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CHEBI:7936 - paroxetine

Default Structure
ChEBI IDCHEBI:7936
ChEBI Nameparoxetine
Stars
DefinitionA 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.
Last Modified4 March 2025
DownloadsMolfile
FormulaC19H20FNO3
Net Charge0
Average Mass329.371
Monoisotopic Mass329.14272
SMILES[H][C@@]1(c2ccc(F)cc2)CCNC[C@H]1COc1ccc2c(c1)OCO2
InChIInChI=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
InChIKeyAHOUBRCZNHFOSL-YOEHRIQHSA-N
Wikipedia
Roles Classification
Biological Roles:
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 exhibiting 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.
Applications:
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.
antidepressant  Antidepressants are mood-stimulating drugs used primarily in the treatment of affective disorders and related 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.
ChEBI Ontology
Outgoing Relation(s)
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 monofluorobenzenes (CHEBI:83575)
paroxetine (CHEBI:7936) is a piperidines (CHEBI:26151)
paroxetine (CHEBI:7936) is conjugate base of paroxetinium(1+) (CHEBI:64197)
Incoming Relation(s)
N-methylparoxetine (CHEBI:94536) has functional parent paroxetine (CHEBI:7936)
6-nitroparoxetine (CHEBI:233619) has functional parent paroxetine (CHEBI:7936)
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  Source
paroxetinaDrugBank
paroxetinumDrugBank
Synonyms  Source
(−)-(3S,4R)-4-(p-fluorophenyl)-3-((3,4-(methylenedioxy)phenoxy)methyl)piperidineChemIDplus
(3S-trans)-3-((1,3-benzodioxol-5-yloxy)methyl)-4-(4-fluorophenyl)piperidineChemIDplus
ParoxetineKEGG COMPOUND
Manual XrefsDatabases
2068DrugCentral
C07415KEGG COMPOUND
D02362KEGG DRUG
DB00715DrugBank
LSM-2843LINCS
ParoxetineWikipedia
Registry NumbersSources
Reaxys:7467879Reaxys
CAS:61869-08-7KEGG COMPOUND
CAS:61869-08-7ChemIDplus
Citations