SR-17018

SR-17018
Identifiers
	IUPAC name 5,6-dichloro-3-[1-[(4-chlorophenyl)methyl]piperidin-4-yl]-1H-benzimidazol-2-one;
CAS Number	2134602-45-0 ;
PubChem CID	130431397;
ChemSpider	67886365;
UNII	2M8P7UAW4W;
ChEMBL	ChEMBL4452384;
PDB ligand	WH9 (PDBe, RCSB PDB);
CompTox Dashboard (EPA)	DTXSID101336689 ;
Chemical and physical data
Formula	C19H18Cl3N3O
Molar mass	410.72 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES C1CN(CCC1N2C3=CC(=C(C=C3NC2=O)Cl)Cl)CC4=CC=C(C=C4)Cl;
	InChI InChI=1S/C19H18Cl3N3O/c20-13-3-1-12(2-4-13)11-24-7-5-14(6-8-24)25-18-10-16(22)15(21)9-17(18)23-19(25)26/h1-4,9-10,14H,5-8,11H2,(H,23,26); Key:LAGUDYUGRSQDKS-UHFFFAOYSA-N;

SR-17018 is a drug which acts as a biased agonist at the μ-opioid receptor, selective for activation of the G-protein signalling pathway over β-arrestin 2 recruitment.^[1] In animal studies it produces analgesic effects but with less respiratory depression and development of tolerance than conventional opioids.^[2]^[3]^[4]^[5]

References

^ Zhuang Y, Wang Y, He B, He X, Zhou XE, Guo S, et al. (November 2022). "Molecular recognition of morphine and fentanyl by the human μ-opioid receptor". Cell. 185 (23): 4361–4375.e19. doi:10.1016/j.cell.2022.09.041. PMID 36368306. S2CID 253426623.
^ Grim TW, Schmid CL, Stahl EL, Pantouli F, Ho JH, Acevedo-Canabal A, et al. (January 2020). "A G protein signaling-biased agonist at the μ-opioid receptor reverses morphine tolerance while preventing morphine withdrawal". Neuropsychopharmacology. 45 (2): 416–425. doi:10.1038/s41386-019-0491-8. PMC 6901606. PMID 31443104.
^ Azevedo Neto J, Costanzini A, De Giorgio R, Lambert DG, Ruzza C, Calò G (August 2020). "Biased versus Partial Agonism in the Search for Safer Opioid Analgesics". Molecules. 25 (17): 3870. doi:10.3390/molecules25173870. PMC 7504468. PMID 32854452.
^ Podlewska S, Bugno R, Kudla L, Bojarski AJ, Przewlocki R (October 2020). "Molecular Modeling of µ Opioid Receptor Ligands with Various Functional Properties: PZM21, SR-17018, Morphine, and Fentanyl-Simulated Interaction Patterns Confronted with Experimental Data". Molecules. 25 (20): 4636. doi:10.3390/molecules25204636. PMC 7594085. PMID 33053718.
^ Pantouli F, Grim TW, Schmid CL, Acevedo-Canabal A, Kennedy NM, Cameron MD, et al. (December 2020). "Comparison of morphine, oxycodone and the biased MOR agonist SR-17018 for tolerance and efficacy in mouse models of pain". Neuropharmacology. 185: 108439. doi:10.1016/j.neuropharm.2020.108439. PMC 7887086. PMID 33345829. S2CID 229306872.

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[pmid36368306-1] Zhuang Y, Wang Y, He B, He X, Zhou XE, Guo S, et al. (November 2022). "Molecular recognition of morphine and fentanyl by the human μ-opioid receptor". Cell. 185 (23): 4361–4375.e19. doi:10.1016/j.cell.2022.09.041. PMID 36368306. S2CID 253426623.

[2] Grim TW, Schmid CL, Stahl EL, Pantouli F, Ho JH, Acevedo-Canabal A, et al. (January 2020). "A G protein signaling-biased agonist at the μ-opioid receptor reverses morphine tolerance while preventing morphine withdrawal". Neuropsychopharmacology. 45 (2): 416–425. doi:10.1038/s41386-019-0491-8. PMC 6901606. PMID 31443104.

[3] Azevedo Neto J, Costanzini A, De Giorgio R, Lambert DG, Ruzza C, Calò G (August 2020). "Biased versus Partial Agonism in the Search for Safer Opioid Analgesics". Molecules. 25 (17): 3870. doi:10.3390/molecules25173870. PMC 7504468. PMID 32854452.

[4] Podlewska S, Bugno R, Kudla L, Bojarski AJ, Przewlocki R (October 2020). "Molecular Modeling of µ Opioid Receptor Ligands with Various Functional Properties: PZM21, SR-17018, Morphine, and Fentanyl-Simulated Interaction Patterns Confronted with Experimental Data". Molecules. 25 (20): 4636. doi:10.3390/molecules25204636. PMC 7594085. PMID 33053718.

[5] Pantouli F, Grim TW, Schmid CL, Acevedo-Canabal A, Kennedy NM, Cameron MD, et al. (December 2020). "Comparison of morphine, oxycodone and the biased MOR agonist SR-17018 for tolerance and efficacy in mouse models of pain". Neuropharmacology. 185: 108439. doi:10.1016/j.neuropharm.2020.108439. PMC 7887086. PMID 33345829. S2CID 229306872.

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Identifiers

IUPAC name 5,6-dichloro-3-[1-[(4-chlorophenyl)methyl]piperidin-4-yl]-1H-benzimidazol-2-one
CAS Number	2134602-45-0^Y
PubChem CID	130431397
ChemSpider	67886365
UNII	2M8P7UAW4W
ChEMBL	ChEMBL4452384
PDB ligand	WH9 (PDBe, RCSB PDB)
CompTox Dashboard (EPA)	DTXSID101336689
Chemical and physical data
Formula	C₁₉H₁₈Cl₃N₃O
Molar mass	410.72 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES C1CN(CCC1N2C3=CC(=C(C=C3NC2=O)Cl)Cl)CC4=CC=C(C=C4)Cl
InChI InChI=1S/C19H18Cl3N3O/c20-13-3-1-12(2-4-13)11-24-7-5-14(6-8-24)25-18-10-16(22)15(21)9-17(18)23-19(25)26/h1-4,9-10,14H,5-8,11H2,(H,23,26) Key:LAGUDYUGRSQDKS-UHFFFAOYSA-N

SR-17018

See also

References