Bioactivation and Reactivity Research Advances - 2021 Year in Review

Overview

Journal Drug Metab Rev

Publisher Informa Healthcare

Specialty Pharmacology

Date 2022 Jul 25

PMID 35876116

Authors

Klarissa D Jackson

Upendra A Argikar

Sungjoon Cho

Rachel D Crouch

James P Driscoll

Carley J S Heck

Lloyd King

Hlaing Holly Maw

Grover P Miller

Herana Kamal Seneviratne

Shuai Wang

Cong Wei

Donglu Zhang

S Cyrus Khojasteh

Affiliations

Soon will be listed here.

Abstract

This year's review on bioactivation and reactivity began as a part of the annual review on biotransformation and bioactivation led by Cyrus Khojasteh (see references). Increased contributions from experts in the field led to the development of a stand alone edition for the first time this year focused specifically on bioactivation and reactivity. Our objective for this review is to highlight and share articles which we deem influential and significant regarding the development of covalent inhibitors, mechanisms of reactive metabolite formation, enzyme inactivation, and drug safety. Based on the selected articles, we created two sections: (1) reactivity and enzyme inactivation, and (2) bioactivation mechanisms and safety (Table 1). Several biotransformation experts have contributed to this effort from academic and industry settings.[Table: see text].

References

Sernoskie S, Jee A, Uetrecht J . The Emerging Role of the Innate Immune Response in Idiosyncratic Drug Reactions. Pharmacol Rev. 2021; 73(3):861-896. DOI: 10.1124/pharmrev.120.000090. View

Baillie T, Dalvie D, Rietjens I, Khojasteh S . Biotransformation and bioactivation reactions - 2015 literature highlights. Drug Metab Rev. 2016; 48(2):113-38. DOI: 10.1080/03602532.2016.1195404. View

Wongrakpanich S, Wongrakpanich A, Melhado K, Rangaswami J . A Comprehensive Review of Non-Steroidal Anti-Inflammatory Drug Use in The Elderly. Aging Dis. 2018; 9(1):143-150. PMC: 5772852. DOI: 10.14336/AD.2017.0306. View

Lim J, Faught P, Chalasani N, Molleston J . Severe liver injury after initiating therapy with atomoxetine in two children. J Pediatr. 2006; 148(6):831-4. DOI: 10.1016/j.jpeds.2006.01.035. View

Lindberg R, Wennberg P, Johansson M, Tysklind M, Andersson B . Screening of human antibiotic substances and determination of weekly mass flows in five sewage treatment plants in Sweden. Environ Sci Technol. 2005; 39(10):3421-9. DOI: 10.1021/es048143z. View

Mulder T, Bobba S, Johnson K, Grandner J, Wang W, Zhang C . Bioactivation of ,-Unsaturated Carboxylic Acids Through Acyl Glucuronidation. Drug Metab Dispos. 2020; 48(9):819-829. DOI: 10.1124/dmd.120.000096. View

Scheible H, Dyroff M, Seithel-Keuth A, Harrison-Moench E, Mammasse N, Port A . Evobrutinib, a covalent Bruton's tyrosine kinase inhibitor: Mass balance, elimination route, and metabolism in healthy participants. Clin Transl Sci. 2021; 14(6):2420-2430. PMC: 8604242. DOI: 10.1111/cts.13108. View

Kazem S, Linssen E, Gibbs S . Skin metabolism phase I and phase II enzymes in native and reconstructed human skin: a short review. Drug Discov Today. 2019; 24(9):1899-1910. DOI: 10.1016/j.drudis.2019.06.002. View

Schleiff M, Crosby S, Blue M, Schleiff B, Boysen G, Miller G . CYP2C9 and 3A4 play opposing roles in bioactivation and detoxification of diphenylamine NSAIDs. Biochem Pharmacol. 2021; 194:114824. PMC: 8710044. DOI: 10.1016/j.bcp.2021.114824. View

10.

de Montellano P . Acetylenes: cytochrome P450 oxidation and mechanism-based enzyme inactivation. Drug Metab Rev. 2019; 51(2):162-177. PMC: 6699906. DOI: 10.1080/03602532.2019.1632891. View

11.

Hrycay E, Bandiera S . Expression, function and regulation of mouse cytochrome P450 enzymes: comparison with human P450 enzymes. Curr Drug Metab. 2010; 10(10):1151-83. DOI: 10.2174/138920009790820138. View

12.

Masubuchi Y, Yamada S, Horie T . Diphenylamine as an important structure of nonsteroidal anti-inflammatory drugs to uncouple mitochondrial oxidative phosphorylation. Biochem Pharmacol. 1999; 58(5):861-5. DOI: 10.1016/s0006-2952(99)00163-x. View

13.

Popovic M, Shenton J, Chen J, Baban A, Tharmanathan T, Mannargudi B . Nevirapine hypersensitivity. Handb Exp Pharmacol. 2009; (196):437-51. DOI: 10.1007/978-3-642-00663-0_15. View

14.

Li Z, Zhang L, Yuan Y, Yang Z . Identification of metabolites of evobrutinib in rat and human hepatocytes by using ultra-high performance liquid chromatography coupled with diode array detector and Q Exactive Orbitrap tandem mass spectrometry. Drug Test Anal. 2018; 11(1):129-139. DOI: 10.1002/dta.2477. View

15.

Buhl A, Waldon D, Baker C, Johnson G . Minoxidil sulfate is the active metabolite that stimulates hair follicles. J Invest Dermatol. 1990; 95(5):553-7. DOI: 10.1111/1523-1747.ep12504905. View

16.

Bailey M, Dickinson R . Acyl glucuronide reactivity in perspective: biological consequences. Chem Biol Interact. 2003; 145(2):117-37. DOI: 10.1016/s0009-2797(03)00020-6. View

17.

Gunduz M, Argikar U, Baeschlin D, Ferreira S, Hosagrahara V, Harriman S . Identification of a novel N-carbamoyl glucuronide: in vitro, in vivo, and mechanistic studies. Drug Metab Dispos. 2009; 38(3):361-7. DOI: 10.1124/dmd.109.030650. View

18.

Khojasteh S, Rietjens I, Dalvie D, Miller G . Biotransformation and bioactivation reactions - 2016 literature highlights. Drug Metab Rev. 2017; 49(3):285-317. DOI: 10.1080/03602532.2017.1326498. View

19.

Inami K, Okazawa M, Mochizuki M . Mutagenicity of aromatic amines and amides with chemical models for cytochrome P450 in Ames assay. Toxicol In Vitro. 2009; 23(6):986-91. DOI: 10.1016/j.tiv.2009.06.025. View

20.

Kanniah G, Kumar S . Clozapine associated cardiotoxicity: Issues, challenges and way forward. Asian J Psychiatr. 2020; 50:101950. DOI: 10.1016/j.ajp.2020.101950. View