Structure via PubChem · Public domain (PubChem)
Nisergolin
Sign in to saveAlso known as (8beta)-10-methoxy-1,6-dimethylergoline-8-methanol 5-bromo-3-pyridinecarboxylate (ester), 10-methoxy-1,6-dimethylergoline-8beta-methanol 5-bromonicotinate
Nicergoline, sold under the brand name Sermion among others, is an ergot derivative used to treat senile dementia and other disorders with vascular origins. Internationally it has been used for frontotemporal dementia as well as early onset in Lewy body dementia and Parkinson's dementia. It decreases vascular resistance and increases arterial blood flow in the brain, improving the utilization of oxygen and glucose by brain cells. It has similar vasoactive properties in other areas of the body, particularly the lungs. Unlike many other ergolines, such as ergotamine, nicergoline is not associate
Key facts
- Drug.Verifiedfields
- changed
- Drug.verifiedrevid
- 462260029
- Drug.IUPAC_name
- [(6aR,9R,10aS)-10a-methoxy-4,7-dimethyl-6a,8,9,10-tetrahydro-6H-indolo[4,3-fg]quinolin-9-yl]methyl 5-bromopyridine-3-carboxylate
- Drug.image
- Nicergoline Structure V.1.svg
- Drug.image_class
- skin-invert-image
- Drug.width
- 200px
- Drug.tradename
- Sermion
- Drug.pregnancy_category
- Not recommended
- Drug.routes_of_administration
- By mouth, intramuscular, intravenous
- Drug.ATC_prefix
- C04
- Drug.ATC_suffix
- AE02
- Drug.legal_EU
- Rx-only
- Drug.bioavailability
- <5%
- Drug.protein_bound
- >90%
- Drug.metabolism
- Extensive First-pass metabolism
- Drug.elimination_half life
- 13–20 hours
- Drug.CAS_number
- 27848-84-6
- Drug.PubChem
- 34040
via Wikipedia infobox
Chemical data
- Formula
- C24H26BrN3O3
- Molecular weight
- 484.4 g/mol
- IUPAC name
- [(6aR,9R,10aS)-10a-methoxy-4,7-dimethyl-6a,8,9,10-tetrahydro-6H-indolo[4,3-fg]quinolin-9-yl]methyl 5-bromopyridine-3-carboxylate
- SMILES
- CN1C[C@@H](C[C@]2([C@H]1CC3=CN(C4=CC=CC2=C34)C)OC)COC(=O)C5=CC(=CN=C5)Br
- InChIKey
- YSEXMKHXIOCEJA-FVFQAYNVSA-N
- XLogP
- 3.2
- Polar surface area
- 56.6 Ų
- H-bond donors
- 0
- H-bond acceptors
- 5
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Approved
- Molecule type
- Small molecule
- Indications
- cardiovascular disease, anxiety, Dementia, depressive disorder
via ChEMBL · EBI
Research
478 papers- Therapeutic use of nicergoline.Clinical drug investigation · 2008
- Ergotamine and nicergoline - facts and myths.Pharmacological reports : PR · 2015
- Safety of nicergoline as an agent for management of cognitive function disorders.BioMed research international · 2014
- Apoptosis in Alzheimer's disease: insight into the signaling pathways and therapeutic avenues.Apoptosis : an international journal on programmed cell death · 2023
- Neurotrophic keratopathy: current challenges and future prospects.Annals of medicine · 2022
via PubMed
Wikidata facts
- Mass
- 483.115754
- Has use
- medication
Show 4 more facts
- subject has role
- vasodilator agent
- chemical formula
- C₂₄H₂₆BrN₃O₃
- canonical SMILES
- CN1CC(CC2(C1CC3=CN(C4=CC=CC2=C34)C)OC)COC(=O)C5=CC(=CN=C5)Br
- isomeric SMILES
- CN1C[C@@H](C[C@]2([C@H]1CC3=CN(C4=CC=CC2=C34)C)OC)COC(=O)C5=CC(=CN=C5)Br
Sources (2)
via Wikidata · CC0