103766-25-2

103766-25-2 structure

Name: Gimeracil
Chemical Name: 5-chloro-4-hydroxy-1H-pyridin-2-one
CAS Number: 103766-25-2
Molecular Formula: C₅H₄ClNO₂
Molecular Weight: 145.544
Catalog: Pharmaceutical intermediate Heterocyclic compound Pyridine compound Pyridine derivative
Create Date: 2018-07-30 06:38:17
Modify Date: 2024-01-02 18:16:52
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:

Name	5-chloro-4-hydroxy-1H-pyridin-2-one
Synonyms	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

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.

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

134878-51-6

2678-54-8

~71%

103766-25-2

Literature: TAIHO PHARMACEUTICAL COMPANY LIMITED Patent: EP1842847 A1, 2007 ; Location in patent: Page/Page column 10 ;

904731-84-6

~33%

103766-25-2

Literature: TAIHO PHARMACEUTICAL COMPANY LIMITED Patent: EP1842847 A1, 2007 ; Location in patent: Page/Page column 9-10 ;

904731-85-7

103766-25-2

Literature: EP1842847 A1, ; Page/Page column 9 ;

103792-80-9

103766-25-2

Literature: Recueil des Travaux Chimiques des Pays-Bas, 73<1954<704,708

856850-46-9

103766-25-2

Literature: Recueil des Travaux Chimiques des Pays-Bas, , vol. 72, p. 285,291

856851-45-1

103766-25-2

Literature: Recueil des Travaux Chimiques des Pays-Bas, , vol. 72, p. 285,291

857991-71-0

103766-25-2

Literature: Recueil des Travaux Chimiques des Pays-Bas, , vol. 72, p. 285,291

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%