General Information of Drug (ID: DM2NUH3)

Drug Name
Imipramine Drug Info
Synonyms
Antideprin; Berkomine; Censtim; Censtin; Declomipramine; Dimipressin; Dpid; Dynaprin; Eupramin; Imavate; Imidobenzyle; Imipramin; Imipramina; Imipraminum; Imiprin; Imizin; Imizinum; Impramine; Intalpram; Iramil; Irmin; Janimine; Melipramin; Melipramine; Nelipramin; Norchlorimipramine; Norfranil; Pramine; Prazepine; Promiben;Psychoforin; Surplix; Timolet; Tofranil; Imipramina [Italian]; Tofraniln A; Antideprin (TN); Deprimin (TN); Deprinol (TN); Depsonil (TN); Dyna-zina; Dynaprin (TN); Eupramin (TN); G-22355; Imipramil (TN); Imipramina [INN-Spanish]; Imipramine (INN); Imipramine [INN:BAN]; Imipraminum [INN-Latin]; Irmin (TN); Janimine (TN); Janimine (hydrochloride); Melipramin (TN); SK-Pramine; Surplix (TN); Tofranil(TN); Tofranil (free base); Tofranil (hydrochloride); Tofranil, base; N-(gamma-Dimethylaminopropyl)iminodibenzyl; N-(gamma.-Dimethylaminopropyl)iminodibenzyl; N-(3-Dimethylaminopropyl)-o-iminodibenzyl; 1-(3-Dimethylaminopropyl)-4,5-dihydro-2,3,6,7-dibenzazepine; 10,11-Dihydro-5-(3-(dimethylamino)propyl)-5H-dibenz[b,f]azepine; 10,11-Dihydro-N,N-dimethyl-5H-dibenz[b,f]azepine-5-propanamine; 2,2'-(3-Dimethylaminopropylimino)bibenzyl; 2,2'-(3-Dimethylaminopropylimino)dibenzyl; 3-(10,11-dihydro-5H-dibenzo[b,f]azepin-5-yl)-N,N-dimethylpropan-1-amine; 3-(5,6-dihydrobenzo[b][1]benzazepin-11-yl)-N,N-dimethylpropan-1-amine; 5,6-Dihydro-N-(3-(dimethylamino)propyl)-11H-dibenz(b,e)azepine; 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; 5H-Dibenz(b,f)azepine,5-[3-(dimethylamino)propyl]-10,11-dihydro-mixed with ethyl alcohol; 5H-Dibenz(b,f)azepine-5-propanamine, 10,11-dihydro-N,N-dimethyl-(9CI)
Indication
Disease Entry ICD 11 Status REF
Depression 6A70-6A7Z Approved [1]
Nocturia MF55 Approved [2]
Therapeutic Class
Antidepressants
Cross-matching ID
PubChem CID
3696
ChEBI ID
CHEBI:47499
CAS Number
CAS 50-49-7
TTD Drug ID
DM2NUH3
VARIDT Drug ID
DR00552
INTEDE Drug ID
DR0861
ACDINA Drug ID
D00325

Molecule(s) Related to This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Norepinephrine transporter (NET) TTAWNKZ SC6A2_HUMAN Inhibitor [3]

Drug Transporter (DTP)
DTP Name DTP ID UniProt ID Highest Status REF
P-glycoprotein 1 (ABCB1) DTUGYRD MDR1_HUMAN Approved [4]

Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID Highest Status REF
Cytochrome P450 3A4 (CYP3A4) DE4LYSA CP3A4_HUMAN Approved [5]
Cytochrome P450 2D6 (CYP2D6) DECB0K3 CP2D6_HUMAN Approved [6]
UDP-glucuronosyltransferase 1A1 (UGT1A1) DEYGVN4 UD11_HUMAN Approved [7]
Mephenytoin 4-hydroxylase (CYP2C19) DEGTFWK CP2CJ_HUMAN Approved [8]
Cytochrome P450 1A2 (CYP1A2) DEJGDUW CP1A2_HUMAN Approved [9]
Cytochrome P450 2B6 (CYP2B6) DEPKLMQ CP2B6_HUMAN Approved [9]
Cytochrome P450 3A7 (CYP3A7) DERD86B CP3A7_HUMAN Approved [10]
Cytochrome P450 2C18 (CYP2C18) DEZMWRE CP2CI_HUMAN Approved [9]
Docosahexaenoic acid omega-hydroxylase (CYP4F11) DEIZLTN CP4FB_HUMAN Approved [11]

