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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

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
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
[Nicergoline to reduce intraoperative blood pressure increases in hypertensive patients].
1985 Nov
Effect of nicergoline on learning and memory.
1988 Jul
[Current strategies of pathogenetic therapy of Alzheimer's disease].
2001
Plasticity of GABA(a) system during ageing: focus on vestibular compensation and possible pharmacological intervention.
2002 Mar 1
First derivative ratio spectrophotometric, HPTLC-densitometric, and HPLC determination of nicergoline in presence of its hydrolysis-induced degradation product.
2002 Oct 15
Antioxidant properties of MDL and MMDL, two nicergoline metabolites, during chronic administration of haloperidol.
2002 Oct 18
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
Treating senile dementia with traditional Chinese medicine.
2007
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
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
Vascular cognitive impairment.
2009 Jan
Sertraline-induced rhabdomyolysis in an elderly patient with dementia and comorbidities.
2009 Jul
[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
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.
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
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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
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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
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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
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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