Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C24H26BrN3O3.C6H10O4 |
Molecular Weight | 630.527 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 5 / 5 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
C[C@H]([C@@H](C)C(O)=O)C(O)=O.[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=PIPPPBXIDXDUCD-IVEQEFCZSA-N
InChI=1S/C24H26BrN3O3.C6H10O4/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;1-3(5(7)8)4(2)6(9)10/h4-7,10-11,13,15,21H,8-9,12,14H2,1-3H3;3-4H,1-2H3,(H,7,8)(H,9,10)/t15-,21-,24+;3-,4-/m11/s1
Molecular Formula | C24H26BrN3O3 |
Molecular Weight | 484.386 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 3 / 3 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
Molecular Formula | C6H10O4 |
Molecular Weight | 146.1412 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 2 / 2 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
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 |
---|---|---|---|
7.26 nM [Ki] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
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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Effects of nicergoline on the cardiovascular system of dogs and rats. | 1981 Jul-Aug |
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[Haemodynamic and metabolic effects of exercise test in diabetic patients with arteritis treated or not with nicergoline (author's transl)]. | 1981 Sep 18-25 |
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Systemic and carotid haemodynamics and plasma renin activity during deliberate hypotension in dogs: a comparison of sodium nitroprusside with nicergoline. | 1984 Mar |
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[Plasma renin activity and prostaglandin E2 in hypotension induced by nicergoline]. | 1985 |
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[Nicergoline to reduce intraoperative blood pressure increases in hypertensive patients]. | 1985 Nov |
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Centrally mediated cardiovascular effects of nicergoline in the dog compared to those of clonidine. | 1985 Oct 29 |
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[The effects of nicergoline on the heart rate in the normotensive or spontaneously hypertensive rat. Possible participation of central alpha-1 receptors]. | 1986 Jan-Mar |
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Effect of nicergoline on learning and memory. | 1988 Jul |
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[Pharmacological analysis of memory disorders of different origins]. | 1989 Jun |
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[A case of parkinsonism induced by an oral contraceptive]. | 1992 Feb |
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Nicergoline in the treatment of dizziness in elderly patients. A review. | 2004 |
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[Nicergoline-induced Prinzmetal angina. "Heartache" instead of headache]. | 2004 Jan 4 |
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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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Treatment of vascular dementia: evidence from trials with non-cholinergic drugs. | 2004 Nov 15 |
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Nicergoline reverts haloperidol-induced loss of detoxifying-enzyme activity. | 2004 Nov 28 |
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[Effect of non-selective alpha-adrenergic receptor antagonist nicergoline on the activity of neurons in the ventral lateral thalamic nucleus]. | 2005 |
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[A case of pseudotumorous course of brain demyelinating disease]. | 2005 |
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Protective effects of nicergoline against neuronal cell death induced by activated microglia and astrocytes. | 2005 Dec 20 |
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Nicergoline, a drug used for age-dependent cognitive impairment, protects cultured neurons against beta-amyloid toxicity. | 2005 Jun 14 |
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Differential modulation of microglia superoxide anion and thromboxane B2 generation by the marine manzamines. | 2005 Mar 11 |
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A phylogenetic survey of biliary lipids in vertebrates. | 2005 Oct |
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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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Preclinical and clinical examinations of Salvia miltiorrhiza and its tanshinones in ischemic conditions. | 2006 Nov 23 |
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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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[Nicergoline, ibudilast, ifenprodil tartrate]. | 2006 Oct 28 |
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Progress update: Pharmacological treatment of Alzheimer's disease. | 2007 |
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Vascular dementia: pharmacological treatment approaches and perspectives. | 2007 |
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Treating senile dementia with traditional Chinese medicine. | 2007 |
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[Treatment of thyroid ophthalmopathy--a clinical case]. | 2007 |
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[Influence of arterial hypertension on the clinical course of Parkinson's disease (PD) among middle-aged patients]. | 2007 Jul-Sep |
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Donepezil in Alzheimer's disease: From conventional trials to pharmacogenetics. | 2007 Jun |
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Therapeutic use of nicergoline. | 2008 |
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Method development and validation for the simultaneous determination of cinnarizine and co-formulated drugs in pharmaceutical preparations by capillary electrophoresis. | 2008 Feb 13 |
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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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Smart stability-indicating spectrophotometric methods for determination of binary mixtures without prior separation. | 2008 Mar-Apr |
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Disruption of GM2/GD2 synthase gene resulted in overt expression of 9-O-acetyl GD3 irrespective of Tis21. | 2008 May |
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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 |
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Natural non-trasgenic animal models for research in Alzheimer's disease. | 2009 Apr |
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Effects of nicergoline on corneal epithelial wound healing in rat eyes. | 2009 Feb |
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Vascular cognitive impairment. | 2009 Jan |
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Sertraline-induced rhabdomyolysis in an elderly patient with dementia and comorbidities. | 2009 Jul |
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[Glaucoma--neurodegenerative disease]. | 2009 Oct-Dec |
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[Therapeutic potential and possibilities of using of sermion (nicergoline) in neurological practice]. | 2010 |
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A systematic review of clinical trials of pharmacological interventions for acute ischaemic stroke (1955-2008) that were completed, but not published in full. | 2010 Apr 22 |
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Nicergoline increases serum substance P levels in patients with an ischaemic stroke. | 2010 Jan |
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Norepinephrine enhances the LPS-induced expression of COX-2 and secretion of PGE2 in primary rat microglia. | 2010 Jan 11 |
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Colloid formation by drugs in simulated intestinal fluid. | 2010 May 27 |
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.
Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Dec 16 07:11:47 GMT 2023
by
admin
on
Sat Dec 16 07:11:47 GMT 2023
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Record UNII |
J7P36Z4900
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Record Status |
Validated (UNII)
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Record Version |
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