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Details

Stereochemistry RACEMIC
Molecular Formula C16H18N2.C4H4O4
Molecular Weight 354.3997
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of NOMIFENSINE MALEATE

SMILES

OC(=O)\C=C/C(O)=O.CN1CC(C2=CC=CC=C2)C3=C(C1)C(N)=CC=C3

InChI

InChIKey=GEOCVSMCLVIOEV-BTJKTKAUSA-N
InChI=1S/C16H18N2.C4H4O4/c1-18-10-14(12-6-3-2-4-7-12)13-8-5-9-16(17)15(13)11-18;5-3(6)1-2-4(7)8/h2-9,14H,10-11,17H2,1H3;1-2H,(H,5,6)(H,7,8)/b;2-1-

HIDE SMILES / InChI

Molecular Formula C16H18N2
Molecular Weight 238.3275
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

Molecular Formula C4H4O4
Molecular Weight 116.0722
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 1
Optical Activity NONE

Description

Nomifensine was developed by Hoechst AG as a potent inhibitor of noradrenaline, dopamine, and 5-HT uptake displayed antidepressant activity. It was first marketed in the UK in 1977 for the treatment of depression. Between 1977 and 1982 there were reports of hemolytic anemia in association with the drug, and this suspected adverse reaction was included in the 1981 edition of the data Sheet Compendium. FDA published a notice of its determination that Merital capsules were removed from the market for safety reasons.

CNS Activity

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
4.7 nM [Ki]
26.0 nM [Ki]
4.0 µM [Ki]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Cmax

ValueDoseCo-administeredAnalytePopulation
84 μg/L
100 mg single, oral
NOMIFENSINE plasma
Homo sapiens
53 ng/mL
100 mg single, oral
NOMIFENSINE plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
196.8 μg × h/L
100 mg single, oral
NOMIFENSINE plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
1.9 h
100 mg single, oral
NOMIFENSINE plasma
Homo sapiens
2.2 h
100 mg single, oral
NOMIFENSINE plasma
Homo sapiens

Funbound

ValueDoseCo-administeredAnalytePopulation
25%
100 mg single, oral
NOMIFENSINE plasma
Homo sapiens

Doses

AEs

PubMed

Patents

Sample Use Guides

In Vivo Use Guide
100 mg at night
Route of Administration: Oral
In Vitro Use Guide
The effect of nomifensine on the uptake of 5-hydroxytryptamine (5-HT) and dopamine (DA) into human platelet-rich plasma has been studied. A significant inhibition of DA uptake was observed at nomifensine 10(-6) M. 5-HT uptake was significantly inhibited only at nomifensine 10(-4) M or more. It was concluded, that the human platelet may be used as a model for studying DA uptake as well as that of 5-HT.
Substance Class Chemical
Record UNII
76S8CUH5MR
Record Status Validated (UNII)
Record Version