belnacasan   

GtoPdb Ligand ID: 9035

Synonyms: HMR3480 | VX-765
Compound class: Synthetic organic
Comment: Belnacasan is a prodrug of VRT-043198, a caspase-1 inhibitor that was developed by Vertex. Pharmacological inhibition of caspase-1 is being investigated as a mechanism to reduce pro-inflammatory cytokine (predominantly IL-1β) production as a novel treatment of inflammatory diseases [1]. Inhibition of caspase-1 is a small molecule strategy developed as an alternative to the use of anti-IL-1β neutralising antibodies, such as canakinumab, or the dimeric fusion protein rilonacept that acts as a IL-1 trap.
2D Structure
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Physico-chemical Properties
Hydrogen bond acceptors 10
Hydrogen bond donors 3
Rotatable bonds 11
Topological polar surface area 140.06
Molecular weight 508.21
XLogP 2
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
Canonical SMILES CCOC1OC(=O)CC1NC(=O)C1CCCN1C(=O)C(C(C)(C)C)NC(=O)c1ccc(c(c1)Cl)N
Isomeric SMILES CCO[C@@H]1OC(=O)C[C@@H]1NC(=O)[C@@H]1CCCN1C(=O)[C@H](C(C)(C)C)NC(=O)c1ccc(c(c1)Cl)N
InChI InChI=1S/C24H33ClN4O6/c1-5-34-23-16(12-18(30)35-23)27-21(32)17-7-6-10-29(17)22(33)19(24(2,3)4)28-20(31)13-8-9-15(26)14(25)11-13/h8-9,11,16-17,19,23H,5-7,10,12,26H2,1-4H3,(H,27,32)(H,28,31)/t16-,17-,19+,23+/m0/s1
InChI Key SJDDOCKBXFJEJB-MOKWFATOSA-N
Classification
Compound class Synthetic organic
Is prodrug? Yes
Active form VRT-043198
IUPAC Name
(2S)-1-[(2S)-2-[(4-amino-3-chlorobenzoyl)amino]-3,3-dimethylbutanoyl]-N-[(2R,3S)-2-ethoxy-5-oxooxolan-3-yl]pyrrolidine-2-carboxamide
Synonyms
HMR3480 | VX-765
Database Links
GtoPdb PubChem SID 315661120
PubChem CID 11398092
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