GtoPdb Ligand ID: 7318

Synonyms: Pyribenzamine®
tripelennamine is an approved drug (FDA (1948))
Compound class: Synthetic organic
Comment: Tripelennamine is a first-generation antihistamine. It also has serotonin reuptake inhibitor (SRI) activity, and was used as the template molecule in the development of the selective serotonin reuptake inhibitor (SSRI) fluvoxamine. In addition, tripelennamine has dopamine reuptake inhibitor (DRI) activity.
2D Structure
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Physico-chemical Properties
Hydrogen bond acceptors 3
Hydrogen bond donors 0
Rotatable bonds 6
Topological polar surface area 19.37
Molecular weight 255.17
XLogP 3.27
No. Lipinski's rules broken 0
Canonical SMILES CN(CCN(c1ccccn1)Cc1ccccc1)C
Isomeric SMILES CN(CCN(c1ccccn1)Cc1ccccc1)C
InChI InChI=1S/C16H21N3/c1-18(2)12-13-19(16-10-6-7-11-17-16)14-15-8-4-3-5-9-15/h3-11H,12-14H2,1-2H3
No information available.
Summary of Clinical Use
Used as an antipruritic and antihistamine in the treatment of asthma, hay fever, rhinitus and urticaria. All formulations of this drug appear to have been discontinued by the US FDA, although other national approval agencies may continue to grant marketing authorisation.
Mechanism Of Action and Pharmacodynamic Effects
Tripelennamine blocks the action of endogenous histamine at the histamine H1 receptor.