Identification

Name
Paroxetine
Accession Number
DB00715
Type
Small Molecule
Groups
Approved, Investigational
Description

Paroxetine hydrochloride and paroxetine mesylate belong to a class of antidepressant agents known as selective serotonin-reuptake inhibitors (SSRIs). Despite distinct structural differences between compounds in this class, SSRIs possess similar pharmacological activity. As with other antidepressant agents, several weeks of therapy may be required before a clinical effect is seen. SSRIs are potent inhibitors of neuronal serotonin reuptake. They have little to no effect on norepinephrine or dopamine reuptake and do not antagonize ⍺- or β-adrenergic, dopamine D2 or histamine H1 receptors. During acute use, SSRIs block serotonin reuptake and increase serotonin stimulation of somatodendritic 5-HT1A and terminal autoreceptors. Chronic use leads to desensitization of somatodendritic 5-HT1A and terminal autoreceptors. The overall clinical effect of increased mood and decreased anxiety is thought to be due to adaptive changes in neuronal function that leads to enhanced serotonergic neurotransmission.

Side effects include dry mouth, nausea, dizziness, drowsiness, sexual dysfunction and headache (see Toxicity section below for a complete listing of side effects). Side effects generally occur during the first two weeks of therapy and are usually less severe and frequent than those observed with tricyclic antidepressants. Paroxetine hydrochloride and mesylate are considered therapeutic alternatives rather than generic equivalents by the US Food and Drug Administration (FDA); both agents contain the same active moiety (i.e. paroxetine), but are formulated as different salt forms. Clinical studies establishing the efficacy of paroxetine in various conditions were performed using paroxetine hydrochloride. Since both agents contain the same active moiety, the clinical efficacy of both agents is thought to be similar. Paroxetine may be used to treat major depressive disorder (MDD), panic disorder with or without agoraphobia, obsessive-compulsive disorder (OCD), social anxiety disorder (social phobia), generalized anxiety disorder (GAD), post-traumatic stress disorder (PTSD) and premenstrual dysphoric disorder (PMDD). Paroxetine has the most evidence supporting its use for anxiety-related disorders of the SSRIs. It has the greatest anticholinergic activity of the agents in this class and compared to other SSRIs, paroxetine may cause greater weight gain, sexual dysfunction, sedation and constipation.

Structure
Thumb
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
  • Paroxetina
  • Paroxetine
  • Paroxetinum
External IDs
BRL 29060 / BRL-29060 / FG-7051
Product Ingredients
IngredientUNIICASInChI Key
Paroxetine hydrochloride3I3T11UD2S78246-49-8GELRVIPPMNMYGS-RVXRQPKJSA-N
Paroxetine hydrochloride hemihydrateX2ELS050D8110429-35-1MQZOATSIFWSKKT-OASXIEIISA-N
Paroxetine mesylateM711N184JE217797-14-3SHIJTGJXUHTGGZ-RVXRQPKJSA-N
Product Images
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Act ParoxetineTablet10 mgOralActavis Pharma Company2005-03-14Not applicableCanada
Act ParoxetineTablet30 mgOralActavis Pharma Company2005-03-14Not applicableCanada
Act ParoxetineTablet20 mgOralActavis Pharma Company2005-03-14Not applicableCanada
BrisdelleCapsule7.5 mg/1OralSebela Pharmaceuticals Inc.2017-05-23Not applicableUs
BrisdelleCapsule7.5 mg/1OralNoven Therapeutics2013-06-282017-11-30Us
M-paroxetineTablet20 mgOralMantra Pharma Inc2018-03-07Not applicableCanada
M-paroxetineTablet10 mgOralMantra Pharma Inc2018-03-07Not applicableCanada
M-paroxetineTablet30 mgOralMantra Pharma IncNot applicableNot applicableCanada
ParoxetineTablet10 mgOralCobalt LaboratoriesNot applicableNot applicableCanada
ParoxetineTablet20 mgOralSivem Pharmaceuticals Ulc2012-06-26Not applicableCanada
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Apo-paroxetineTablet10 mgOralApotex Corporation2003-10-24Not applicableCanada
Apo-paroxetineTablet30 mgOralApotex Corporation2003-10-24Not applicableCanada
Apo-paroxetineTablet20 mgOralApotex Corporation2003-10-24Not applicableCanada
Auro-paroxetineTablet20 mgOralAuro Pharma Inc2012-07-24Not applicableCanada
Auro-paroxetineTablet10 mgOralAuro Pharma Inc2012-07-24Not applicableCanada
Auro-paroxetineTablet30 mgOralAuro Pharma Inc2012-07-24Not applicableCanada
Bio-paroxetineTablet10 mgOralBiomed Pharma2016-12-21Not applicableCanada
Bio-paroxetineTablet30 mgOralBiomed Pharma2016-12-21Not applicableCanada
Bio-paroxetineTablet20 mgOralBiomed Pharma2016-12-21Not applicableCanada
Dom-paroxetineTablet40 mgOralDominion PharmacalNot applicableNot applicableCanada
International/Other Brands
Aropax / PAXILCR / Sereupin / Seroxat / Seroxat CR
Categories
UNII
41VRH5220H
CAS number
61869-08-7
Weight
Average: 329.3654
Monoisotopic: 329.142721716
Chemical Formula
C19H20FNO3
InChI Key
AHOUBRCZNHFOSL-YOEHRIQHSA-N
InChI
InChI=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
IUPAC Name
(3S,4R)-3-[(2H-1,3-benzodioxol-5-yloxy)methyl]-4-(4-fluorophenyl)piperidine
SMILES
FC1=CC=C(C=C1)[C@@H]1CCNC[C@H]1COC1=CC2=C(OCO2)C=C1

Pharmacology

Indication

Labeled indications include: major depressive disorder (MDD), panic disorder with or without agoraphobia, obsessive-compulsive disorder (OCD), social anxiety disorder (social phobia), generalized anxiety disorder (GAD), post-traumatic stress disorder (PTSD), and premenstrual dysphoric disorder (PMDD). Unlabeled indications include: eating disorders, impulse control disorders, vasomotor symptoms of menopause, obsessive-compulsive disorder (OCD) in children, and mild dementia-associated agitation in nonpsychotic individuals. Brisdelle, which consists of paroxetine mesylate is indicated for the treatment of moderate to severe vasomotor symptoms (like hot flashes) associated with menopause.

Associated Conditions
Pharmacodynamics

Paroxetine, an antidepressant drug of the selective serotonin reuptake inhibitor (SSRI) type, has no active metabolites and has the highest specificity for serotonin receptors of all the SSRIs. It is used to treat depression resistant to other antidepressants, depression complicated by anxiety, panic disorder, social and general anxiety disorder, obsessive-compulsive disorder (OCD), premenstrual dysphoric disorder, premature ejaculation, and hot flashes of menopause in women with breast cancer. In human platelets, paroxetine blocks the uptake of serotonin. It has weak effects on norepinephrine and dopamine neuronal reuptake. In vitro radioligand binding studies indicate that paroxetine has little affinity for muscarinic alpha1-, alpha2-, beta-adrenergic-, dopamine (D2)-, 5-HT1-, 5-HT2-, and histamine (H1)-receptors.

