Rutecarpine

COX-2 inhibitor compound From Wikipedia, the free encyclopedia

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]

Quick facts Names, Identifiers ...
Rutecarpine
Names
Preferred IUPAC name
8,13-Hydroindolo[2′,3′:3,4]pyrido[2,1-b]quinazolin-5(7H)-one
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.163.752 Edit this at Wikidata
EC Number
  • 635-907-6
KEGG
UNII
  • InChI=1S/C18H13N3O/c22-18-13-6-2-4-8-15(13)20-17-16-12(9-10-21(17)18)11-5-1-3-7-14(11)19-16/h1-8,19H,9-10H2
    Key: ACVGWSKVRYFWRP-UHFFFAOYSA-N
  • InChI=1/C18H13N3O/c22-18-13-6-2-4-8-15(13)20-17-16-12(9-10-21(17)18)11-5-1-3-7-14(11)19-16/h1-8,19H,9-10H2
    Key: ACVGWSKVRYFWRP-UHFFFAOYAZ
  • C1CN2C(=NC3=CC=CC=C3C2=O)C4=C1C5=CC=CC=C5N4
Properties
C18H13N3O
Molar mass 287.322 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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]

References

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