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Drug

D0441 | paroxetine

Molecular Formula C19H20FNO3
Molecular Weight 329.4
Structure
State solid
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.
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.
Protein binding ~ 95% bound to plasma proteins.
Half life 21-24 hours
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.

N

N06AB05 Paroxetine


[N06AB] Selective serotonin reuptake inhibitors


[N06A] ANTIDEPRESSANTS


[N06] PSYCHOANALEPTICS


[N] Nervous system

Toxicity Dose Time Species Model Method Action Positive criterion Reference
ELECTRON TRANSPORT CHAIN 50 μM bovine heart mitochondria Measurement of complex I activity decrease p < 0.01 3
ELECTRON TRANSPORT CHAIN 50 μM bovine heart mitochondria Measurement of complex II + III activity decrease p < 0.001 3
ELECTRON TRANSPORT CHAIN 50 μM bovine heart mitochondria Measurement of complex II + III activity decrease p < 0.001 3
ELECTRON TRANSPORT CHAIN 50 μM bovine heart mitochondria Measurement of complex IV activity Negative p < 0.05 3
ELECTRON TRANSPORT CHAIN 50 μM bovine heart mitochondria Measurement of complex V activity decrease p < 0.001 3
ELECTRON TRANSPORT CHAIN decrease 35
ELECTRON TRANSPORT CHAIN decrease 35
ELECTRON TRANSPORT CHAIN decrease 35
ELECTRON TRANSPORT CHAIN decrease 35
GLUCOSE GALACTOSE IC50 RATIO 37.5 ± 15.9, 36.9 ± 27.9, 1, 37.1 ± 11.3, 32.3 ± 17.8, 1.2 4hr H9c2 cells high-glucose–galactose cell viability assay with JC-1 mitochondrial membrane potential and ATP-depletion assays (CellTiter-Glo reagent ). glucose/galactose IC50 ratio (JC-1 IC50 in glucose, JC-1 IC50 in galactose, JC-1 glu/gla, ATP IC50 in glucose, ATP IC50 in galactose, ATP glu/gla ) 50

Target Dose Time Species Model Method Action Positive criterion Reference
NADH:ubiquinone reductase 50 μM bovine heart mitochondria Measurement of complex I activity inhibitor p < 0.01 3
NADH:ubiquinone reductase inhibitor 35
Succinate dehydrogenase 50 μM bovine heart mitochondria Measurement of complex II + III activity inhibitor p < 0.001 3
Succinate dehydrogenase inhibitor 35
Quinol--cytochrome-c reductase 50 μM bovine heart mitochondria Measurement of complex II + III activity inhibitor p < 0.001 3
Quinol--cytochrome-c reductase inhibitor 35
Cytochrome c oxidase 50 μM bovine heart mitochondria Measurement of complex IV activity Negative p < 0.05 3
ATP synthase 50 μM bovine heart mitochondria Measurement of complex V activity inhibitor p < 0.001 3
ATP synthase inhibitor 35

Pictogram Signal Statements Precautionary Statement Codes
Danger

Aggregated GHS information provided by 6 companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.


Reported as not meeting GHS hazard criteria by 1 of 6 companies. For more detailed information, please visit ECHA C&L website


Of the 3 notification(s) provided by 5 of 6 companies with hazard statement code(s):


H302 (80%): Harmful if swallowed [Warning Acute toxicity, oral]


H360 (60%): May damage fertility or the unborn child [Danger Reproductive toxicity]


H361 (20%): Suspected of damaging fertility or the unborn child [Warning Reproductive toxicity]


H400 (20%): Very toxic to aquatic life [Warning Hazardous to the aquatic environment, acute hazard]


H410 (60%): Very toxic to aquatic life with long lasting effects [Warning Hazardous to the aquatic environment, long-term hazard]


Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown.


 P201, P202, P264, P270, P273, P281, P301+P312, P308+P313, P330, P391, P405, and P501; (The corresponding statement to each P-code can be found at the GHS Classification page.)
Warning

Aggregated GHS information provided by 77 companies from 11 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.


H302 (98.7%): Harmful if swallowed [Warning Acute toxicity, oral]


H315 (55.84%): Causes skin irritation [Warning Skin corrosion/irritation]


H319 (93.51%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]


H335 (66.23%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure


Respiratory tract irritation]


H361 (12.99%): Suspected of damaging fertility or the unborn child [Warning Reproductive toxicity]


H411 (40.26%): Toxic to aquatic life with long lasting effects [Hazardous to the aquatic environment, long-term hazard]


Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown.


 P201, P202, P261, P264, P270, P271, P273, P280, P281, P301+P312, P302+P352, P304+P340, P305+P351+P338, P308+P313, P312, P321, P330, P332+P313, P337+P313, P362, P391, P403+P233, P405, and P501; (The corresponding statement to each P-code can be found at the GHS Classification page.)
Warning

H302: Harmful if swallowed [Warning Acute toxicity, oral]


H315: Causes skin irritation [Warning Skin corrosion/irritation]


H319: Causes serious eye irritation [Warning Serious eye damage/eye irritation]


H335: May cause respiratory irritation [Warning Specific target organ toxicity, single exposure


Respiratory tract irritation]


 P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P340, P305+P351+P338, P312, P321, P330, P332+P313, P337+P313, P362, P403+P233, P405, and P501; (The corresponding statement to each P-code can be found at the GHS Classification page.)