Mechanism of action

Paroxetine is a potent and highly selective inhibitor of neuronal serotonin reuptake. Paroxetine likely inhibits the reuptake of serotonin at the neuronal membrane, enhances serotonergic neurotransmission by reducing turnover of the neurotransmitter, therefore it prolongs its activity at synaptic receptor sites and potentiates 5-HT in the CNS; paroxetine is more potent than both sertraline and fluoxetine in its ability to inhibit 5-HT reuptake. Compared to the tricyclic antidepressants, SSRIs have dramatically decreased binding to histamine, acetylcholine, and norepinephrine receptors. The mechanism of action for the treatment of vasomotor symptoms is unknown.

TargetActionsOrganism
ASodium-dependent serotonin transporter
inhibitor
Human
USodium-dependent noradrenaline transporter
inhibitor
Human
U5-hydroxytryptamine receptor 2A
other/unknown
Human
NMuscarinic acetylcholine receptor M1
antagonist
Human
NMuscarinic acetylcholine receptor M2
antagonist
Human
NMuscarinic acetylcholine receptor M3
antagonist
Human
NMuscarinic acetylcholine receptor M4
antagonist
Human
NMuscarinic acetylcholine receptor M5
antagonist
Human
Absorption

Paroxetine hydrochloride is slowly, but completely absorbed following oral administration. Paroxetine mesylate salt is also completely absorbed after oral dosing. The oral bioavailability appears to be low due to extensive first-pass metabolism. Paroxetine hydrochloride oral tablets and suspension are reportedly bioequivalent. Absorption of either salt form is not substantially affected by food. Peak concentrations of Brisbelle (mesylate salt) were reached at 6 hours (3 to 8 hours range). Steady state Cmax was 13.10 ng/mL. The steady state AUC (0-last) was 237 hr*ng/mL. Paroxetine mesylate generally follows non-linear pharmacokinetics because CYP2D6, the enzyme that is part responisible for paroxetine metabolism, is readily saturable.

Volume of distribution

3.1-28 L/kg observed in animal studies. Paroxetine distributes throughout the body, including the central nervous system, with only 1% remaining in the plasma.

Protein binding

~ 95% bound to plasma proteins.

Metabolism

Paroxetine is extensively metabolized after oral administration, likely in the liver. The main metabolites are polar and conjugated products of oxidation and methylation, which are readily eliminated by the body. The predominant metabolites are glucuronic acid and sulfate conjugates. Paroxetine metabolites do not possess significant pharmacologic activity (less than 2% that of parent compound). Paroxetine is metabolized by cytochrome P450 (CYP) 2D6. Enzyme saturation appears to account for the nonlinear pharmacokinetics observed with increasing dose and duration of therapy.

Route of elimination

Approximately 64% of a 30 mg oral solution of paroxetine was excreted in the urine with 2% as the parent compound and 62% as metabolites. Approximately 36% of the dose was excreted in the feces (via bile), mostly as metabolites and less than 1% as parent compound.

Half life

21-24 hours

Clearance
Not Available
Toxicity

LD50=500mg/kg (orally in mice). Symptoms of overdose include: coma, dizziness, drowsiness, facial flushing, nausea, sweating, tremor, vomiting. Side effects include: nervous system effects such as asthenia, somnolence, dizziness, insomnia, tremor, and nervousness; GI effects such as nausea, decreased appetite, constipation, diarrhea, and dry mouth; impotence, ejaculatory dysfunction (principally ejaculatory delay), and other male genital disorders; female genital disorders (principally anorgasmia or difficulty reaching climax/orgasm); and sweating. Discontinuation syndrome may occur with abrupt withdrawal. Symptoms of discontinuation syndrome include flu-like symptoms, insomnia, nausea, imbalance, sensory changes, and hyperactivity.

Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Interacting Gene/EnzymeAllele nameGenotype(s)Defining Change(s)Type(s)DescriptionDetails
Multidrug resistance protein 1---(C;C) / (C;T)C AlleleEffect Directly StudiedPatients with this genotype have an increased likelihood of remission when using paroxetine to treat major depressive disorder.Details
Cytochrome P450 2D6CYP2D6*3Not Available2549delAEffect Directly StudiedThe presence of this polymorphism in CYP2D6 is associated with reduced or poor metabolism of paroxetine.Details
Cytochrome P450 2D6CYP2D6*4Not AvailableA alleleEffect Directly StudiedThe presence of this polymorphism in CYP2D6 is associated with reduced or poor metabolism of paroxetine.Details
Cytochrome P450 2D6CYP2D6*5Not AvailableWhole-gene deletionEffect Directly StudiedThe presence of this polymorphism in CYP2D6 is associated with reduced or poor metabolism of paroxetine.Details
Cytochrome P450 2D6CYP2D6*6Not Available1707delTEffect Directly StudiedThe presence of this polymorphism in CYP2D6 is associated with reduced or poor metabolism of paroxetine.Details
Cytochrome P450 2D6CYP2D6*7Not Available2935A>CEffect InferredPoor drug metabolizer. For individual with two non-functional alleles, alternative drug or dose reduction recommended.Details
Cytochrome P450 2D6CYP2D6*8Not Available1758G>TEffect InferredPoor drug metabolizer. For individual with two non-functional alleles, alternative drug or dose reduction recommended.Details
Cytochrome P450 2D6CYP2D6*11Not Available883G>CEffect InferredPoor drug metabolizer. For individual with two non-functional alleles, alternative drug or dose reduction recommended.Details
Cytochrome P450 2D6CYP2D6*12Not Available124G>AEffect InferredPoor drug metabolizer. For individual with two non-functional alleles, alternative drug or dose reduction recommended.Details
Cytochrome P450 2D6CYP2D6*13Not AvailableCYP2D7/2D6 hybrid gene structureEffect InferredPoor drug metabolizer. For individual with two non-functional alleles, alternative drug or dose reduction recommended.Details
Cytochrome P450 2D6CYP2D6*14ANot Available1758G>AEffect InferredPoor drug metabolizer. For individual with two non-functional alleles, alternative drug or dose reduction recommended.Details
Cytochrome P450 2D6CYP2D6*15Not Available137insT, 137_138insTEffect InferredPoor drug metabolizer. For individual with two non-functional alleles, alternative drug or dose reduction recommended.Details
Cytochrome P450 2D6CYP2D6*19Not Available2539_2542delAACTEffect InferredPoor drug metabolizer. For individual with two non-functional alleles, alternative drug or dose reduction recommended.Details
Cytochrome P450 2D6CYP2D6*20Not Available1973_1974insGEffect InferredPoor drug metabolizer. For individual with two non-functional alleles, alternative drug or dose reduction recommended.Details
Cytochrome P450 2D6CYP2D6*21Not Available2573insCEffect InferredPoor drug metabolizer. For individual with two non-functional alleles, alternative drug or dose reduction recommended.Details
Cytochrome P450 2D6CYP2D6*31Not Available-1770G>A / -1584C>G  … show all Effect InferredPoor drug metabolizer. For individual with two non-functional alleles, alternative drug or dose reduction recommended.Details
Cytochrome P450 2D6CYP2D6*36Not Available100C>T / -1426C>T  … show all Effect InferredPoor drug metabolizer. For individual with two non-functional alleles, alternative drug or dose reduction recommended.Details
Cytochrome P450 2D6CYP2D6*38Not Available2587_2590delGACTEffect InferredPoor drug metabolizer. For individual with two non-functional alleles, alternative drug or dose reduction recommended.Details
Cytochrome P450 2D6CYP2D6*40Not Available1863_1864ins(TTT CGC CCC)2Effect InferredPoor drug metabolizer. For individual with two non-functional alleles, alternative drug or dose reduction recommended.Details
Cytochrome P450 2D6CYP2D6*42Not Available3259_3260insGTEffect InferredPoor drug metabolizer. For individual with two non-functional alleles, alternative drug or dose reduction recommended.Details
Cytochrome P450 2D6CYP2D6*44Not Available2950G>CEffect InferredPoor drug metabolizer. For individual with two non-functional alleles, alternative drug or dose reduction recommended.Details
Cytochrome P450 2D6CYP2D6*47Not Available100C>T / -1426C>T  … show all Effect InferredPoor drug metabolizer. For individual with two non-functional alleles, alternative drug or dose reduction recommended.Details
Cytochrome P450 2D6CYP2D6*51Not Available-1584C>G / -1235A>G  … show all Effect InferredPoor drug metabolizer. For individual with two non-functional alleles, alternative drug or dose reduction recommended.Details
Cytochrome P450 2D6CYP2D6*56Not Available3201C>TEffect InferredPoor drug metabolizer. For individual with two non-functional alleles, alternative drug or dose reduction recommended.Details
Cytochrome P450 2D6CYP2D6*57Not Available100C>T / 310G>T  … show all Effect InferredPoor drug metabolizer. For individual with two non-functional alleles, alternative drug or dose reduction recommended.Details
Cytochrome P450 2D6CYP2D6*62Not Available4044C>TEffect InferredPoor drug metabolizer. For individual with two non-functional alleles, alternative drug or dose reduction recommended.Details
Cytochrome P450 2D6CYP2D6*68ANot Available-1426C>T / -1235A>G  … show all Effect InferredPoor drug metabolizer. For individual with two non-functional alleles, alternative drug or dose reduction recommended.Details
Cytochrome P450 2D6CYP2D6*68BNot AvailableSimilar but not identical switch region compared to CYP2D6*68A. Found in tandem arrangement with CYP2D6*4.Effect InferredPoor drug metabolizer. For individual with two non-functional alleles, alternative drug or dose reduction recommended.Details
Cytochrome P450 2D6CYP2D6*69Not Available2988G>A / -1426C>T  … show all Effect InferredPoor drug metabolizer. For individual with two non-functional alleles, alternative drug or dose reduction recommended.Details
Cytochrome P450 2D6CYP2D6*92Not Available1995delCEffect InferredPoor drug metabolizer. For individual with two non-functional alleles, alternative drug or dose reduction recommended.Details
Cytochrome P450 2D6CYP2D6*100Not Available-1426C>T / -1235A>G  … show all Effect InferredPoor drug metabolizer. For individual with two non-functional alleles, alternative drug or dose reduction recommended.Details
Cytochrome P450 2D6CYP2D6*101Not Available-1426C>T / -1235A>G  … show all Effect InferredPoor drug metabolizer. For individual with two non-functional alleles, alternative drug or dose reduction recommended.Details
Cytochrome P450 2D6CYP2D6*3Not AvailableG alleleEffect Directly StudiedThe presence of this polymorphism in CYP2D6 is associated with reduced or poor metabolism of paroxetine.Details
Cytochrome P450 2D6CYP2D6*4Not Available3877G>AEffect Directly StudiedThe presence of this polymorphism in CYP2D6 is associated with reduced or poor metabolism of paroxetine.Details

Interactions

Drug Interactions
DrugInteraction
(R)-warfarinThe risk or severity of hemorrhage can be increased when Paroxetine is combined with (R)-warfarin.
(S)-WarfarinThe risk or severity of hemorrhage can be increased when Paroxetine is combined with (S)-Warfarin.
1,10-PhenanthrolineThe therapeutic efficacy of Paroxetine can be decreased when used in combination with 1,10-Phenanthroline.
2,4-thiazolidinedioneThe risk or severity of hypoglycemia can be increased when Paroxetine is combined with 2,4-thiazolidinedione.
2,5-Dimethoxy-4-ethylamphetamineThe risk or severity of serotonin syndrome can be increased when Paroxetine is combined with 2,5-Dimethoxy-4-ethylamphetamine.
2,5-Dimethoxy-4-ethylthioamphetamineThe risk or severity of adverse effects can be increased when 2,5-Dimethoxy-4-ethylthioamphetamine is combined with Paroxetine.
3,4-MethylenedioxyamphetamineThe risk or severity of adverse effects can be increased when 3,4-Methylenedioxyamphetamine is combined with Paroxetine.
3,5-diiodothyropropionic acidThe metabolism of 3,5-diiodothyropropionic acid can be decreased when combined with Paroxetine.
4-Bromo-2,5-dimethoxyamphetamineThe risk or severity of adverse effects can be increased when 4-Bromo-2,5-dimethoxyamphetamine is combined with Paroxetine.
4-hydroxycoumarinThe metabolism of 4-hydroxycoumarin can be decreased when combined with Paroxetine.
Food Interactions
  • Take without regard to meals. Avoid alcohol.

References

Synthesis Reference

Charles M. Zepp, Yun Gao, Donald L. Heefner, "Method of preparing optically pure precursors of paroxetine." U.S. Patent US5258517, issued November 1993.

