Paroxetine (CED0001984)

Record Information

Version

1.0

Creation Date

2009-07-21 20:27:29 UTC

Update Date

2026-05-14 16:46:54 UTC

SynCED ID

CED0001984

Secondary Accession Numbers

CHEM002256
T3D2868

Identification

Common Name

Paroxetine

Class

Small Molecule

Description

Paroxetine belongs to the phenylpiperidines, a subclass of piperidines within the organic compounds. This exogenous compound has the formula C19H20FNO3 and an average molecular weight of 329.37 g/mol. At room temperature, it exists as a solid. It is classified within the superclass of organoheterocyclic compounds. Paroxetine is used as an antidepressant and anxiolytic drug. Biologically, it functions as a serotonin uptake inhibitor and a P450 inhibitor, and it is identified as a hepatotoxic agent. Its protein targets include the sodium-dependent serotonin transporter (SLC6A4), the sodium-dependent noradrenaline transporter (SLC6A2), and the 5-hydroxytryptamine receptor 2A (HTR2A). As a potent and highly selective inhibitor of neuronal serotonin reuptake, paroxetine likely inhibits serotonin reuptake at the neuronal membrane, which enhances serotonergic neurotransmission by reducing neurotransmitter turnover. This process prolongs serotonin activity at synaptic receptor sites and potentiates 5-HT in the CNS; paroxetine is more potent than fluoxetine and sertraline in its ability to inhibit 5-HT reuptake. Additionally, it is a binder, inhibitor, or other unknown modulator of Muscarinic acetylcholine receptors M1 (CHRM1), M2 (CHRM2), M3 (CHRM3), and M4 (CHRM4), among 21 other proteins. The compound is recorded in 12 sources, including antidepressants in healthcare, pharmaceuticals, and veterinary products; drinking water; food processing for fish and hops; household cleaning and consumer products such as non-electric simulated smoking devices and other smoking requisites; and electrical and electronic equipment, including discharge lamps, electric hearing aids, electric switches, electrically stimulated smoking devices, and radio transmission systems. The recorded exposure route for paroxetine is oral.

Contaminant Type

Amine
Antidepressant
Antidepressant, Second-Generation
Antidepressive Agent
Drug
Ether
Food Toxin
Metabolite
Organic Compound
Organofluoride
Selective Serotonin Reuptake Inhibitor
Serotonin Uptake Inhibitor
Synthetic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(-)-(3S,4R)-4-(p-Fluorophenyl)-3-((3,4-(methylenedioxy)phenoxy)methyl)piperidine	ChEBI
(3S-trans)-3-((1,3-Benzodioxol-5-yloxy)methyl)-4-(4-fluorophenyl)piperidine	ChEBI
Paroxetina	ChEBI
Paroxetinum	ChEBI
Hydrochloride hemihydrate, paroxetine	HMDB
Hydrochloride, hemihydrate paroxetine	HMDB
Acetate, paroxetine	HMDB
Maleate, paroxetine	HMDB
Paroxetine acetate	HMDB
Paroxetine hydrochloride hemihydrate	HMDB
Paroxetine, trans-(+)-isomer	HMDB
Seroxat	HMDB
Aropax	HMDB
Hemihydrate paroxetine hydrochloride	HMDB
Paroxetine hydrochloride anhydrous	HMDB
Paroxetine, cis-(+)-isomer	HMDB
Paxil	HMDB
Anhydrous, paroxetine hydrochloride	HMDB
Hemihydrate, paroxetine hydrochloride	HMDB
Hydrochloride anhydrous, paroxetine	HMDB
Hydrochloride, paroxetine	HMDB
Paroxetine hydrochloride	HMDB
Paroxetine hydrochloride, hemihydrate	HMDB
Paroxetine maleate	HMDB
Paroxetine, cis-(-)-isomer	HMDB

