75523-11-4 Usage
Description
Indomethacin Acyl-β-D-glucuronide is a metabolite of Indomethacin, a nonsteroidal anti-inflammatory drug (NSAID) commonly used for pain relief, reducing inflammation, and lowering fever. It is formed through the glucuronidation process, where a glucuronic acid molecule is attached to the parent drug, facilitating its elimination from the body. Acyl glucuronides, including Indomethacin Acyl-β-D-glucuronide, have been associated with the toxicity of various xenobiotics and marketed drugs.
Uses
Used in Pharmaceutical Industry:
Indomethacin Acyl-β-D-glucuronide is used as a research compound for understanding the metabolism and toxicity of Indomethacin and other NSAIDs. Its study helps in the development of safer and more effective drugs with reduced side effects.
Used in Toxicology Research:
Indomethacin Acyl-β-D-glucuronide is utilized as a model compound in toxicology research to investigate the role of acyl glucuronides in the adverse effects of certain drugs. This research aids in the identification of potential drug-drug interactions and the development of strategies to mitigate toxicity.
Used in Drug Metabolism Studies:
Indomethacin Acyl-β-D-glucuronide serves as a valuable tool in drug metabolism studies, providing insights into the glucuronidation pathway and its impact on drug efficacy and safety. This knowledge is crucial for the optimization of drug dosing regimens and the design of prodrugs with improved pharmacokinetic properties.
Check Digit Verification of cas no
The CAS Registry Mumber 75523-11-4 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 7,5,5,2 and 3 respectively; the second part has 2 digits, 1 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 75523-11:
(7*7)+(6*5)+(5*5)+(4*2)+(3*3)+(2*1)+(1*1)=124
124 % 10 = 4
So 75523-11-4 is a valid CAS Registry Number.
InChI:InChI=1/C25H24ClNO10/c1-11-15(10-18(28)36-25-21(31)19(29)20(30)22(37-25)24(33)34)16-9-14(35-2)7-8-17(16)27(11)23(32)12-3-5-13(26)6-4-12/h3-9,19-22,25,29-31H,10H2,1-2H3,(H,33,34)/t19-,20-,21-,22?,25+/m1/s1
75523-11-4Relevant articles and documents
Comparative in vitro metabolism of phospho-tyrosol-indomethacin by mice, rats and humans
Xie, Gang,Zhou, Dingying,Cheng, Ka-Wing,Wong, Chi C.,Rigas, Basil
, p. 1195 - 1202 (2013/05/22)
Phospho-tyrosol-indomethacin (PTI; MPI 621), a novel anti-cancer agent, is more potent and safer than conventional indomethacin. Here, we show that PTI was extensively metabolized in vitro and in vivo. PTI was rapidly hydrolyzed by carboxylesterases to generate indomethacin as its major metabolite in the liver microsomes and rats. PTI additionally undergoes cytochromes P450 (CYP)-mediated hydroxylation at its tyrosol moiety and O-demethylation at its indomethacin moiety. Of the five major human CYPs, CYP3A4 and CYP2D6 catalyze the hydroxylation and O-demethylation reactions of PTI, respectively; whereas CYP1A2, 2C9 and 2C19 are inactive towards PTI. In contrast to PTI, indomethacin is primarily O-demethylated by CYP2C9, which prefers acidic substrates. The hydrolyzed and O-demethylated metabolites of PTI are further glucuronidated and sulfated, facilitating drug elimination and detoxification. We observed substantial inter-species differences in the metabolic rates of PTI. Among the liver microsomes from various species, PTI was the most rapidly hydrolyzed, hydroxylated and O-demethylated in mouse, human and rat liver microsomes, respectively. These results reflect the differential expression patterns of carboxylesterase and CYP isoforms among these species. Of the human microsomes from various tissues, PTI underwent more rapid carboxylesterase- and CYP-catalyzed reactions in liver and intestine microsomes than in kidney and lung microsomes. Together, our results establish the metabolic pathways of PTI, reveal significant inter-species differences in its metabolism, and provide insights into the underlying biochemical mechanisms.