US5258517
General References
  1. Baldwin DS, Anderson IM, Nutt DJ, Bandelow B, Bond A, Davidson JR, den Boer JA, Fineberg NA, Knapp M, Scott J, Wittchen HU: Evidence-based guidelines for the pharmacological treatment of anxiety disorders: recommendations from the British Association for Psychopharmacology. J Psychopharmacol. 2005 Nov;19(6):567-96. [PubMed:16272179]
  2. Baldwin D, Bobes J, Stein DJ, Scharwachter I, Faure M: Paroxetine in social phobia/social anxiety disorder. Randomised, double-blind, placebo-controlled study. Paroxetine Study Group. Br J Psychiatry. 1999 Aug;175:120-6. [PubMed:10627793]
  3. Yonkers KA, Gullion C, Williams A, Novak K, Rush AJ: Paroxetine as a treatment for premenstrual dysphoric disorder. J Clin Psychopharmacol. 1996 Feb;16(1):3-8. [PubMed:8834412]
  4. Waldinger MD, Hengeveld MW, Zwinderman AH, Olivier B: Effect of SSRI antidepressants on ejaculation: a double-blind, randomized, placebo-controlled study with fluoxetine, fluvoxamine, paroxetine, and sertraline. J Clin Psychopharmacol. 1998 Aug;18(4):274-81. [PubMed:9690692]
  5. Waldinger MD, Zwinderman AH, Olivier B: SSRIs and ejaculation: a double-blind, randomized, fixed-dose study with paroxetine and citalopram. J Clin Psychopharmacol. 2001 Dec;21(6):556-60. [PubMed:11763001]
External Links
Human Metabolome Database
HMDB0014853
KEGG Drug
D02362
KEGG Compound
C07415
PubChem Compound
43815
PubChem Substance
46504821
ChemSpider
39888
BindingDB
50331515
ChEBI
7936
ChEMBL
CHEMBL490
Therapeutic Targets Database
DAP001428
PharmGKB
PA450801
HET
8PR
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Paroxetine
ATC Codes
N06AB05 — Paroxetine
AHFS Codes
  • 28:16.04.20 — Selective-serotonin Reuptake Inhibitors
PDB Entries
3v5w / 4jlt / 4l9i / 4mm4 / 5i6x / 6awn / 6f6i
FDA label
Download (299 KB)
MSDS
Download (51.2 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
0CompletedNot AvailableHealthy Volunteers1
1CompletedNot AvailableDrug Drug Interaction (DDI)1
1CompletedNot AvailableHealthy Volunteers8
1CompletedNot AvailableMetabolic Detoxication, Phase I1
1CompletedBasic ScienceAnovulatory cycle / Cytochrome P450 CYP3A Enzyme Deficiency / Disorder Due Cytochrome P450 CYP2D6 Variant1
1CompletedDiagnosticDepressive Disorders / Healthy Volunteers / Two Single Doses of Controlled Release Paroxetine Given 14 Days Apart1
1CompletedOtherDepressive Disorders / Healthy Volunteers1
1CompletedTreatmentDiabetic Neuropathies / Fibromyalgia / Major Depressive Disorder (MDD) / Vasomotor Symptoms1
1CompletedTreatmentHealthy Adults1
1CompletedTreatmentHealthy Volunteers3
1CompletedTreatmentPostmenopausal Syndrome1
1RecruitingHealth Services ResearchGeneralized Anxiety Disorder (GAD) / Healthy Volunteers / Major Depressive Disorder (MDD) / Obsessive Compulsive Disorder (OCD) / Panic Disorders / Social Anxiety Disorder (SAD)1
1, 2CompletedTreatmentFibromyalgia1
1, 2CompletedTreatmentHIV Associated Neurocognitive Disorders (HAND)1
2Active Not RecruitingTreatmentMajor Depressive Disorder (MDD)1
2CompletedPreventionMenopausal Hot Flushes1
2CompletedTreatmentAnxiety Disorders2
2CompletedTreatmentAnxiety Disorders / Social Anxiety Disorder (SAD)1
2CompletedTreatmentDepression / Parkinson's Disease (PD)1
2CompletedTreatmentDepressive Disorder and Anxiety Disorders / Social Anxiety Disorder (SAD)1
2CompletedTreatmentDepressive Disorders1
2CompletedTreatmentMajor Depressive Disorder (MDD)3
2CompletedTreatmentSocial Anxiety Disorder (SAD) / Social Phobia2
2CompletedTreatmentSocial Phobia1
2CompletedTreatmentTinnitus1
2RecruitingTreatmentCardiac Remodeling / Myocardial Infarction1
2TerminatedNot AvailableDepression / Hepatitis C Infection1
2TerminatedTreatmentMajor Depressive Disorder With Panic Attacks / Panic Disorders1
2TerminatedTreatmentPost Traumatic Stress Disorder (PTSD)1
3CompletedNot AvailablePremenstrual Dysphoric Disorder1
3CompletedTreatmentAlcohol Dependence / Depression / Post Traumatic Stress Disorder (PTSD)1
3CompletedTreatmentBipolar Disorder (BD) / Depression / Depression, Bipolar1
3CompletedTreatmentChronic Hepatitis C Virus (HCV) Infection1
3CompletedTreatmentDepression1
3CompletedTreatmentDepression / Depressive Disorders / Major Depressive Disorder (MDD) / Moods Disorders / Psychiatric Disorder NOS1
3CompletedTreatmentDepression / Parkinson's Disease (PD)1
3CompletedTreatmentDepressive Disorders1
3CompletedTreatmentDisseminated Sclerosis / Pain, Neuropathic1
3CompletedTreatmentGeneralized Anxiety Disorder (GAD)1
3CompletedTreatmentMajor Depressive Disorder (MDD)12
3CompletedTreatmentMenopausal Hot Flushes1
3CompletedTreatmentPanic Disorders1
3CompletedTreatmentPost Traumatic Stress Disorder (PTSD)2
3CompletedTreatmentPostmenopausal Syndrome1
3CompletedTreatmentPremature Ejaculation1
3CompletedTreatmentSocial Anxiety Disorder (SAD)1
3CompletedTreatmentUnipolar Depression1
3RecruitingTreatmentMajor Depressive Disorder (MDD)1
3TerminatedTreatmentAnxiety Disorders1
