NICERGOLINE TARTRATE

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 Search

SMILES

C[C@H]([C@@H](C)C(O)=O)C(O)=O.CO[C@]12C[C@@H](COC(=O)C3=CN=CC(Br)=C3)CN(C)[C@@H]1CC4=CN(C)C5=CC=CC2=C45

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	C6H10O4
Molecular Weight	146.1412
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	2 / 2
E/Z Centers	0
Optical Activity	UNSPECIFIED

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

Description
Sources: http://www.ema.europa.eu/docs/en_GB/document_library/Referrals_document/Ergot_derivatives-containing_products/WC500161305.pdf
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
Alpha-1a adrenergic receptor 67 Target ID: CHEMBL319 Sources: http://www.ema.europa.eu/docs/en_GB/document_library/Referrals_document/Ergot_derivatives-containing_products/WC500161305.pdf	Antagonist 2849		7.26 nM [Ki]

Conditions

Condition	Modality	Highest Phase	Product
Dementia 27 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18666801	Palliative	Approved 8583	SERMION Approved Use Dementia (including Alzheimer's disease and vascular dementia)
Alzheimer’s disease 278 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18666801	Palliative	Approved 8583	SERMION Approved Use Dementia (including Alzheimer's disease and vascular dementia)
Vascular dementia 12 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18666801	Palliative	Approved 8583	SERMION Approved Use Dementia (including Alzheimer's disease and vascular dementia)

C_max

Value	Dose	Co-administered	Analyte	Population
34.504 ng/mL CLINICAL TRIAL https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5760819/pdf/main.pdf	30 mg single, oral dose: 30 mg route of administration: Oral experiment type: SINGLE co-administered:		NICERGOLINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN

AUC

Value	Dose	Co-administered	Analyte	Population
388.38 ng × h/mL CLINICAL TRIAL https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5760819/pdf/main.pdf	30 mg single, oral dose: 30 mg route of administration: Oral experiment type: SINGLE co-administered:		NICERGOLINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN

T_1/2

Value	Dose	Co-administered	Analyte	Population
8.427 h CLINICAL TRIAL https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5760819/pdf/main.pdf	30 mg single, oral dose: 30 mg route of administration: Oral experiment type: SINGLE co-administered:		NICERGOLINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN

Doses

Dose	Population	Adverse events
60 mg 1 times / day multiple, oral Studied dose Dose: 60 mg, 1 times / day Route: oral Route: multiple Dose: 60 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/2646350/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/2646350/	Disc. AE: Gastric pain, Hot flushes... AEs leading to discontinuation/dose reduction: Gastric pain (grade 2, 0.65%) Hot flushes (grade 2, 0.65%) Hypertensive crisis (0.65%) Confusional state (0.65%) Syncopal attack (0.65%) Sources: https://pubmed.ncbi.nlm.nih.gov/2646350/

AEs

AE	Significance	Dose	Population
Confusional state	0.65% Disc. AE	60 mg 1 times / day multiple, oral Studied dose Dose: 60 mg, 1 times / day Route: oral Route: multiple Dose: 60 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/2646350/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/2646350/
Hypertensive crisis	0.65% Disc. AE	60 mg 1 times / day multiple, oral Studied dose Dose: 60 mg, 1 times / day Route: oral Route: multiple Dose: 60 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/2646350/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/2646350/
Syncopal attack	0.65% Disc. AE	60 mg 1 times / day multiple, oral Studied dose Dose: 60 mg, 1 times / day Route: oral Route: multiple Dose: 60 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/2646350/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/2646350/
Gastric pain	grade 2, 0.65% Disc. AE	60 mg 1 times / day multiple, oral Studied dose Dose: 60 mg, 1 times / day Route: oral Route: multiple Dose: 60 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/2646350/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/2646350/
Hot flushes	grade 2, 0.65% Disc. AE	60 mg 1 times / day multiple, oral Studied dose Dose: 60 mg, 1 times / day Route: oral Route: multiple Dose: 60 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/2646350/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/2646350/

PubMed

Title	Date	PubMed
DDT-induced myoclonus: serotonin and alpha noradrenergic interaction.	1979 Feb	37558
[Haemodynamic and metabolic effects of exercise test in diabetic patients with arteritis treated or not with nicergoline (author's transl)].	1981 Sep 18-25	6270809
Systemic and carotid haemodynamics and plasma renin activity during deliberate hypotension in dogs: a comparison of sodium nitroprusside with nicergoline.	1984 Mar	6399253
[Neurotransmitter mechanism of the tropoxin effect in comparison with other antimigraine preparations].	2003 May-Jun	12924226
Sudden hearing loss as a first complication of long-standing Type 1 diabetes mellitus: a case report.	2004 Jan	14706062
[A case of pseudotumorous course of brain demyelinating disease].	2005	15822744
Progress update: Pharmacological treatment of Alzheimer's disease.	2007	19300586
Donepezil in Alzheimer's disease: From conventional trials to pharmacogenetics.	2007 Jun	19300564
Therapeutic use of nicergoline.	2008	18666801
Second-derivative synchronous fluorescence spectroscopy for the simultaneous determination of cinnarizine and nicergoline in pharmaceutical preparations.	2008 Mar-Apr	18476347
Smart stability-indicating spectrophotometric methods for determination of binary mixtures without prior separation.	2008 Mar-Apr	18476341
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	18565728
Natural non-trasgenic animal models for research in Alzheimer's disease.	2009 Apr	19355852
Effects of nicergoline on corneal epithelial wound healing in rat eyes.	2009 Feb	18836171
Sertraline-induced rhabdomyolysis in an elderly patient with dementia and comorbidities.	2009 Jul	19567656

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

In Vitro Use Guide

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 `Mon Mar 31 21:40:46 GMT 2025` Edited by `admin` on `Mon Mar 31 21:40:46 GMT 2025`
Record UNII	J7P36Z4900
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ERGOLINE-8-METHANOL, 10-METHOXY-1,6-DIMETHYL-, 5-BROMO-3-PYRIDINECARBOXYLATE (ESTER), (8.BETA.)-, (2R,3R)-2,3-DIHYDROXYBUTANEDIOATE (SALT)

Preferred Name

English

NICERGOLINE TARTRATE

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

Code System Code Type Description

CAS

32222-75-6