Details of the Drug

General Information of Drug (ID: DMCP2TS)

Drug Name

Nomifensine

Synonyms

Linamiphen; Nomifenison; Nomifensin; Nomifensina; Nomifensinum; Nomiphensine; Nomifensina [INN-Spanish]; Nomifensine [INN:BAN]; Nomifensine maleate(USAN); Nomifensinum [INN-Latin]; D,L-nomifensine; Nomifensine Maleate (1:1); R/S-nomifensine; (+)-Nomifensine; (+)-Nomiphensine; (+-)-1,2,3,4-Tetrahydro-2-methyl-4-phenyl-8-isoquinolinamine; (+-)-Nomifensin; (+-)-Nomifensine; (R)-1,2,3,4-Tetrahydro-2-methyl-4-phenyl-8-isoquinolinamine; 2-Methyl-4-phenyl-1,2,3,4-tetrahydro-8-isoquinolinamine; 2-Methyl-4-phenyl-1,2,3,4-tetrahydro-8-isoquinolinamine 2-butenedioate; 2-Methyl-4-phenyl-1,2,3,4-tetrahydro-isoquinolin-8-ylamine; 2-methyl-4-phenyl-1,2,3,4-tetrahydroisoquinolin-8-amine; 2-methyl-4-phenyl-3,4-dihydro-1H-isoquinolin-8-amine; 8-Amino-1,2,3,4-tetrahydro-2-methyl-4-phenylisochinolin; 8-Amino-1,2,3,4-tetrahydro-2-methyl-4-phenylisoquinoline; 8-Amino-1,2,3,4-tetrahydro-2-methyl-4-phenylisoquinoline maleate (1:1); 8-Amino-2-methyl-4-phenyl-1,2,3,4-tetrahydroisoquinoline; 8-Isoquinolinamine, 1,2,3,4-tetrahydro-2-methyl-4-phenyl; 8-Isoquinolinamine, 1,2,3,4-tetrahydro-2-methyl-4-phenyl-(9CI)

Indication

Disease Entry	ICD 11	Status	REF
Breast cancer	2C60-2C65	Withdrawn from market	[1]

Affected Organisms

Humans and other mammals

ATC Code

N06AX04: Nomifensine

N06AX: Other antidepressants

N06A: ANTIDEPRESSANTS

N06: PSYCHOANALEPTICS

N: NERVOUS SYSTEM

Drug Type

Small molecular drug

Structure

3D MOL

2D MOL

#Ro5 Violations (Lipinski): 0

Molecular Weight (mw)

238.33

Logarithm of the Partition Coefficient (xlogp)

2.6

Rotatable Bond Count (rotbonds)

Hydrogen Bond Donor Count (hbonddonor)

Hydrogen Bond Acceptor Count (hbondacc)

ADMET Property

BDDCS Class: Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 1: high solubility and high permeability [2]
Clearance: The drug present in the plasma can be removed from the body at the rate of 22 mL/min/kg [3]
Half-life: The concentration or amount of drug in body reduced by one-half in 6.5 hours [3]
MRTD: The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 11.988 micromolar/kg/day [4]
Unbound Fraction: The unbound fraction of drug in plasma is 0.4% [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 L/kg [3]

Chemical Identifiers

Formula: C16H18N2
IUPAC Name: 2-methyl-4-phenyl-3,4-dihydro-1H-isoquinolin-8-amine
Canonical SMILES: CN1CC(C2=C(C1)C(=CC=C2)N)C3=CC=CC=C3
InChI: InChI=1S/C16H18N2/c1-18-10-14(12-6-3-2-4-7-12)13-8-5-9-16(17)15(13)11-18/h2-9,14H,10-11,17H2,1H3
InChIKey: XXPANQJNYNUNES-UHFFFAOYSA-N

Cross-matching ID

PubChem CID: 4528
ChEBI ID: CHEMBL273575
CAS Number: 24526-64-5
UNII: 1LGS5JRP31
DrugBank ID: DB04821
TTD ID: D06BPG
VARIDT ID: DR00944

Drug-Molecule Activity Atlas (DMA)^NEW

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Drug Pharmacogenomic Perturbation (DPP)^NEW

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Drug ADMET Endpoint Profile (DAE)^NEW

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Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
Dopamine D2 receptor (D2R)	TTEX248	DRD2_HUMAN	Antagonist	[5]

Drug-Metabolizing Enzyme (DME)

DME Name	DME ID	UniProt ID	MOA	REF
Dimethylaniline oxidase 5 (FMO5)_{Main DME}	DEBMX7C	FMO5_HUMAN	Substrate	[6]

Drug Off-Target (DOT)

DOT Name	DOT ID	UniProt ID	Interaction	REF
Antileukoproteinase (SLPI)	OTUNFUU8	SLPI_HUMAN	Gene/Protein Processing	[7]
Hepatocyte growth factor receptor (MET)	OT7K55MU	MET_HUMAN	Gene/Protein Processing	[7]
Phosphatidylcholine translocator ABCB4 (ABCB4)	OTE6PY83	MDR3_HUMAN	Gene/Protein Processing	[8]
PTB-containing, cubilin and LRP1-interacting protein (PID1)	OT5YJ7FI	PCLI1_HUMAN	Gene/Protein Processing	[7]

Molecular Interaction Atlas (MIA)

MIA Detail

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Molecular Expression Atlas of This Drug

The Studied Disease

Breast cancer

ICD Disease Classification

2C60-2C65

Molecule Name	Molecule Type	Gene Name	p-value	Fold-Change	Z-score
Dopamine D2 receptor (D2R)	DTT	DRD2	2.50E-02	-0.08	-0.49
Dimethylaniline oxidase 5 (FMO5)	DME	FMO5	6.17E-04	1.66E-01	5.17E-01

Molecular Expression Atlas (MEA)

MEA Detail

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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: 4792).
2	BDDCS predictions, self-correcting aspects of BDDCS assignments, BDDCS assignment corrections, and classification for more than 175 additional drugs
3	Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds
4	Estimating the safe starting dose in phase I clinical trials and no observed effect level based on QSAR modeling of the human maximum recommended daily dose
5	Pharmacologically induced, subsecond dopamine transients in the caudate-putamen of the anesthetized rat. Synapse. 2007 Jan;61(1):37-9.
6	Drug metabolism by flavin-containing monooxygenases of human and mouse. Expert Opin Drug Metab Toxicol. 2017 Feb;13(2):167-181.
7	An in vitro coculture system of human peripheral blood mononuclear cells with hepatocellular carcinoma-derived cells for predicting drug-induced liver injury. Arch Toxicol. 2021 Jan;95(1):149-168. doi: 10.1007/s00204-020-02882-4. Epub 2020 Aug 20.
8	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.