3TerminatedTreatmentAnxiety Disorders / Dementias / Depression / Psychosomatic Disorders / Schizophrenic Disorders1
3TerminatedTreatmentGeneralized Anxiety Disorder (GAD)3
3TerminatedTreatmentMajor Depressive Disorder (MDD)1
4CompletedNot AvailableDepression1
4CompletedNot AvailableMajor Depressive Disorder (MDD)1
4CompletedBasic SciencePost Traumatic Stress Disorder (PTSD)2
4CompletedHealth Services ResearchObsessive Compulsive Disorder (OCD)1
4CompletedOtherHealthy Controls / Major Depressive Disorder (MDD)1
4CompletedPreventionPost Traumatic Stress Disorder (PTSD)1
4CompletedTreatmentAlcohol Abuse / Alcohol Dependence / Alcohol Use Disorder (AUD) / Social Anxiety Disorder (SAD) / Social Phobia1
4CompletedTreatmentBipolar Disorder (BD)1
4CompletedTreatmentCardiovascular Risk Factors / Endothelial Dysfunction / Postmenopausal Flushing1
4CompletedTreatmentCombat Disorders / Post Traumatic Stress Disorder (PTSD)1
4CompletedTreatmentDementias1
4CompletedTreatmentDepression2
4CompletedTreatmentDepression / High Blood Pressure (Hypertension)1
4CompletedTreatmentDepression / Primary Insomnia1
4CompletedTreatmentDepression / Suicidal Thoughts1
4CompletedTreatmentFear of open spaces / Panic Disorders1
4CompletedTreatmentFibromyalgia Syndrome1
4CompletedTreatmentHealthy Volunteers1
4CompletedTreatmentIrritable Bowel Syndrome (IBS)1
4CompletedTreatmentMajor Depressive Disorder (MDD)5
4CompletedTreatmentMenopause1
4CompletedTreatmentObstructive Sleep Apnea (OSA)1
4CompletedTreatmentPanic Disorders4
4CompletedTreatmentPhobic Disorders1
4CompletedTreatmentPost Traumatic Stress Disorder (PTSD)2
4CompletedTreatmentPosttraumatic Stress Disorders1
4CompletedTreatmentPremenstrual Dysphoric Disorder / Premenstrual Syndrome1
4CompletedTreatmentPsychiatric Disorder NOS1
4CompletedTreatmentUnipolar Depression1
4RecruitingNot AvailableDepressive Disorders / Lactation1
4RecruitingTreatmentAnxiety Disorders / Obsessive Compulsive Disorder (OCD) / Psychiatric Disorder NOS1
4RecruitingTreatmentGeneralized Anxious Disorders1
4TerminatedTreatmentDepression1
4TerminatedTreatmentDepressive Disorders1
4TerminatedTreatmentMajor Depressive Disorder (MDD)1
4TerminatedTreatmentPost Traumatic Stress Disorder (PTSD)1
4Unknown StatusNot AvailableMajor Depressive Disorder (MDD)1
4Unknown StatusTreatmentDepression / Pain NOS1
4Unknown StatusTreatmentMajor Depression Disorder1
4Unknown StatusTreatmentMajor Depressive Disorder (MDD)2
Not AvailableActive Not RecruitingNot AvailableAnxiety Disorders / Generalized Anxiety Disorder (GAD) / Obsessive Compulsive Disorder (OCD) / Panic Disorders / Post Traumatic Stress Disorder (PTSD) / Social Anxiety Disorder (SAD)1
Not AvailableActive Not RecruitingNot AvailableMajor Depressive Disorder (MDD)1
Not AvailableActive Not RecruitingBasic ScienceHealthy Volunteers1
Not AvailableActive Not RecruitingTreatmentAdverse Reaction to Drug / Continuous Antidepressant Abuse / Depression1
Not AvailableActive Not RecruitingTreatmentDepression2
Not AvailableCompletedNot AvailableAcute Kidney Injury (AKI) / Depression1
Not AvailableCompletedNot AvailablePanic Disorders2
Not AvailableCompletedNot AvailablePsychiatric Disorder NOS3
Not AvailableCompletedNot AvailableSocial Phobia1
Not AvailableCompletedBasic ScienceAnxiety Disorders1
Not AvailableCompletedBasic ScienceMajor Depressive Disorder (MDD)1
Not AvailableCompletedPreventionDepression / Hepatitis C Viral Infection / Interferon-alpha Associated Side Effects1
Not AvailableCompletedTreatmentBipolar Disorder (BD)1
Not AvailableCompletedTreatmentDepression1
Not AvailableCompletedTreatmentMajor Depression With Panic Attacks / Panic Disorders1
Not AvailableCompletedTreatmentPost Traumatic Stress Disorder (PTSD) / Sleep disorders and disturbances1
Not AvailableCompletedTreatmentTobacco Use Disorders1
Not AvailableCompletedTreatmentUnipolar Depression1
Not AvailableEnrolling by InvitationNot AvailableBipolar Disorder (BD)1
Not AvailableRecruitingOtherObsessive Compulsive Disorder (OCD)1
Not AvailableRecruitingTreatmentAdverse Reaction to Drug / Depression1
Not AvailableRecruitingTreatmentAlcohol-Related Disorders / Brain Injury / Depression / Disease, Chronic / Mild Cognitive Impairment (MCI) / Pain NOS / Posttraumatic Stress Disorders / Quality of Life / Substance-Related Disorders / Suicidal Thoughts / Wounds and Injuries1
Not AvailableRecruitingTreatmentAntidepressant Drug Adverse Reaction / Depression1
Not AvailableRecruitingTreatmentDepression / Depressive Symptoms1
Not AvailableTerminatedTreatmentMenopausal Hot Flushes1
Not AvailableTerminatedTreatmentPost Traumatic Stress Disorder (PTSD) / Sleep disorders and disturbances1
Not AvailableUnknown StatusNot AvailableHealthy Volunteers1
Not AvailableUnknown StatusTreatmentAnxiety Disorders / Panic Disorders / Psychiatric Disorder NOS1
Not AvailableUnknown StatusTreatmentMajor Depressive Disorder (MDD)1
Not AvailableUnknown StatusTreatmentTreatment Resistant Depression (TRD)1
Not AvailableWithdrawnTreatmentPost Traumatic Stress Disorder (PTSD)1