Chemical Formula

C₁₉H₂₀FNO₃

Average Molecular Mass

329.365 g/mol

Monoisotopic Mass

329.143 g/mol

CAS Registry Number

61869-08-7

IUPAC Name

(3S,4R)-3-[(2H-1,3-benzodioxol-5-yloxy)methyl]-4-(4-fluorophenyl)piperidine

Traditional Name

paroxetine

SMILES

FC1=CC=C(C=C1)[C@@H]1CCNC[C@H]1COC1=CC2=C(OCO2)C=C1

InChI Identifier

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

InChI Key

AHOUBRCZNHFOSL-YOEHRIQHSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenylpiperidines. Phenylpiperidines 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

Substituents

Phenylpiperidine
Benzodioxole
Alkyl aryl ether
Fluorobenzene
Halobenzene
Aralkylamine
Aryl fluoride
Aryl halide
Monocyclic benzene moiety
Benzenoid
Ether
Secondary aliphatic amine
Acetal
Oxacycle
Secondary amine
Azacycle
Organooxygen compound
Organonitrogen compound
Organofluoride
Organohalogen compound
Hydrocarbon derivative
Organopnictogen compound
Organic oxygen compound
Amine
Organic nitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

piperidines (CHEBI:7936 )
organofluorine compound (CHEBI:7936 )
aromatic ether (CHEBI:7936 )
benzodioxoles (CHEBI:7936 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Applications

Biological Roles

serotonin uptake inhibitor (PMC8620498 )?
P450 inhibitor (PMC12155096 )?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 exihibiting itself through the ability to induce damage to the liver in animals.
inhibitor (PMC5962350 )?
Antidepressant (PMC5962350 , PMC5962350 )?

Chemical Roles

P450 inhibitor ?

Organoleptic Effects

bitter taste ?

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	147-150°C (mesylate salt)
Boiling Point	Not Available
Solubility	>1 g/mL (mesylate salt)

Predicted Properties

Property	Value	Source
Water Solubility	0.0085 g/L	ALOGPS
logP	3.1	ALOGPS
logP	3.15	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Basic)	9.77	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	39.72 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	88.02 m³·mol⁻¹	ChemAxon
Polarizability	34.48 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum	splash10-0f9i-1911000000-12c3e68d4fb152fcf19a	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-001i-3709000000-7d029049c2e6d638ecbe	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-001i-2409000000-077fb077fbf0e4210f51	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-001i-0009000000-56cd88a7bae65159b40e	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-00di-9300000000-95d57654f38599951250	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-001i-3609000000-814e80528f9dde6c33a5	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-001l-6809000000-6461647e2077c359be2e	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-001l-2906000000-a8c78adc02d4f098ec53	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-001i-2309000000-dae2fa8b8f5f0d2d9c83	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-001i-0409000000-034c664e49ac69cc6701	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0uel-1915000000-1cceed9b83dba502dc39	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0006-6900000000-a45d96d1002ba6a0049e	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-004i-0409000000-7b0c408204b05629f155	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-002r-1829000000-c76de0eff9bcad218ff4	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-000i-4900000000-77810e81d9b6e4cb0cf7	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-001i-0409000000-52ccb63e39824262697a	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-001r-0915000000-6663900bf83beabe3f50	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-004r-0901000000-7e65658f2aa91b98e293	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-000i-0903000000-8712cfe4d48fe9ccd484	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-004r-0927000000-031f43eecdb967cf56ae	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0a4i-1900000000-6adcbe9a9b2a0603a1ce	Not Available	View Spectrum
MS	MS Spectrum	splash10-0006-8900000000-0a273deac3c7836cdc76	Not Available	View Spectrum

Toxicity Profile

Toxicity Values

Toxicity Value	Organism	Dose Descriptor	Route of Exposure	Predicted or Experimental	Toxicity Rating	Reference
500.0 mg/kg	Mouse	LD50	Oral	experimental	Not Available	1
262.0 Log mg/kg [150:470]	Rat	LD50	oral	predicted	Not Available	Not Available

Toxicity / Toxin Class

Not Available

Mechanism of Toxicity

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.

