MRI-1867   

GtoPdb Ligand ID: 10521

Synonyms: (-)-MRI-1867 | MRI1867
Compound class: Synthetic organic
Comment: MRI-1867 is a hybrid molecule that acts both as an inverse agonist of peripheral cannabinoid receptor 1 (CB1) and as an inhibitor of inducible nitric oxide synthase (iNOS) [1]. It is orally active, and the (S)-enantiomer is the more active form of the molecule. MRI-1867 was initially shown to exhibit anti-fibrotic activity in mouse models of liver fibrosis [1] and it has subsequently been demonstrated to reduce signs of inflammation, fibrosis, oxidative stress and overall renal injury in a mouse model of obesity-induced chronic kidney disease [2]. The therapeutic effect of MRI-1867 is two-fold; it both reduces fibrotic progression and is able to attenuate established fibrosis. Activities at both of its molecular targets are involved in mediating its in vivo efficacy.
2D Structure
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Physico-chemical Properties
Hydrogen bond acceptors 7
Hydrogen bond donors 1
Rotatable bonds 6
Topological polar surface area 108.86
Molecular weight 513.08
XLogP 5.32
No. Lipinski's rules broken 1
SMILES / InChI / InChIKey
Canonical SMILES Clc1ccc(cc1)C1=NN(CC1c1ccccc1)C(=NS(=O)(=O)c1ccc(cc1)Cl)N=C(N)C
Isomeric SMILES Clc1ccc(cc1)C1=NN(C[C@@H]1c1ccccc1)/C(=N/S(=O)(=O)c1ccc(cc1)Cl)/N=C(\N)/C
InChI InChI=1S/C24H21Cl2N5O2S/c1-16(27)28-24(30-34(32,33)21-13-11-20(26)12-14-21)31-15-22(17-5-3-2-4-6-17)23(29-31)18-7-9-19(25)10-8-18/h2-14,22H,15H2,1H3,(H2,27,28,30)/t22-/m1/s1
InChI Key GZPQTZIUWCQXCF-JOCHJYFZSA-N
Classification
Compound class Synthetic organic
IUPAC Name
(4S)-N-(1-aminoethylidene)-5-(4-chlorophenyl)-N'-(4-chlorophenyl)sulfonyl-4-phenyl-3,4-dihydropyrazole-2-carboximidamide
Synonyms
(-)-MRI-1867 | MRI1867
Database Links
GtoPdb PubChem SID 387065603
PubChem CID 132937648
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