| Identification | More | [Name]
5-Chlorouracil | [CAS]
1820-81-1 | [Synonyms]
5-CHLORO-2,4-DIHYDROXYPYRIMIDINE
5-CHLORO-5-URACIL
5-CHLOROPYRIMIDINE-2,4(1H,3H)-DIONE
5-CHLOROURACIL
TIMTEC-BB SBB004103
2,4(1H,3H)-Pyrimidinedione,5-chloro-
2,4-Pyrimidinediol,5-chloro-
3h)-pyrimidinedione,5-chloro-4(1h
5-Chlor-2,4-dihydroxypyrimidin
5-Chloro-1H-pyrimidine-2,4-dione
5-Chloro-2,4-pyrimidinedione
5-chloro-uraci
Uracil,5-chloro-
5-CHLOROURACIL CRYSTALLINE
5-Chlorouracil,98%
2,4(1H,3H)-Pyrimidinedione, 5-chloro-(9CI)
5-Chloro-2,4(1H,3H)-pyrimidinedione
NSC 28172
5-CHLOROURACIL,5-CHLORO-2,4-DIHYDROXYPYRIMIDINE
5-Chloro-1,2,3,4-tetrahydropyrimidine-2,4-dione | [EINECS(EC#)]
217-339-7 | [Molecular Formula]
C4H3ClN2O2 | [MDL Number]
MFCD00006019 | [Molecular Weight]
146.53 | [MOL File]
1820-81-1.mol |
| Chemical Properties | Back Directory | [Appearance]
white to light beige crystalline powder | [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 | [form ]
Solid | [pka]
6.77±0.10(Predicted) | [color ]
White to Off-White | [Water Solubility ]
2.501g/L(25 ºC) | [Usage]
Used for the experimental and clinical treatment of neoplastic and viral diseases | [Detection Methods]
HPLC,NMR | [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]
1820-81-1(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S22:Do not breathe dust .
S24/25:Avoid contact with skin and eyes .
S36:Wear suitable protective clothing .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice . | [RIDADR ]
UN2811 | [WGK Germany ]
3
| [RTECS ]
YQ9410000
| [HazardClass ]
6.1 | [HS Code ]
29335995 |
| Hazard Information | Back Directory | [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. | [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.
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