Nicergoline

Identification

Summary

Nicergoline is an ergot derivative use for the treatment of symptoms associated with cerebrovascular abnormalities.

Generic Name
Nicergoline
DrugBank Accession Number
DB00699
Background

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.

Type
Small Molecule
Groups
Approved, Investigational
Structure
Weight
Average: 484.386
Monoisotopic: 483.11575436
Chemical Formula
C24H26BrN3O3
Synonyms
  • (8β)-10-methoxy-1,6-dimethylergoline-8-methanol 5-bromo-3-pyridinecarboxylate (ester)
  • 10-methoxy-1,6-dimethylergoline-8β-methanol 5-bromonicotinate
  • Nicergolin
  • Nicergolina
  • Nicergoline
  • Nicergolinum
External IDs
  • FI-6714

Pharmacology

Indication

For the treatment of senile dementia, migraines of vascular origin, transient ischemia, platelet hyper-aggregability, and macular degeneration.

Reduce drug development failure rates
Build, train, & validate machine-learning models
with evidence-based and structured datasets.
See how
Build, train, & validate predictive machine-learning models with structured datasets.
See how
Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Symptomatic treatment ofStroke, ischemic••••••••••••••••••• •••• ••••••
Symptomatic treatment ofTransient ischemic attack (tia)••••••••••••••••••• •••• ••••••
Associated Therapies
Contraindications & Blackbox Warnings
Prevent Adverse Drug Events Today
Tap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.
Learn more
Avoid life-threatening adverse drug events with our Clinical API
Learn more
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.

TargetActionsOrganism
AAlpha-1A adrenergic receptor
antagonist
Humans
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism

Hover over products below to view reaction partners

Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
Improve decision support & research outcomes
With structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!
See the data
Improve decision support & research outcomes with our structured adverse effects data.
See a data sample
Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
AbataceptThe metabolism of Nicergoline can be increased when combined with Abatacept.
AbirateroneThe metabolism of Nicergoline can be decreased when combined with Abiraterone.
AcebutololAcebutolol may increase the vasoconstricting activities of Nicergoline.
AceclofenacThe risk or severity of hypertension can be increased when Nicergoline is combined with Aceclofenac.
AcemetacinThe risk or severity of hypertension can be increased when Nicergoline is combined with Acemetacin.
Food Interactions
Not Available

Products

Drug product information from 10+ global regions
Our datasets provide approved product information including:
dosage, form, labeller, route of administration, and marketing period.
Access now
Access drug product information from over 10 global regions.
Access now
International/Other Brands
Sermion

Categories

ATC Codes
C04AE02 — Nicergoline
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as indoloquinolines. These are polycyclic aromatic compounds containing an indole fused to a quinoline.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Quinolines and derivatives
Sub Class
Indoloquinolines
Direct Parent
Indoloquinolines
Alternative Parents
Ergoline and derivatives / Benzoquinolines / Pyrroloquinolines / 3-alkylindoles / N-alkylindoles / Pyridinecarboxylic acids / Isoindoles and derivatives / Aralkylamines / Piperidines / N-methylpyrroles
show 13 more
Substituents
3-alkylindole / Alkaloid or derivatives / Amine / Amino acid or derivatives / Aralkylamine / Aromatic heteropolycyclic compound / Aryl bromide / Aryl halide / Azacycle / Benzenoid
show 32 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
JCV8365FWN
CAS number
27848-84-6
InChI Key
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
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=CN=CC(Br)=C1)CN2C)OC

References

General References
  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. [Article]
Human Metabolome Database
HMDB0014837
KEGG Drug
D01290
PubChem Compound
34040
PubChem Substance
46508741
ChemSpider
31373
RxNav
7398
ChEBI
31902
ChEMBL
CHEMBL1372950
ZINC
ZINC000003873817
Therapeutic Targets Database
DAP000902
PharmGKB
PA164743014
Wikipedia
Nicergoline

