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
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-
Molecular Formula | C16H18N2 |
Molecular Weight | 238.3275 |
Charge | 0 |
Count |
|
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 |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 1 |
Optical Activity | NONE |
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.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: GO:0051620 Sources: https://www.ncbi.nlm.nih.gov/pubmed/844493 |
4.7 nM [Ki] | ||
Target ID: GO:0090494 Sources: https://www.ncbi.nlm.nih.gov/pubmed/844493 |
26.0 nM [Ki] | ||
Target ID: GO:0051610 Sources: https://www.ncbi.nlm.nih.gov/pubmed/844493 |
4.0 µM [Ki] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | Unknown Approved UseUnknown |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
84 μg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7082545 |
100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered: |
NOMIFENSINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
53 ng/mL |
100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered: |
NOMIFENSINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
196.8 μg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7082545 |
100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered: |
NOMIFENSINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
1.9 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7082545 |
100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered: |
NOMIFENSINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
2.2 h |
100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered: |
NOMIFENSINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
Funbound
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
25% |
100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered: |
NOMIFENSINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
Doses
Dose | Population | Adverse events |
---|---|---|
150 mg 2 times / day multiple, oral Studied dose Dose: 150 mg, 2 times / day Route: oral Route: multiple Dose: 150 mg, 2 times / day Sources: |
unhealthy, 18-44 years n = 18 Health Status: unhealthy Condition: attention deficit disorder Age Group: 18-44 years Sex: M+F Population Size: 18 Sources: |
Disc. AE: Skin rash, Fever... AEs leading to discontinuation/dose reduction: Skin rash (severe, 1 patient) Sources: Fever (severe, 1 patient) Back pain (severe, 1 patient) |
100 mg single, intravenous Dose: 100 mg Route: intravenous Route: single Dose: 100 mg Sources: |
healthy, 22-41 years Health Status: healthy Age Group: 22-41 years Sex: M+F Sources: |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Back pain | severe, 1 patient Disc. AE |
150 mg 2 times / day multiple, oral Studied dose Dose: 150 mg, 2 times / day Route: oral Route: multiple Dose: 150 mg, 2 times / day Sources: |
unhealthy, 18-44 years n = 18 Health Status: unhealthy Condition: attention deficit disorder Age Group: 18-44 years Sex: M+F Population Size: 18 Sources: |
Fever | severe, 1 patient Disc. AE |
150 mg 2 times / day multiple, oral Studied dose Dose: 150 mg, 2 times / day Route: oral Route: multiple Dose: 150 mg, 2 times / day Sources: |
unhealthy, 18-44 years n = 18 Health Status: unhealthy Condition: attention deficit disorder Age Group: 18-44 years Sex: M+F Population Size: 18 Sources: |
Skin rash | severe, 1 patient Disc. AE |
150 mg 2 times / day multiple, oral Studied dose Dose: 150 mg, 2 times / day Route: oral Route: multiple Dose: 150 mg, 2 times / day Sources: |
unhealthy, 18-44 years n = 18 Health Status: unhealthy Condition: attention deficit disorder Age Group: 18-44 years Sex: M+F Population Size: 18 Sources: |
PubMed
Title | Date | PubMed |
---|---|---|
Effects of sibutramine on the central dopaminergic system in rodents. | 2001 Jul |
|
In vivo evidence for a lack of central effect of ebastine, an antihistaminic agent, in rats: a microdialysis study. | 2002 Dec |
|
Destruction of serotonergic nerve terminals prevents fluoxetine-induced desensitization of hypothalamic 5-HT(1A) receptors. | 2002 Dec |
|
Dopamine, but not norepinephrine or serotonin, reuptake inhibition reverses motor deficits in 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine-treated primates. | 2002 Dec |
|
Selective blockade of drug-induced place preference conditioning by ACPC, a functional NDMA-receptor antagonist. | 2002 Nov |
|
Kinetic analysis of striatal clearance of exogenous dopamine recorded by chronoamperometry in freely-moving rats. | 2002 Nov 15 |
|
Aged Fischer 344 rats exhibit altered locomotion in the absence of decreased locomotor activity: exacerbation by nomifensine. | 2002 Nov 29 |
|
In vivo temporal sequence of rat striatal glutamate, aspartate and dopamine efflux during apomorphine, nomifensine, NMDA and PDC in situ administration. | 2002 Oct |
|
Modification of the striatal dopaminergic neuron system by carbon monoxide exposure in free-moving rats, as determined by in vivo brain microdialysis. | 2002 Oct |
|
FR143166 attenuates spinal pain transmission through activation of the serotonergic system. | 2002 Oct 11 |
|
A role for presynaptic mechanisms in the actions of nomifensine and haloperidol. | 2003 |
|
Tetrahydrobiopterin precursor sepiapterin provides protection against neurotoxicity of 1-methyl-4-phenylpyridinium in nigral slice cultures. | 2003 Apr |
|
The effects of systemically administered taurine and N-pivaloyltaurine on striatal extracellular dopamine and taurine in freely moving rats. | 2003 Aug |
|
Identification of dopamine transporter in bovine pineal gland using [3H]GBR 12935. | 2003 Aug |
|
Differential effects of amphetamine transport vs. dopamine reverse transport on particulate PKC activity in striatal synaptoneurosomes. | 2003 Aug |
|
Dopamine induces autophagic cell death and alpha-synuclein increase in human neuroblastoma SH-SY5Y cells. | 2003 Aug 1 |
|
In vitro pharmacological characterization of (+/-)-4-[2-(1-methyl-2-pyrrolidinyl)ethyl]thio]phenol hydrochloride (SIB-1553A), a nicotinic acetylcholine receptor ligand. | 2003 Aug 15 |
|
