terfenadine   Click here for help

GtoPdb Ligand ID: 2608

Synonyms: RMI-9918 | Seldane® | Triludan®
Approved drug Immunopharmacology Ligand
terfenadine is an approved drug (FDA)
Compound class: Synthetic organic
Comment: Due to adverse effects on cardiac function, terfenadine has largely been superseded by its carboxylic acid metabolite fexofenadine. Terfenadine was completely withdrawn in the US in 1998.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 3
Hydrogen bond donors 2
Rotatable bonds 9
Topological polar surface area 43.7
Molecular weight 471.31
XLogP 7.11
No. Lipinski's rules broken 1
SMILES / InChI / InChIKey
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Canonical SMILES OC(c1ccc(cc1)C(C)(C)C)CCCN1CCC(CC1)C(c1ccccc1)(c1ccccc1)O
Isomeric SMILES OC(c1ccc(cc1)C(C)(C)C)CCCN1CCC(CC1)C(c1ccccc1)(c1ccccc1)O
InChI InChI=1S/C32H41NO2/c1-31(2,3)26-18-16-25(17-19-26)30(34)15-10-22-33-23-20-29(21-24-33)32(35,27-11-6-4-7-12-27)28-13-8-5-9-14-28/h4-9,11-14,16-19,29-30,34-35H,10,15,20-24H2,1-3H3
InChI Key GUGOEEXESWIERI-UHFFFAOYSA-N
No information available.
Summary of Clinical Use Click here for help
Terfenadine is an antihistamine used to treat allergic rhinitis, hay fever, and allergic skin disorders. Due to adverse effects on cardiac function, terfenadine has largely been superseded by fexofenadine. Marketing authorisation for terfenadine was completely withdrawn in the US in 1998. Other national approval agencies may continue to grant marketing authorisation.
Mechanism Of Action and Pharmacodynamic Effects Click here for help
Following reversible binding of histamine H1 receptors, terfenadine competes with histamine and thus supresses the effects of histaminic activity.