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
3Not Yet RecruitingTreatmentDysphagia1
3TerminatedTreatmentAnxiety Disorders / Dementia / Depression / Psychosomatic Disorders / Schizophrenia1
1CompletedOtherPharmacokinetics1
Not AvailableCompletedNot AvailableAlzheimer's Disease (AD) / Dementia / Vascular Dementia (VaD)1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
Capsule
Tablet, film coatedOral10 MG
Powder, for solutionOral
Solution / dropsOral
Tablet, effervescent
TabletOral30 MG
Tablet, soluble
Injection, powder, for solution
Powder, for solutionOral10 MG/ML
TabletOral10.000 mg
Tablet, coatedOral5 MG
Tablet, film coatedOral
Tablet, soluble30 MG
Tablet, coatedOral10 mg
Tablet, coatedOral30 mg
Tablet, sugar coatedOral
Tablet, sugar coatedOral10 mg
Tablet, film coatedOral30 mg
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
logP3.3Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0127 mg/mLALOGPS
logP3.99ALOGPS
logP3.7Chemaxon
logS-4.6ALOGPS
pKa (Strongest Basic)8.12Chemaxon
Physiological Charge1Chemaxon
Hydrogen Acceptor Count4Chemaxon
Hydrogen Donor Count0Chemaxon
Polar Surface Area56.59 Å2Chemaxon
Rotatable Bond Count5Chemaxon
Refractivity123.3 m3·mol-1Chemaxon
Polarizability48.08 Å3Chemaxon
Number of Rings5Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9908
Blood Brain Barrier+0.9396
Caco-2 permeable+0.5782
P-glycoprotein substrateSubstrate0.7569
P-glycoprotein inhibitor IInhibitor0.8563
P-glycoprotein inhibitor IIInhibitor0.9233
Renal organic cation transporterInhibitor0.5733
CYP450 2C9 substrateNon-substrate0.8512
CYP450 2D6 substrateNon-substrate0.7141
CYP450 3A4 substrateSubstrate0.6869
CYP450 1A2 substrateInhibitor0.9107
CYP450 2C9 inhibitorNon-inhibitor0.9072
CYP450 2D6 inhibitorInhibitor0.8932
CYP450 2C19 inhibitorInhibitor0.8994
CYP450 3A4 inhibitorNon-inhibitor0.8126
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.5988
Ames testNon AMES toxic0.7004
CarcinogenicityNon-carcinogens0.9091
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.6401 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.914
hERG inhibition (predictor II)Inhibitor0.5933
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-01oy-0490000000-9946900f54448caef05c
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0ue9-0020900000-5ceafbec4ed6eb8a5d44
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-001i-0000900000-8814d0f9bb97aa3b8a78
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0f89-0000900000-88442dbd903a48761b61
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-9010400000-2374a1397180765c1d20
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-001i-0592300000-b2b83c30b0f3bef9cc33
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-056r-9513500000-3edf86370267b2655fe8
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-207.0600016
predicted
DarkChem Lite v0.1.0
[M-H]-196.02808
predicted
DeepCCS 1.0 (2019)
[M+H]+207.6140016
predicted
DarkChem Lite v0.1.0
[M+H]+198.42363
predicted
DeepCCS 1.0 (2019)
[M+Na]+207.2365016
predicted
DarkChem Lite v0.1.0
[M+Na]+204.33617
predicted
DeepCCS 1.0 (2019)

Targets

Build, predict & validate machine-learning models
Use our structured and evidence-based datasets to unlock new
insights and accelerate drug research.
Learn more
Use our structured and evidence-based datasets to unlock new insights and accelerate drug research.
Learn more
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Antagonist
General Function
Protein heterodimerization activity
Specific Function
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) prot...
Gene Name
ADRA1A
Uniprot ID
P35348
Uniprot Name
Alpha-1A adrenergic receptor
Molecular Weight
51486.005 Da
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. [Article]

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Steroid hydroxylase activity
Specific Function
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...
Gene Name
CYP2D6
Uniprot ID
P10635
Uniprot Name
Cytochrome P450 2D6
Molecular Weight
55768.94 Da
References
  1. Bottiger Y, Dostert P, Benedetti MS, Bani M, Fiorentini F, Casati M, Poggesti I, Alm C, Alvan G, Bertilsson L: Involvement of CYP2D6 but not CYP2C19 in nicergoline metabolism in humans. Br J Clin Pharmacol. 1996 Dec;42(6):707-11. [Article]
  2. Saletu B, Garg A, Shoeb A: Safety of nicergoline as an agent for management of cognitive function disorders. Biomed Res Int. 2014;2014:610103. doi: 10.1155/2014/610103. Epub 2014 Aug 28. [Article]

Drug created at June 13, 2005 13:24 / Updated at December 02, 2023 06:54