Pharmacoeconomics

Manufacturers
  • Glaxosmithkline
  • Apotex inc
  • Mylan pharmaceuticals inc
  • Actavis elizabeth llc
  • Alphapharm pty ltd
  • Aurobindo pharma ltd
  • Caraco pharmaceutical laboratories ltd
  • Roxane laboratories inc
  • Sandoz inc
  • Teva pharmaceuticals usa inc
  • Teva pharmaceuticals usa
  • Zydus pharmaceuticals usa inc
  • Noven therapeutics llc
Packagers
  • Advanced Pharmaceutical Services Inc.
  • Aidarex Pharmacuticals LLC
  • Alphapharm Party Ltd.
  • Amerisource Health Services Corp.
  • Apotex Inc.
  • A-S Medication Solutions LLC
  • Aurobindo Pharma Ltd.
  • Bryant Ranch Prepack
  • Cadila Healthcare Ltd.
  • Caraco Pharmaceutical Labs
  • Cardinal Health
  • Comprehensive Consultant Services Inc.
  • Corepharma LLC
  • Dept Health Central Pharmacy
  • Dispensing Solutions
  • Diversified Healthcare Services Inc.
  • Excella GmbH
  • GlaxoSmithKline Inc.
  • Golden State Medical Supply Inc.
  • Greenstone LLC
  • H.J. Harkins Co. Inc.
  • Heartland Repack Services LLC
  • Innoviant Pharmacy Inc.
  • International Laboratories Inc.
  • Kaiser Foundation Hospital
  • Lake Erie Medical and Surgical Supply
  • Major Pharmaceuticals
  • Mallinckrodt Inc.
  • Mckesson Corp.
  • Murfreesboro Pharmaceutical Nursing Supply
  • Mylan
  • Neuman Distributors Inc.
  • Norwich Pharmaceuticals Inc.
  • Noven Pharmaceuticals Inc.
  • Nucare Pharmaceuticals Inc.
  • Palmetto Pharmaceuticals Inc.
  • PD-Rx Pharmaceuticals Inc.
  • Penn Labs
  • Pharmacy Service Center
  • Physicians Total Care Inc.
  • Preferred Pharmaceuticals Inc.
  • Prepackage Specialists
  • Prepak Systems Inc.
  • Rebel Distributors Corp.
  • Remedy Repack
  • Resource Optimization and Innovation LLC
  • Rubin Neudecker Medical Research Laboratories Ltd.
  • Sandhills Packaging Inc.
  • Sandoz
  • Southwood Pharmaceuticals
  • Stat Rx Usa
  • Synthon Pharmaceuticals Inc.
  • Teva Pharmaceutical Industries Ltd.
  • Torpharm Inc.
  • UDL Laboratories
  • Vangard Labs Inc.
  • Watson Pharmaceuticals
  • Zydus Pharmaceuticals
Dosage forms
FormRouteStrength
CapsuleOral7.5 mg/1
TabletOral10 mg/1
TabletOral20 mg/1
TabletOral30 mg/1
TabletOral40 mg/1
Tablet, film coatedOral10 mg/1
Tablet, film coatedOral20 mg/1
Tablet, film coatedOral30 mg/1
Tablet, film coatedOral40 mg/1
Tablet, film coated, extended releaseOral37.5 mg/1
TabletOral37.5 mg/1
SuspensionOral10 mg/5mL
Tablet, extended releaseOral12.5 mg
Tablet, extended releaseOral25 mg
Tablet, extended releaseOral37.5 mg
Tablet, film coated, extended releaseOral12.5 mg/1
Tablet, film coated, extended releaseOral25 mg/1
TabletOral10 mg
TabletOral20 mg
TabletOral30 mg
TabletOral40 mg
Prices
Unit descriptionCostUnit
Paxil 30 40 mg tablet Bottle138.39USD bottle
Paxil 30 30 mg tablet Bottle131.0USD bottle
Paxil 30 10 mg tablet Bottle121.87USD bottle
Pexeva 40 mg tablet6.29USD tablet
Pexeva 30 mg tablet6.11USD tablet
Pexeva 20 mg tablet5.84USD tablet
Pexeva 10 mg tablet5.6USD tablet
Paxil CR 37.5 mg 24 Hour tablet4.5USD tablet
Paxil 40 mg tablet4.44USD tablet
Paxil CR 25 mg 24 Hour tablet4.37USD tablet
Paxil cr 37.5 mg tablet4.32USD tablet
Paxil 30 mg tablet4.2USD tablet
Paxil cr 25 mg tablet4.2USD tablet
Paxil CR 12.5 mg 24 Hour tablet4.18USD tablet
Paxil 20 mg tablet4.16USD tablet
PARoxetine HCl 37.5 mg 24 Hour tablet4.04USD tablet
Paxil cr 12.5 mg tablet4.02USD tablet
PARoxetine HCl 25 mg 24 Hour tablet3.93USD tablet
Paxil 10 mg tablet3.91USD tablet
PARoxetine HCl 12.5 mg 24 Hour tablet3.76USD tablet
Paroxetine hcl 40 mg tablet2.93USD tablet
Paroxetine hcl 30 mg tablet2.78USD tablet
Paroxetine hcl 20 mg tablet2.7USD tablet
Paroxetine hcl 10 mg tablet2.58USD tablet
Paxil 30 mg Tablet2.16USD tablet
Pms-Paroxetine 40 mg Tablet2.1USD tablet
Paxil 20 mg Tablet2.03USD tablet
Apo-Paroxetine 30 mg Tablet1.12USD tablet
Co Paroxetine 30 mg Tablet1.12USD tablet
Mylan-Paroxetine 30 mg Tablet1.12USD tablet
Novo-Paroxetine 30 mg Tablet1.12USD tablet
Phl-Paroxetine 30 mg Tablet1.12USD tablet
Pms-Paroxetine 30 mg Tablet1.12USD tablet
Ratio-Paroxetine 30 mg Tablet1.12USD tablet
Sandoz Paroxetine 30 mg Tablet1.12USD tablet
Apo-Paroxetine 20 mg Tablet1.05USD tablet
Co Paroxetine 20 mg Tablet1.05USD tablet
Mylan-Paroxetine 20 mg Tablet1.05USD tablet
Novo-Paroxetine 20 mg Tablet1.05USD tablet
Phl-Paroxetine 20 mg Tablet1.05USD tablet
Pms-Paroxetine 20 mg Tablet1.05USD tablet
Ratio-Paroxetine 20 mg Tablet1.05USD tablet
Sandoz Paroxetine 20 mg Tablet1.05USD tablet
Paxil 10 mg/5ml Suspension0.85USD ml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US6703408No2004-03-092022-10-21Us
US5789449No1998-08-042009-07-06Us
CA2445678No2009-11-242016-07-19Canada
CA2168829No1997-12-162016-02-05Canada
US7598271No2009-10-062023-02-12Us
US6121291Yes2000-09-192017-09-17Us
US5811436Yes1998-09-222016-03-22Us
US6063927Yes2000-05-162019-10-23Us
US6172233Yes2001-01-092018-07-15Us
US7229640Yes2007-06-122017-01-19Us
US6548084Yes2003-04-152017-01-19Us
US5874447No1999-02-232017-06-10Us
US8658663No2014-02-252029-04-06Us
US8946251No2015-02-032026-08-04Us
US6133289Yes2000-10-172015-11-19Us
US5900423Yes1999-05-042015-11-19Us
US5872132Yes1999-02-162015-11-19Us
US6080759Yes2000-06-272015-11-19Us
US9393237No2016-07-192026-08-04Us

