caffeine   Click here for help

GtoPdb Ligand ID: 407

Synonyms: Peyona®
Approved drug PDB Ligand
caffeine is an approved drug (FDA (no history prior to 1999), EMA (2009))
Comment: Caffeine is a central nervous system stimulant that causes increased alertness and agitation.
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View more information in the IUPHAR Pharmacology Education Project: caffeine

2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 3
Hydrogen bond donors 0
Rotatable bonds 0
Topological polar surface area 61.82
Molecular weight 194.08
XLogP 1.55
No. Lipinski's rules broken 0
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Canonical SMILES Cn1cnc2c1c(=O)n(C)c(=O)n2C
Isomeric SMILES Cn1cnc2c1c(=O)n(C)c(=O)n2C
InChI InChI=1S/C8H10N4O2/c1-10-4-9-6-5(10)7(13)12(3)8(14)11(6)2/h4H,1-3H3
No information available.
Summary of Clinical Use Click here for help
Used in the management of orthostatic hypotension, fatigue and for the short term treatment of apnea (due to a lack of respiratory effort) in premature infants.
Mechanism Of Action and Pharmacodynamic Effects Click here for help
The mechanism(s) by which caffeine exerts its effects are not fully resolved, but appear to involve inhibition of cyclic nucleotide phosphodiesterases, antagonism of adenosine receptors, and modulation of intracellular calcium handling. The stimulatory effects of caffeine can be explained by antagonism of adenosine receptors and subsequent increase of neurotransmitter release, indeed blocking the adenosine A1 receptor in the heart leads to the sensation of an accelerated and pounding heartbeat experienced following caffeine intake.
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