| Identification | More | [Name]
Gimeracil | [CAS]
103766-25-2 | [Synonyms]
5-chloropyridine-2,4-diol
GIMERACIL
gimestat
5-Chloro-2,4-dihydroxypyridine
5-Chloro-4-hydroxy-2(1H)-pyridinone
5-Chloro-4-hydroxy-2-pyridone
2(1H)-Pyridinone,5-chloro-4-hydroxy-(9CI)
2(1H)-Pyridinone, 5-chloro-4-hydroxy-
Gimeracil,(CDHP)
CDHP
5-Chloro-2,4-pyridinediol
（CDHP）Gimeracil | [EINECS(EC#)]
1312995-182-4 | [Molecular Formula]
C5H4ClNO2 | [MDL Number]
MFCD08458352 | [Molecular Weight]
145.54 | [MOL File]
103766-25-2.mol |
| Chemical Properties | Back Directory | [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). | [form ]
solid | [pka]
4.50±1.00(Predicted) | [color ]
White | [Usage]
Antitumor agent. A potent inhibitor of dihydropyrimidine dehydrogenase (DPD) | [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 Data | Back Directory | [Safety Statements ]
24/25 | [WGK Germany ]
WGK 3 | [HS Code ]
29337900 | [Storage Class]
11 - Combustible Solids | [Hazard Classifications]
Acute Tox. 4 Oral |
| Hazard Information | Back Directory | [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]
Antitumor agent. A potent inhibitor of dihydropyrimidine dehydrogenase (DPD) | [Uses]
Gimeracil is an antitumor agent. Gimeracil is a potent inhibitor of dihydropyrimidine dehydrogenase (DPD). | [Uses]
Gimeracil is an inhibitor of dihydropyrimidine dehydrogenase, which inhibits the early step in homologous recombination for double strand breaks repair. | [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]
Gimeracil (2.5-25 mg/kg, orally) may inhibit the rapid repair of X-ray-induced DNA damage in tumors[3].
| Animal Model: | Nude mice (Lu-99, LC-11, KB/C3 and PAN-4 tumors were xenografted)[3].
| | Dosage: | 2.5-25 mg/kg. | | Administration: | Orally. | | Result: | Exhibited anti-tumor activity. |
| [References]
1) Diasio (1999)?Clinical implications of dihydropyrimidine dehydrogenase inhibition; Oncology(Williston Park),?13?17
2) Kobayakawa and Kojima (2011),?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; Onco. Targets Ther.,?4?193
3) Sakata?et al.?(2011),?Gimeracil, an inhibitor of dihydropyrimidine dehydrogenase, inhibits the early step in homologous recombination; Cancer Sci.,?102?1712 |
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