Gimeracil Chemical Properties

Melting point:

274 °C

Boiling point:

255.1±40.0 °C(Predicted)

Density 

1.56±0.1 g/cm3(Predicted)

storage temp. 

Inert atmosphere,Store in freezer, under -20°C

solubility 

Soluble in DMSO (up to 5 mg/ml).

pka

4.50±1.00(Predicted)

form 

solid

color 

White

Stability:

Stable for 1 year from date of purchase as supplied. Solutions in DMSO may be stored at -20°C for up to 3 months.

InChI

InChI=1S/C5H4ClNO2/c6-3-2-7-5(9)1-4(3)8/h1-2H,(H2,7,8,9)

InChIKey

ZPLQIPFOCGIIHV-UHFFFAOYSA-N

SMILES

C1(=O)NC=C(Cl)C(O)=C1

CAS DataBase Reference

103766-25-2(CAS DataBase Reference)

Safety Information

Safety Statements 

24/25

HS Code 

29337900

Gimeracil Usage And Synthesis

Description

Gimeracil (103766-25-2) is a dihydropyrimidine dehydrogenase (DPD) inhibitor.? DPD is involved in the degradation of pyrimidine-based chemotherapeutic drugs such as 5-fluorouracil (5-FU).? Gimeracil is used along with 5-FU or Tegafur to prolong circulating concentrations of the drugs.1,2? Gimeracil has also been shown to act as a radiosensitizer via inhibition of homologous recombination in the repair of DNA double strand breaks.3

Chemical Properties

Off-White Solid

Uses

Gimeracil is an inhibitor of dihydropyrimidine dehydrogenase, which inhibits the early step in homologous recombination for double strand breaks repair.

Uses

Gimeracil is an antitumor agent. Gimeracil is a potent inhibitor of dihydropyrimidine dehydrogenase (DPD).

Uses

Antitumor agent. A potent inhibitor of dihydropyrimidine dehydrogenase (DPD)

Definition

ChEBI: Gimeracil is an organic molecular entity.

Synthesis

Compound 6 (8.0 g, 44 mmol) was used as a raw material, which was mixed with acetonitrile (100 mL), acetic acid (3 mL) and sodium iodide (13.2 g, 88 mmol), and the reaction was heated at 60°C for 8 hours. Upon completion of the reaction, the mixture was cooled to room temperature and poured into 10% sodium thiosulfate solution (200 mL) to precipitate a colorless solid. Purification by aqueous recrystallization afforded the target product 5-chloro-4-hydroxypyridin-2(1H)-one (Compound 2) in a yield of 5.6 g in 86%. The product characterization data were as follows: melting point 272-273 °C (literature value 273-274 °C); 1H NMR (400 MHz, DMSO-d6) δ 5.70 (s, 1H), 7.51 (s, 1H), 11.29 (br, 2H); 13C NMR (100 MHz, DMSO-d6) δ 163.5, 163.2, 134.6 , 105.6, 98.7; LRMS (ESI) m/z (%): 146 (100) [M(35Cl)+H]+, 148 (30) [M(37Cl)+H]+; HRMS (ESI) m/z calculated value of C5H535ClNO2: [M+H]+: 146.0003, measured value: 146.0012; C5H537ClNO2: [M+H]+: 147.9975, measured value: 147.9975.

in vivo

References

[1] DIASIO R B. Clinical implications of dihydropyrimidine dehydrogenase inhibition.[C]//13 7 Suppl 3. 1999: 17-21.
[2] MASAO KOBAYAKAWA  Yasushi K. Tegafur/gimeracil/oteracil (S-1) approved for the treatment of advanced gastric cancer in adults when given in combination with cisplatin: a review comparing it with other fluoropyrimidine-based therapies.[J]. OncoTargets and therapy, 2011, 4: 193-201. DOI:10.2147/ott.s19059
[3] KOH-ICHI SAKATA. Gimeracil, an inhibitor of dihydropyrimidine dehydrogenase, inhibits the early step in homologous recombination[J]. Cancer Science, 2011, 102 9: 1712-1716. DOI:10.1111/j.1349-7006.2011.02004.x

Gimeracil(103766-25-2)Related Product Information

• 2,4-Dihydroxypyridine
• 2-Chloro-5-chloromethylpyridine
• Clopidol
• 5-CHLORO-1,2-DIHYDRO-4-METHOXY-2-OXO-3-PYRIDINECARBONITRILE
• 5-Chloropyridine-2,3-diol
• 2,4-Dihydroxypyridine
• Gimeracil-13C3
• Gimeracil
• AURORA KA-4855
• AURORA KA-6096
• AURORA KA-3471
• AURORA KA-2491
• AURORA KA-8145
• AURORA KA-3473
• AURORA KA-6035
• AURORA KA-4741
• AURORA KA-3807
• AURORA KA-4737