NICERGOLINE

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

Structure Search

SMILES

CO[C@]12C[C@@H](COC(=O)C3=CN=CC(Br)=C3)CN(C)[C@@H]1CC4=CN(C)C5=C4C2=CC=C5

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

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

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
Colloid formation by drugs in simulated intestinal fluid.	2010-05-27	20426472
A systematic review of clinical trials of pharmacological interventions for acute ischaemic stroke (1955-2008) that were completed, but not published in full.	2010-04-22	20412562
[Glaucoma--neurodegenerative disease].	2010-03-03	20191885
Norepinephrine enhances the LPS-induced expression of COX-2 and secretion of PGE2 in primary rat microglia.	2010-01-11	20064241
Nicergoline increases serum substance P levels in patients with an ischaemic stroke.	2010-01	20029189
[Therapeutic potential and possibilities of using of sermion (nicergoline) in neurological practice].	2010	21434467
Sertraline-induced rhabdomyolysis in an elderly patient with dementia and comorbidities.	2009-07	19567656
Natural non-trasgenic animal models for research in Alzheimer's disease.	2009-04	19355852
Effects of nicergoline on corneal epithelial wound healing in rat eyes.	2009-02	18836171
Vascular cognitive impairment.	2009-01	21416020
Second-derivative synchronous fluorescence spectroscopy for the simultaneous determination of cinnarizine and nicergoline in pharmaceutical preparations.	2008-05-15	18476347
Smart stability-indicating spectrophotometric methods for determination of binary mixtures without prior separation.	2008-05-15	18476341
Disruption of GM2/GD2 synthase gene resulted in overt expression of 9-O-acetyl GD3 irrespective of Tis21.	2008-05	18194438
[Influence of arterial hypertension on the clinical course of Parkinson's disease (PD) among middle-aged patients].	2008-04-18	18416166
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.	2008-03-06	18565728
Method development and validation for the simultaneous determination of cinnarizine and co-formulated drugs in pharmaceutical preparations by capillary electrophoresis.	2008-02-13	18164891
Therapeutic use of nicergoline.	2008	18666801
Donepezil in Alzheimer's disease: From conventional trials to pharmacogenetics.	2007-06	19300564
Progress update: Pharmacological treatment of Alzheimer's disease.	2007	19300586
Vascular dementia: pharmacological treatment approaches and perspectives.	2007	18044183
Treating senile dementia with traditional Chinese medicine.	2007	18044136
[Treatment of thyroid ophthalmopathy--a clinical case].	2007	17605272
[Treatment by medicine which improves cerebral circulation and metabolism].	2006-11-28	17469538
Preclinical and clinical examinations of Salvia miltiorrhiza and its tanshinones in ischemic conditions.	2006-11-23	17302964
Supraspinal control of external anal sphincter motility: effects of vesical distension in humans and cats.	2006-11	17040414
[Nicergoline, ibudilast, ifenprodil tartrate].	2006-10-28	17461212
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.	2006-10-11	16766155
Protective effects of nicergoline against neuronal cell death induced by activated microglia and astrocytes.	2005-12-20	16325157
A phylogenetic survey of biliary lipids in vertebrates.	2005-10	16061950
Nicergoline, a drug used for age-dependent cognitive impairment, protects cultured neurons against beta-amyloid toxicity.	2005-06-14	15882840
Differential modulation of microglia superoxide anion and thromboxane B2 generation by the marine manzamines.	2005-03-11	15762999
[Effect of non-selective alpha-adrenergic receptor antagonist nicergoline on the activity of neurons in the ventral lateral thalamic nucleus].	2005	16201147
[A case of pseudotumorous course of brain demyelinating disease].	2005	15822744
Nicergoline reverts haloperidol-induced loss of detoxifying-enzyme activity.	2004-11-28	15556144
Treatment of vascular dementia: evidence from trials with non-cholinergic drugs.	2004-11-15	15537523
Prolongevity medicine: Antagonic-Stress drug in distress, geriatrics, and related diseases. II. Clinical review--2003.	2004-06	15247054
Nicergoline enhances glutamate uptake via glutamate transporters in rat cortical synaptosomes.	2004-06	15187425
[Nicergoline-induced Prinzmetal angina. "Heartache" instead of headache].	2004-01-04	15222138
Nicergoline in the treatment of dizziness in elderly patients. A review.	2004	15207410
[A case of parkinsonism induced by an oral contraceptive].	1992-02	1567736
[Pharmacological analysis of memory disorders of different origins].	1989-06	2571367
Effect of nicergoline on learning and memory.	1988-07	3419247
[The effects of nicergoline on the heart rate in the normotensive or spontaneously hypertensive rat. Possible participation of central alpha-1 receptors].	1986-01-01	3012204
[Nicergoline to reduce intraoperative blood pressure increases in hypertensive patients].	1985-11	4092160
Centrally mediated cardiovascular effects of nicergoline in the dog compared to those of clonidine.	1985-10-29	4085539
[Plasma renin activity and prostaglandin E2 in hypotension induced by nicergoline].	1985	3893236
Systemic and carotid haemodynamics and plasma renin activity during deliberate hypotension in dogs: a comparison of sodium nitroprusside with nicergoline.	1984-03	6399253
[Haemodynamic and metabolic effects of exercise test in diabetic patients with arteritis treated or not with nicergoline (author's transl)].	1981-09-18	6270809
Effects of nicergoline on the cardiovascular system of dogs and rats.	1981-07-01	6167799
DDT-induced myoclonus: serotonin and alpha noradrenergic interaction.	1979-02	37558

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 `Wed Apr 02 07:04:55 GMT 2025` Edited by `admin` on `Wed Apr 02 07:04:55 GMT 2025`
Record UNII	JCV8365FWN
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

NICERGOLINE

Official Name

English

SERMION

Preferred Name

English

VASOSPAN

Brand Name

English

NSC-150531

Code

English

CERGODUM

Brand Name

English

Nicergoline [WHO-DD]

Common Name

English

nicergoline [INN]

Common Name

English

NICERGOLINE [MART.]

Common Name

English

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

Common Name

English

DURACEBROL

Brand Name

English

ERGOBEL

Brand Name

English

NICERGOLINE [JAN]

Common Name

English

MEMOQ

Brand Name

English

ERGOTOP

Brand Name

English

NICERGOLINE [MI]

Common Name

English

FI-6714

Code

English

NICERGOLINE [EP MONOGRAPH]

Common Name

English

10-Methoxy-1,6-dimethylergoline-8?-methanol 5-bromonicotinate (ester)

Common Name

English

NILOGRIN

Brand Name

English

CIRCO-MAREN

Brand Name

English

DILASENIL

Brand Name

English

NICERGOLENT

Brand Name

English

NICERGOLINE [USAN]

Common Name

English

Classification Tree Code System Code

WHO-ATC

C04AE02