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Minimum Risk Level

Not Available

Symptoms

Coma, dizziness, drowsiness, facial flushing, nausea, sweating, tremor, vomiting

Treatment

Treatment should consist of those general measures employed in the management of overdosage with any drugs effective in the treatment of major depressive disorder. Ensure an adequate airway, oxygenation, and ventilation. Monitor cardiac rhythm and vital signs. General supportive and symptomatic measures are also recommended. Induction of emesis is not recommended. Gastric lavage with a large-bore orogastric tube with appropriate airway protection, if needed, may be indicated if performed soon after ingestion, or in symptomatic patients. Activated charcoal should be administered. Due to the large volume of distribution of this drug, forced diuresis, dialysis, hemoperfusion, and exchange transfusion are unlikely to be of benefit. No specific antidotes for paroxetine are known. (8)

Health Effects

Health Effect	Relationship	Direction	Description	Reference
anxiety disorder	Not Available	Not Available	Not Available	PMC8620498
sexual dysfunction	Associated With?	Not Available	Not Available	PMC11831715
Oxidative Stress	Associated With?	Not Available	Not Available	PMC11831715
depressive disorder	Not Available	Not Available	Not Available	PMC1492602 , PMC3595243
depressive disorder	Has Therapeutic Effect On	Not Available	Not Available	PMC13282955
Erythema	Has Therapeutic Effect On	Not Available	Not Available	PMC13282955
tricuspid valve insufficiency	Associated With?	Not Available	Not Available	PMC12903827
Pulmonary Valve Insufficiency	Associated With?	Not Available	Not Available	PMC12903827

