Available from stock

Gimeracil

SKU: G0209

Category: API's & Intermediates

Synonyms: 5-Chloro-4-hydroxy-2(1H)-pyridinone , 5-Chloro-2,4-dihydroxypyridine , 5-Chloro-4-hydroxy-2-pyridone , Gimestat , CDHP; 103766-25-2
CAS-Number: C₅H₄ClNO₂
Molecular Formula: 145.54
Molecular Weight

For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.

Product Data
Handling
Safety Information
Details

Specifications

Purity: ≥99%
Appearance: White to yellow crystalline powder
Identity: 1H-NMR

Properties

Solvents: DMSO (25 mg/ml), DMF (20 mg/ml)
Melting Point: 274°C (dec.) (lit.)
Boiling Point: ~524.2° C at 760 mmHg (Predicted) (tautomer)
Refractive Index: n20D ~1.62 (Predicted)
Density: ~1.6 g/cm3 (Predicted) (tautomer)

Shipping: AMBIENT
Short Term Storage: +4°C
Long Term Storage: -20°C
Handling Advice: Protect from light and moisture.
Use / Stability: Stable for at least 6 months after receipt when stored at RT.

Hazard statements: H302
Precautionary statements: P264
GHS Symbol: GHS07
Signal word: Warning
Transportation: Not dangerous goods

Description: Gimeracil is an orally active inhibitor against dihydropyrimidine dehydrogenase (DPYD), the rate limiting enzyme for the catabolism of pyrimidines, including the chemotherapeutic drug 5-fluorouracil (5FU). It has been administered concomitantly with 5-fluorouracil in a chemotherapy regimen termed S-1 to block 5-fluorouracil degradation, thus prolonging circulating 5-fluorouracil concentrations. Furthermore, Gimeracil has been shown to inhibit homologous recombination in the repair of DNA double strand breaks, which can sensitize cancer cells to radiotherapy.
Smiles: ClC1=CNC(C=C1O)=O
InChi Key: ZPLQIPFOCGIIHV-UHFFFAOYSA-N
References: (1) T. Shirasaka, et al., Cancer Res. 56, 2602 (1996) , (2) A.A. Adjei, Br. J. Clin. Pharmacol. 48, 265 (1999) (Review) , (3) M.D. Wyatt & D.M. Wilson, Cell Mol. Life Sci. 66, 788 (2009) , (4) M. Fukushima, et al., Oncol. Rep. 24, 1307 (2010) , (5) K.I. Sakata, et al., Cancer Sci. 102, 1712 (2011) , (6) K. Harada, et al., Anticancer Res. 36, 5923 (2016)
InChi: InChI=1S/C5H4ClNO2/c6-3-2-7-5(9)1-4(3)8/h1-2H,(H2,7,8,9)

Gimeracil is an orally active inhibitor against dihydropyrimidine dehydrogenase (DPYD), the rate limiting enzyme for the catabolism of pyrimidines, including the chemotherapeutic drug 5-fluorouracil (5FU). It has been administered concomitantly with 5-fluorouracil in a chemotherapy regimen termed S-1 to block 5-fluorouracil degradation, thus prolonging circulating 5-fluorouracil concentrations. Furthermore, Gimeracil has been shown to inhibit homologous recombination in the repair of DNA double strand breaks, which can sensitize cancer cells to radiotherapy.

SKU: G0209 Category: API's & Intermediates

Additional information

Additional information

Synonyms	5-Chloro-4-hydroxy-2(1H)-pyridinone, 5-Chloro-2,4-dihydroxypyridine, 5-Chloro-4-hydroxy-2-pyridone, Gimestat, CDHP
Purity	≥99%
Appearance	White to yellow crystalline powder
CAS-Number	103766-25-2
Molecular Formula	C5H4ClNO2
Molecular Weight	145.54
Identity	1H-NMR
Solvents	DMSO (25 mg/ml), DMF (20 mg/ml)
Melting Point	274°C (dec.) (lit.)
Boiling Point	~524.2° C at 760 mmHg (Predicted) (tautomer)
Refractive Index	n20D ~1.62 (Predicted)
Density	~1.6 g/cm3 (Predicted) (tautomer)
Smiles	ClC1=CNC(C=C1O)=O
InChi Key	ZPLQIPFOCGIIHV-UHFFFAOYSA-N
Shipping	AMBIENT
Short Term Storage	+4°C
Long Term Storage	-20°C
Handling Advice	Protect from light and moisture.
Use / Stability	Stable for at least 6 months after receipt when stored at RT.
Hazard statements	H302
Precautionary statements	P264
GHS Symbol	GHS07
Signal word	Warning
Transportation	Not dangerous goods
References	(1) T. Shirasaka, et al., Cancer Res. 56, 2602 (1996), (2) A.A. Adjei, Br. J. Clin. Pharmacol. 48, 265 (1999) (Review), (3) M.D. Wyatt & D.M. Wilson, Cell Mol. Life Sci. 66, 788 (2009), (4) M. Fukushima, et al., Oncol. Rep. 24, 1307 (2010), (5) K.I. Sakata, et al., Cancer Sci. 102, 1712 (2011), (6) K. Harada, et al., Anticancer Res. 36, 5923 (2016)
InChi	InChI=1S/C5H4ClNO2/c6-3-2-7-5(9)1-4(3)8/h1-2H,(H2,7,8,9)
Quantity	1 g, 5 g, Bulk