The Expression Level of Molecule(s) in Normal Tissue of Major ADME-Related Organs

Molecule Molecule Type Gene Name Liver Colon Kidney Small Intestine
Norepinephrine transporter (NET) DTT SLC6A2 2.459 3.426 3.322 3.35
P-glycoprotein 1 (ABCB1) DTP P-GP 7.009 6.988 7.442 8.135
Cytochrome P450 2C18 (CYP2C18) DME CYP2C18 8.485 5.28 4.621 8.889
Cytochrome P450 1A2 (CYP1A2) DME CYP1A2 10.036 5.779 6.508 6.481
Mephenytoin 4-hydroxylase (CYP2C19) DME CYP2C19 7.867 5.142 5.52 7.08
Cytochrome P450 2D6 (CYP2D6) DME CYP2D6 3.307 5.005 3.921 5.327
Cytochrome P450 3A4 (CYP3A4) DME CYP3A4 11.692 6.58 4.984 9.089
Molecule Expression Atlas in Normal Tissue of Major ADME-related organs

The Expression Level of Molecule(s) between Disease Section and Healthy Individual Tissue

The Studied Disease Depression
ICD Disease Classification 6A70-6A7Z
Molecule Name Molecule Type Gene Name p-value Fold-Change Z-score
Norepinephrine transporter (NET) DTT SLC6A2 7.05E-01 7.02E-03 0.07
P-glycoprotein 1 (ABCB1) DTP P-GP 7.83E-01 4.69E-02 1.89E-01
Cytochrome P450 2C18 (CYP2C18) DME CYP2C18 7.90E-01 3.72E-02 2.95E-01
UDP-glucuronosyltransferase 1A1 (UGT1A1) DME UGT1A1 1.87E-01 4.98E-02 3.61E-01
Cytochrome P450 2B6 (CYP2B6) DME CYP2B6 5.79E-01 -1.30E-02 -9.78E-02
Cytochrome P450 1A2 (CYP1A2) DME CYP1A2 8.68E-01 3.64E-02 2.72E-01
Docosahexaenoic acid omega-hydroxylase (CYP4F11) DME CYP4F11 6.86E-01 -4.38E-02 -2.46E-01
Mephenytoin 4-hydroxylase (CYP2C19) DME CYP2C19 7.66E-01 9.19E-03 4.88E-02
Cytochrome P450 2D6 (CYP2D6) DME CYP2D6 5.64E-01 2.36E-02 1.75E-01
Cytochrome P450 3A4 (CYP3A4) DME CYP3A4 6.06E-01 -2.42E-02 -1.64E-01
Molecular Expression Atlas between Disease Section and Healthy Individual Tissue

References

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).
2 Imipramine FDA Label
3 Invivo antioxidant status: a putative target of antidepressant action. Prog Neuropsychopharmacol Biol Psychiatry. 2009 Mar 17;33(2):220-8.
4 Caco-2 permeability, P-glycoprotein transport ratios and brain penetration of heterocyclic drugs. Int J Pharm. 2003 Sep 16;263(1-2):113-22.
5 Variability in metabolism of imipramine and desipramine using urinary excretion data. J Anal Toxicol. 2014 Jul-Aug;38(6):368-74.
6 QTc prolongation associated with combination therapy of levofloxacin, imipramine, and fluoxetine. Ann Pharmacother. 2005 Mar;39(3):543-6.
7 Liquid chromatography-tandem mass spectrometry method for measurement of nicotine N-glucuronide: a marker for human UGT2B10 inhibition. J Pharm Biomed Anal. 2011 Jul 15;55(5):964-71.
8 Inhibitory effects of tricyclic antidepressants (TCAs) on human cytochrome P450 enzymes in vitro: mechanism of drug interaction between TCAs and phenytoin. Drug Metab Dispos. 2002 Oct;30(10):1102-7.
9 Reappraisal of human CYP isoforms involved in imipramine N-demethylation and 2-hydroxylation: a study using microsomes obtained from putative extensive and poor metabolizers of S-mephenytoin and eleven recombinant human CYPs. J Pharmacol Exp Ther. 1997 Jun;281(3):1199-210.
10 Catalysis of drug oxidation during embryogenesis in human hepatic tissues using imipramine as a model substrate. Drug Metab Dispos. 1999 Nov;27(11):1306-8.
11 Expression and characterization of human cytochrome P450 4F11: putative role in the metabolism of therapeutic drugs and eicosanoids. Toxicol Appl Pharmacol. 2004 Sep 15;199(3):295-304.