CHEBI:64194 - paroxetine maleate

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ChEBI Name paroxetine maleate
ChEBI ID CHEBI:64194
Definition A maleate salt obtained by reaction of paroxetine with one equivalent of maleic acid. 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.
Supplier Information eMolecules:26754657
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Formula C23H24FNO7
Net Charge 0
Average Mass 445.43760
Monoisotopic Mass 445.15368
InChI InChI=1S/C19H20FNO3.C4H4O4/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;5-3(6)1-2-4(7)8/h1-6,9,14,17,21H,7-8,10-12H2;1-2H,(H,5,6)(H,7,8)/b;2-1-/t14-,17-;/m0./s1
InChIKey AEIUZSKXSWGSRU-QXGDPHCHSA-N
SMILES OC(=O)\C=C/C(O)=O.[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 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.
Application(s): antidepressant
Antidepressants are mood-stimulating drugs used primarily in the treatment of affective disorders and related conditions.
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.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing paroxetine maleate (CHEBI:64194) has part paroxetinium(1+) (CHEBI:64197)
paroxetine maleate (CHEBI:64194) has role antidepressant (CHEBI:35469)
paroxetine maleate (CHEBI:64194) has role anxiolytic drug (CHEBI:35474)
paroxetine maleate (CHEBI:64194) has role hepatotoxic agent (CHEBI:50908)
paroxetine maleate (CHEBI:64194) has role P450 inhibitor (CHEBI:50183)
paroxetine maleate (CHEBI:64194) has role serotonin uptake inhibitor (CHEBI:50949)
paroxetine maleate (CHEBI:64194) is a maleate salt (CHEBI:50221)
IUPAC Name
(3S,4R)-3-[(1,3-benzodioxol-5-yloxy)methyl]-4-(4-fluorophenyl)piperidine (2Z)-but-2-enedioate
Synonyms Sources
(-)-alpha-4-(4-Fluorophenyl)-3-(1,3-benzdioxolyl-(3))-oxymethyl piperidine maleate ChemIDplus
(3S,4R)-3-[(1,3-benzodioxol-5-yloxy)methyl]-4-(4-fluorophenyl)piperidine maleate ChEBI
(3S,4R)-3-[(1,3-benzodioxol-5-yloxy)methyl]-4-(4-fluorophenyl)piperidinium (2Z)-3-carboxyacrylate IUPAC
trans-(-)-3-((1,3-Benzodioxol-5-yloxy)methyl)-4-(4-fluorophenyl)piperidine maleate ChemIDplus
Manual Xrefs Databases
DB00715 DrugBank
EP1078925 Patent
EP269303 Patent
US4745122 Patent
US5874447 Patent
US6440459 Patent
View more database links
Registry Numbers Types Sources
14623212 Reaxys Registry Number Reaxys
64006-44-6 CAS Registry Number ChemIDplus
Last Modified
15 March 2012