Exposure Sources

Source ID	Source	Sector	Reference
CEDs000010	Insecticides?Insecticides are synthetic chemicals designed to control or eliminate insect pests that threaten crops and other agricultural products.	Agriculture & land management	PubChem
CEDs000115	Drinking water?Drinking water can be a medium for synthetic chemical contamination, often originating from various industrial processes and agricultural practices.	Drinking water & water supply	Not Available
CEDs000377	Antidepressants?Antidepressants, a class of synthetic chemicals designed to alleviate symptoms of depression and anxiety, can enter the environment through various pathways, leading to contamination of water systems.	Healthcare, pharmaceuticals & veterinary products	Not Available
CEDs000483	WWTP effluent?Wastewater treatment plant (WWTP) effluent can serve as a significant source of synthetic chemical contamination in the environment.	Wastewater, sanitation & biosolids	PMC12707372
CEDs000514	Discharge Lamps?Discharge lamps, including fluorescent and high-intensity discharge (HID) lamps, are commonly used for lighting applications due to their energy efficiency and brightness.	Electrical & Electronic Equipment	PubChem
CEDs000516	Electric Hearing Aids?Electric hearing aids are small electronic devices designed to amplify sound for individuals with hearing loss.	Electrical & Electronic Equipment	PubChem
CEDs000517	Electric Switches?Electric switches, integral components in numerous devices, can be a source of synthetic chemical contamination due to the materials and manufacturing processes involved in their production.	Electrical & Electronic Equipment	PubChem
CEDs000518	Electrically Stimulated Smoking Devices?Electrically stimulated smoking devices, commonly known as e-cigarettes or vape pens, utilize electrical components to heat a liquid solution, often containing nicotine, flavorings, and other additives, to produce an aerosol for inhalation.	Electrical & Electronic Equipment	PubChem
CEDs000519	Electrodes?Electrodes, used in various electrical and electronic applications, can be a source of synthetic chemical contamination due to the materials from which they are constructed and the processes involved in their manufacturing.	Electrical & Electronic Equipment	PubChem
CEDs000530	Radio Transmission Systems?Radio transmission systems utilize a variety of synthetic chemicals in their manufacturing and maintenance processes.	Electrical & Electronic Equipment	PubChem
CEDs000537	Television Systems?Television systems can be a source of synthetic chemical contamination due to the various materials and components used in their manufacture and operation.	Electrical & Electronic Equipment	PubChem
CEDs000545	Food Preservation?Food preservation often involves the use of synthetic chemicals, such as preservatives, flavor enhancers, and color additives, to extend shelf life and enhance the sensory qualities of food products.	Food, food processing & cookware	PubChem
CEDs000551	Processing Fish?Processing fish can lead to synthetic chemical contamination through various stages of production and preservation.	Food, food processing & cookware	PubChem
CEDs000553	Treatment Of Hops?Hops, a key ingredient in brewing and food flavoring, can be a source of synthetic chemical contamination due to various agricultural practices.	Food, food processing & cookware	PubChem
CEDs000559	Non Electric Simulated Smoking Devices?Non-electric simulated smoking devices, often designed to mimic the experience of smoking without combustion, can be sources of synthetic chemical contamination due to the materials and chemicals used in their construction and operation.	Household cleaning & consumer products	PubChem
CEDs000560	Other Smoking Requisites?Other smoking requisites, including items such as lighters, matches, and rolling papers, can introduce synthetic chemical contamination through various components and additives.	Household cleaning & consumer products	PubChem
CEDs000561	Perfumes Within Detergents And Soaps?Perfumes within detergents and soaps are synthetic fragrance compounds added to enhance the sensory experience of cleaning products.	Household cleaning & consumer products	PubChem
CEDs000569	Tobacco Smoke Filters?Tobacco smoke filters are designed to reduce the inhalation of harmful substances in cigarette smoke, including tar and other particulate matter.	Household cleaning & consumer products	PubChem
CEDs000580	Manufacture Preparation Of Tobacco Products?The manufacture and preparation of tobacco products involve various processes that can result in the introduction of synthetic chemicals into the environment.	Industrial manufacturing & chemical processing	PubChem
CEDs000596	Acaricides?Acaricides are synthetic chemicals specifically designed to target and control mite populations that can damage crops and plants.	Agriculture & land management	PubChem
