U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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
Structure of NICERGOLINE TARTRATE

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

HIDE SMILES / InChI

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

Description
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.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
SERMION

Approved Use

Dementia (including Alzheimer's disease and vascular dementia)
Palliative
SERMION

Approved Use

Dementia (including Alzheimer's disease and vascular dementia)
Palliative
SERMION

Approved Use

Dementia (including Alzheimer's disease and vascular dementia)
PubMed

PubMed

TitleDatePubMed
DDT-induced myoclonus: serotonin and alpha noradrenergic interaction.
1979 Feb
Effects of nicergoline on the cardiovascular system of dogs and rats.
1981 Jul-Aug
[Haemodynamic and metabolic effects of exercise test in diabetic patients with arteritis treated or not with nicergoline (author's transl)].
1981 Sep 18-25
Systemic and carotid haemodynamics and plasma renin activity during deliberate hypotension in dogs: a comparison of sodium nitroprusside with nicergoline.
1984 Mar
[Plasma renin activity and prostaglandin E2 in hypotension induced by nicergoline].
1985
[Nicergoline to reduce intraoperative blood pressure increases in hypertensive patients].
1985 Nov
Centrally mediated cardiovascular effects of nicergoline in the dog compared to those of clonidine.
1985 Oct 29
[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
Effect of nicergoline on learning and memory.
1988 Jul
[Pharmacological analysis of memory disorders of different origins].
1989 Jun
[A case of parkinsonism induced by an oral contraceptive].
1992 Feb
Nicergoline in the treatment of dizziness in elderly patients. A review.
2004
[Nicergoline-induced Prinzmetal angina. "Heartache" instead of headache].
2004 Jan 4
Prolongevity medicine: Antagonic-Stress drug in distress, geriatrics, and related diseases. II. Clinical review--2003.
2004 Jun
Nicergoline enhances glutamate uptake via glutamate transporters in rat cortical synaptosomes.
2004 Jun
Treatment of vascular dementia: evidence from trials with non-cholinergic drugs.
2004 Nov 15
Nicergoline reverts haloperidol-induced loss of detoxifying-enzyme activity.
2004 Nov 28
[Effect of non-selective alpha-adrenergic receptor antagonist nicergoline on the activity of neurons in the ventral lateral thalamic nucleus].
2005
[A case of pseudotumorous course of brain demyelinating disease].
2005
Protective effects of nicergoline against neuronal cell death induced by activated microglia and astrocytes.
2005 Dec 20
Nicergoline, a drug used for age-dependent cognitive impairment, protects cultured neurons against beta-amyloid toxicity.
2005 Jun 14
Differential modulation of microglia superoxide anion and thromboxane B2 generation by the marine manzamines.
2005 Mar 11
A phylogenetic survey of biliary lipids in vertebrates.
2005 Oct
Supraspinal control of external anal sphincter motility: effects of vesical distension in humans and cats.
2006 Nov
Preclinical and clinical examinations of Salvia miltiorrhiza and its tanshinones in ischemic conditions.
2006 Nov 23
[Treatment by medicine which improves cerebral circulation and metabolism].
2006 Nov 28
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
[Nicergoline, ibudilast, ifenprodil tartrate].
2006 Oct 28
Progress update: Pharmacological treatment of Alzheimer's disease.
2007
Vascular dementia: pharmacological treatment approaches and perspectives.
2007
Treating senile dementia with traditional Chinese medicine.
2007
[Treatment of thyroid ophthalmopathy--a clinical case].
2007
[Influence of arterial hypertension on the clinical course of Parkinson's disease (PD) among middle-aged patients].
2007 Jul-Sep
Donepezil in Alzheimer's disease: From conventional trials to pharmacogenetics.
2007 Jun
Therapeutic use of nicergoline.
2008
Method development and validation for the simultaneous determination of cinnarizine and co-formulated drugs in pharmaceutical preparations by capillary electrophoresis.
2008 Feb 13
Second-derivative synchronous fluorescence spectroscopy for the simultaneous determination of cinnarizine and nicergoline in pharmaceutical preparations.
2008 Mar-Apr
Smart stability-indicating spectrophotometric methods for determination of binary mixtures without prior separation.
2008 Mar-Apr
Disruption of GM2/GD2 synthase gene resulted in overt expression of 9-O-acetyl GD3 irrespective of Tis21.
2008 May
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
Natural non-trasgenic animal models for research in Alzheimer's disease.
2009 Apr
Effects of nicergoline on corneal epithelial wound healing in rat eyes.
2009 Feb
Vascular cognitive impairment.
2009 Jan
Sertraline-induced rhabdomyolysis in an elderly patient with dementia and comorbidities.
2009 Jul
[Glaucoma--neurodegenerative disease].
2009 Oct-Dec
[Therapeutic potential and possibilities of using of sermion (nicergoline) in neurological practice].
2010
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
Nicergoline increases serum substance P levels in patients with an ischaemic stroke.
2010 Jan
Norepinephrine enhances the LPS-induced expression of COX-2 and secretion of PGE2 in primary rat microglia.
2010 Jan 11
Colloid formation by drugs in simulated intestinal fluid.
2010 May 27
Patents