Functionally distinct dopamine and octopamine transporters in the CNS of the cabbage looper moth. | 2003 Feb |
|
Mechanism by which brain-derived neurotrophic factor increases dopamine release from the rabbit retina. | 2003 Feb |
|
Strain-dependent modification of behavior following antidepressant treatment. | 2003 Feb |
|
Discriminative stimulus effects of (-)-ephedrine in rats: analysis with catecholamine transporter and receptor ligands. | 2003 Jun 5 |
|
Aged Fischer 344 rats exhibit altered orolingual motor function: relationships with nigrostriatal neurochemical measures. | 2003 Mar-Apr |
|
Differences in norepinephrine clearance in cerebellar slices from low-alcohol-sensitive and high-alcohol-sensitive rats. | 2003 May |
|
8-[3H]-hydroxy-2-(di-n-propylamino)tetralin binding sites in blood lymphocytes of rats and the modulation by mitogens and immobilization. | 2003 May |
|
High-frequency stimulation of the subthalamic nucleus enhances striatal dopamine release and metabolism in rats. | 2003 May |
|
Mechanisms underlying domoic acid-induced dopamine release from striatum: an in vivo microdialysis study. | 2003 Oct |
|
Enhanced attention in rhesus monkeys as a common factor for the cognitive effects of drugs with abuse potential. | 2003 Sep |
|
Nomifensine amplifies subsecond dopamine signals in the ventral striatum of freely-moving rats. | 2004 Aug |
|
Prenatal cocaine exposure decreases nigrostriatal dopamine release in vitro: effects of age and sex. | 2004 Aug |
|
Dopamine release evoked by beta scorpion toxin, tityus gamma, in prefrontal cortical slices is mediated by intracellular calcium stores. | 2004 Dec |
|
Sibutramine induces potential-dependent exocytotic release but not carrier-mediated release of dopamine and 5-hydroxytryptamine. | 2004 Jan 26 |
|
[Effects of anxiolytic drugs on rewarding and aversive behaviors induced by intracranial stimulation]. | 2004 Jun |
|
Uptake inhibitors but not substrates induce protease resistance in extracellular loop two of the dopamine transporter. | 2004 Mar |
|
(-)-Deprenyl inhibits tyramine-induced noradrenaline release, but not tyramine-induced dopamine release or potassium-induced noradrenaline release, from rat brain synaptosomes. | 2004 Mar |
|
[Dopaminergic regulation of theta activity of septohippocampal neuron in the awake rabbit]. | 2004 Mar-Apr |
|
Methylphenidate restores ventral tegmental area dopamine neuron activity in prenatal ethanol-exposed rats by augmenting dopamine neurotransmission. | 2004 May |
|
Induction of gp130-related cytokines and activation of JAK2/STAT3 pathway in astrocytes precedes up-regulation of glial fibrillary acidic protein in the 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine model of neurodegeneration: key signaling pathway for astrogliosis in vivo? | 2004 May 7 |
|
Involvement of dopamine receptors in the anti-immobility effects of dopamine re-uptake inhibitors in the forced swimming test. | 2004 Nov 19 |
|
Voltammetric study of the control of striatal dopamine release by glutamate. | 2004 Oct |
|
Methamphetamine neurotoxicity in dopamine nerve endings of the striatum is associated with microglial activation. | 2004 Oct |
|
Reduced inhibitory action of a GABAB receptor agonist on [3H]-dopamine release from rat ventral tegmental area in vitro after chronic nicotine administration. | 2004 Oct 20 |
|
Inhibitory effect of nitric oxide on dopamine transporters: interneuronal communication without receptors. | 2004 Sep |
|
Opioid and monoamine systems mediate the discriminative stimulus of tramadol in rats. | 2004 Sep 13 |
|
D2 autoreceptor inhibition reveals oxygen-glucose deprivation-induced release of dopamine in guinea-pig cochlea. | 2005 |
|
Dopamine transporter function differences between male and female CD-1 mice. | 2005 Feb 28 |
|
Antidepressant-like effect of D(2/3) receptor-, but not D(4) receptor-activation in the rat forced swim test. | 2005 Jul |
|
Dopamine transporters are involved in the onset of hypoxia-induced dopamine efflux in striatum as revealed by in vivo microdialysis. | 2005 Jun |
|
Dyskinesias in normal squirrel monkeys induced by nomifensine and levodopa. | 2005 Mar |
|
Monoamine transporter inhibitors and norepinephrine reduce dopamine-dependent iron toxicity in cells derived from the substantia nigra. | 2005 Mar |
|
Nicotine and epibatidine alter differently nomifensine-elevated dopamine output in the rat dorsal and ventral striatum. | 2005 Mar 28 |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/3091156
100 mg at night
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/911650
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
Created
by
admin
on
Edited
Fri Dec 15 16:19:49 UTC 2023
by
admin
on
Fri Dec 15 16:19:49 UTC 2023
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Record UNII |
76S8CUH5MR
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Record Status |
Validated (UNII)
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Record Version |
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-
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Classification Tree | Code System | Code | ||
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NCI_THESAURUS |
C265
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289114
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100000080020
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CHEMBL273575
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251-223-7
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m8030
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262302
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32795-47-4
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5358907
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C73808
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DBSALT002854
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DTXSID1045790
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SUB14663MIG
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76S8CUH5MR
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PARENT -> SALT/SOLVATE |
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ACTIVE MOIETY |