Safotibant

Safotibant

Names
IUPAC name N-[[4-(4,5-Dihydro-1H-imidazol-2-yl)phenyl]methyl]-2-[2-[[(4-methoxy-2,6-dimethylphenyl) sulfonyl]methylamino]ethoxy]-N-methylacetamide
Identifiers
CAS Number	633698-99-4
3D model (Jmol)	Interactive image
ChemSpider	10127675
PubChem	11953367
InChI InChI=1S/C25H34N4O5S/c1-18-14-22(33-5)15-19(2)24(18)35(31,32)29(4)12-13-34-17-23(30)28(3)16-20-6-8-21(9-7-20)25-26-10-11-27-25/h6-9,14-15H,10-13,16-17H2,1-5H3,(H,26,27) Key: AMTQCENHQIDBHQ-UHFFFAOYSA-N InChI=1/C25H34N4O5S/c1-18-14-22(33-5)15-19(2)24(18)35(31,32)29(4)12-13-34-17-23(30)28(3)16-20-6-8-21(9-7-20)25-26-10-11-27-25/h6-9,14-15H,10-13,16-17H2,1-5H3,(H,26,27) Key: AMTQCENHQIDBHQ-UHFFFAOYAH
SMILES Cc1cc(cc(c1S(=O)(=O)N(C)CCOCC(=O)N(C)Cc2ccc(cc2)C3=NCCN3)C)OC
Properties
Chemical formula	C25H34N4O5S
Molar mass	502.63 g·mol^−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Safotibant (INN^[1]) also known by the research code LF22-0542 is a non-peptide bradykinin B₁ antagonist. It displayed binding Ki values of 0.35 and 6.5 nM at cloned human and mouse B₁ receptors, respectively, while having no affinity for either human, mouse, or rat B₂ receptors at concentrations up to 10 μM. This means that LF22-0542 is at least 4000 times selective for the B₁ receptor over the B₂ receptor. Systemic administration of LF22-0542 inhibited acute pain induced by acetic acid, formalin, and a hot plate. It also reversed acute inflammatory pain induced by carrageenan, and persistent inflammatory pain induced by CFA. In a neuropathic pain model, LF22-0542 reversed the thermal hyperalgesia, but not the mechanical hyperalgesia.^[2]

References

1. "Safotibant INN". Mednet. Retrieved 31 March 2016.
2. Porreca, Frank (July 2006). "Antinociceptive Pharmacology of N-[[4-(4,5-Dihydro-1H-imidazol-2-yl)phenyl]methyl]-2-[2-[[(4-methoxy-2,6-dimethylphenyl)sulfonyl]methylamino]ethoxy]-N-methylacetamide, Fumarate (LF22-0542), a Novel Nonpeptidic Bradykinin B1 Receptor Antagonist". The Journal of Pharmacology and Experimental Therapeutics. 318 (1): 195–205. doi:10.1124/jpet.105.098368. PMID 16565167.