firategrast   Click here for help

GtoPdb Ligand ID: 11486

Synonyms: SB-683699 | SB683699
Immunopharmacology Ligand
Compound class: Synthetic organic
Comment: Firategrast (SB-683699) is an orally bioavailable, short-acting small molecule α4-integrin antagonist. It was designed to reduce α4β1/α4β7 integrin-mediated trafficking of lymphocytes into the central nervous system (CNS). Anti-α4-integrin natalizumab is currently approved to treat MS, but its long half-life is problematic, and it has to be administered by infusion. This short acting small molecule was developed as an alternative to antibody therapy.
2D Structure
Click here for help
Click here for structure editor
Physico-chemical Properties
Click here for help
Hydrogen bond acceptors 5
Hydrogen bond donors 2
Rotatable bonds 12
Topological polar surface area 94.09
Molecular weight 499.18
XLogP 5
No. Lipinski's rules broken 2
SMILES / InChI / InChIKey
Click here for help
Canonical SMILES CCOCc1cc(OC)c(c(c1)OC)c1ccc(cc1)C[C@@H](C(=O)O)NC(=O)c1c(F)cccc1F
Isomeric SMILES CCOCc1cc(OC)c(c(c1)OC)c1ccc(cc1)C[C@@H](C(=O)O)NC(=O)c1c(F)cccc1F
InChI InChI=1S/C27H27F2NO6/c1-4-36-15-17-13-22(34-2)24(23(14-17)35-3)18-10-8-16(9-11-18)12-21(27(32)33)30-26(31)25-19(28)6-5-7-20(25)29/h5-11,13-14,21H,4,12,15H2,1-3H3,(H,30,31)(H,32,33)/t21-/m0/s1
InChI Key YLFZHHDVRSYTKT-NRFANRHFSA-N
Classification Click here for help
Compound class Synthetic organic
International Nonproprietary Names Click here for help
INN number INN
8755 firategrast
Synonyms Click here for help
SB-683699 | SB683699
Database Links Click here for help
CAS Registry No. 402567-16-2 (source: WHO INN record)
ChEMBL Ligand CHEMBL2104967
DrugBank Ligand DB12732
GtoPdb PubChem SID 440816854
PubChem CID 9935681
Search Google for chemical match using the InChIKey YLFZHHDVRSYTKT-NRFANRHFSA-N
Search Google for chemicals with the same backbone YLFZHHDVRSYTKT
Search PubMed clinical trials firategrast
Search PubMed titles firategrast
Search PubMed titles/abstracts firategrast
Search UniChem for chemical match using the InChIKey YLFZHHDVRSYTKT-NRFANRHFSA-N
Search UniChem for chemicals with the same backbone YLFZHHDVRSYTKT