Gimeracil

Modify Date: 2025-08-22 13:16:42

Gimeracil Structure
Gimeracil structure
 Common Name Gimeracil
CAS Number 103766-25-2 Molecular Weight 145.544
Density 1.6±0.1 g/cm3 Boiling Point 524.2±45.0 °C at 760 mmHg
Molecular Formula C5H4ClNO2 Melting Point 274 °C
MSDS N/A Flash Point 270.8±28.7 °C

 Use of Gimeracil


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:

 Names

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

 Gimeracil 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
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.

 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

 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

3-chloro-1,5-dioxaspiro[5.5]undec-3-en-2-one structure

3-chloro-1,5-di...

CAS#:134878-51-6

1,1-Diethoxyethene structure

1,1-Diethoxyethene

CAS#:2678-54-8

~71%

Gimeracil Structure

Gimeracil

CAS#:103766-25-2

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

N/A

CAS#:904731-84-6

~33%

Gimeracil Structure

Gimeracil

CAS#:103766-25-2

Literature: TAIHO PHARMACEUTICAL COMPANY LIMITED Patent: EP1842847 A1, 2007 ; Location in patent: Page/Page column 9-10 ;
5-chloro-2-methoxy-2-t-butyldimethylsilyloxy-2,3-dihydropyran-4-one structure

5-chloro-2-meth...

CAS#:904731-85-7

~%

Gimeracil Structure

Gimeracil

CAS#:103766-25-2

Literature: EP1842847 A1, ; Page/Page column 9 ;
3,5-dichloro-4-hydroxy-1H-pyridin-2-one structure

3,5-dichloro-4-...

CAS#:103792-80-9

~%

Gimeracil Structure

Gimeracil

CAS#:103766-25-2

Literature: Recueil des Travaux Chimiques des Pays-Bas, 73<1954<704,708
2,4-diethoxy-5-chloro-pyridine structure

2,4-diethoxy-5-...

CAS#:856850-46-9

~%

Gimeracil Structure

Gimeracil

CAS#:103766-25-2

Literature: Recueil des Travaux Chimiques des Pays-Bas, , vol. 72, p. 285,291
4-Chloro-2-ethoxypyridine structure

4-Chloro-2-etho...

CAS#:856851-45-1

~%

Gimeracil Structure

Gimeracil

CAS#:103766-25-2

Literature: Recueil des Travaux Chimiques des Pays-Bas, , vol. 72, p. 285,291
4,5-Dichloro-2-ethoxypyridine structure

4,5-Dichloro-2-...

CAS#:857991-71-0

~%

Gimeracil Structure

Gimeracil

CAS#:103766-25-2

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

 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%

 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
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Chemsrc provides Gimeracil(CAS#:103766-25-2) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of Gimeracil are included as well.>> amp version: Gimeracil

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