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Product Details:

  • CAS No: 123441-03-2
  • AHFC code: 12:04.0
  • Synonyms: (S)-3-(1-(Dimethylamino)ethyl)phenyl ethylmethylcarbamate, 3-((1S)-1-(Dimethylamino)ethyl)phenyl ethylmethylcarbamate, Carbamic acid, ethylmethyl-, 3-((1S)-1-(dimethylamino)ethyl)phenyl ester, ENA 713, ENA 713 free base, ENA-713, Exelon, Exelon Patch, m-((S)-1-(Dimethylamino)ethyl)phenyl ethylmethylcarbamate, Nimvastid, Prometax, Rivastigmine, Rivastigmine Teva, Rivastigmine transdermal system, SDZ 212-713, SDZ ENA 713, SDZ-212-713, SDZ-ENA-713, UNII-PKI06M3IW0
  • ATC Code: N06DA03
  • Chemical Formula: C14-H22-N2-O2
  • Molecular Weight: 250.34
  • Assay/Purity: Typically NLT 98%
  • DrugBank: DB00989 (APRD00321)
  • SMILES: c1c(OC(=O)N(C)CC)cc([C,,H](N(C)C)C)cc1
  • InChl: 1S/C14H22N2O2/c1-6-16(5)14(17)18-13-9-7-8-12(10-13)11(2)15(3)4/h7-11H,6H2,1-5H3/t11-/m0/s1
  • PubChem: 77991
  • IUPAC: Carbamic acid, ethylmethyl-, 3-(1-(dimethylamino)ethyl)phenyl ester, (S)-

Additional Details

Indication:
For the treatment of mild to moderate dementia associated with Parkinson's disease or of the Alzheimer's type.
Pharmacodynamics:
Rivastigmine is a parasympathomimetic and a reversible cholinesterase inhibitor. An early pathophysiological feature of Alzheimer's disease that is associated with memory loss and cognitive deficits is a deficiency of acetylcholine as a result of selective loss of cholinergic neurons in the cerebral cortex, nucleus basalis, and hippocampus. Tacrine is postulated to exert its therapeutic effect by enhancing cholinergic function. While the precise mechanism of rivastigmine's action is unknown, it is postulated to exert its therapeutic effect by enhancing cholinergic function. This is accomplished by increasing the concentration of acetylcholine through reversible inhibition of its hydrolysis by cholinesterase. If this proposed mechanism is correct, rivastigmine's effect may lessen as the disease progresses and fewer cholinergic neurons remain functionally intact.
Mode of Action:
Rivastigmine is a carbamate derivative that is structurally related to physostigmine, but not to donepezil and tacrine. The precise mechanism of rivastigmine has not been fully determined, but it is suggested that rivastigmine binds reversibly with and inactivates chlolinesterase (eg. acetylcholinesterase, butyrylcholinesterase), preventing the hydrolysis of acetycholine, and thus leading to an increased concentration of acetylcholine at cholinergic synapses. The anticholinesterase activity of rivastigmine is relatively specific for brain acetylcholinesterase and butyrylcholinesterase compared with those in peripheral tissues.
Metabolism:
Rivastigmine is rapidly metabolized by cholinesterase-mediated hydrolysis.
Toxicity:
General Reference:
Camps P, Munoz-Torrero D: Cholinergic drugs in pharmacotherapy of Alzheimerês disease. Mini Rev Med Chem. 2002 Feb;2(1):11-25. Pubmed Rosler M, Anand R, Cicin-Sain A, Gauthier S, Agid Y, Dal-Bianco P, Stahelin HB, Hartman R, Gharabawi M: Efficacy and safety of rivastigmine in patients with Alzheimerês disease: international randomised controlled trial. BMJ. 1999 Mar 6;318(7184):633-8. Pubmed Finkel SI: Effects of rivastigmine on behavioral and psychological symptoms of dementia in Alzheimerês disease. Clin Ther. 2004 Jul;26(7):980-90. Pubmed Rosler M, Retz W, Retz-Junginger P, Dennler HJ: Effects of two-year treatment with the cholinesterase inhibitor rivastigmine on behavioural symptoms in Alzheimerês disease. Behav Neurol. 1998;11(4):211-216. Pubmed Emre M, Aarsland D, Albanese A, Byrne EJ, Deuschl G, De Deyn PP, Durif F, Kulisevsky J, van Laar T, Lees A, Poewe W, Robillard A, Rosa MM, Wolters E, Quarg P, Tekin S, Lane R: Rivastigmine for dementia associated with Parkinsonês disease. N Engl J Med. 2004 Dec 9;351(24):2509-18. Pubmed Birks J, Grimley Evans J, Iakovidou V, Tsolaki M, Holt FE: Rivastigmine for Alzheimerês disease. Cochrane Database Syst Rev. 2009 Apr 15;(2):CD001191. Pubmed# Naik RS, Hartmann J, Kiewert C, Duysen EG, Lockridge O, Klein J: Effects of rivastigmine and donepezil on brain acetylcholine levels in acetylcholinesterase-deficient mice. J Pharm Pharm Sci. 2009;12(1):79-85. Pubmed Farlow MR: Update on rivastigmine. Neurologist. 2003 Sep;9(5):230-4. Pubmed
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