fexofenadine   

GtoPdb Ligand ID: 4819

Synonyms: Allegra® | fexofenadine HCl
fexofenadine is an approved drug (FDA (1996))
Compound class: Synthetic organic
Comment: Fexofenadine is a metabolite of terfenadine. Fexofenadine is an antihistamine (histamine H1 receptor antagonist), non-sedating antiallergic agent. The approved drug is a racemic mixture of two enatiomers (CID 9870655) and (CID 6603853). The structure shown here does not specify stereochemistry and represents the mixture.
2D Structure
Click here for structure editor
Physico-chemical Properties
Hydrogen bond acceptors 5
Hydrogen bond donors 3
Rotatable bonds 10
Topological polar surface area 81
Molecular weight 501.29
XLogP 5.64
No. Lipinski's rules broken 1
SMILES / InChI / InChIKey
Canonical SMILES OC(=O)C(c1ccc(cc1)C(CCCN1CCC(CC1)C(c1ccccc1)(c1ccccc1)O)O)(C)C
Isomeric SMILES OC(=O)C(c1ccc(cc1)C(CCCN1CCC(CC1)C(c1ccccc1)(c1ccccc1)O)O)(C)C
InChI InChI=1S/C32H39NO4/c1-31(2,30(35)36)25-17-15-24(16-18-25)29(34)14-9-21-33-22-19-28(20-23-33)32(37,26-10-5-3-6-11-26)27-12-7-4-8-13-27/h3-8,10-13,15-18,28-29,34,37H,9,14,19-23H2,1-2H3,(H,35,36)
InChI Key RWTNPBWLLIMQHL-UHFFFAOYSA-N
Transporters Moving this Compound Across a Lipid Membrane
Transporter EC number Reaction Reference
OATP1B3
OATP2B1
OATP1B1
OATP1A2
Selectivity at GPCRs
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
H1 receptor Hs Antagonist Antagonist 7.6 pKi - 1
pKi 7.6 (Ki 2.7x10-8 M) [1]