Rutecarpine Explained

Rutecarpine or rutaecarpine is a COX-2 inhibitor isolated from Tetradium ruticarpum, a tree native to China.[1] It is classified as a non-basic alkaloid.[2]

In contrast to synthetic COX-2 inhibitors like etoricoxib and celecoxib, rutecarpine does not appear to cause negative effects on the cardiovascular system.[3]

Metabolism

Microsome studies suggest that rutaecarpine may be at least a weak inhibitor of CYP1A2, CYP2C9, CYP2C19, CYP2E1, and CYP3A4 enzymes.[4] [5] At the same time, it is believed to be a strong inducer of CYP1A2 and CYP1A1.[6]

Rutecarpine metabolism is complex and proceeds along several routes, primarily involving the addition of a single hydroxyl group by CYP3A4. Six monohydroxylated and four dihydroxylated metabolites have been identified. To a much lesser extent, rutecarpine may be metabolized by CYP2C9 and CYP1A2, according to liver microsome studies.[7]

Supplementation

Rutecarpine has been shown to decrease the overall bioavailability of caffeine in rats by up to 80 percent,[8] likely through induction of enzymes CYP1A2 and CYP2E1.[9]

Notes and References

  1. Moon . T. C. . Murakami . M. . Kudo . I. . Son . K. H. . Kim . H. P. . Kang . S. S. . Chang . H. W. . 1999 . A new class of COX-2 inhibitor, rutaecarpine from Evodia rutaecarpa . Inflammation Research . 48 . 12 . 621–625 . 10.1007/s000110050512 . 10669112 . 19555209.
  2. Book: Manske, R. H. F. . 1950 . Sources of alkaloids and their isolation . Manske . R. H. F. . Holmes . H. L. . The Alkaloids: Chemistry and Physiology . 1 . Academic Press . 1–14 . 10.1016/S1876-0813(08)60184-0 . 978-0-12-469501-6 . 82529003.
  3. Jia . Sujie . Hu . Changping . 2010 . Pharmacological effects of rutaecarpine as a cardiovascular protective agent . doi . Molecules . 15 . 3 . 1873–1881 . 10.3390/molecules15031873 . free . 6257227 . 20336017 . 21968872 . free.
  4. Zhang . Fang-Liang . He . Xin . Zhai . Yi-Ran . He . Li-Na . Zhang . Si-Chao . Wang . Li-Li . Yang . Ai-Hong . An . Li-Jun . Mechanism-based inhibition of CYPs and RMs-induced hepatoxicity by rutaecarpine . Xenobiotica . 2 November 2015 . 45 . 11 . 978–989 . 10.3109/00498254.2015.1038742. 26053557 . 6293291 .
  5. Ueng . Yune-Fang . Jan . Woan-Ching . Lin . Lie-Chwen . Chen . Ta-Liang . Guengerich . F. Peter . Chen . Chieh-Fu . The Alkaloid Rutaecarpine Is a Selective Inhibitor of Cytochrome P450 1A in Mouse and Human Liver Microsomes . Drug Metabolism and Disposition . 1 March 2002 . 30 . 3 . 349–353 . 10.1124/dmd.30.3.349. 11854157 .
  6. Ueng . Yune-Fang . Wang . Jong-Jing . Lin . Lie-Chwen . Park . Sang Shin . Chen . Chieh-Fu . Induction of cytochrome P450-dependent monooxygenase in mouse liver and kidney by rutaecarpine, an alkaloid of the herbal drug Evodia rutaecarpa . Life Sciences . November 2001 . 70 . 2 . 207–217 . 10.1016/S0024-3205(01)01390-X. 11787945 .
  7. Lee . Seung . Son . Jong-Keun . Jeong . Byeong . Jeong . Tae-Cheon . Chang . Hyeon . Lee . Eung-Seok . Jahng . Yurngdong . Progress in the Studies on Rutaecarpine . Molecules . 6 February 2008 . 13 . 2 . 272–300 . 10.3390/molecules13020272. 18305418 . 6245441 . free .
  8. Estari . Rohit Kumar . Dong . Jin . Chan . William K. . Park . Miki Susanto . Zhou . Zhu . Time effect of rutaecarpine on caffeine pharmacokinetics in rats . Biochemistry and Biophysics Reports . 1 December 2021 . 28 . 101121 . 10.1016/j.bbrep.2021.101121. 34527815 . 8429912 . free .
  9. Noh . Keumhan . Seo . Young Min . Lee . Sang Kyu . Bista . Sudeep R. . Kang . Mi Jeong . Jahng . Yurngdong . Kim . Eunyoung . Kang . Wonku . Jeong . Tae Cheon . Effects of rutaecarpine on the metabolism and urinary excretion of caffeine in rats . Archives of Pharmacal Research . January 2011 . 34 . 1 . 119–125 . 10.1007/s12272-011-0114-3. 21468923 . 44752343 .

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