Gimeracil
Synonym(s):5-chloro-4-hydroxypyridin-2(1H)-one;5-Chloropyridine-2,4-diol;CDHP;Gimestat
- CAS NO.:103766-25-2
- Empirical Formula: C5H4ClNO2
- Molecular Weight: 145.54
- MDL number: MFCD08458352
- EINECS: 1312995-182-4
- SAFETY DATA SHEET (SDS)
- Update Date: 2024-10-31 20:01:59
What is Gimeracil?
Absorption
Mean 5-FU maximum plasma concentration (Cmax) and area under the concentration-time curve (AUC) values were approximately 3-fold higher after Teysuno administration than after administration of tegafur alone, despite a 16-fold lower Teysuno dose (50 mg of tegafur) compared to tegafur alone (800 mg), and are attributed to inhibition of DPD by gimeracil. Maximum plasma uracil concentration was observed at 4 hours, with a return to baseline levels within approximately 48 hours after dosing, indicating the reversibility of the DPD inhibition by gimeracil.
After administration of a single dose of 50 mg Teysuno (expressed as tegafur content), median Tmax for Teysuno components tegafur, gimeracil, and oteracil was 0.5, 1.0, and 2.0 hours, respectively .
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
The Uses of Gimeracil
Gimeracil is an inhibitor of dihydropyrimidine dehydrogenase, which inhibits the early step in homologous recombination for double strand breaks repair.
The Uses of Gimeracil
Antitumor agent. A potent inhibitor of dihydropyrimidine dehydrogenase (DPD)
The Uses of Gimeracil
Gimeracil is an antitumor agent. Gimeracil is a potent inhibitor of dihydropyrimidine dehydrogenase (DPD).
What are the applications of Application
Gimeracil is a potent inhibitor of dihydropyrimidine dehydrogenase (DPD)
Background
Gimeracil is an adjunct to antineoplastic therapy, used to increase the concentration and effect of the main active componets within chemotherapy regimens. Approved by the European Medicines Agency (EMA) in March 2011, Gimeracil is available in combination with Oteracil and Tegafur within the commercially available product "Teysuno". The main active ingredient in Teysuno is Tegafur, a pro-drug of Fluorouracil (5-FU), which is a cytotoxic anti-metabolite drug that acts on rapidly dividing cancer cells. By mimicking a class of compounds called "pyrimidines" that are essential components of RNA and DNA, 5-FU is able to insert itself into strands of DNA and RNA, thereby halting the replication process necessary for continued cancer growth.
Gimeracil's main role within Teysuno is to prevent the breakdown of Fluorouracil (5-FU), which helps to maintin high enough concentrations for sustained effect against cancer cells . It functions by reversibly and selectively blocking the enzyme dihydropyrimidine dehydrogenase (DPD), which is involved in the degradation of 5-FU . This allows higher concentrations of 5-FU to be achieved with a lower dose of tegafur, thereby also reducing toxic side effects.
Indications
Gimeracil is used as an adjunct to antineoplastic therapy. When used within the product Teysuno, gimeracil is indicated for the treatment of adults with advanced gastric (stomach) cancer when given in combination with cisplatin.
Definition
ChEBI: Gimeracil is an organic molecular entity.
Metabolism
Not Available
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
Properties of Gimeracil
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 |
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. |
CAS DataBase Reference | 103766-25-2(CAS DataBase Reference) |
Safety information for Gimeracil
Signal word | Warning |
Pictogram(s) |
Exclamation Mark Irritant GHS07 |
GHS Hazard Statements |
H302:Acute toxicity,oral |
Precautionary Statement Codes |
P264:Wash hands thoroughly after handling. P264:Wash skin thouroughly after handling. P270:Do not eat, drink or smoke when using this product. P301+P312:IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell. P501:Dispose of contents/container to..… |
Computed Descriptors for Gimeracil
InChIKey | ZPLQIPFOCGIIHV-UHFFFAOYSA-N |
Abamectin manufacturer
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