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Drug

D0460 | clomipramine

Molecular Formula C19H23ClN2
Molecular Weight 314.9
Structure
State solid
Volume of distribution ~ 17 L/kg (range: 9-25 L/kg). Clomipramine is capable of distributing into the cerebrospinal fluid, the brain, and into breast milk.
Route of elimination Urine (51-60%) and feces via biliary elimination (24-32%)
Protein binding Clomipramine is approximately 97-98% bound to plasma proteins, principally to albumin and possibly to &alpha;<sub>1</sub>-acid glycoprotein. Desmethylclomipramine is 97-99% bound to plasma proteins.
Half life Following oral administration of a single 150 mg dose of clomipramine, the average elimination half-life of clomipramine was 32 hours (range: 19-37 hours) and of desmethylclomipramine was 69 hours (range: 54-77 hours). Elimination half-life may vary substantially with different doses due to saturable kinetics (i.e. metabolism).
Absorption Well absorbed from the GI tract following oral administration. Bioavailability is approximately 50% orally due to extensive first-pass metabolism. Bioavailability is not affected by food. Peak plasma concentrations occurred 2-6 hours following oral administration of a single 50 mg dose. The peak plasma concentration ranged from 56 ng/mL to 154 mg/mL (mean, 92 ng/mL). There are large interindividual variations in plasma concentrations occur, partly due to genetic differences in clomipramine metabolism. On average, steady state plasma concentrations are achieved in 1-2 weeks following multiple dose oral administration. Smoking appears to lower the steady-state plasma concentration of clomipramine, but not its active metabolite desmethylclomipramine.

N

N06AA04 Clomipramine


[N06AA] Non-selective monoamine reuptake inhibitors


[N06A] ANTIDEPRESSANTS


[N06] PSYCHOANALEPTICS


[N] Nervous system

Toxicity Dose Time Species Model Method Action Positive criterion Reference
STATE 3 RESPIRATION decrease 22
STATE 4 RESPIRATION increase 22
ELECTRON TRANSPORT CHAIN decrease 38
POTASSIUM RELEASE increase 22

Target Dose Time Species Model Method Action Positive criterion Reference
potassium not specified 22

Pictogram Signal Statements Precautionary Statement Codes
Warning

Aggregated GHS information provided by 42 companies from 2 notifications to the ECHA C&L Inventory.


H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]


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.


 P264, P270, P301+P312, P330, and P501; (The corresponding statement to each P-code can be found at the GHS Classification page.)


