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
Structure for Nicergoline (DB00699)
- 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 ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Associated Conditions
Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Symptomatic treatment of Stroke, ischemic •••••••••••• ••••••• •••• •••••• Symptomatic treatment of Transient ischemic attack (tia) •••••••••••• ••••••• •••• •••••• - Associated Therapies
- Contraindications & Blackbox Warnings
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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.
Target Actions Organism AAlpha-1A adrenergic receptor antagonistHumans - Absorption
Not Available
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
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- Route of elimination
Not Available
- Half-life
Not Available
- Clearance
Not Available
- Adverse Effects
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Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
- Not Available
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
- 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.
Drug Interaction Integrate drug-drug
interactions in your softwareAbatacept The metabolism of Nicergoline can be increased when combined with Abatacept. Abiraterone The metabolism of Nicergoline can be decreased when combined with Abiraterone. Acebutolol Acebutolol may increase the vasoconstricting activities of Nicergoline. Aceclofenac The risk or severity of hypertension can be increased when Nicergoline is combined with Aceclofenac. Acemetacin The risk or severity of hypertension can be increased when Nicergoline is combined with Acemetacin. - Food Interactions
- Not Available
Products
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- Sermion
Categories
- ATC Codes
- C04AE02 — Nicergoline
- Drug Categories
- Adrenergic Agents
- Adrenergic alpha-1 Receptor Antagonists
- Adrenergic alpha-Antagonists
- Adrenergic Antagonists
- Agents that produce hypertension
- Alkaloids
- Cardiovascular Agents
- Central Nervous System Agents
- Cytochrome P-450 CYP2D6 Substrates
- Cytochrome P-450 Substrates
- Ergolines
- Ergot Alkaloids and Derivatives
- Heterocyclic Compounds, Fused-Ring
- Neurotransmitter Agents
- Nootropic Agents
- Peripheral Vasodilators
- Vasodilating Agents
- 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
- 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]
- External Links
- Human Metabolome Database
- HMDB0014837
- KEGG Drug
- D01290
- PubChem Compound
- 34040
- PubChem Substance
- 46508741
- ChemSpider
- 31373
- 7398
- ChEBI
- 31902
- ChEMBL
- CHEMBL1372950
- ZINC
- ZINC000003873817
- Therapeutic Targets Database
- DAP000902
- PharmGKB
- PA164743014
- Wikipedia
- Nicergoline
Clinical Trials
- Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count 3 Not Yet Recruiting Treatment Dysphagia 1 3 Terminated Treatment Anxiety Disorders / Dementia / Depression / Psychosomatic Disorders / Schizophrenia 1 1 Completed Other Pharmacokinetics 1 Not Available Completed Not Available Alzheimer's Disease (AD) / Dementia / Vascular Dementia (VaD) 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Capsule Tablet, film coated Oral 10 MG Powder, for solution Oral Solution / drops Oral Tablet, effervescent Tablet Oral 30 MG Tablet, soluble Injection, powder, for solution Powder, for solution Oral 10 MG/ML Tablet Oral 10.000 mg Tablet, coated Oral 5 MG Tablet, film coated Oral Tablet, soluble 30 MG Tablet, coated Oral 10 mg Tablet, coated Oral 30 mg Tablet, sugar coated Oral Tablet, sugar coated Oral 10 mg Tablet, film coated Oral 30 mg - 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 0.0127 mg/mL ALOGPS logP 3.99 ALOGPS logP 3.7 Chemaxon logS -4.6 ALOGPS pKa (Strongest Basic) 8.12 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 4 Chemaxon Hydrogen Donor Count 0 Chemaxon Polar Surface Area 56.59 Å2 Chemaxon Rotatable Bond Count 5 Chemaxon Refractivity 123.3 m3·mol-1 Chemaxon Polarizability 48.08 Å3 Chemaxon Number of Rings 5 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9908 Blood Brain Barrier + 0.9396 Caco-2 permeable + 0.5782 P-glycoprotein substrate Substrate 0.7569 P-glycoprotein inhibitor I Inhibitor 0.8563 P-glycoprotein inhibitor II Inhibitor 0.9233 Renal organic cation transporter Inhibitor 0.5733 CYP450 2C9 substrate Non-substrate 0.8512 CYP450 2D6 substrate Non-substrate 0.7141 CYP450 3A4 substrate Substrate 0.6869 CYP450 1A2 substrate Inhibitor 0.9107 CYP450 2C9 inhibitor Non-inhibitor 0.9072 CYP450 2D6 inhibitor Inhibitor 0.8932 CYP450 2C19 inhibitor Inhibitor 0.8994 CYP450 3A4 inhibitor Non-inhibitor 0.8126 CYP450 inhibitory promiscuity High CYP Inhibitory Promiscuity 0.5988 Ames test Non AMES toxic 0.7004 Carcinogenicity Non-carcinogens 0.9091 Biodegradation Not ready biodegradable 1.0 Rat acute toxicity 2.6401 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.914 hERG inhibition (predictor II) Inhibitor 0.5933
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS splash10-01oy-0490000000-9946900f54448caef05c Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-0ue9-0020900000-5ceafbec4ed6eb8a5d44 Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-001i-0000900000-8814d0f9bb97aa3b8a78 Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-0f89-0000900000-88442dbd903a48761b61 Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-004i-9010400000-2374a1397180765c1d20 Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-001i-0592300000-b2b83c30b0f3bef9cc33 Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-056r-9513500000-3edf86370267b2655fe8 Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 207.0600016 predictedDarkChem Lite v0.1.0 [M-H]- 196.02808 predictedDeepCCS 1.0 (2019) [M+H]+ 207.6140016 predictedDarkChem Lite v0.1.0 [M+H]+ 198.42363 predictedDeepCCS 1.0 (2019) [M+Na]+ 207.2365016 predictedDarkChem Lite v0.1.0 [M+Na]+ 204.33617 predictedDeepCCS 1.0 (2019)
Targets
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- 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
- 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
- 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]
- 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