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)147-150 °C (mesylate salt) FDA label
water solubility>1 g/mL (mesylate salt) Not Available
logP3.6Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.00853 mg/mLALOGPS
logP3.1ALOGPS
logP3.15ChemAxon
logS-4.6ALOGPS
pKa (Strongest Basic)9.77ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area39.72 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity88.02 m3·mol-1ChemAxon
Polarizability34.48 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.9869
Caco-2 permeable+0.5195
P-glycoprotein substrateSubstrate0.6555
P-glycoprotein inhibitor IInhibitor0.8564
P-glycoprotein inhibitor IIInhibitor0.6771
Renal organic cation transporterInhibitor0.5222
CYP450 2C9 substrateNon-substrate0.9265
CYP450 2D6 substrateSubstrate0.8918
CYP450 3A4 substrateNon-substrate0.6004
CYP450 1A2 substrateInhibitor0.9107
CYP450 2C9 inhibitorInhibitor0.8948
CYP450 2D6 inhibitorNon-inhibitor0.9231
CYP450 2C19 inhibitorNon-inhibitor0.9025
CYP450 3A4 inhibitorInhibitor0.8298
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.8649
Ames testNon AMES toxic0.6722
CarcinogenicityNon-carcinogens0.9046
BiodegradationNot ready biodegradable0.995
Rat acute toxicity2.8239 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Strong inhibitor0.5554
hERG inhibition (predictor II)Non-inhibitor0.5879
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Mass Spectrum (Electron Ionization)MSsplash10-0006-8900000000-0a273deac3c7836cdc76
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-001i-3709000000-7d029049c2e6d638ecbe
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-001i-2409000000-077fb077fbf0e4210f51

Taxonomy

Description
This compound belongs to the class of organic compounds known as phenylpiperidines. These are compounds containing a phenylpiperidine skeleton, which consists of a piperidine bound to a phenyl group.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Piperidines
Sub Class
Phenylpiperidines
Direct Parent
Phenylpiperidines
Alternative Parents
Benzodioxoles / Fluorobenzenes / Aralkylamines / Alkyl aryl ethers / Aryl fluorides / Oxacyclic compounds / Dialkylamines / Azacyclic compounds / Acetals / Organopnictogen compounds
show 2 more
Substituents
Phenylpiperidine / Benzodioxole / Alkyl aryl ether / Fluorobenzene / Halobenzene / Aralkylamine / Aryl fluoride / Aryl halide / Monocyclic benzene moiety / Benzenoid
show 16 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
piperidines, organofluorine compound, aromatic ether, benzodioxoles (CHEBI:7936)

Targets

Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Inhibitor
General Function
Serotonin:sodium symporter activity
Specific Function
Serotonin transporter whose primary function in the central nervous system involves the regulation of serotonergic signaling via transport of serotonin molecules from the synaptic cleft back into t...
Gene Name
SLC6A4
Uniprot ID
P31645
Uniprot Name
Sodium-dependent serotonin transporter
Molecular Weight
70324.165 Da
References
  1. Scholze P, Zwach J, Kattinger A, Pifl C, Singer EA, Sitte HH: Transporter-mediated release: a superfusion study on human embryonic kidney cells stably expressing the human serotonin transporter. J Pharmacol Exp Ther. 2000 Jun;293(3):870-8. [PubMed:10869387]
  2. Preuss UW, Soyka M, Bahlmann M, Wenzel K, Behrens S, de Jonge S, Kruger M, Bondy B: Serotonin transporter gene regulatory region polymorphism (5-HTTLPR), [3H]paroxetine binding in healthy control subjects and alcohol-dependent patients and their relationships to impulsivity. Psychiatry Res. 2000 Sep 25;96(1):51-61. [PubMed:10980326]
  3. Haughey HM, Fleckenstein AE, Metzger RR, Hanson GR: The effects of methamphetamine on serotonin transporter activity: role of dopamine and hyperthermia. J Neurochem. 2000 Oct;75(4):1608-17. [PubMed:10987842]
  4. Pollock BG, Ferrell RE, Mulsant BH, Mazumdar S, Miller M, Sweet RA, Davis S, Kirshner MA, Houck PR, Stack JA, Reynolds CF, Kupfer DJ: Allelic variation in the serotonin transporter promoter affects onset of paroxetine treatment response in late-life depression. Neuropsychopharmacology. 2000 Nov;23(5):587-90. [PubMed:11027924]
  5. Wihlback AC, Sundstrom-Poromaa I, Allard P, Mjorndal T, Spigset O, Backstrom T: Influence of postmenopausal hormone replacement therapy on platelet serotonin uptake site and serotonin 2A receptor binding. Obstet Gynecol. 2001 Sep;98(3):450-7. [PubMed:11530128]
  6. Tatsumi M, Groshan K, Blakely RD, Richelson E: Pharmacological profile of antidepressants and related compounds at human monoamine transporters. Eur J Pharmacol. 1997 Dec 11;340(2-3):249-58. [PubMed:9537821]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Norepinephrine:sodium symporter activity
Specific Function
Amine transporter. Terminates the action of noradrenaline by its high affinity sodium-dependent reuptake into presynaptic terminals.
Gene Name
SLC6A2
Uniprot ID
P23975
Uniprot Name
Sodium-dependent noradrenaline transporter
Molecular Weight
69331.42 Da
References
  1. Rubin RT: Paroxetine binding to the rat norepinephrine transporter in vivo. Biol Psychiatry. 2000 Nov 1;48(9):954-6. [PubMed:11203183]
  2. Gilmor ML, Owens MJ, Nemeroff CB: Inhibition of norepinephrine uptake in patients with major depression treated with paroxetine. Am J Psychiatry. 2002 Oct;159(10):1702-10. [PubMed:12359676]
  3. Nemeroff CB, Owens MJ: Neuropharmacology of paroxetine. Psychopharmacol Bull. 2003 Spring;37 Suppl 1:8-18. [PubMed:14566196]
  4. Tatsumi M, Groshan K, Blakely RD, Richelson E: Pharmacological profile of antidepressants and related compounds at human monoamine transporters. Eur J Pharmacol. 1997 Dec 11;340(2-3):249-58. [PubMed:9537821]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Other/unknown
General Function
Virus receptor activity
Specific Function
G-protein coupled receptor for 5-hydroxytryptamine (serotonin). Also functions as a receptor for various drugs and psychoactive substances, including mescaline, psilocybin, 1-(2,5-dimethoxy-4-iodop...
Gene Name
HTR2A
Uniprot ID
P28223
Uniprot Name
5-hydroxytryptamine receptor 2A
Molecular Weight
52602.58 Da
References
  1. Bixo M, Allard P, Backstrom T, Mjorndal T, Nyberg S, Spigset O, Sundstrom-Poromaa I: Binding of [3H]paroxetine to serotonin uptake sites and of [3H]lysergic acid diethylamide to 5-HT2A receptors in platelets from women with premenstrual dysphoric disorder during gonadotropin releasing hormone treatment. Psychoneuroendocrinology. 2001 Aug;26(6):551-64. [PubMed:11403977]
  2. Meyer JH, Kapur S, Eisfeld B, Brown GM, Houle S, DaSilva J, Wilson AA, Rafi-Tari S, Mayberg HS, Kennedy SH: The effect of paroxetine on 5-HT(2A) receptors in depression: an [(18)F]setoperone PET imaging study. Am J Psychiatry. 2001 Jan;158(1):78-85. [PubMed:11136637]
Kind
Protein
Organism
Human
Pharmacological action
No
Actions
Antagonist
General Function
Phosphatidylinositol phospholipase c activity
Specific Function
The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the...
Gene Name
CHRM1
Uniprot ID
P11229
Uniprot Name
Muscarinic acetylcholine receptor M1
Molecular Weight
51420.375 Da
References
  1. Cusack B, Nelson A, Richelson E: Binding of antidepressants to human brain receptors: focus on newer generation compounds. Psychopharmacology (Berl). 1994 May;114(4):559-65. [PubMed:7855217]
Kind
Protein
Organism
Human
Pharmacological action
No
Actions
Antagonist
General Function
G-protein coupled acetylcholine receptor activity
Specific Function
The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the...
Gene Name
CHRM2
Uniprot ID
P08172
Uniprot Name
Muscarinic acetylcholine receptor M2
Molecular Weight
51714.605 Da
References
  1. Cusack B, Nelson A, Richelson E: Binding of antidepressants to human brain receptors: focus on newer generation compounds. Psychopharmacology (Berl). 1994 May;114(4):559-65. [PubMed:7855217]
Kind
Protein
Organism
Human
Pharmacological action
No
Actions
Antagonist
General Function
Receptor activity
Specific Function
The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the...
Gene Name
CHRM3
Uniprot ID
P20309
Uniprot Name
Muscarinic acetylcholine receptor M3
Molecular Weight
66127.445 Da
References
  1. Cusack B, Nelson A, Richelson E: Binding of antidepressants to human brain receptors: focus on newer generation compounds. Psychopharmacology (Berl). 1994 May;114(4):559-65. [PubMed:7855217]
Kind
Protein
Organism
Human
Pharmacological action
No
Actions
Antagonist
General Function
Guanyl-nucleotide exchange factor activity
Specific Function
The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the...
Gene Name
CHRM4
Uniprot ID
P08173
Uniprot Name
Muscarinic acetylcholine receptor M4
Molecular Weight
53048.65 Da
References
  1. Cusack B, Nelson A, Richelson E: Binding of antidepressants to human brain receptors: focus on newer generation compounds. Psychopharmacology (Berl). 1994 May;114(4):559-65. [PubMed:7855217]
Kind
Protein
Organism
Human
Pharmacological action
No
Actions
Antagonist
General Function
Phosphatidylinositol phospholipase c activity
Specific Function
The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the...
Gene Name
CHRM5
Uniprot ID
P08912
Uniprot Name
Muscarinic acetylcholine receptor M5
Molecular Weight
60073.205 Da
References
  1. Cusack B, Nelson A, Richelson E: Binding of antidepressants to human brain receptors: focus on newer generation compounds. Psychopharmacology (Berl). 1994 May;114(4):559-65. [PubMed:7855217]