  • (3-{5-chloro-2-azatricyclo[9.4.0.0^{3,8}]pentadeca-1(11),3(8),4,6,12,14-hexaen-2-yl}propyl)dimethylamine 10,11-dihydro-3-chloro-5-(3-(dimethylamino)propyl)-5H-dibenz(b,f)azepine 2241983-11-7
    3-(2-chloranyl-5,6-dihydrobenzo[b][1]benzazepin-11-yl)-N,N-dimethyl-propan-1-amine;hydrochloride 3-(2-chloro-5,6-dihydrobenzo[b][1]benzazepin-11-yl)-N,N-dimethyl-1-propanamine;hydrochloride; 3-(2-chloro-5,6-dihydrobenzo[b][1]benzazepin-11-yl)-N,N-dimethyl-propan-1-amine
    3-(2-chloro-5,6-dihydrobenzo[b][1]benzazepin-11-yl)-N,N-dimethylpropan-1-amine 3-(2-chloro-5,6-dihydrobenzo[b][1]benzazepin-11-yl)propyl-dimethyl-amine;hydrochloride 3-(3-CHLORO-5H-DIBENZO[B,F]AZEPIN-5-YL)-N,N-DIMETHYLPROPAN-1-AMINE
    3-(3-Chloro-10,11-dihydro-5H-dibenzo[b,f]azepin-5-yl)-N,N-dimethyl-1-propanamine 3-(3-Chloro-10,11-dihydro-5H-dibenzo[b,f]azepin-5-yl)-N,N-dimethyl-1-propanamine # 3-(3-chloro-10,11-dihydro-5H-dibenzo[b,f]azepin-5-yl)-N,N-dimethylpropan-1-amine
    3-(9-chloro-5,6-dihydrobenzo[b][1]benzazepin-11-yl)-N,N-dimethylpropan-1-amine 3-Chloro-5-(3-(dimethylamino)propyl)-10,11-dihydro-5H-dibenz(b,f)azepine 3-Chloro-5-[3-(dimethylamino)propyl]-10,f]azepine
    3-Chloroimipramine 3-chloro-10,11-dihydro-N,N-dimethyl-5H-Dibenz(b,f)azepine-5-propanamine 3-chloro-5-(3-(dimethylamino)propyl)-10,11-dihydro-5H-dibenz[b,f]azepine
    303-49-1 303C491 5-20-08-00103 (Beilstein Handbook Reference)
    5H-Dibenz(b,f)azepine, 10,11-dihydro-3-chloro-5-(3-(dimethylamino)propyl)- 5H-Dibenz(b,f)azepine, 3-chloro-5-(3-(dimethylamino)propyl)-10,11-dihydro- 5H-Dibenz(b,f)azepine, 3-chloro-5-(3-(dimethylamino)propyl)-10,11-dihydro- (8CI)
    5H-Dibenz(b,f)azepine-5-propanamine, 3-chloro-10,11-dihydro-N,N-dimethyl- 5H-Dibenz[b, 10,11-dihydro-3-chloro-5-[3-(dimethylamino)propyl]- 5H-Dibenz[b, 3-chloro-10,11-dihydro-N,N-dimethyl-
    5H-Dibenz[b, 3-chloro-5-[3-(dimethylamino)propyl]-10,11-dihydro- 5H-Dibenz[b,f]azepine, 3-chloro-5-[3-(dimethylamino)propyl]-10,11-dihydro- 5H-Dibenz[b,f]azepine-5-propanamine, 3-chloro-10,11-dihydro-N,N-dimethyl-
    AB00053695 AB00053695-14 AB00053695_15
    AB00053695_16 AB05476 ACM303491
    AK122641 AKOS001487687 API0002067
    AX8246819 Anafranil (TN) Anafranil (free base)
    Anafranil base BBL028455 BDBM77970
    BIDD:PXR0151 BPBio1_000130 BPBio1_000661
    BRD-K52989797-001-01-1 BRD-K52989797-003-05-8 BRD-K52989797-003-16-5
    BRN 1323477 BSPBio_000118 BSPBio_003294
    Biomol-NT_000151 C06918 C14H12ClN.C6H15N
    CAS-17321-77-6 CAS-303-49-1 CCG-110307
    CHEBI:47780 CHEMBL415 CLOMIPRIMINE
    Chlomipramine Chlorimipramine Clomicalm
    Clomipramina Clomipramina [INN-Spanish] Clomipramine (INN)
    Clomipramine [INN:BAN] Clomipraminum Clomipraminum [INN-Latin]
    D07727 DB01242 DS-6718
    DSSTox_CID_2844 DSSTox_GSID_22844 DSSTox_RID_76755
    DTXSID6022844 DivK1c_000797 EINECS 206-144-2
    G 34586 G-34586 GDLIGKIOYRNHDA-UHFFFAOYSA-N
    GTPL2398 HMS3428J14 HSDB 7746
    Hydiphen IDI1_000797 KBio1_000797
    KBio2_000924 KBio2_003492 KBio2_006060
    KBio3_002514 KBioGR_000759 KBioSS_000924
    L000890 LS-60386 Lopac-C-7291
    Lopac0_000307 MCULE-6443168248 Monochlorimipramine
    N-[3-(3-chloro-10,11-dihydro-5H-dibenzo[b,f]azepin-5-yl)propyl]-N,N-dimethylamine NCGC00015264-01 NCGC00015264-02
    NCGC00015264-03 NCGC00015264-04 NCGC00015264-05
    NCGC00015264-06 NCGC00015264-07 NCGC00015264-08
    NCGC00015264-09 NCGC00015264-10 NCGC00015264-13
    NCGC00024355-02 NCGC00024355-04 NCGC00024355-05
    NINDS_000797 NSC 169865 NSC-169865
    NSC169865 NUV44L116D Oprea1_312582
    PDSP1_000241 PDSP2_000240 Prestwick0_000269
    Prestwick1_000269 Prestwick2_000269 Prestwick3_000269
    PubChem17200 Q58713 SBI-0050295.P003
    SC-80642 SCHEMBL35423 SPBio_001778
    SPBio_002337 STK534842 SY246341
    Spectrum2_001729 Spectrum3_001707 Spectrum4_000350
    Spectrum5_001235 Spectrum_000444 Tocris-0457
    Tox21_110117 Tox21_110117_1 UNII-NUV44L116D
    WLN: T C676 BN & T & J B3N1 & 1 EG ZINC20248 cid_68539
    clomipramine

    DrugBank Name clomipramine
    DrugBank DB01242
    CAS Number 17321-77-6, 2241983-11-7, 303-49-1
    PubChem Compound 2801
    KEGG Compound ID C06918
    KEGG Drug D07727
    ChEBI 47780
    PharmGKB PA449048