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Drug

D0501 | citalopram

Molecular Formula C20H21FN2O
Molecular Weight 324.4
Structure
State solid
Clearance The systemic clearance of citalopram is 330 mL/min, with approximately 20% renal clearance [FDA label].
Volume of distribution 12 L/kg [FDA label] Citalopram is highly lipophilic and likely widely distributed throughout the body, including the blood-brain-barrier. However, its metabolite, _demethylcitalopram_ does not penetrate the blood-brain-barrier well [FDA label].
Route of elimination 12-23% of an oral dose of citalopram is found unchanged in the urine, while 10% of the dose is found in the faeces [FDA label].
Protein binding Citalopram, dimethylcitalopram, and didemethylcitalopram are 80% bound to plasma proteins [FDA label].
Half life About 35 hours [FDA label].
Absorption Rapidly and well absorbed from the GI tract. Peak plasma concentrations occur within 4 hours of a single orally administered dose. Bioavailability is 80% following oral administration. Food does not affect absorption [FDA label].

N

N06AB04 Citalopram


[N06AB] Selective serotonin reuptake inhibitors


[N06A] ANTIDEPRESSANTS


[N06] PSYCHOANALEPTICS


[N] Nervous system

Toxicity Dose Time Species Model Method Action Positive criterion Reference
UNCOUPLING rat isolated liver mitochondria measurements of mitochondrial respiration; RST inhibition assay, RST uncoupling assay; IC 50ratio of glucose/galactose assay Negative 53
ELECTRON TRANSPORT CHAIN pig brain mitochondria decrease 62
ELECTRON TRANSPORT CHAIN pig brain mitochondria decrease 62
ELECTRON TRANSPORT CHAIN pig brain mitochondria decrease 62
ELECTRON TRANSPORT CHAIN rat isolated liver mitochondria measurements of mitochondrial respiration; RST inhibition assay, RST uncoupling assay; IC 50ratio of glucose/galactose assay Negative 53

Target Dose Time Species Model Method Action Positive criterion Reference
NADH:ubiquinone reductase pig brain mitochondria inhibitor 62
Succinate dehydrogenase pig brain mitochondria inhibitor 62

Pictogram Signal Statements Precautionary Statement Codes
Warning

Aggregated GHS information provided by 4 companies from 3 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 4 companies. For more detailed information, please visit ECHA C&L website


Of the 2 notification(s) provided by 3 of 4 companies with hazard statement code(s):


H302 (66.67%): Harmful if swallowed [Warning Acute toxicity, oral]


H317 (66.67%): May cause an allergic skin reaction [Warning Sensitization, Skin]


H319 (33.33%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]


H335 (33.33%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure


Respiratory tract irritation]


H361 (33.33%): Suspected of damaging fertility or the unborn child [Warning Reproductive toxicity]


H410 (66.67%): 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, P261, P264, P270, P271, P272, P273, P280, P281, P301+P312, P302+P352, P304+P340, P305+P351+P338, P308+P313, P312, P321, P330, P333+P313, P337+P313, P363, P391, P403+P233, P405, and P501; (The corresponding statement to each P-code can be found at the GHS Classification page.)


