diphenhydramine   Click here for help

GtoPdb Ligand ID: 1224

Synonyms: Benadryl® | benzhydramine | dimehydrinate
Approved drug PDB Ligand
diphenhydramine is an approved drug (FDA (1946))
Compound class: Synthetic organic
Comment: Diphenhydramine has anti-histamine action.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 2
Hydrogen bond donors 0
Rotatable bonds 6
Topological polar surface area 12.47
Molecular weight 255.16
XLogP 3.16
No. Lipinski's rules broken 0
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Canonical SMILES CN(CCOC(c1ccccc1)c1ccccc1)C
Isomeric SMILES CN(CCOC(c1ccccc1)c1ccccc1)C
InChI InChI=1S/C17H21NO/c1-18(2)13-14-19-17(15-9-5-3-6-10-15)16-11-7-4-8-12-16/h3-12,17H,13-14H2,1-2H3
No information available.
Summary of Clinical Use Click here for help
Diphenhydramine is a histamine antagonist, but is often used for its antiemetic effects to treat conditions such as vertigo, nausea and vomiting and motion sickness. It is also used to treat hypersensitivity reactions and irritant coughs. Diphenhydramine is an ingredient in some common cold preparations, but does cause undesirable drowsiness.
Mechanism Of Action and Pharmacodynamic Effects Click here for help
In addition to anti-histaminergic actions, diphenhydramine also has antimuscarinic/anticholinergic action which is believed to account for both the drowsiness side-effect and also for the beneficial antiemetic and antidyskinesia (ie may help with movement disorders such as parkansinism) effects.