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

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 of NICERGOLINE

SMILES

[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=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

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
[Sermion in the treatment of patients with neurological diseases].
2001 Aug
Effect of an alpha-blocker (Nicergoline) and of a beta-blocker (Acebutolol) on the in vitro biosynthesis of vascular extracellular matrix.
2001 May
Neuroprotection: a realistic goal for aged brain?
2004
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
Supraspinal control of external anal sphincter motility: effects of vesical distension in humans and cats.
2006 Nov
[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
Progress update: Pharmacological treatment of Alzheimer's disease.
2007
Therapeutic use of nicergoline.
2008
Second-derivative synchronous fluorescence spectroscopy for the simultaneous determination of cinnarizine and nicergoline in pharmaceutical preparations.
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
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
EP   INN   MART.   MI   USAN   WHO-DD  
INN   USAN  
Official 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
SERMION
Brand 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-8β-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
Created by admin on Sat Dec 16 16:04:19 GMT 2023 , Edited by admin on Sat Dec 16 16:04:19 GMT 2023
NCI_THESAURUS C29713
Created by admin on Sat Dec 16 16:04:19 GMT 2023 , Edited by admin on Sat Dec 16 16:04:19 GMT 2023
WHO-VATC QC04AE02
Created by admin on Sat Dec 16 16:04:19 GMT 2023 , Edited by admin on Sat Dec 16 16:04:19 GMT 2023
Code System Code Type Description
ChEMBL
CHEMBL1372950
Created by admin on Sat Dec 16 16:04:19 GMT 2023 , Edited by admin on Sat Dec 16 16:04:19 GMT 2023
PRIMARY
DRUG BANK
DB00699
Created by admin on Sat Dec 16 16:04:19 GMT 2023 , Edited by admin on Sat Dec 16 16:04:19 GMT 2023
PRIMARY
CAS
27848-84-6
Created by admin on Sat Dec 16 16:04:19 GMT 2023 , Edited by admin on Sat Dec 16 16:04:19 GMT 2023
PRIMARY
NCI_THESAURUS
C84006
Created by admin on Sat Dec 16 16:04:19 GMT 2023 , Edited by admin on Sat Dec 16 16:04:19 GMT 2023
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PUBCHEM
34040
Created by admin on Sat Dec 16 16:04:19 GMT 2023 , Edited by admin on Sat Dec 16 16:04:19 GMT 2023
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FDA UNII
JCV8365FWN
Created by admin on Sat Dec 16 16:04:19 GMT 2023 , Edited by admin on Sat Dec 16 16:04:19 GMT 2023
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DRUG CENTRAL
1910
Created by admin on Sat Dec 16 16:04:19 GMT 2023 , Edited by admin on Sat Dec 16 16:04:19 GMT 2023
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MERCK INDEX
m7851
Created by admin on Sat Dec 16 16:04:19 GMT 2023 , Edited by admin on Sat Dec 16 16:04:19 GMT 2023
PRIMARY Merck Index
NSC
150531
Created by admin on Sat Dec 16 16:04:19 GMT 2023 , Edited by admin on Sat Dec 16 16:04:19 GMT 2023
PRIMARY
EVMPD
SUB09226MIG
Created by admin on Sat Dec 16 16:04:19 GMT 2023 , Edited by admin on Sat Dec 16 16:04:19 GMT 2023
PRIMARY
RXCUI
7398
Created by admin on Sat Dec 16 16:04:19 GMT 2023 , Edited by admin on Sat Dec 16 16:04:19 GMT 2023
PRIMARY RxNorm
WIKIPEDIA
NICERGOLINE
Created by admin on Sat Dec 16 16:04:19 GMT 2023 , Edited by admin on Sat Dec 16 16:04:19 GMT 2023
PRIMARY
EPA CompTox
DTXSID7045607
Created by admin on Sat Dec 16 16:04:19 GMT 2023 , Edited by admin on Sat Dec 16 16:04:19 GMT 2023
PRIMARY
ECHA (EC/EINECS)
248-694-6
Created by admin on Sat Dec 16 16:04:19 GMT 2023 , Edited by admin on Sat Dec 16 16:04:19 GMT 2023
PRIMARY
INN
3088
Created by admin on Sat Dec 16 16:04:19 GMT 2023 , Edited by admin on Sat Dec 16 16:04:19 GMT 2023
PRIMARY
SMS_ID
100000092017
Created by admin on Sat Dec 16 16:04:19 GMT 2023 , Edited by admin on Sat Dec 16 16:04:19 GMT 2023
PRIMARY
MESH
D009530
Created by admin on Sat Dec 16 16:04:19 GMT 2023 , Edited by admin on Sat Dec 16 16:04:19 GMT 2023
PRIMARY