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PMID: 18665582 Published · ppublish English Journal Article

3-(1H-tetrazol-5-yl)-1,4,5,6-tetrahydro-cyclopentapyrazole (MK-0354): a partial agonist of the nicotinic acid receptor, G-protein coupled receptor 109a, with antilipolytic but no vasodilatory activity in mice.

Journal of medicinal chemistry ·Vol. 51 ·No. 16 ·2008-08-28 ·Pages 5101-8

Semple G, Skinner PJ, Gharbaoui T, Shin YJ, Jung JK, Cherrier MC, Webb PJ, Tamura SY, Boatman PD, Sage CR, Schrader TO, Chen R, Colletti SL, Tata JR, Waters MG, Cheng K, Taggart AK, Cai TQ, Carballo-Jane E, Behan DP, Connolly DT, Richman JG

Abstract

The discovery and profiling of 3-(1H-tetrazol-5-yl)-1,4,5,6-tetrahydro-cyclopentapyrazole (5a, MK-0354), a partial agonist of GPR109a, is described. Compound 5a retained the plasma free fatty acid lowering effects in mice associated with GPR109a agonism, but did not induce vasodilation at the maximum feasible dose. Moreover, preadministration of 5a blocked the flushing effect induced by nicotinic acid but not that induced by PGD2. This profile made 5a a suitable candidate for further study for the treatment of dyslipidemia.

MeSH Terms
Adipocytes/drug effects Animals Fatty Acids, Nonesterified/blood Humans Hypolipidemic Agents/chemical synthesis,pharmacology,therapeutic use Lipolysis/drug effects Male Mice Mice, Inbred C57BL Pyrazoles/chemical synthesis,pharmacokinetics Receptors, G-Protein-Coupled/agonists Receptors, Nicotinic Tetrazoles/chemical synthesis,pharmacokinetics Vasodilation/drug effects
Chemicals
3-(1H-tetrazol-5-yl)-1,4,5,6-tetrahydrocyclopentapyrazole Fatty Acids, Nonesterified HCAR2 protein, human HCAR3 protein, human Hypolipidemic Agents Pyrazoles Receptors, G-Protein-Coupled Receptors, Nicotinic Tetrazoles
Authors & Affiliations
22 authors, click to expand affiliations / ORCID
Semple Graeme
Department of Medicinal Chemistry, Arena Pharmaceuticals, 6166 Nancy Ridge Drive, San Diego, California 92121, USA. gsemple@arenapharm.com
Skinner Philip J
Gharbaoui Tawfik
Shin Young-Jun
Jung Jae-Kyu
Cherrier Martin C
Webb Peter J
Tamura Susan Y
Boatman P Douglas
Sage Carleton R
Schrader Thomas O
Chen Ruoping
Colletti Steven L
Tata James R
Waters M Gerard
Cheng Kang
Taggart Andrew K
Cai Tian-Quan
Carballo-Jane Ester
Behan Dominic P
Connolly Daniel T
Richman Jeremy G
Article Info
Journal
Journal of medicinal chemistry
Abbr.
J Med Chem
ISSN
1520-4804
Published
2008-08-28
Epub
2008-00-30
Pages
5101-8
Language
English
Region
United States
NLM ID
9716531
Subset
IM
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