  • (-)-(3S,4R)-4-(p-Fluorophenyl)-3-((3,4-(methylenedioxy)phenoxy)methyl)piperidine (-)-(3S,4R)-4-(p-Fluorophenyl)-3-((3,4-methylenedioxy)phenoxy)methyl)piperidine (-)-Paroxetine
    (-)-trans-4-(4-Fluorophenyl)-3-(3,4-methylenedioxyphenoxymethyl)piperidine (-)-trans-4-(p-fluorophenyl)-3-[[3,4-(methylenedioxy)phenoxy]methyl]-piperidine (3S,4R)-3-(1,3-benzodioxol-5-yloxymethyl)-4-(4-fluorophenyl)piperidine
    (3S,4R)-3-[(1,3-benzodioxol-5-yloxy)methyl]-4-(4-fluorophenyl)piperidine (3S,4R)-3-[(2H-1,3-benzodioxol-5-yloxy)methyl]-4-(4-fluorophenyl)piperidine (3S,4R)-3-{[(2H-1,3-Benzodioxol-5-yl)oxy]methyl}-4-(4-fluorophenyl)piperidine
    (3S-trans)-3-((1,3-benzodioxol-5-yloxy)methyl)-4-(4-fluorophenyl)piperidine (3S-trans)-3-[(1,3-Benzodioxol-5-yl-oxy)methyl]-4-(4-fluorophenyl)piperidine (3s,4r)-3-((benzo[d][1,3]dioxol-5-yloxy)methyl)-4-(4-fluorophenyl)piperidine
    110429-35-1 3h-paroxetine 41VRH5220H
    61869-08-7 869P087 8PR
    AB00053704-21 AB00053704_22 AB00053704_23
    AB00514724 AC-8185 AHOUBRCZNHFOSL-YOEHRIQHSA-N
    AKOS015888636 Aropax BDBM22416
    BDBM50331515 BIDD:GT0673 BPBio1_000949
    BRD-K37991163-003-02-7 BRD-K37991163-050-05-1 BRL 29060
    BRL-29060 BSPBio_000861 C-19975
    C07415 C19H20FNO3 CAS-61869-08-7
    CC-33477 CHEBI:7936 CHEMBL1708
    CHEMBL490 Casbol D02362
    DB00715 DSSTox_CID_3425 DSSTox_GSID_23425
    DSSTox_RID_77022 DTXSID3023425 DivK1c_006884
    FG 7051 FG-7051 FT-0085087
    Frosinor GTPL4790 HMS2090H05
    HSDB 7175 KBio1_001828 KBio2_002232
    KBio2_004800 KBio2_007368 KBioSS_002232
    KS-00000JK2 LS-114249 Motivan
    NCGC00025355-02 NCGC00025355-03 NCGC00025355-04
    NCGC00025355-05 NCGC00025355-06 NCGC00025355-07
    NCGC00025355-08 NCGC00025355-09 NCGC00025355-12
    NCGC00182968-01 NNC-20-7051 PAROXETINE HCL HEMIHYDRATE
    Paroxetin HCL Paroxetina Paroxetina [INN-Spanish]
    Paroxetine (TN) Paroxetine (USP/INN) Paroxetine Hydrochloride Anhydrous EP Impurity E
    Paroxetine USP Related Compound D;[(3S,4R)-4-(p-Fluorophenyl)-3-piperidyl](1,3-dioxa-5-indanyloxy)methane; Paroxetine [USAN:INN:BAN] Paroxetine.HCl
    Paroxetinum Paroxetinum [INN-Latin] PaxPar
    Paxetil Paxil Paxil CR
    Pexeva Piperidine, 3-((1,3-benzodioxol-5-yloxy)methyl)-4-(4-fluorophenyl)-, (3S,4R)- Piperidine, 3-((1,3-benzodioxol-5-yloxy)methyl)-4-(4-fluorophenyl)-, (3S-trans)-
    Piperidine, 3-[(1,3-benzodioxol-5-yloxy)methyl]-4-(4-fluorophenyl)-, (3S-trans)- Piperidine, 3-[(1,3-benzodioxol-5-yloxy)methyl]-4-(4-fluorophenyl)-,(3S,4R)- Prestwick3_000851
    Q408471 SBI-0051908.P002 SC-16100
    SC-22977 SCHEMBL27799 Seroxat
    SpecPlus_000788 Spectrum5_001665 Spectrum_001752
    Tox21_113123 Tox21_113123_1 UNII-41VRH5220H
    ZINC527386 [3H]Paroxetine cis-Paroxetine
    paroxetine paroxetine hydrochloride (anhydrous or hemihydrate) piperidine, 3-[(1,3-benzodioxol-5-yloxy)methyl]-4-(4-fluorophenyl)-, (3S,4R)-

    DrugBank Name paroxetine
    DrugBank DB00715
    CAS Number 110429-35-1, 61869-08-7, 78246-49-8
    PubChem Compound 43815
    KEGG Compound ID C07415
    KEGG Drug D02362
    ChEBI 7936
    PharmGKB PA450801
    ChemSpider 39888
    BindingDB 50331515.0
    TTD DAP001428
    Wikipedia Paroxetine