  • (1S)-1-[3-(dimethylamino)propyl]-1-(4-fluorophenyl)-3H-2-benzofuran-5-carbonitrile 1,3-Dihydro-1-(3-(dimethylamino)propyl)-1-(4-fluorophenyl)-5-isobenzofurancarbonitrile 1-(3'-dimethylaminopropyl)-1-(4'-fluorophenyl)-1,3-dihydroisobenzofuran-5-carbonitrile
    1-(3-(Dimethylamino)propyl)-1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-5-carbonitrile 1-(3-(Dimethylamino)propyl)-1-(p-fluorophenyl)-5-phthalancarbonitrile 1-(3-(dimethylamino)propyl)-1-(4'-fluorophenyl)-1,3-dihydroisobenzofuran-5-carbonitrile
    1-(3-Dimethylamino-propyl)-1-(4-fluoro-phenyl)-1,3-dihydro-isobenzofuran-5-carbonitrile 1-(3-dimethylaminopropyl)-1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-5-carbonitrile 1-[3-(dimethylamino) propyl]-1-(4-fluorophenyl)-1,3-dihydro-5-isobenzofuran carbonitrile
    1-[3-(dimethylamino)propyl]-1-(4-fluorophenyl)-1,3-dihydro-2-benzofuran-5-carbonitrile 1-[3-(dimethylamino)propyl]-1-(4-fluorophenyl)-1,3-dihydro-5-isobenzo[b]furancarbonitrile 1-[3-(dimethylamino)propyl]-1-(4-fluorophenyl)-1,3-dihydro-5-isobenzofurancarbonitrile
    1-[3-(dimethylamino)propyl]-1-(4-fluorophenyl)-1,3-dihydro[3,4]benzofuran-5-carbonitrile 1-[3-(dimethylamino)propyl]-1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-5-carb onitrile 1-[3-(dimethylamino)propyl]-1-(4-fluorophenyl)-3H-2-benzofuran-5-carbonitrile
    1-[3-(dimethylamino)propyl]-1-(4-fluorophenyl)-3H-isobenzofuran-5-carbonitrile 1-[3-(dimethylamino)propyl]-1-(p-fluorophenyl)-5-phthalancarbonitrile 4793-EP2275420A1
    4793-EP2284166A1 4793-EP2298764A1 4793-EP2298765A1
    4793-EP2305648A1 5-Cyano-1-(4-fluorophenyl)-1-(3-dimethylaminopropyl)-1,3-dihydro-isobenzofuran 5-Isobenzofurancarbonitrile, 1,3-dihydro-1-(3-(dimethylamino)propyl)-1-(4-fluorophenyl)-
    5-Isobenzofurancarbonitrile, 1-(3-(dimethylamino)propyl)-1-(4-fluorophenyl)-1,3-dihydro- 5-Isobenzofurancarbonitrile, 1-[3-(dimethylamino)propyl]-1-(4-fluorophenyl)-1,3-dihydro- 59729-33-8
    729C338 AB00513896 AB00513896-09
    AB00513896-11 AB00513896_12 AB00513896_13
    AC-8894 ACT02666 AKOS005711003
    BBL029066 BDBM25870 BPBio1_000929
    BRD-A47598013-004-02-0 BRD-A47598013-004-06-1 BSPBio_000843
    Bonitrile C07572 C20H21FN2O
    CCG-204353 CHEBI:77397 CHEMBL549
    CPD000465669 Celexa Cipram
    Citadur (TN) Citalopram (USP/INN) Citalopram [Celexa]
    Citalopram [INN:BAN] Citalopram [USP:INN:BAN] Citalopram-d4 oxalate
    Citalopramum Citalopramum [INN-Latin] Cytalopram
    D07704 DB00215 DTXSID8022826
    EINECS 261-891-1 EN300-304884 Escitalopram Impurity A
    FT-0657967 GTPL4621 GTPL7547
    HMS2090O09 HMS2093A14 HMS3259B10
    InChI=1/C20H21FN2O/c1-23(2)11-3-10-20(17-5-7-18(21)8-6-17)19-9-4-15(13-22)12-16(19)14-24-20/h4-9,12H,3,10-11,14H2,1-2H3; L001223 LS-84327
    LU-10171B Lopac0_000258 Lu 10-171
    Lu-10-171 MCULE-5882770916 MLS000028578
    MLS006011858 MRF-0000302 NC00711
    NCGC00015267-04 NCGC00015267-05 NCGC00015267-07
    NCGC00015267-09 NCGC00015267-12 NCGC00025160-02
    Nitalapram Perrigo citalopram Prestwick3_000692
    Q409672 SAM002589960 SBI-0050246.P002
    SC-16253 SCHEMBL946 SMR000465669
    SR-01000003129-8 ST069372 STL058639
    VA10838 WSEQXVZVJXJVFP-UHFFFAOYSA- WSEQXVZVJXJVFP-UHFFFAOYSA-N
    [3H]-Citalopram [3H]Citalopram [3H]Cytalopram
    [3H]Escitalopram [3H]Lexapro citalopram

    DrugBank Name citalopram
    DrugBank DB00215
    CAS Number 128196-01-0, 207559-01-1, 59729-32-7, 59729-33-8
    PubChem Compound 2771
    KEGG Compound ID C07572
    KEGG Drug D07704
    ChEBI 3723
    PharmGKB PA449015