CEDs000600	Herbicides And Algicides?Herbicides and algicides are synthetic chemicals primarily used to control unwanted plants and algae in various environments.	Agriculture & land management	PubChem
CEDs000605	Pest Repellants?Pest repellents, often formulated from synthetic chemicals, are widely used to protect crops from insect infestations and other pests.	Agriculture & land management	PubChem
CEDs000610	Aftersun Products?Aftersun products are designed to soothe and hydrate the skin after sun exposure, often containing various synthetic chemicals such as emollients, preservatives, and fragrances.	Personal care & cosmetics	PubChem
CEDs000611	Anti Perspirants Or Body Deoderants?Antiperspirants and body deodorants commonly contain synthetic chemicals such as aluminum compounds, parabens, and synthetic fragrances.	Personal care & cosmetics	PubChem
CEDs000614	Essential Oils Or Perfumes?Essential oils and perfumes are complex mixtures of volatile compounds derived from natural or synthetic sources, commonly used for their aromatic properties.	Personal care & cosmetics	PubChem
CEDs000615	Eye Makeup Products?Eye makeup products, including mascaras, eyeliners, and eyeshadows, often contain a variety of synthetic chemicals such as pigments, preservatives, and film-forming agents.	Personal care & cosmetics	PubChem
CEDs000618	Lip Makeup Products?Lip makeup products, such as lipsticks, lip glosses, and lip liners, often contain a variety of synthetic chemicals, including pigments, preservatives, and emollients.	Personal care & cosmetics	PubChem
CEDs000632	Apparel?Apparel production often involves the use of various synthetic chemicals, including dyes, finishing agents, and preservatives.	Textiles, leather & furnishings	PubChem
CEDs000642	Footwear?Footwear production often involves the use of various synthetic chemicals, such as adhesives, dyes, and treatments, which can contribute to environmental contamination.	Textiles, leather & furnishings	PubChem
CEDs000671	Airplanes And Helicopters?Airplanes and helicopters are significant sources of synthetic chemical contamination primarily through the use of aviation fuels, lubricants, and de-icing agents.	Aviation & Aerospace	PubChem
CEDs000685	Ceramics?Ceramics can be a source of synthetic chemical contamination through various additives and processing agents used in their production.	Building & Construction	PubChem
CEDs000688	Glass Coatings?Glass coatings are synthetic chemical formulations applied to glass surfaces to enhance properties such as durability, UV resistance, and aesthetic appeal.	Building & Construction	PubChem
CEDs000695	Treatment Of Milk Or Cream?The treatment of milk or cream involves various processes such as pasteurization, homogenization, and the addition of preservatives to enhance shelf life and safety.	Food, food processing & cookware	PubChem
CEDs000696	Nanotechnology?Nanotechnology involves the manipulation of materials at the molecular or atomic level, typically within the range of 1 to 100 nanometers.	Industrial manufacturing & chemical processing	PubChem
CEDs000735	Explosives?Explosives are chemical compounds or mixtures designed to undergo rapid decomposition, releasing energy in the form of gas and heat.	Defense & military infrastructure	PubChem
CEDs000739	Inks?Inks are complex mixtures composed of pigments or dyes, solvents, resins, and additives used primarily for printing and writing applications.	Paper, pulp & fiber products	PubChem
CEDs000740	Paper?Paper production involves the processing of wood fibers and the use of various chemicals, which can lead to synthetic chemical contamination.	Paper, pulp & fiber products	PubChem
CEDs000741	Pigment Pastes?Pigment pastes are concentrated dispersions of pigments used to impart color and properties to materials.	Paper, pulp & fiber products	PubChem
CEDs000743	Sludge Treatment?Sludge treatment involves the processing of waste materials generated from wastewater treatment plants, which often contain a variety of organic and inorganic substances.	Wastewater, sanitation & biosolids	PubChem
CEDs000744	Water, Wastewater, & Sewage Treatment?Water, wastewater, and sewage treatment processes are critical for managing and mitigating pollutants in water systems.	Wastewater, sanitation & biosolids	PubChem
CEDs02255	Water	Aquatic systems & sediments	PMC5306312
CEDs02265	River Water	Aquatic systems & sediments	PMC5306312
CEDs02268	Water Samples	Aquatic systems & sediments	PMC12303642
CEDs02319	Lake Water	Aquatic systems & sediments	PMC5306312
CEDs02330	River Sediments	Aquatic systems & sediments	PMC10675236
CEDs02376	Ponds	Aquatic systems & sediments	PMC12303642
CEDs02431	Estuarine Sediment	Aquatic systems & sediments	PMC8537644
CEDs03017	Sludge	Wastewater, sanitation & biosolids	PMC8537644

