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
Effects of nicergoline on the cardiovascular system of dogs and rats.	1981 Jul-Aug	6167799
[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
[Nicergoline to reduce intraoperative blood pressure increases in hypertensive patients].	1985 Nov	4092160
Nicergoline in the treatment of dizziness in elderly patients. A review.	2004	15207410
Neuroprotection: a realistic goal for aged brain?	2004	14977213
Sudden hearing loss as a first complication of long-standing Type 1 diabetes mellitus: a case report.	2004 Jan	14706062
Prolongevity medicine: Antagonic-Stress drug in distress, geriatrics, and related diseases. II. Clinical review--2003.	2004 Jun	15247054
Nicergoline enhances glutamate uptake via glutamate transporters in rat cortical synaptosomes.	2004 Jun	15187425
Supraspinal control of external anal sphincter motility: effects of vesical distension in humans and cats.	2006 Nov	17040414
Preclinical and clinical examinations of Salvia miltiorrhiza and its tanshinones in ischemic conditions.	2006 Nov 23	17302964
[Treatment by medicine which improves cerebral circulation and metabolism].	2006 Nov 28	17469538
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	16766155

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