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.

firategrast is commercially available from our sponsors

2D Structure
Click here for help

2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

✖
Click here for structure editor
Physico-chemical Properties
Click here for help

Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

✖
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

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
SMILES / InChI / InChIKey
Click here for help

SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

✖
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

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
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
UniChem Compound Search for chemical match using the InChIKey YLFZHHDVRSYTKT-NRFANRHFSA-N
UniChem Connectivity Search for chemical match using the InChIKey YLFZHHDVRSYTKT-NRFANRHFSA-N

Product suppliers

View disclaimer

Sponsored products disclaimer

Product supplier links are provided as a service to assist in identifying commercial suppliers of reagents that are mentioned on the IUPHAR/BPS Guide to PHARMACOLOGY database website, and do not imply their endorsement by NC-IUPHAR.

Links are provided in return for sponsorship, used to fund improvements to this database. The sponsorship account is managed and audited by the University of Edinburgh, a charitable body registered in Scotland, SC005336. If you are interested in sponsoring the database, please contact us.

✖

MedChemExpress
Firategrast (links to external site)
Cat. No. HY-14951