Sample Use Guides

In Vivo Use Guide
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
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 Sat Dec 16 07:11:47 GMT 2023
Edited
by admin
on Sat Dec 16 07:11:47 GMT 2023
Record UNII
J7P36Z4900
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
NICERGOLINE TARTRATE
WHO-DD  
Common Name English
NIMERGOLINE
Common Name English
NICOTINIC ACID, 5-BROMO-, (10-METHOXY-1,6-DIMETHYLERGOLIN-8.BETA.-YL)METHYL ESTER, TARTRATE
Common Name English
Nicergoline tartrate [WHO-DD]
Common Name English
ERGOLINE-8-METHANOL, 10-METHOXY-1,6-DIMETHYL-, 5-BROMO-3-PYRIDINECARBOXYLATE (ESTER), (8.BETA.)-, (R-(R*,R*))-2,3-DIHYDROXYBUTANEDIOATE (SALT)
Common Name English
ERGOLINE-8-METHANOL, 10-METHOXY-1,6-DIMETHYL-, 5-BROMO-3-PYRIDINECARBOXYLATE (ESTER), (8.BETA.)-, (2R,3R)-2,3-DIHYDROXYBUTANEDIOATE (SALT)
Common Name English
Code System Code Type Description
CAS
32222-75-6
Created by admin on Sat Dec 16 07:11:47 GMT 2023 , Edited by admin on Sat Dec 16 07:11:47 GMT 2023
PRIMARY
ECHA (EC/EINECS)
250-964-3
Created by admin on Sat Dec 16 07:11:47 GMT 2023 , Edited by admin on Sat Dec 16 07:11:47 GMT 2023
PRIMARY
FDA UNII
J7P36Z4900
Created by admin on Sat Dec 16 07:11:47 GMT 2023 , Edited by admin on Sat Dec 16 07:11:47 GMT 2023
PRIMARY
PUBCHEM
139033071
Created by admin on Sat Dec 16 07:11:47 GMT 2023 , Edited by admin on Sat Dec 16 07:11:47 GMT 2023
PRIMARY
EPA CompTox
DTXSID10954060
Created by admin on Sat Dec 16 07:11:47 GMT 2023 , Edited by admin on Sat Dec 16 07:11:47 GMT 2023
PRIMARY
SMS_ID
100000089076
Created by admin on Sat Dec 16 07:11:47 GMT 2023 , Edited by admin on Sat Dec 16 07:11:47 GMT 2023
PRIMARY
EVMPD
SUB23254
Created by admin on Sat Dec 16 07:11:47 GMT 2023 , Edited by admin on Sat Dec 16 07:11:47 GMT 2023
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY