Drug Details

General Information of the Drug (ID: DR3248)
Name
Imipramine
Synonyms
imipramine; Melipramine; Imidobenzyle; 50-49-7; Antideprin; Berkomine; Dimipressin; Melipramin; Tofranil; Intalpram; Nelipramin; Dynaprin; Janimine; Timolet; Irmin; Dpid; Dyna-zina; Impramine; Promiben; Censtim; Censtin; Imiprin; Iramil; Imipramina; Declomipramine; Eupramin; Imipramin; Imipraminum; Psychoforin; 3-(10,11-dihydro-5H-dibenzo[b,f]azepin-5-yl)-N,N-dimethylpropan-1-amine; Imavate; Imizine; Surplix; Imizin; Tofranil, base; Imipramine Hcl; Tofranil-PM; Imizinum; Pramine; N-(gamma-Dimethylaminopropyl)iminodibenzyl; N-(3-Dimethylaminopropyl)-o-iminodibenzyl; 2,2'-(3-Dimethylaminopropylimino)bibenzyl; 2,2'-(3-Dimethylaminopropylimino)dibenzyl; Tofranil (free base); SK-Pramine; UNII-OGG85SX4E4; NSC 169866; CHEMBL11; 1-(3-Dimethylaminopropyl)-4,5-dihydro-2,3,6,7-dibenzazepine; 10,11-Dihydro-N,N-dimethyl-5H-dibenz[b,f]azepine-5-propanamine; 5,6-Dihydro-N-(3-(dimethylamino)propyl)-11H-dibenz(b,e)azepine; 5-(3-(Dimethylamino)propyl)-10,11-dihydro-5H-dibenz(b,f)azepine; 5-(3-Dimethylaminopropyl)-10,11-dihydro-5H-dibenzo(b,f)azepine; OGG85SX4E4; 3-(5,6-dihydrobenzo[b][1]benzazepin-11-yl)-N,N-dimethylpropan-1-amine; CHEBI:47499; 5,e)azepine; 5,e]azepine; 5H-Dibenz(b,f)azepine, 10,11-dihydro-5-(3-(dimethylamino)propyl)-; 5H-Dibenz(b,f)azepine-5-propanamine, 10,11-dihydro-N,N-dimethyl-; 5H-Dibenz[b,f]azepine-5-propanamine, 10,11-dihydro-N,N-dimethyl-; Imipramine-d6; Imidol; NSC-169866; 113-52-0 (HCl); NCGC00015563-07; Imipramina [Italian]; Tofranil (TN); 10,11-Dihydro-5-(3-(dimethylamino)propyl)-5H-dibenz[b,f]azepine; 3-(5H-DIBENZO[B,F]AZEPIN-5-YL)-N,N-DIMETHYLPROPAN-1-AMINE; N-(.gamma.-Dimethylaminopropyl)iminodibenzyl; 5H-Dibenz(b,f)azepine, 5-(3-(dimethylamino)propyl)-10,11-dihydro-; 3-(10,11-Dihydro-5H-dibenzo[b,f]azepin-5-yl)-N,N-dimethyl-1-propanamine; Imipramine [INN:BAN]; DSSTox_CID_23881; DSSTox_RID_80080; DSSTox_GSID_43881; Imipraminum [INN-Latin]; Imipramina [INN-Spanish]; 3-(10,11-dihydro-5h-dibenz[b,f]azepin-5-yl)propyldimethylamine; G-22355; 5-[3-(dimethylamino)propyl]-10,11-dihydro-5H-dibenz[b,f]azepine; 3-(10,11-dihydro-5H-dibenzo[b,f]azepin-5-yl)-N,N-dimethylpropan-1-amine hydrochloride; CAS-50-49-7; 3-(10,11-Dihydro-5H-dibenzo[b,f]azepin-5-yl)-N,N-dimethylpropan-1-amine;3-(10,11-Dihydro-5H-dibenzo[b,f]azepin-5-yl)-N,N-dimethylpropan-1-amine; Imipramine (INN); CCRIS 9173; HSDB 3100; 3-(5,6-dihydrobenzo[b][1]benzazepin-11-yl)-N,N-dimethyl-propan-1-amine; Janimine (hydrochloride); Tofranil (hydrochloride); CAS-113-52-0; EINECS 200-042-1; BRN 0256892; 5H-Dibenz(b, 5-(3-(dimethylamino)propyl)-10,11-dihydro-; 5H-Dibenz[b, 5-[3-(dimethylamino)propyl]-10,11-dihydro-; Tofranil base; 5H-Dibenz[b,f]azepine, 5-[3-(dimethylamino)propyl]-10,11-dihydro-; Imipramine-d3 HCl; Imizin (Salt/Mix); Imavate (Salt/Mix); Imizine (Salt/Mix); Surplix (Salt/Mix); Eupramin (Salt/Mix); Imizinum (Salt/Mix); Tofranil (Salt/Mix); PubChem21397; Spectrum_000915; Psychoforin (Salt/Mix); Prestwick0_000072; Prestwick1_000072; Prestwick2_000072; Prestwick3_000072; SK-Pramine (Salt/Mix); Spectrum2_000990; Spectrum3_000466; Spectrum4_000016; Spectrum5_000864; Lopac-I-7379; Lopac0_000702; Oprea1_200908; SCHEMBL34282; BSPBio_000283; BSPBio_002172; GTPL357; KBioGR_000391; KBioSS_001395; BIDD:GT0116; DivK1c_000559; SPBio_001059; SPBio_002204; G-22355 (Salt/Mix); BPBio1_000313; Clomipramine HCl EP Impurity B; DTXSID1043881; KBio1_000559; KBio2_001395; KBio2_003963; KBio2_006531; KBio3_001392; ZINC20245; NINDS_000559; HMS2089G08; ORG-2463; Tox21_110174; BDBM50010859; CCG-36485; MFCD31699979; NSC169866; STL416211; AKOS016010320; N,N-Dimethyl-10,11-dihydro-5H-dibenzo[b,f]azepine-5-propanamine-2,8-D2; Tox21_110174_1; DB00458; MCULE-9471074673; SDCCGSBI-0050680.P005; IDI1_000559; MRF-0000592; NCGC00015563-01; NCGC00015563-02; NCGC00015563-03; NCGC00015563-04; NCGC00015563-05; NCGC00015563-06; NCGC00015563-08; NCGC00015563-09; NCGC00015563-10; NCGC00015563-11; NCGC00015563-13; NCGC00015563-25; NCGC00024253-03; NCGC00024253-04; 112898-42-7; 2241983-10-6; 5-(3-Dimethylaminopropyl)-10,f)azepine; SY246340; Trimipramine maleate impurity, imipramine-; SBI-0050680.P004; WLN: T C676 BN&T&J B3N1&1; 5-(3-(Dimethylamino)propyl)-10,f)azepine; AB00053486; FT-0670319; FT-0697093; W0042; 5H-Dibenz[b, 10,11-dihydro-N,N-dimethyl-; C07049; D08070; Q58396; AB00053486-15; AB00053486_16; AB00053486_17; 1-(3-Dimethylaminopropyl)-4,3,6,7-dibenzazepine; L000739; W-109253; BRD-K38436528-003-05-5; BRD-K38436528-003-15-4; 5H-Dibenz(b, 10,11-dihydro-5-(3-(dimethylamino)propyl)-; 5H-Dibenz(b,f)azepine-5-propanamine, 10,11-dihydro-N,N-dimethyl- (9CI); 3-(10,11-Dihydro-5H-dibenzo[b,f]azepin-5-yl)-N,N-dimethyl-1-propanamine #; 5H-Dibenz(b,5-[3-(dimethylamino)propyl]-10,11-dihydro-mixed with ethyl alcohol; Clomipramine EP Impurity B; 10,11-Dihydro-N,N-dimethyl-5H-dibenz[b,f]azepine-5-propanamine; (3-{2-azatricyclo[9.4.0.0^{3,8}]pentadeca-1(11),3(8),4,6,12,14-hexaen-2-yl}propyl)dimethylamine; 5-(3-(dimethylamino)propyl)-10,11-dihydro-5H-dibenz[b,f]azepine;10,11-Dehydroimipramine;Depramine
    Click to Show/Hide
Molecular Type
Small molecule
Disease Depression [ICD-11: 6A70-6A71] Approved [1]
Structure
Click to Download Mol
2D MOL

3D MOL

ADMET Property
Absorption Tmax
The time to maximum plasma concentration (Tmax) is 1-1.5 h
BDDCS Class
Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 1: high solubility and high permeability
Bioavailability
The bioavailability of drug is 62%
Clearance
The clearance of drug is 1 L/h/kg
Elimination
Imipramine is primarily excreted in the urine with less than 5% present as the parent compound
Half-life
The concentration or amount of drug in body reduced by one-half in 12 hours
Metabolism
The drug is metabolized via the liver
MRTD
The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 5.0944 micromolar/kg/day
Unbound Fraction
The unbound fraction of drug in plasma is 0.075%
Vd
The volume of distribution (Vd) of drug is 10-20 L/kg
    Click to Show/Hide
    Click to Show/Hide the Molecular Information and External Link(s) of This Natural Product
Formula
C19H24N2
PubChem CID
3696
Canonical SMILES
CN(C)CCCN1C2=CC=CC=C2CCC3=CC=CC=C31
InChI
1S/C19H24N2/c1-20(2)14-7-15-21-18-10-5-3-8-16(18)12-13-17-9-4-6-11-19(17)21/h3-6,8-11H,7,12-15H2,1-2H3
InChIKey
BCGWQEUPMDMJNV-UHFFFAOYSA-N
CAS Number
CAS 50-49-7
ChEBI ID
CHEBI:47499
TTD Drug ID
D06ZUK
DrugBank ID
DB00458
Combinatorial Therapeutic Effect(s) Validated Clinically or Experimentally
    α. A List of Natural Product(s) Able to Enhance the Efficacy of This Drug
          Beta caryophyllene      Syzygium aromaticum     Click to Show/Hide the Molecular Data of This NP
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [2]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    In-vivo Model To establish experimental autoimmune encephalomyelitis (EAE) mice, female C57BL/6 mice were actively immunized using two subcutaneous injections with an emulsion containing myelin MOG35-55 (250 g) and an equal volume of CFA (250 g) into dierent sites of each hind ank.
                    Experimental
                    Result(s)		 They reduced the clinical and pathological defects in EAE mice through modulation of both local (microglia) and systemic (lymphocytes and blood) immunity from inflammatory (Th1/Th17/M1) towards anti-inflammatory (Th2/Treg/M2) phenotypes.
          Yohimbine      Corynanthe johimbe     Click to Show/Hide the Molecular Data of This NP
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [3]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    Molecule(s)
                    Regulation		 Down-regulation Expression ADRA2A  Molecule Info 
Pathway MAP
Down-regulation Expression HTR2C  Molecule Info 
Pathway MAP
Down-regulation Expression SSTR1  Molecule Info 
Pathway MAP
                    In-vivo Model Animals received yohimbine (2 mg/kg) 30 min prior to administration of imipramine(20 mg/kg) (Y + I group) or received vehicle treatment (Ctl group), once a day for seven consecutive days in adult male Wistar rats (250-400 g, 2-3 months of age) and adult male nestin-GFP transgenic mice (25-35 g, 2-3 months of age).
                    Experimental
                    Result(s)		 Yohimbine and Imipramine combination treatment enhanced the quiescent neural progenitor pool in the hippocampal neurogenic niche similar to ECS, and distinct from chronic imipramine treatment.
Target and Pathway
Target(s) Norepinephrine transporter (NET)  Molecule Info  [4]
Panther Pathway Adrenaline and noradrenaline biosynthesis Click to Show/Hide
Reactome Na+/Cl- dependent neurotransmitter transporters Click to Show/Hide
WikiPathways Monoamine Transport Click to Show/Hide
2 NRF2 pathway
3 Transport of glucose and other sugars, bile salts and organic acids, metal ions and amine compounds
References
Reference 1 URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 357).
Reference 2 Combination of Imipramine, a sphingomyelinase inhibitor, and Beta-caryophyllene improve their therapeutic effects on experimental autoimmune encephalomyelitis (EAE). Int Immunopharmacol. 2019 Dec;77:105923.
Reference 3 Hippocampal transcriptional and neurogenic changes evoked by combination yohimbine and imipramine treatment. Prog Neuropsychopharmacol Biol Psychiatry. 2015 Aug 3;61:1-9.
Reference 4 Invivo antioxidant status: a putative target of antidepressant action. Prog Neuropsychopharmacol Biol Psychiatry. 2009 Mar 17;33(2):220-8.
 Download Picture         KEGG Link      
 Download Picture         KEGG Link      
 Download Picture         KEGG Link      
 Download Picture         KEGG Link