WARNING: This product is for research use only, not for human or veterinary use.
MedKoo CAT#: 206066
CAS#: 103766-25-2
Description: Gimeracil is a pyridine derivative with antitumor activity. Gimeracil enhances the antitumor activity of fluoropyrimidines by competitively and reversibly inhibiting the enzyme dihydropyrimidine dehydrogenase causing decreased degradation of the fluoropyrimidines. Check for active clinical trials or closed clinical trials using this agent. (NCI Thesaurus).
MedKoo Cat#: 206066
Name: Gimeracil
CAS#: 103766-25-2
Chemical Formula: C5H4ClNO2
Exact Mass: 144.99306
Molecular Weight: 145.542
Elemental Analysis: C, 41.26; H, 2.77; Cl, 24.36; N, 9.62; O, 21.99
Synonym: Gimeracil; chlorodihydroxypyridine. Abbreviation: CDHP.
IUPAC/Chemical Name: 5-chloro-2-hydroxypyridin-4(1H)-one
InChi Key: ZPLQIPFOCGIIHV-UHFFFAOYSA-N
InChi Code: InChI=1S/C5H4ClNO2/c6-3-2-7-5(9)1-4(3)8/h1-2H,(H2,7,8,9)
SMILES Code: O=C1C=C(O)NC=C1Cl
Appearance: Solid powder
Purity: >98% (or refer to the Certificate of Analysis)
Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility: Soluble in DMSO, not in water
Shelf Life: >5 years if stored properly
Drug Formulation: This drug may be formulated in DMSO
Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code: 2934.99.9001
| Biological target: | Gimeracil, a component of an oral fluoropyrimidine derivative S-1, inhibits DNA DSB repair and is a potent inhibitor of DPYD (dihydropyrimidine dehydrogenase, DPD). |
| In vitro activity: | Results of gamma-H2AX focus assay indicated that 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. Reference: Radiother Oncol. 2010 Aug;96(2):259-66. https://pubmed.ncbi.nlm.nih.gov/20584556/ |
| In vivo activity: | These experiments demonstrated that gimeracil enhanced the efficacy of X-ray irradiation against lung as well as head and neck cancer xenografts in a dose-dependent manner. Furthermore, this study observed decreased expression of γ-H2AX protein, a marker of DNA repair, in LC-11 tumors treated with X-ray irradiation and gimeracil compared to that observed in tumors treated with X-ray irradiation alone, suggesting that gimeracil may inhibit rapid repair of X-ray-induced DNA damage in tumors. Reference: Oncol Rep. 2010 Nov;24(5):1307-13. https://pubmed.ncbi.nlm.nih.gov/20878125/ |
| Solvent | Max Conc. mg/mL | Max Conc. mM | |
|---|---|---|---|
| Solubility | |||
| DMF | 20.0 | 137.42 | |
| DMSO | 51.33 | 352.7 | |
| DMSO:PBS (pH 7.2) (1:1) | 0.5 | 3.44 | |
| Ethanol | 0.1 | 0.69 |
The following data is based on the product molecular weight 145.542 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass | 1 mg | 5 mg | 10 mg |
|---|---|---|---|
| 1 mM | 1.15 mL | 5.76 mL | 11.51 mL |
| 5 mM | 0.23 mL | 1.15 mL | 2.3 mL |
| 10 mM | 0.12 mL | 0.58 mL | 1.15 mL |
| 50 mM | 0.02 mL | 0.12 mL | 0.23 mL |
| Formulation protocol: | 1. Sakata K, Someya M, Matsumoto Y, Tauchi H, Kai M, Toyota M, Takagi M, Hareyama M, Fukushima M. Gimeracil, an inhibitor of dihydropyrimidine dehydrogenase, inhibits the early step in homologous recombination. Cancer Sci. 2011 Sep;102(9):1712-6. doi: 10.1111/j.1349-7006.2011.02004.x. Epub 2011 Jul 21. PMID: 21668582. 2. Takagi M, Sakata K, Someya M, Tauchi H, Iijima K, Matsumoto Y, Torigoe T, Takahashi A, Hareyama M, Fukushima M. Gimeracil sensitizes cells to radiation via inhibition of homologous recombination. Radiother Oncol. 2010 Aug;96(2):259-66. doi: 10.1016/j.radonc.2010.05.020. Epub 2010 Jun 26. PMID: 20584556. 3. Fukushima M, Sakamoto K, Sakata M, Nakagawa F, Saito H, Sakata Y. Gimeracil, a component of S-1, may enhance the antitumor activity of X-ray irradiation in human cancer xenograft models in vivo. Oncol Rep. 2010 Nov;24(5):1307-13. doi: 10.3892/or_00000987. PMID: 20878125. |
