| Candidate ID: | R0251 |
| Source ID: | DB00715 |
| Source Type: | approved; investigational |
| Compound Type: |
small molecule
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| Compound Name: |
Paroxetine
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| Synonyms: |
(−)-(3S,4R)-4-(p-fluorophenyl)-3-((3,4-(methylenedioxy)phenoxy)methyl)piperidine; (3S-trans)-3-((1,3-benzodioxol-5-yloxy)methyl)-4-(4-fluorophenyl)piperidine; Paroxetine
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| Molecular Formula: |
C19H20FNO3
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| SMILES: |
FC1=CC=C(C=C1)[C@@H]1CCNC[C@H]1COC1=CC2=C(OCO2)C=C1
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| Structure: |
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| DrugBank Description: |
Paroxetine is a selective serotonin reuptake inhibitor (SSRI) drug commonly known as Paxil. It has a variety of uses, including the treatment of anxiety disorders, major depression, posttraumatic stress disorder, and symptoms of menopause, among others. It was approved by the FDA in the early 1990s and marketed by SmithKline Beecham. A unique feature of this drug is that it is highly potent and selective in its inhibition of serotonin reuptake and has little effect on other neurotransmitters. Because of its potent inhibition of serotonin reuptake, paroxetine is more likely to cause withdrawal effects upon cessation. Paroxetine is well tolerated in most patients with a similar adverse effect profile to other members of its drug class. The controlled release formulation was designed to decrease the likelihood of nausea that is sometimes associated with paroxetine.
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| CAS Number: |
61869-08-7
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| Molecular Weight: |
329.3654
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| DrugBank Indication: |
Paroxetine is indicated for the management of depression, obsessive-compulsive disorder, panic disorder, social anxiety disorder, generalized anxiety disorder, posttraumatic stress disorder. One form of paroxetine, commercially known as Brisdelle, is used to manage mild to moderate vasomotor symptoms of menopause. Off-label, paroxetine may be used for the treatment of premature ejaculation or irritable bowel syndrome (IBS).
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| DrugBank Pharmacology: |
Paroxetine treats the symptoms of depression, various anxiety disorders, posttraumatic stress disorder, obsessive-compulsive disorder, and the vasomotor symptoms of menopause via the inhibition of serotonin reuptake. The onset of action of paroxetine is reported to be approximately 6 weeks.
Due its serotonergic activity, paroxetine, like other SSRI drugs, may potentiate serotonin syndrome. This risk is especially high when monoamine oxidase (MAO) inhibitors are given within 2 weeks of paroxetine administration. Upon cessation of MAO inhibitors, a 2-week interval before paroxetine administration is recommended. Do not coadminister these agents.
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| DrugBank MoA: |
Paroxetine enhances serotonergic activity via the inhibition presynaptic reuptake of serotonin by the serotonin (SERT) receptor. This inhibition raises the level of serotonin in the synaptic cleft, relieving various symptoms. This drug has been demonstrated to be a stronger inhibitor of serotonin reuptake than other members of the same drug class, including , , and . The mechanism of action of paroxetine in relieving the vasomotor symptoms of menopause is unknown, according to the Brisdelle prescribing information, but may occur due to its effects on thermoregulation.
Paroxetine shows a clinically insignificant affinity for adrenergic alpha-1 and alpha-2 receptors and β-adrenergic receptors, dopamine D1 and D2 receptors, histamine H1 receptors and serotonin 5-HT1A, 5-HT2A and 5-HT2C receptors. This drug shows some affinity for muscarinic cholinergic receptors and 5-H2B receptors. The delayed onset of paroxetine therapeutic effects may be explained by the initial paroxetine actions on the 5-HT neurons. In rats, paroxetine activates 5-HT1A receptors when it is first administered, inhibiting the stimulation of the 5-HT neurons and subsequent release of serotonin at the synaptic cleft.
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| Targets: |
Sodium-dependent serotonin transporter inhibitor; Sodium-dependent noradrenaline transporter inhibitor; 5-hydroxytryptamine receptor 2A agonist; Alpha-1 adrenergic receptors binder; Alpha-2 adrenergic receptors binder; Beta adrenergic receptor inhibitor; Dopamine D2 receptor other/unknown; Histamine H1 receptor inhibitor; Serotonin Receptors; Muscarinic acetylcholine receptor inhibitor; 5-hydroxytryptamine receptor 2B agonist; D(1) dopamine receptor other/unknown
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| Inclusion Criteria: |
Indication associated
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