General Information
Drug ID
DR00552
Drug Name
Imipramine
Synonyms
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); Antideprin; Antideprin (TN); Berkomine; Censtim; Censtin; Declomipramine; Deprimin (TN); Deprinol (TN); Depsonil (TN); Dimipressin; Dpid; Dyna-zina; Dynaprin; Dynaprin (TN); Eupramin; Eupramin (TN); G-22355; Imavate; Imidobenzyle; Imipramil (TN); Imipramin; Imipramina; Imipramina [INN-Spanish]; Imipramina [Italian]; Imipramine (INN); Imipramine [INN:BAN]; Imipraminum; Imipraminum [INN-Latin]; Imiprin; Imizin; Imizinum; Impramine; Intalpram; Iramil; Irmin; Irmin (TN); Janimine; Janimine (TN); Janimine (hydrochloride); Melipramin; Melipramin (TN); Melipramine; N-(3-Dimethylaminopropyl)-o-iminodibenzyl; N-(gamma-Dimethylaminopropyl)iminodibenzyl; N-(gamma.-Dimethylaminopropyl)iminodibenzyl; Nelipramin; Norchlorimipramine; Norfranil; Pramine; Prazepine; Promiben;Psychoforin; SK-Pramine; Surplix; Surplix (TN); Timolet; Tofranil; Tofranil (free base); Tofranil (hydrochloride); Tofranil(TN); Tofranil, base; Tofraniln A
Drug Type
Small molecular drug
Indication Major depressive disorder [ICD11:6A70.3] Approved [1]
Therapeutic Class
Antidepressants
Structure
3D MOL 2D MOL
Formula
C19H24N2
Canonical SMILES
CN(C)CCCN1C2=CC=CC=C2CCC3=CC=CC=C31
InChI
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
Pharmaceutical Properties Molecular Weight 280.4 Topological Polar Surface Area 6.5
Heavy Atom Count 21 Rotatable Bond Count 4
Hydrogen Bond Donor Count 0 Hydrogen Bond Acceptor Count 2
XLogP
4.8
PubChem CID
3696
PubChem SID
10524418 ,11111330 ,11111331 ,11335734 ,11360973 ,11363809 ,11366371 ,11368933 ,11371492 ,11373530 ,11377095 ,11461945 ,11466100 ,11467220 ,11484795 ,11485940 ,11488806 ,11490282 ,11491831 ,11494729 ,15222228 ,26751600 ,29214791 ,29222819 ,3249403 ,442469 ,46507351 ,47365159 ,47588968 ,47736449 ,47736450 ,47736451 ,47810727 ,47885381 ,48110430 ,48110431 ,49698865 ,49761601 ,49961519 ,50100256 ,50104254 ,53788900 ,57288535 ,57321945 ,615226 ,7548657 ,7849629 ,7979599 ,8152336 ,9261
ChEBI ID
ChEBI:47499
TTD Drug ID
D06ZUK
DT(s) Transporting This Drug P-GP Transporter Info P-glycoprotein 1 Substrate [2]
References
1 Imipramine was approved by FDA. The official website of the U.S. Food and Drug Administration. (2019)
2 Caco-2 permeability, P-glycoprotein transport ratios and brain penetration of heterocyclic drugs. Int J Pharm. 2003 Sep 16;263(1-2):113-22.

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