reparixin   Click here for help

GtoPdb Ligand ID: 8498

Synonyms: DF 1681Y | repertaxin
Immunopharmacology Ligand
Compound class: Synthetic organic
Comment: Reparixin is an orally bioavailable compound that has been explored for potential to disrupt IL-8/CXCR1/2 signalling in cancer and transplant indications. It negatively modulates CXCR1 and CXCR2 dependent functions [1], but without inhibiting chemokine binding to either receptor. Direct binding to CXCR1 has only been indicated by molecular modelling, so the mechanism of action of this molecule remains to be fully resolved.
Click here for help
2D Structure
Click here for help
Click here for structure editor
Physico-chemical Properties
Click here for help
Hydrogen bond acceptors 4
Hydrogen bond donors 1
Rotatable bonds 6
Topological polar surface area 71.62
Molecular weight 283.12
XLogP 3.02
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
Click here for help
Canonical SMILES CC(Cc1ccc(cc1)C(C(=O)NS(=O)(=O)C)C)C
Isomeric SMILES CC(Cc1ccc(cc1)[C@H](C(=O)NS(=O)(=O)C)C)C
InChI InChI=1S/C14H21NO3S/c1-10(2)9-12-5-7-13(8-6-12)11(3)14(16)15-19(4,17)18/h5-8,10-11H,9H2,1-4H3,(H,15,16)/t11-/m1/s1
InChI Key KQDRVXQXKZXMHP-LLVKDONJSA-N
Classification Click here for help
Compound class Synthetic organic
IUPAC Name Click here for help
(2R)-2-[4-(2-methylpropyl)phenyl]-N-methylsulfonylpropanamide
International Nonproprietary Names Click here for help
INN number INN
8224 reparixin
Synonyms Click here for help
DF 1681Y | repertaxin
Database Links Click here for help
CAS Registry No. 266359-83-5
ChEMBL Ligand CHEMBL191413
GtoPdb PubChem SID 252166706
PubChem CID 9838712
Search Google for chemical match using the InChIKey KQDRVXQXKZXMHP-LLVKDONJSA-N
Search Google for chemicals with the same backbone KQDRVXQXKZXMHP
Search PubMed clinical trials reparixin
Search PubMed titles reparixin
Search PubMed titles/abstracts reparixin
Search UniChem for chemical match using the InChIKey KQDRVXQXKZXMHP-LLVKDONJSA-N
Search UniChem for chemicals with the same backbone KQDRVXQXKZXMHP