Gimeracil

Names

[ Name ]:
Gimeracil

[Synonym ]:
1,2-Dihydro-5-chloro-4-hydroxybenzene
5-Chloro-4-hydroxy-2(1H)-pyridinone
2(1H)-Pyridinone, 5-chloro-4-hydroxy-
5-chloropyridine-2,4-diol
Gimeracil
2,4-dihydroxy-5-chloropyridine
5-Chloro-2,4-pyridinediol
5-Chloro-2,4-dihydroxypyridine
5-Chlor-pyridin-2,4-diol
5-Chloro-4-hydroxypyridin-2(1H)-one
MFCD08458352

Biological Activity

[Description]:

Gimeracil(Gimestat) is an inhibitor of dihydropyrimidine dehydrogenase (DPYD), which degrades pyrimidine including 5-fluorouracil in the blood; inhibits homologous recombination.IC50 Value: Target: DPYDin vitro: Gimeracil had radiosensitizing effects by partially inhibiting homologous recombination (HR) in the repair of DNA double strand breaks. Tail moments in neutral comet assay increased in gimeracil-treated cells. Gimeracil restrained the formation of foci of Rad51 and replication protein A (RPA), whereas it increased the number of foci of Nbs1, Mre11, Rad50, and FancD2. Gimeracil did not sensitize DPYD-depleted cells [1]. Gimeracil inhibited DNA DSB repair. It did not sensitize cells deficient in HR but sensitized those deficient in NHEJ. In SCneo assay, Gimeracil reduced the frequency of neo-positive clones. Additionally, it sensitized the cells in S-phase more than in G0/G1 [2].in vivo:

[Related Catalog]:

Signaling Pathways >> Others >> Others

Research Areas >> Cancer

[References]

[1]. Sakata K, et al. Gimeracil, an inhibitor of dihydropyrimidine dehydrogenase, inhibits the early step in homologous recombination. Cancer Sci. 2011 Sep;102(9):1712-6.

[2]. Takagi M, et al. Gimeracil sensitizes cells to radiation via inhibition of homologous recombination. Radiother Oncol. 2010 Aug;96(2):259-66.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.6±0.1 g/cm3

[ Boiling Point ]:
524.2±45.0 °C at 760 mmHg

[ Melting Point ]:
274 °C

[ Molecular Formula ]:
C₅H₄ClNO₂

[ Molecular Weight ]:
145.544

[ Flash Point ]:
270.8±28.7 °C

[ Exact Mass ]:
144.993057

[ PSA ]:
53.09000

[ LogP ]:
-1.50

[ Vapour Pressure ]:
0.0±1.4 mmHg at 25°C

[ Index of Refraction ]:
1.641

[ Storage condition ]:
Refrigerator

MSDS

Click to get detail MSDS

Safety Information

[ Hazard Codes ]:
F,C

[ Risk Phrases ]:
R11:Highly Flammable. R14:Reacts violently with water. R34:Causes burns.

[ Safety Phrases ]:
S16-S26-S33-S36/37/39-S45

[ RIDADR ]:
UN 2985 3/PG 2

[ WGK Germany ]:
1

[ Packaging Group ]:
II

[ Hazard Class ]:
3

[ HS Code ]:
2942000000

Synthetic Route

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Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2933399090

[ Summary ]:
2933399090. other compounds containing an unfused pyridine ring (whether or not hydrogenated) in the structure. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%