Pathways

3 pathwaysPathway Source: PathBank

Paroxetine Mechanism of Action Action Pathway New

Paroxetine Drug Metabolism Action Pathway

Paroxetine Predicted Metabolism Pathway

Targets

Structure	Protein	UniProt ID	Organism	Relationship	Details
Click to view 3D structure	Cytochrome P450 2D6	P10635	Humans	Known	Not Available
Click to view 3D structure	Beta-adrenergic receptor kinase 1	P21146	Bos taurus	Predicted (SEA)	Prediction Confidence Score 0.742 Applicability Domain 1.0 Statistical Significance 1.00e-05 Supporting Reference Compounds 16 E-value 0.0778492
Click to view 3D structure	Beta-adrenergic receptor kinase 1	P25098	Humans	Predicted (SEA)	Prediction Confidence Score 0.577 Applicability Domain 1.0 Statistical Significance 1.50e-04 Supporting Reference Compounds 76 E-value 1.16774
Click to view 3D structure	Cytochrome P450 2D6	P10635	Humans	Predicted (SEA)	Prediction Confidence Score 0.554 Applicability Domain 1.0 Statistical Significance 0.0014 Supporting Reference Compounds 1130 E-value 11.2103
Click to view 3D structure	Sodium-dependent dopamine transporter	P23977	Rattus norvegicus	Predicted (SEA)	Prediction Confidence Score 0.547 Applicability Domain 1.0 Statistical Significance 9.00e-04 Supporting Reference Compounds 203 E-value 7.00643
Click to view 3D structure	Sodium-dependent serotonin transporter	P31652	Rattus norvegicus	Predicted (SEA)	Prediction Confidence Score 0.547 Applicability Domain 1.0 Statistical Significance 0.0014 Supporting Reference Compounds 297 E-value 10.8989
Click to view 3D structure	Sodium-dependent dopamine transporter	Q01959	Humans	Predicted (SEA)	Prediction Confidence Score 0.415 Applicability Domain 1.0 Statistical Significance 0.0045 Supporting Reference Compounds 506 E-value 35.2657
Click to view 3D structure	Sodium-dependent noradrenaline transporter	P23975	Humans	Predicted (SEA)	Prediction Confidence Score 0.415 Applicability Domain 1.0 Statistical Significance 0.0039 Supporting Reference Compounds 451 E-value 30.2833
Click to view 3D structure	Sodium-dependent serotonin transporter	P31645	Humans	Predicted (SEA)	Prediction Confidence Score 0.414 Applicability Domain 1.0 Statistical Significance 0.0086 Supporting Reference Compounds 593 E-value 66.7168
Click to view 3D structure	Voltage-gated inwardly rectifying potassium channel KCNH2	Q12809	Humans	Predicted (SEA)	Prediction Confidence Score 0.407 Applicability Domain 1.0 Statistical Significance 0.0258 Supporting Reference Compounds 1498 E-value 200.929
Click to view 3D structure	5-hydroxytryptamine receptor 6	P50406	Humans	Predicted (SEA)	Prediction Confidence Score 0.402 Applicability Domain 1.0 Statistical Significance 0.0085 Supporting Reference Compounds 536 E-value 66.3275
Click to view 3D structure	Norepinephrine transporter	Q9WTR4	Rattus norvegicus	Predicted (SEA)	Prediction Confidence Score 0.402 Applicability Domain 1.0 Statistical Significance 0.0021 Supporting Reference Compounds 112 E-value 16.6597
Click to view 3D structure	5-hydroxytryptamine receptor 2A	P14842	Rattus norvegicus	Predicted (SEA)	Prediction Confidence Score 0.396 Applicability Domain 1.0 Statistical Significance 0.009 Supporting Reference Compounds 380 E-value 69.7529
Click to view 3D structure	Sigma non-opioid intracellular receptor 1	Q99720	Humans	Predicted (SEA)	Prediction Confidence Score 0.392 Applicability Domain 1.0 Statistical Significance 0.0133 Supporting Reference Compounds 562 E-value 103.773
Click to view 3D structure	5-hydroxytryptamine receptor 1A	P19327	Rattus norvegicus	Predicted (SEA)	Prediction Confidence Score 0.39 Applicability Domain 1.0 Statistical Significance 0.0141 Supporting Reference Compounds 541 E-value 109.534
Click to view 3D structure	Muscarinic acetylcholine receptor M2	P08172	Humans	Predicted (SEA)	Prediction Confidence Score 0.382 Applicability Domain 1.0 Statistical Significance 0.0035 Supporting Reference Compounds 373 E-value 26.9358
Click to view 3D structure	Muscarinic acetylcholine receptor M4	P08173	Humans	Predicted (SEA)	Prediction Confidence Score 0.382 Applicability Domain 1.0 Statistical Significance 0.0027 Supporting Reference Compounds 297 E-value 21.4085
Click to view 3D structure	Muscarinic acetylcholine receptor M1	P11229	Humans	Predicted (SEA)	Prediction Confidence Score 0.381 Applicability Domain 1.0 Statistical Significance 0.0047 Supporting Reference Compounds 385 E-value 36.9784
Click to view 3D structure	Muscarinic acetylcholine receptor M5	P08912	Humans	Predicted (SEA)	Prediction Confidence Score 0.374 Applicability Domain 1.0 Statistical Significance 0.0028 Supporting Reference Compounds 266 E-value 21.9535
