Rivastigmine

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Structural formula
Structural formula of rivastigmine
General
Non-proprietary name Rivastigmine
other names

( S ) - {3- [α- (Dimethylamino) ethyl] phenyl} - N -ethyl- N -methylcarbamate ( IUPAC )

Molecular formula
  • C 14 H 22 N 2 O 2 (rivastigmine)
  • C 14 H 22 N 2 O 2 · C 4 H 6 O 6 [rivastigmine · hydrogen tartrate]
External identifiers / databases
CAS number
  • 123441-03-2 (rivastigmine)
  • 129101-54-8 [rivastigmine hydrogen (2 R , 3 R ) tartrate]
PubChem 77991
DrugBank DB00989
Wikidata Q411887
Drug information
ATC code

N06 DA03

Drug class
properties
Molar mass 250.34 g · mol -1
Physical state

firmly

Melting point

123-125 ° C [rivastigmine hydrogen (2 R , 3 R ) tartrate]

boiling point

viscous liquid at room temperature [rivastigmine base]

safety instructions
Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed
GHS hazard labeling
no classification available
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Rivastigmine is used as a medicinal substance for the symptomatic treatment of mild to moderate Alzheimer's disease . It is the only antidementia drug that is also approved for the treatment of Parkinson's disease. Rivastigmine can be administered orally (hard capsule, solution) and transdermally as a patch.

Pharmacotherapeutically, the active ingredient belongs to the group of cholinesterase inhibitors . Rivastigmine inhibits acetylcholinesterase and butyrylcholinesterase . The purpose of this inhibition is to reduce the lack of acetylcholine that occurs in Alzheimer's dementia. By inhibiting the degrading enzymes (acetyl and butyrylcholinesterase), the degradation of acetylcholine is reduced and the messenger substance is still available. For this reason, rivastigmine can favorably influence the cholinergically mediated cognitive deficits that occur in Alzheimer's disease and improve the symptoms.

Studies have shown a small but significant effect of rivastigmine on cognitive function and quality of life. However, side effects such as nausea , vomiting , diarrhea , anorexia , headache and syncope lead to high treatment discontinuation rates (9% higher than with placebo ).

With the galenic preparation form as a plaster (TTS), a constant release of the active ingredient and thus a constant effective level is achieved. This enables better tolerance than with tablets or solutions. The authorization of the plaster cast is based on the IDEAL study ( I nvestigation of trans D ermal E Xelon in AL zheimer's Disease) with 195 patients. The results of this study showed that daily use of a patch (9.5 mg / day) improved cognitive skills and everyday skills just as much as the highest approved capsule dose (2 × 6 mg / day). Otherwise frequently observed side effects such as nausea and vomiting occurred three times less often when using the patch than after taking the capsules. The frequency of side effects was no higher than with a placebo preparation (preparation without active ingredient). But there are also studies that show that acetylcholinesterase inhibitors have little effect. In contrast to the other antidementia drugs donepezil and galantamine, rivastigmine is not metabolized in a cytochrome P450-dependent manner, which is why fewer drug interactions are to be expected.

Trade names

  • Novartis : Exelon (D, A, CH), Protemax (I, E, P etc.)
  • Nimvastid (D, A), other generics

Web links

Individual evidence

  1. ^ The Merck Index . An Encyclopaedia of Chemicals, Drugs and Biologicals . 14th edition, 2006, pp. 1422-1423, ISBN 978-0-911910-00-1 .
  2. PHARMEUROPA 23.2 The European Pharmacopoeia Forum. 23.2, April 2011, pp. 376-379.
  3. This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.
  4. Birks J: Cholinesterase inhibitors for Alzheimer's disease . In: Cochrane Database Syst Rev . No. 1, 2006, p. CD005593. doi : 10.1002 / 14651858.CD005593 . PMID 16437532 .
  5. Lanctôt KL, Herrmann N, Yau KK, et al. : Efficacy and safety of cholinesterase inhibitors in Alzheimer's disease: a meta-analysis . In: CMAJ . 169, No. 6, September 2003, pp. 557-564. PMID 12975222 . PMC 191283 (free full text).
  6. ^ B. Winblad et al .: A six-month double-blind, randomized, placebo-controlled study of a transdermal patch in Alzheimer's disease - rivastigmine patch versus capsule . Int J Geriatric Psychiatry. 2007, 22 (5), 456-467, PMID 17380489 .
  7. Kaduszkiewicz H, Zimmermann T, Beck-Bornholdt HP, Hendrik van den Bussche : Cholinesterase inhibitors for patients with Alzheimer's disease: systematic review of randomized clinical trials . In: BMJ (Clinical Research Ed.) . 331, No. 7512, August 2005, pp. 321-327. PMID 16081444 . PMC 1183129 (free full text).