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CHEBI:7936 - paroxetine

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.
P450 inhibitor  An enzyme inhibitor that interferes with the activity of cytochrome P450 involved in catalysis of organic substances.
hepatotoxic agent  A role played by a chemical compound exhibiting itself through the ability to induce damage to the liver in animals.
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.
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.
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
paroxetinumDrugBank
paroxetinaDrugBank
Synonyms  Source
ParoxetineKEGG COMPOUND
(3S-trans)-3-((1,3-benzodioxol-5-yloxy)methyl)-4-(4-fluorophenyl)piperidineChemIDplus
(−)-(3S,4R)-4-(p-fluorophenyl)-3-((3,4-(methylenedioxy)phenoxy)methyl)piperidineChemIDplus
Manual XrefsDatabases
C07415KEGG COMPOUND
D02362KEGG DRUG
ParoxetineWikipedia
DB00715DrugBank
LSM-2843LINCS
2068DrugCentral
Registry NumbersSources
Reaxys:7467879Reaxys
CAS:61869-08-7KEGG COMPOUND
CAS:61869-08-7ChemIDplus
Citations