Banner
targets (1) enzymes (1)
for drugs
Identification
Name Nicergoline
Accession Number DB00699 (APRD00617)
Type small molecule
Groups approved
Description

An ergot derivative that has been used as a cerebral vasodilator and in peripheral vascular disease. It has been suggested to ameliorate cognitive deficits in cerebrovascular disease. [PubChem]
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms Not Available
Salts Not Available
Brand names
Name Company
MNE
Nargoline
Nicergolin [German]
Nicergolina [Dcit]
Nicergoline [Usan:Ban:Inn:Jan]
Nicergolinum [INN-Latin]
Nicotergoline
Nimergoline
Nimergoline Base
Sermion
Brand mixtures Not Available
Categories
  • Vasodilator Agents
  • Adrenergic alpha-Antagonists
  • Nootropic Agents
CAS number 27848-84-6
Weight Average: 484.386
Monoisotopic: 483.11575436
Chemical Formula C24H26BrN3O3
InChI Key InChIKey=YSEXMKHXIOCEJA-FVFQAYNVSA-N
InChI
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
Plain Text
IUPAC Name
[(2S,4R,7R)-2-methoxy-6,11-dimethyl-6,11-diazatetracyclo[7.6.1.0^{2,7}.0^{12,16}]hexadeca-1(16),9,12,14-tetraen-4-yl]methyl 5-bromopyridine-3-carboxylate
SMILES
[H][C@@]12CC3=CN(C)C4=CC=CC(=C34)[C@]1(C[C@@H](COC(=O)C1=CC(Br)=CN=C1)CN2C)OC
Plain Text
Mass Spec Not Available
Taxonomy
Kingdom Organic
Classes
  • Ergolines
  • Indoloquinolines
Substructures
  • Carboxylic Acids and Derivatives
  • Benzyl Alcohols and Derivatives
  • Acetates
  • Indoles and Indole Derivatives
  • Pyrroles
  • Pyridines and Derivatives
  • Ethers
  • Benzene and Derivatives
  • Phenylpiperidines
  • Ergolines
  • Aliphatic and Aryl Amines
  • Aryl Halides
  • Phenethylamines
  • Heterocyclic compounds
  • Aromatic compounds
  • Tryptamines and Derivatives
  • Amphetamines
  • Piperidines
  • Indoloquinolines
Pharmacology
Indication For the treatment of senile dementia, migraines of vascular origin, transient ischemia, platelet hyper-aggregability, and macular degeneration.
Pharmacodynamics Nicergoline is a potent vasodilator (improves brain blood flow). On the cerebral level it prompts a lowering of vascular resistance, an increase in arterial flow and stimulates the use of oxygen and glucose. Nicergoline also improves blood circulation in the lungs and limbs and has been shown to inhibit blood platelet aggregation.
Mechanism of action Nicergoline acts by inhibiting the postsynaptic alpha(1)-adrenoceptors on vascular smooth muscle. This inhibits the vasoconstrictor effect of circulating and locally released catecholamines (epinephrine and norepinephrine), resulting in peripheral vasodilation. Therefore the mechanism of Nicergoline is to increase vascular circulation in the brain, thereby enhancing the transmission of nerve signals across the nerve fibres, which secrete acetylcholine as a neural transmitter.
Absorption Not Available
Volume of distribution Not Available
Protein binding Not Available
Metabolism Not Available
Route of elimination Not Available
Half life Not Available
Clearance Not Available
Toxicity Not Available
Affected organisms
  • Humans and other mammals
Pathways Not Available
Pharmacoeconomics
Manufacturers Not Available
Packagers Not Available
Dosage forms Not Available
Prices Not Available
Patents Not Available
Properties
State solid
Experimental Properties
Property Value Source
logP 3.3 Not Available
Predicted Properties
Property Value Source
water solubility 1.27e-02 g/l ALOGPS
logP 3.99 ALOGPS
logP 3.7 ChemAxon
logS -4.6 ALOGPS
pKa (strongest basic) 8.14 ChemAxon
physiological charge 1 ChemAxon
hydrogen acceptor count 4 ChemAxon
hydrogen donor count 0 ChemAxon
polar surface area 56.59 ChemAxon
rotatable bond count 5 ChemAxon
refractivity 123.3 ChemAxon
polarizability 48.08 ChemAxon
References
Synthesis Reference Not Available
General Reference
  1. Winblad B, Fioravanti M, Dolezal T, Logina I, Milanov IG, Popescu DC, Solomon A: Therapeutic use of nicergoline. Clin Drug Investig. 2008;28(9):533-52. Pubmed 18666801
External Links
Resource Link
KEGG Drug D01290 Link_out
PubChem Compound 34040 Link_out
PubChem Substance 46508741 Link_out
ChemSpider 31373 Link_out
Therapeutic Targets Database DAP000902 Link_out
PharmGKB PA164743014 Link_out
Wikipedia http://en.wikipedia.org/wiki/Nicergoline Link_out
ATC Codes
  • C04AE02
AHFS Codes Not Available
PDB Entries Not Available
FDA label Not Available
MSDS Not Available
Interactions
Drug Interactions Not Available
Food Interactions Not Available
Targets

1. Alpha-1A adrenergic receptor

Pharmacological action: yes
Actions: agonist

This alpha-adrenergic receptor mediates its action by association with G proteins that activate a phosphatidylinositol- calcium second messenger system. Its effect is mediated by G(q) and G(11) proteins

Organism class: human
UniProt ID: P35348 Link_out
Gene: ADRA1A Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Alvarez-Guerra M, Bertholom N, Garay RP: Selective blockade by nicergoline of vascular responses elicited by stimulation of alpha 1A-adrenoceptor subtype in the rat. Fundam Clin Pharmacol. 1999;13(1):50-8. Pubmed
Enzymes

1. Cytochrome P450 2D6

Actions: substrate

Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic antidepressants

UniProt ID: P10635 Link_out
Gene: CYP2D6 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed
Comments
Drug created on June 13, 2005 07:24 / Updated on February 08, 2013 16:19