KSC-12-192: Difference between revisions

KSC-12-192
Clinical data
Other names	"probe 1.1"
ATC code	None;
Identifiers
	IUPAC name 2-[4-(furan-2-ylmethyl)-5-[[4-methyl-3-(trifluoromethyl)phenyl]methylsulfanyl]-1,2,4-triazol-3-yl]pyridine;
PubChem CID	46245518;
ChemSpider	58145205;
ChEMBL	ChEMBL4458783;
Chemical and physical data
Formula	C21H17F3N4OS
Molar mass	430.45 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CC1=C(C=C(C=C1)CSC2=NN=C(N2CC3=CC=CO3)C4=CC=CC=N4)C(F)(F)F;
	InChI InChI=1S/C21H17F3N4OS/c1-14-7-8-15(11-17(14)21(22,23)24)13-30-20-27-26-19(18-6-2-3-9-25-18)28(20)12-16-5-4-10-29-16/h2-11H,12-13H2,1H3; Key:OQJGZGAYSCWFCK-UHFFFAOYSA-N;

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Revision as of 08:38, 21 March 2023

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KSC-12-192 is a drug that is used in scientific research to study the κ-opioid receptor, where it acts as a biased agonist.^[1]

KSC-12-192 preferentially activates G-protein coupling over β-arrestin 2 recruitment in vitro, an intrinsic activity shared with many other KOR ligands developed to separate KOR-mediated analgesia from accompanying dysphoria.

Compared with most of the known KOR G-protein biased agonists, KSC-12-192 and its parent compound ML138 have no stereoisomers.

	X	R₁	R₂	R₃
KSC-12-192	O	H	CH₃	CF₃
ML138	O	H	Cl	Cl
KUC103903N	S	H	Cl	Cl

References

^ Zhou, Lei; Lovell, Kimberly M.; Frankowski, Kevin J.; Slauson, Stephen R.; Phillips, Angela M.; Streicher, John M.; Stahl, Edward; Schmid, Cullen L.; Hodder, Peter; Madoux, Franck; Cameron, Michael D.; Prisinzano, Thomas E.; Aubé, Jeffrey; Bohn, Laura M. (2013-12-20). "Development of functionally selective, small molecule agonists at kappa opioid receptors". The Journal of Biological Chemistry. 288 (51): 36703–36716. doi:10.1074/jbc.M113.504381. ISSN 1083-351X. PMC 3868780. PMID 24187130.{{cite journal}}: CS1 maint: unflagged free DOI (link)

[1] Zhou, Lei; Lovell, Kimberly M.; Frankowski, Kevin J.; Slauson, Stephen R.; Phillips, Angela M.; Streicher, John M.; Stahl, Edward; Schmid, Cullen L.; Hodder, Peter; Madoux, Franck; Cameron, Michael D.; Prisinzano, Thomas E.; Aubé, Jeffrey; Bohn, Laura M. (2013-12-20). "Development of functionally selective, small molecule agonists at kappa opioid receptors". The Journal of Biological Chemistry. 288 (51): 36703–36716. doi:10.1074/jbc.M113.504381. ISSN 1083-351X. PMC 3868780. PMID 24187130.{{cite journal}}: CS1 maint: unflagged free DOI (link)

[1]

@@ Line 29: / Line 29: @@
 Compared with most of the known KOR G-protein biased agonists, KSC-12-192 and its parent compound [[ML138]] have no [[Stereoisomerism|stereoisomers]].
-[[File:KSC-12-192 common scaffold.png|left|frameless]]
+[[File:KSC-12-192_common_scaffold.png|frameless|274x274px]]
-{| class="wikitable" style=""
+{| class="wikitable" style="display:inline-table;text-align:right;"
 |-
 ! !! X !! R<sub>1</sub> !! R<sub>2</sub> !!  R<sub>3</sub>