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CHEBI:64194 - paroxetine maleate

Default Structure
ChEBI IDCHEBI:64194
ChEBI Nameparoxetine maleate
Stars
DefinitionA 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.
Last Modified15 March 2012
SubmitterSteve
DownloadsMolfile
FormulaC19H20FNO3.C4H4O4
Net Charge0
Average Mass445.443
Monoisotopic Mass445.15368
SMILESO=C(O)/C=C\C(=O)O.[H][C@@]1(c2ccc(F)cc2)CCNC[C@H]1COc1ccc2c(c1)OCO2
InChIInChI=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
InChIKeyAEIUZSKXSWGSRU-QXGDPHCHSA-N
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 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  Source
(3S,4R)-3-[(1,3-benzodioxol-5-yloxy)methyl]-4-(4-fluorophenyl)piperidine maleateChEBI
(3S,4R)-3-[(1,3-benzodioxol-5-yloxy)methyl]-4-(4-fluorophenyl)piperidinium (2Z)-3-carboxyacrylateIUPAC
(-)-alpha-4-(4-Fluorophenyl)-3-(1,3-benzdioxolyl-(3))-oxymethyl piperidine maleateChemIDplus
trans-(-)-3-((1,3-Benzodioxol-5-yloxy)methyl)-4-(4-fluorophenyl)piperidine maleateChemIDplus
Manual XrefsDatabases
DB00715DrugBank
EP1078925Patent
EP269303Patent
US4745122Patent
US5874447Patent
US6440459Patent
Registry NumbersSources
Reaxys:14623212Reaxys
CAS:64006-44-6ChemIDplus