CHEBI:7936 - paroxetine

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ChEBI Name paroxetine
ChEBI ID CHEBI:7936
Definition A benzodioxole that consists of piperidine bearing 1,3-benzodioxol-5-yloxy)methyl and 4-fluorophenyl substituents at positions 3 and 4 respectively; the (3S,4R)-diastereomer. Highly potent and selective 5-HT uptake inhibitor that binds with high affinity to the serotonin transporter (Ki = 0.05 nM). Ki values are 1.1, 350 and 1100 nM for inhibition of [3H]-5-HT, [3H]-l-NA and [3H]-DA uptake respectively. Displays minimal affinity for α1-, α2- or β-adrenoceptors, 5-HT2A, 5-HT1A, D2 or H1 receptors at concentrations below 1000 nM, however displays weak affinity for muscarinic ACh receptors (Ki = 42 nM). Antidepressant and anxiolytic in vivo.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C19H20FNO3
Net Charge 0
Average Mass 329.36540
InChI InChI=1S/C19H20FNO3/c20-15-3-1-13(2-4-15)17-7-8-21-10-14(17)11-22-16-5-6-18-19(9-16)24-12-23-18/h1-6,9,14,17,21H,7-8,10-12H2/t14-,17-/m0/s1
InChIKey AHOUBRCZNHFOSL-YOEHRIQHSA-N
SMILES [H][C@]1(CCNC[C@H]1COc1ccc2OCOc2c1)c1ccc(F)cc1
Roles Classification
Biological Role(s): serotonin uptake inhibitor
A compound that specifically inhibits the reuptake of serotonin in the brain. This increases the serotonin concentration in the synaptic cleft which then activates serotonin receptors to a greater extent.
hepatotoxic agent
A role played by a chemical compound exihibiting itself through the ability to induce damage to the liver in animals.
P450 inhibitor
An enzyme inhibitor that interferes with the activity of cytochrome P450 involved in catalysis of organic substances.
Application(s): anxiolytic drug
Anxiolytic drugs are agents that alleviate anxiety, tension, and anxiety disorders, promote sedation, and have a calming effect without affecting clarity of consciousness or neurologic conditions.
serotonin uptake inhibitor
A compound that specifically inhibits the reuptake of serotonin in the brain. This increases the serotonin concentration in the synaptic cleft which then activates serotonin receptors to a greater extent.
antidepressant
Antidepressants are mood-stimulating drugs used primarily in the treatment of affective disorders and related conditions.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing paroxetine (CHEBI:7936) has functional parent monofluorobenzene (CHEBI:5115)
paroxetine (CHEBI:7936) has role antidepressant (CHEBI:35469)
paroxetine (CHEBI:7936) has role anxiolytic drug (CHEBI:35474)
paroxetine (CHEBI:7936) has role hepatotoxic agent (CHEBI:50908)
paroxetine (CHEBI:7936) has role P450 inhibitor (CHEBI:50183)
paroxetine (CHEBI:7936) has role serotonin uptake inhibitor (CHEBI:50949)
paroxetine (CHEBI:7936) is a aromatic ether (CHEBI:35618)
paroxetine (CHEBI:7936) is a benzodioxoles (CHEBI:38298)
paroxetine (CHEBI:7936) is a organofluorine compound (CHEBI:37143)
paroxetine (CHEBI:7936) is a piperidines (CHEBI:26151)
paroxetine (CHEBI:7936) is conjugate base of paroxetinium(1+) (CHEBI:64197)
Incoming paroxetinium(1+) (CHEBI:64197) is conjugate acid of paroxetine (CHEBI:7936)
IUPAC Name
(3S,4R)-3-[(1,3-benzodioxol-5-yloxy)methyl]-4-(4-fluorophenyl)piperidine
INNs Sources
paroxetina DrugBank
paroxetinum DrugBank
Synonyms Sources
(−)-(3S,4R)-4-(p-fluorophenyl)-3-((3,4-(methylenedioxy)phenoxy)methyl)piperidine ChemIDplus
(3S-trans)-3-((1,3-benzodioxol-5-yloxy)methyl)-4-(4-fluorophenyl)piperidine ChemIDplus
Paroxetine KEGG COMPOUND
Database Links Databases
C07415 KEGG COMPOUND
D02362 KEGG DRUG
DB00715 DrugBank
LSM-2843 LINCS
Paroxetine Wikipedia
View more database links
Registry Numbers Types Sources
61869-08-7 CAS Registry Number KEGG COMPOUND
61869-08-7 CAS Registry Number ChemIDplus
7467879 Beilstein Registry Number Beilstein
7467879 Reaxys Registry Number Reaxys
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Last Modified
25 February 2016