Enzymes

Details
1. Cytochrome P450 2D6
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
General Function
Steroid hydroxylase activity
Specific Function
Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic...
Gene Name
CYP2D6
Uniprot ID
P10635
Uniprot Name
Cytochrome P450 2D6
Molecular Weight
55768.94 Da
References
  1. Urichuk L, Prior TI, Dursun S, Baker G: Metabolism of atypical antipsychotics: involvement of cytochrome p450 enzymes and relevance for drug-drug interactions. Curr Drug Metab. 2008 Jun;9(5):410-8. [PubMed:18537577]
  2. Baumann P: Pharmacokinetic-pharmacodynamic relationship of the selective serotonin reuptake inhibitors. Clin Pharmacokinet. 1996 Dec;31(6):444-69. [PubMed:8968657]
  3. Ozdemir V, Naranjo CA, Herrmann N, Reed K, Sellers EM, Kalow W: Paroxetine potentiates the central nervous system side effects of perphenazine: contribution of cytochrome P4502D6 inhibition in vivo. Clin Pharmacol Ther. 1997 Sep;62(3):334-47. [PubMed:9333110]
  4. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
  5. Drug Interactions: Cytochrome P450 Drug Interaction Table [Link]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Steroid hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP2C9
Uniprot ID
P11712
Uniprot Name
Cytochrome P450 2C9
Molecular Weight
55627.365 Da
References
  1. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014]
  2. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Steroid hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP2B6
Uniprot ID
P20813
Uniprot Name
Cytochrome P450 2B6
Molecular Weight
56277.81 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
  2. Walsky RL, Astuccio AV, Obach RS: Evaluation of 227 drugs for in vitro inhibition of cytochrome P450 2B6. J Clin Pharmacol. 2006 Dec;46(12):1426-38. [PubMed:17101742]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Steroid hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP2C8
Uniprot ID
P10632
Uniprot Name
Cytochrome P450 2C8
Molecular Weight
55824.275 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP1A2
Uniprot ID
P05177
Uniprot Name
Cytochrome P450 1A2
Molecular Weight
58293.76 Da
References
  1. Ozdemir V, Naranjo CA, Shulman RW, Herrmann N, Sellers EM, Reed K, Kalow W: Determinants of interindividual variability and extent of CYP2D6 and CYP1A2 inhibition by paroxetine and fluvoxamine in vivo. J Clin Psychopharmacol. 1998 Jun;18(3):198-207. [PubMed:9617978]
  2. Begre S, von Bardeleben U, Ladewig D, Jaquet-Rochat S, Cosendai-Savary L, Golay KP, Kosel M, Baumann P, Eap CB: Paroxetine increases steady-state concentrations of (R)-methadone in CYP2D6 extensive but not poor metabolizers. J Clin Psychopharmacol. 2002 Apr;22(2):211-5. [PubMed:11910269]
Kind
Protein
Organism
Human
Pharmacological action
No
Actions
Inhibitor
General Function
Vitamin d3 25-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. Gerotziafas GT, Mahe I, Elalamy I: New orally active anticoagulant agents for the prevention and treatment of venous thromboembolism in cancer patients. Ther Clin Risk Manag. 2014 Jun 13;10:423-36. doi: 10.2147/TCRM.S49063. eCollection 2014. [PubMed:24966680]

Transporters

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Xenobiotic-transporting atpase activity
Specific Function
Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
Gene Name
ABCB1
Uniprot ID
P08183
Uniprot Name
Multidrug resistance protein 1
Molecular Weight
141477.255 Da
References
  1. Weiss J, Dormann SM, Martin-Facklam M, Kerpen CJ, Ketabi-Kiyanvash N, Haefeli WE: Inhibition of P-glycoprotein by newer antidepressants. J Pharmacol Exp Ther. 2003 Apr;305(1):197-204. [PubMed:12649369]

Drug created on June 13, 2005 07:24 / Updated on December 14, 2018 17:07