 5-CHLORO-6-METHYLURACIL
• 4-AMINOPYRAZOLO[3,4-D]PYRIMIDINE
• 6-Chlorouracil
• 6-methyl-5-chlorouracil
• 1,3-Dimethyl-4-chlorouracil,1,3-DIMETHYL-6-CHLOROURACIL
• 3-Methyl-6-chlorouracil, GC 97%,3-METHYL-6-CHLOROURACIL
• 2,4(1H,3H)-Pyrimidinedione,5-chloro-6-(chloromethyl)-(9CI)
• 5-CHLORO-2'-DEOXYURIDINE
• 1-(3-Fluoro-2,3-dideoxy-β-D-erythro-pentofuranosyl)-5-chlorouracil
• 5-Chloro-2',3'-O-isopropylidene-D-uridine
• 5-Chloro-5'-deoxy-5'-iodo-2',3'-O-isopropylidene-D-uridine
• 5-Chlorouracil-15N2,13C
• 1,3,5-TRICHLOROURACIL
• 5-CHLORO-5'-DEOXYURIDINE