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Nicergoline

From Wikipedia, the free encyclopedia
Chemical compound

Pharmaceutical compound
Nicergoline
Clinical data
Trade namesSermion
Other names[(8β)-10-Methoxy-1,6-dimethylergolin-8-yl]methyl 5-bromopyridine-3-carboxylate
AHFS/Drugs.comInternational Drug Names
Pregnancy
category
  • Not recommended
Routes of
administration		By mouth,intramuscular,intravenous
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability<5%
Protein binding>90%
MetabolismExtensiveFirst-pass metabolism
Eliminationhalf-life13–20 hours
Identifiers
  • [(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
CAS Number
PubChemCID
DrugBank
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard(EPA)
ECHA InfoCard100.044.252Edit this at Wikidata
Chemical and physical data
FormulaC24H26BrN3O3
Molar mass484.394 g·mol−1
3D model (JSmol)
  • Brc1cc(cnc1)C(=O)OC[C@@H]3C[C@]4(OC)c5cccc2c5c(cn2C)C[C@H]4N(C3)C
  • 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 checkY
  • Key:YSEXMKHXIOCEJA-FVFQAYNVSA-N checkY
 ☒NcheckY (what is this?)  (verify)

Nicergoline, sold under the brand nameSermion among others, is anergotderivative used to treatsenile dementia and other disorders withvascular origins. Internationally it has been used forfrontotemporal dementia as well as early onset inLewy body dementia andParkinson's dementia. It decreasesvascular 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 otherergolines, such asergotamine, nicergoline is not associated withcardiac fibrosis.[2]

It is used for vascular disorders such as cerebralthrombosis andatherosclerosis, arterial blockages in the limbs,Raynaud's disease, vascularmigraines, andretinopathy.

Nicergoline has been registered in over fifty countries and has been used for more than three decades for the treatment of cognitive, affective, and behavioral disorders of older people.[3]

Medical uses

[edit]

Nicergoline is used in the following cases:

  • Acute and chronic cerebral metabolic-vascular disorders (cerebral arteriosclerosis,thrombosis andcerebral embolism, transitory cerebral ischaemia). Acute and chronic peripheral metabolic-vascular disorders (organic and functional arteriopathies of the limbs),Raynaud's disease and other syndromes caused by altered peripheral irrigation.
  • Migraines of vascular origin
  • Coadjutant therapy in clinical situations accompanied by platelet hyper-aggregability, arterial tension.
  • Corio-retinal vascular disorders: diabetic retinopathy,macular degeneration and retinal angiosclerosis
  • Oto-vestibular problems of a vascular nature: dizziness, auditory hallucinations,hypoacusis.

Dosages for known conditions are usually administered at 5–10 mg three times a day, however anti-aging preventative purposes may want to consider 5 mg once or twice a day more adequate.[4]

Contraindications

[edit]

Persons suffering from acute bleeding,myocardial infarction (heart conditions), hypertension,bradycardia or using alpha or beta receptor agonists should consult with their physician before use.Although toxicology studies have not shown nicergoline to have anyteratogenic effect, the use of this medicine during pregnancy should be limited to those cases where it is absolutely necessary.

On 28 June 2013, theEuropean Medicines Agency recommended restricting the use of medicines containing ergot derivatives, including nicergoline. They stated that "these medicines should no longer be used to treat several conditions involving blood circulation problems or problems with memory and sensation, or to prevent migraine headaches, since the risks are greater than the benefits in these indications. This is based on a review of data showing an increased risk of fibrosis (formation of excess connective tissue that can damage organs and body structures) and ergotism (symptoms of ergot poisoning, such as spasms and obstructed blood circulation) with these medicines."[5] However, only a subset ofergolines are associated with fibrosis and evidence suggests that nicergoline does not carry the same fibrotic risk like other ergoline derivatives such asergotamine.[2]

Nicergoline is considered unsafe inporphyria.[6]

Side effects

[edit]

The side effects of nicergoline are usually limited to nausea, hot flushes, mild gastric upset, hypotension and dizziness.[6] At high drug dosages, bradycardia, increased appetite, agitation, diarrhea and perspiration were reported. Most of the available literature suggests that the side effects of nicergoline are mild and transient.[2]

Interactions

[edit]

Nicergoline is known to enhance the cardiac depressive effects ofpropranolol.[6] At high dosages, it is advisable to seek one's physician's guidance if combining with potentvasodilators such asbromocriptine,Ginkgo biloba,picamilon,vinpocetine orxantinol nicotinate.

