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CHEBI:64194 - paroxetine maleate

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:
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.
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.
Applications:
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.
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.
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
trans-(-)-3-((1,3-Benzodioxol-5-yloxy)methyl)-4-(4-fluorophenyl)piperidine maleateChemIDplus
(-)-alpha-4-(4-Fluorophenyl)-3-(1,3-benzdioxolyl-(3))-oxymethyl piperidine maleateChemIDplus
(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
Manual XrefsDatabases
EP269303Patent
EP1078925Patent
US4745122Patent
US6440459Patent
US5874447Patent
DB00715DrugBank
Registry NumbersSources
Reaxys:14623212Reaxys
CAS:64006-44-6ChemIDplus