Click to view 3D structure	Substance-P receptor	P25103	Humans	Predicted (SEA)	Prediction Confidence Score 0.374 Applicability Domain 1.0 Statistical Significance 0.0129 Supporting Reference Compounds 122 E-value 100.348
Click to view 3D structure	Muscarinic acetylcholine receptor M3	P20309	Humans	Predicted (SEA)	Prediction Confidence Score 0.371 Applicability Domain 1.0 Statistical Significance 0.0039 Supporting Reference Compounds 310 E-value 30.0498
Click to view 3D structure	Transporter	Q63380	Rattus norvegicus	Predicted (SEA)	Prediction Confidence Score 0.368 Applicability Domain 0.958 Statistical Significance 0.0012 Supporting Reference Compounds 54 E-value 9.41976
Click to view 3D structure	Cytochrome P450 1A2	P05177	Humans	Predicted (SEA)	Prediction Confidence Score 0.368 Applicability Domain 0.958 Statistical Significance 0.0163 Supporting Reference Compounds 793 E-value 126.739
Click to view 3D structure	Sodium-dependent serotonin transporter	Q60857	Mus musculus	Predicted (SEA)	Prediction Confidence Score 0.325 Applicability Domain 1.0 Statistical Significance 8.50e-04 Supporting Reference Compounds 20 E-value 6.61718
Click to view 3D structure	Myeloperoxidase	P05164	Humans	Predicted (SEA)	Prediction Confidence Score 0.321 Applicability Domain 1.0 Statistical Significance 0.0022 Supporting Reference Compounds 43 E-value 17.4382
Click to view 3D structure	P2X purinoceptor 4	Q99571	Humans	Predicted (SEA)	Prediction Confidence Score 0.319 Applicability Domain 1.0 Statistical Significance 0.0035 Supporting Reference Compounds 32 E-value 27.3251
Click to view 3D structure	Sodium-dependent serotonin transporter	P31645	Humans	Known	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.
Click to view 3D structure	Sodium-dependent noradrenaline transporter	P23975	Humans	Known	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.
Click to view 3D structure	5-hydroxytryptamine receptor 2A	P28223	Humans	Known	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.
Click to view 3D structure	Sodium-dependent dopamine transporter	Q01959	Humans	Known	Not Available
Click to view 3D structure	Muscarinic acetylcholine receptor M1	P11229	Humans	Known	Not Available
Click to view 3D structure	5-hydroxytryptamine receptor 1A	P08908	Humans	Known	Not Available
Click to view 3D structure	5-hydroxytryptamine receptor 2C	P28335	Humans	Known	Not Available
Click to view 3D structure	Alpha-2A adrenergic receptor	P08913	Humans	Known	Not Available
Click to view 3D structure	Muscarinic acetylcholine receptor M2	P08172	Humans	Known	Not Available
Click to view 3D structure	Muscarinic acetylcholine receptor M3	P20309	Humans	Known	Not Available
Click to view 3D structure	Muscarinic acetylcholine receptor M4	P08173	Humans	Known	Not Available
Click to view 3D structure	5-hydroxytryptamine receptor 2B	P41595	Humans	Known	Not Available
Click to view 3D structure	Cytochrome P450 2D6	P10635	Humans	Known	Not Available
Click to view 3D structure	Histamine H1 receptor	P35367	Humans	Known	Not Available
Click to view 3D structure	Muscarinic acetylcholine receptor M5	P08912	Humans	Known	Not Available
Click to view 3D structure	P2X purinoceptor 4	Q99571	Humans	Known	Not Available
Click to view 3D structure	Substance-P receptor	P25103	Humans	Known	Not Available

Concentrations

Not Available

External Links

DrugBank ID

DB00715

HMDB ID

HMDB0014853

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Chemspider ID

ChEBI ID

PubChem Compound ID

Kegg Compound ID

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Charles M. Zepp, Yun Gao, Donald L. Heefner, “Method of preparing optically pure precursors of paroxetine.” U.S. Patent US5258517, issued January, 1976.

MSDS

Link

General References

Wishart DS, Knox C, Guo AC, Cheng D, Shrivastava S, Tzur D, Gautam B, Hassanali M: DrugBank: a knowledgebase for drugs, drug actions and drug targets. Nucleic Acids Res. 2008 Jan;36(Database issue):D901-6. Epub 2007 Nov 29. [PubMed: 18048412]
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]
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]
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]
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]
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]
Drugs.com - http://www.drugs.com/cons/Paroxetine.html
RxList: The Internet Drug Index (2009). - http://www.rxlist.com/

Paroxetine (CED0001984)

Structure for CHEM002256: Paroxetine

Structure