Details of the Drug

General Information of Drug (ID: DMNI3U2)

Drug Name
ZIMELIDINE
Synonyms
Prestwick0_000092; Prestwick1_000092; 56775-88-3; AC1L26VA; NCIStruc1_001846; NCIStruc2_001359; SPBio_001983; 2-Propen-1-amine, 3-(4-bromophenyl)-N,N-dimethyl-3-(3-pyridinyl)-; CTK1F3832; OYPPVKRFBIWMSX-UHFFFAOYSA-N; DB04832; NCI60_002580; FT-0675907; N,N-dimethyl-3-(4-bromophenyl)-3-(pyrid-3-yl)allylamine; N,N-dimethyl-3-(4-bromophenyl)-3-(3-pyridyl)-allylamine; (Z)-3-[1-(p-Bromophenyl)-3-(dimethylamino)propenyl]pyridine; 3-(4-bromophenyl)-N,N-dimethyl-3-pyridin-3-ylprop-2-en-1-amine
Indication
Disease Entry ICD 11 Status REF
Depression 6A70-6A7Z Withdrawn from market [1]
Major depressive disorder 6A70.3 Withdrawn from market [2]
Affected Organisms
Humans and other mammals
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 317.22
Logarithm of the Partition Coefficient (xlogp) 3.9
Rotatable Bond Count (rotbonds) 4
Hydrogen Bond Donor Count (hbonddonor) 0
Hydrogen Bond Acceptor Count (hbondacc) 2
ADMET Property
Clearance
The drug present in the plasma can be removed from the body at the rate of 13.8 mL/min/kg [3]
Half-life
The concentration or amount of drug in body reduced by one-half in 8.4 +/- 2.0 hours [3]
Unbound Fraction
The unbound fraction of drug in plasma is 0.086% [3]
Vd
Fluid volume that would be required to contain the amount of drug present in the body at the same concentration as in the plasma 6.8 L/kg [3]
Chemical Identifiers
Formula
C16H17BrN2
IUPAC Name
(Z)-3-(4-bromophenyl)-N,N-dimethyl-3-pyridin-3-ylprop-2-en-1-amine
Canonical SMILES
CN(C)C/C=C(/C1=CC=C(C=C1)Br)\\C2=CN=CC=C2
InChI
InChI=1S/C16H17BrN2/c1-19(2)11-9-16(14-4-3-10-18-12-14)13-5-7-15(17)8-6-13/h3-10,12H,11H2,1-2H3/b16-9-
InChIKey
OYPPVKRFBIWMSX-SXGWCWSVSA-N
Cross-matching ID
PubChem CID
5365247
ChEBI ID
CHEMBL92824
CAS Number
56775-88-3
UNII
3J928617DW
DrugBank ID
DB04832
TTD ID
D0C1XS
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Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Serotonin transporter (SERT) TT3ROYC SC6A4_HUMAN Inhibitor [4]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
Acid ceramidase (ASAH1) OT1DNGXL ASAH1_HUMAN Gene/Protein Processing [5]
Alpha-1-antichymotrypsin (SERPINA3) OT9BP2S0 AACT_HUMAN Gene/Protein Processing [5]
AP-1 complex subunit sigma-1A (AP1S1) OTQ2H8DN AP1S1_HUMAN Gene/Protein Processing [6]
Fibronectin type III domain-containing protein 4 (FNDC4) OTOQK0WK FNDC4_HUMAN Gene/Protein Processing [5]
Inhibin beta E chain (INHBE) OTOI2NYG INHBE_HUMAN Gene/Protein Processing [5]
Lysophospholipase D GDPD3 (GDPD3) OTOHM9QM GDPD3_HUMAN Gene/Protein Processing [6]
Nuclear protein 1 (NUPR1) OT4FU8C0 NUPR1_HUMAN Gene/Protein Processing [5]
Nuclear receptor subfamily 0 group B member 2 (NR0B2) OT7UVICX NR0B2_HUMAN Gene/Protein Processing [6]
Phosphatidylcholine translocator ABCB4 (ABCB4) OTE6PY83 MDR3_HUMAN Gene/Protein Processing [7]
Protein DEPP1 (DEPP1) OTB36PHJ DEPP1_HUMAN Gene/Protein Processing [5]
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Molecular Expression Atlas of This Drug

ICD Disease Classification 06 Mental, behavioural or neurodevelopmental disorder
Disease Class ICD-11: 6A20 Schizophrenia
The Studied Tissue Pre-frontal cortex
The Studied Disease Major depressive disorder [ICD-11:6A20]
Molecule Name Molecule Type Gene Name p-value Fold-Change Z-score
Serotonin transporter (SERT) DTT SLC6A4 1.17E-01 0.07 0.59
Molecular Expression Atlas (MEA) Jump to Detail Molecular Expression Atlas of This Drug

References

1 Pharmacokinetic study of zimelidine using a new GLC method. Clin Pharmacokinet. 1983 Nov-Dec;8(6):530-40.
2 Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services. 2015
3 Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds
4 Nontricyclic antidepressant agents derived from cis- and trans-1-amino-4-aryltetralins. J Med Chem. 1984 Nov;27(11):1508-15.
5 A toxicogenomic approach to drug-induced phospholipidosis: analysis of its induction mechanism and establishment of a novel in vitro screening system. Toxicol Sci. 2005 Feb;83(2):282-92.
6 Determination of phospholipidosis potential based on gene expression analysis in HepG2 cells. Toxicol Sci. 2007 Mar;96(1):101-14.
7 Evaluating the Role of Multidrug Resistance Protein 3 (MDR3) Inhibition in Predicting Drug-Induced Liver Injury Using 125 Pharmaceuticals. Chem Res Toxicol. 2017 May 15;30(5):1219-1229. doi: 10.1021/acs.chemrestox.7b00048. Epub 2017 May 4.