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
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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
References
1. Aslanian R, Piwinski JJ, Zhu X, Priestley T, Sorota S, Du XY, Zhang XS, McLeod RL, West RE, Williams SM et al.. (2009)
Structural determinants for histamine H(1) affinity, hERG affinity and QTc prolongation in a series of terfenadine analogs.
Bioorg. Med. Chem. Lett., 19 (17): 5043-7. [PMID:19660947]