| In vitro protocol: | 1. Sakata K, Someya M, Matsumoto Y, Tauchi H, Kai M, Toyota M, Takagi M, Hareyama M, Fukushima M. Gimeracil, an inhibitor of dihydropyrimidine dehydrogenase, inhibits the early step in homologous recombination. Cancer Sci. 2011 Sep;102(9):1712-6. doi: 10.1111/j.1349-7006.2011.02004.x. Epub 2011 Jul 21. PMID: 21668582. 2. Takagi M, Sakata K, Someya M, Tauchi H, Iijima K, Matsumoto Y, Torigoe T, Takahashi A, Hareyama M, Fukushima M. Gimeracil sensitizes cells to radiation via inhibition of homologous recombination. Radiother Oncol. 2010 Aug;96(2):259-66. doi: 10.1016/j.radonc.2010.05.020. Epub 2010 Jun 26. PMID: 20584556. |
| In vivo protocol: | 1. Fukushima M, Sakamoto K, Sakata M, Nakagawa F, Saito H, Sakata Y. Gimeracil, a component of S-1, may enhance the antitumor activity of X-ray irradiation in human cancer xenograft models in vivo. Oncol Rep. 2010 Nov;24(5):1307-13. doi: 10.3892/or_00000987. PMID: 20878125. |
1: Otsuka H, Fujii T, Toh U, Iwakuma N, Takahashi R, Mishima M, Takenaka M, Kakuma T, Tanaka M, Shirouzu K. Phase II clinical trial of metronomic chemotherapy with combined irinotecan and tegafur-gimeracil-oteracil potassium in metastatic and recurrent breast cancer. Breast Cancer. 2013 Jul 5. [Epub ahead of print] PubMed PMID: 23827973.
2: Tegafur + gimeracil + oteracil. Just another fluorouracil precursor. Prescrire Int. 2013 May;22(138):122. PubMed PMID: 23819172.
3: Meng C, Chen X, Luo Z. [Inhibitive effect of celecoxib combined with tegafur gimeracil oteracil potassium on the growth of xenograft tumor of gastric cancer in nude mice]. Xi Bao Yu Fen Zi Mian Yi Xue Za Zhi. 2013 May;29(5):458-61. Chinese. PubMed PMID: 23643260.
4: Yamamoto Y, Nakai N, Wakabayashi Y, Okuzawa Y, Asai J, Takenaka H, Katoh N. A case of advanced cutaneous squamous cell carcinoma of the lower eyelid that was successfully treated with tegafur-gimeracil-oteracil potassium monotherapy. J Am Acad Dermatol. 2012 Nov;67(5):e233-4. doi: 10.1016/j.jaad.2012.04.038. PubMed PMID: 23062933.
5: Takagi M, Sakata K, Someya M, Matsumoto Y, Tauchi H, Hareyama M, Fukushima M. The combination of hyperthermia or chemotherapy with gimeracil for effective radiosensitization. Strahlenther Onkol. 2012 Mar;188(3):255-61. doi: 10.1007/s00066-011-0043-6. Epub 2012 Feb 11. PubMed PMID: 22322869.
6: Kawahara H, Watanabe K, Ushigome T, Noaki R, Kobayashi S, Yanaga K. Feasibility study of adjuvant chemotherapy with S-1 (TS-1; tegafur, gimeracil and oteracil potassium) for colorectal cancer. Hepatogastroenterology. 2012 Jan-Feb;59(113):134-7. doi: 10.5754/hge09684. PubMed PMID: 22251528.
7: Kobayakawa M, Kojima Y. 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. 2011;4:193-201. doi: 10.2147/OTT.S19059. Epub 2011 Nov 15. PubMed PMID: 22162925; PubMed Central PMCID: PMC3233278.
8: Matt P, van Zwieten-Boot B, Calvo Rojas G, Ter Hofstede H, Garcia-Carbonero R, Camarero J, Abadie E, Pignatti F. The European Medicines Agency review of Tegafur/Gimeracil/Oteracil (Teysuno™) for the treatment of advanced gastric cancer when given in combination with cisplatin: summary of the Scientific Assessment of the Committee for medicinal products for human use (CHMP). Oncologist. 2011;16(10):1451-7. doi: 10.1634/theoncologist.2011-0224. Epub 2011 Sep 30. Review. PubMed PMID: 21963999; PubMed Central PMCID: PMC3228070.
9: Sakata K, Someya M, Matsumoto Y, Tauchi H, Kai M, Toyota M, Takagi M, Hareyama M, Fukushima M. Gimeracil, an inhibitor of dihydropyrimidine dehydrogenase, inhibits the early step in homologous recombination. Cancer Sci. 2011 Sep;102(9):1712-6. doi: 10.1111/j.1349-7006.2011.02004.x. Epub 2011 Jul 21. PubMed PMID: 21668582.
10: Fukushima M, Sakamoto K, Sakata M, Nakagawa F, Saito H, Sakata Y. Gimeracil, a component of S-1, may enhance the antitumor activity of X-ray irradiation in human cancer xenograft models in vivo. Oncol Rep. 2010 Nov;24(5):1307-13. PubMed PMID: 20878125.