Pharmacology

[edit]

Pharmacodynamics

[edit]

Nicergoline is an ergot alkaloid derivative that acts as a potent and selectiveα1A-adrenergic receptorantagonist.[7] TheIC50 of nicergolinein vitro has been reported to be 0.2 nM.[8] The primary action of nicergoline is to increase arterial blood flow by vasodilation. Furthermore, it is known that nicergoline inhibitsplatelet aggregation. Studies have shown that nicergoline also increasesnerve growth factor in the aged brain.[9][10] In addition to the α1A-adrenergic receptor, nicergoline is an antagonist of theserotonin5-HT1A receptor (IC50 = 6 nM) and shows moderateaffinity for serotonin5-HT2 andα2-adrenergic receptors and low affinity for thedopamineD1 andD2 andmuscarinic acetylcholineM1 andM2 receptors.[2] The majormetabolites of nicergoline, MMDL and MDL, show low or no affinity foradrenergic,serotonin,dopamine, oracetylcholine receptors.[2]

Society and culture

[edit]

Generic names

[edit]

Nicergoline is thegeneric name of the drug and itsINNTooltip International Nonproprietary Name,USANTooltip United States Adopted Name,BANTooltip British Approved Name, andDCFTooltip Dénomination Commune Française.[11][12]

Brand names

[edit]

In some countries, Sermion is marketed byViatris after Upjohn was spun off from Pfizer.[13][14]

References

[edit]
  1. ^"List of nationally authorised medicinal products"(PDF).Archived(PDF) from the original on 11 July 2024. Retrieved11 July 2024.
  2. ^abcdeZajdel P, Bednarski M, Sapa J, Nowak G (April 2015). "Ergotamine and nicergoline - facts and myths".Pharmacological Reports.67 (2):360–363.doi:10.1016/j.pharep.2014.10.010.PMID 25712664.S2CID 22768662.
  3. ^Fioravanti M, Flicker L (2001)."Efficacy of nicergoline in dementia and other age associated forms of cognitive impairment".The Cochrane Database of Systematic Reviews.2001 (4) CD003159.doi:10.1002/14651858.CD003159.PMC 7025776.PMID 11687175.
  4. ^Nicergoline drug insert, Pharmacia & Upjohn, October 2000
  5. ^European Medicines Agency (28 June 2013), "New restrictions on use of medicines containing ergot derivatives",Press Release, archived fromthe original on 10 September 2018, retrieved18 December 2013
  6. ^abcSweetman SC, ed. (2009). "Supplementary drugs and other substances".Martindale: It should be considered as last option in temporal impediments and build up of Lewy Bodies and obstructions contributed to "dementia" The complete drug reference (36th ed.). London: Pharmaceutical Press. p. 2352.ISBN 978-0-85369-840-1.
  7. ^Alvarez-Guerra M, Bertholom N, Garay RP (1999). "Selective blockade by nicergoline of vascular responses elicited by stimulation of alpha 1A-adrenoceptor subtype in the rat".Fundamental & Clinical Pharmacology.13 (1):50–58.doi:10.1111/j.1472-8206.1999.tb00320.x.PMID 10027088.S2CID 43871763.
  8. ^Moretti A, Carfagna N, Caccia C, Carpentieri M (1988). "Effect of ergolines on neurotransmitter systems in the rat brain".Archives Internationales de Pharmacodynamie et de Therapie.294:33–45.PMID 2906797.
  9. ^Nishio T, Sunohara N, Furukawa S, Akiguchi I, Kudo Y (March 1998)."Repeated injections of nicergoline increase the nerve growth factor level in the aged rat brain".Japanese Journal of Pharmacology.76 (3):321–323.doi:10.1254/jjp.76.321.PMID 9593228.
  10. ^Mizuno T, Kuno R, Nitta A, Nabeshima T, Zhang G, Kawanokuchi J, et al. (December 2005). "Protective effects of nicergoline against neuronal cell death induced by activated microglia and astrocytes".Brain Research.1066 (1–2):78–85.doi:10.1016/j.brainres.2005.10.050.PMID 16325157.S2CID 34963522.{{cite journal}}: CS1 maint: overridden setting (link)
  11. ^J. Elks (14 November 2014).The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 864–.ISBN 978-1-4757-2085-3.
  12. ^Index Nominum 2000: International Drug Directory. Taylor & Francis. 2000. pp. 727–.ISBN 978-3-88763-075-1.Archived from the original on 15 April 2021. Retrieved15 April 2021.
  13. ^"Pfizer Completes Transaction to Combine Its Upjohn Business with Mylan". Pfizer. 16 November 2020. Retrieved17 June 2024 – via Business Wire.
  14. ^"Brands".Viatris. 16 November 2020.Archived from the original on 17 June 2024. Retrieved17 June 2024.
Phenylethanolamine derivatives
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