Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C24H26BrN3O3 |
Molecular Weight | 484.386 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 3 / 3 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
[H][C@@]12CC3=CN(C)C4=C3C(=CC=C4)[C@]1(C[C@@H](COC(=O)C5=CN=CC(Br)=C5)CN2C)OC
InChI
InChIKey=YSEXMKHXIOCEJA-FVFQAYNVSA-N
InChI=1S/C24H26BrN3O3/c1-27-13-17-8-21-24(30-3,19-5-4-6-20(27)22(17)19)9-15(12-28(21)2)14-31-23(29)16-7-18(25)11-26-10-16/h4-7,10-11,13,15,21H,8-9,12,14H2,1-3H3/t15-,21-,24+/m1/s1
DescriptionCurator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/mesh/68009530
Curator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/mesh/68009530
Nicergoline is a semisynthetic ergoline derivative that has been used as a cerebral vasodilator and in peripheral vascular disease. Nicergoline seems to have an action: (i) as an alpha1-adrenoceptor antagonist, it induces vasodilation and increases arterial blood flow; (ii) it enhances cholinergic and catecholaminergic neurotransmitter function; (iii) it inhibits platelet aggregation; (iv) it promotes metabolic activity, resulting in increased utilization of oxygen and glucose; and (v) it has neurotrophic and antioxidant properties. Nicergoline has been suggested to ameliorate cognitive deficits in cerebrovascular disease.
CNS Activity
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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7.26 nM [Ki] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Palliative | SERMION Approved UseDementia (including Alzheimer's disease and vascular dementia) |
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Palliative | SERMION Approved UseDementia (including Alzheimer's disease and vascular dementia) |
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Palliative | SERMION Approved UseDementia (including Alzheimer's disease and vascular dementia) |
PubMed
Title | Date | PubMed |
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DDT-induced myoclonus: serotonin and alpha noradrenergic interaction. | 1979 Feb |
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[Sermion in the treatment of patients with neurological diseases]. | 2001 Aug |
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Effect of an alpha-blocker (Nicergoline) and of a beta-blocker (Acebutolol) on the in vitro biosynthesis of vascular extracellular matrix. | 2001 May |
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Neuroprotection: a realistic goal for aged brain? | 2004 |
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Prolongevity medicine: Antagonic-Stress drug in distress, geriatrics, and related diseases. II. Clinical review--2003. | 2004 Jun |
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Nicergoline enhances glutamate uptake via glutamate transporters in rat cortical synaptosomes. | 2004 Jun |
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Supraspinal control of external anal sphincter motility: effects of vesical distension in humans and cats. | 2006 Nov |
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[Treatment by medicine which improves cerebral circulation and metabolism]. | 2006 Nov 28 |
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An efficient separation and method development for the quantifying of two basic impurities of Nicergoline by reversed-phase high performance liquid chromatography using ion-pairing counter ions. | 2006 Oct 11 |
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Progress update: Pharmacological treatment of Alzheimer's disease. | 2007 |
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Therapeutic use of nicergoline. | 2008 |
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Second-derivative synchronous fluorescence spectroscopy for the simultaneous determination of cinnarizine and nicergoline in pharmaceutical preparations. | 2008 Mar-Apr |
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Amyloid precursor protein 96-110 and beta-amyloid 1-42 elicit developmental anomalies in sea urchin embryos and larvae that are alleviated by neurotransmitter analogs for acetylcholine, serotonin and cannabinoids. | 2008 Nov-Dec |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://nootriment.com/nicergoline/
5-10 mg (1-2 tablets or 20-40 drops) 3 times daily at regular intervals over prolonged periods of time. To facilitate absorption, take this medicine between meals.
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/10482351
The ability of the antidementia agent, nicergoline, to stimulate PKC mediated alpha-secretase amyloid precursor protein (APP) processing in cultured human neuroblastoma SH-SY5Y cells was investigated. Western immunoblotting of cell conditioned media using the Mabs 22C11 and 6E10 revealed the presence of 2 bands with molecular mass of 90 and 120 kDa, corresponding to possible alternatively glycosylated forms of secreted APP (APPs). Short-term (30 min and 2 h) treatment of cells with nicergoline gave an increased intensity of both bands, compared to non-treated cells. Maximal nicergoline effects, of the order of 150-200% over basal APPs release, were seen at concentrations between 1 and 10 microM. 2 h treatment with nicergoline had no effect on cellular full-length APP levels. Immunoblotting with PKC isoform specific antibodies of soluble and membrane fractions prepared from 2 h treated cells, showed that nicergoline (50 microM) induced translocation of PKC alpha, gamma and epsilon, but not PKC beta. These results indicate that nicergoline can modulate alpha-secretase APP processing by a PKC dependent mechanism that is likely to involve the gamma and epsilon isoforms of this enzyme.
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WHO-ATC |
C04AE02
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NCI_THESAURUS |
C29713
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WHO-VATC |
QC04AE02
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CHEMBL1372950
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DB00699
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27848-84-6
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C84006
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34040
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m7851
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150531
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7398
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NICERGOLINE
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DTXSID7045607
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D009530
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ACTIVE MOIETY
SALT/SOLVATE (PARENT)