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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:51 UTC
Update Date2021-09-14 14:59:01 UTC
HMDB IDHMDB0015124
Secondary Accession Numbers
  • HMDB15124
Metabolite Identification
Common NameRivastigmine
DescriptionRivastigmine is only found in individuals that have used or taken this drug. It is a parasympathomimetic or cholinergic agent for the treatment of mild to moderate dementia of the Alzheimer's type. Rivastigmine is a cholinesterase inhibitor that inhibits both butyrylcholinesterase and acetylcholinesterase.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.
Structure
Data?1582753261
Synonyms
ValueSource
(S)-3-(1-(Dimethylamino)ethyl)phenyl ethylmethylcarbamateChEBI
m-((S)-1-(Dimethylamino)ethyl)phenyl ethylmethylcarbamateChEBI
ExelonKegg
PrometaxKegg
(S)-3-(1-(Dimethylamino)ethyl)phenyl ethylmethylcarbamic acidGenerator
m-((S)-1-(Dimethylamino)ethyl)phenyl ethylmethylcarbamic acidGenerator
Ena 713 free baseHMDB
(S)-N-Ethyl-3-((1-dimethyl-amino)ethyl)-N-methylphenylcarbamateHMDB
713, ENAHMDB
SDZ ENA 713HMDB
713, SDZ ENAHMDB
ENA 713HMDB
Rivastigmine hydrogen tartrateHMDB
Tartrate, rivastigmine hydrogenHMDB
ENA-713HMDB
RivastigmineTartrateHMDB
ENA 713, SDZHMDB
Hydrogen tartrate, rivastigmineHMDB
Chemical FormulaC14H22N2O2
Average Molecular Weight250.3367
Monoisotopic Molecular Weight250.168127958
IUPAC Name3-[(1S)-1-(dimethylamino)ethyl]phenyl N-ethyl-N-methylcarbamate
Traditional Nameexelon
CAS Registry Number123441-03-2
SMILES
CCN(C)C(=O)OC1=CC=CC(=C1)[C@H](C)N(C)C
InChI Identifier
InChI=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
InChI KeyXSVMFMHYUFZWBK-NSHDSACASA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as phenoxy compounds. These are aromatic compounds contaning a phenoxy group.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassPhenoxy compounds
Direct ParentPhenoxy compounds
Alternative Parents
Substituents
  • Phenoxy compound
  • Aralkylamine
  • Carbamic acid ester
  • Carbonic acid derivative
  • Tertiary amine
  • Tertiary aliphatic amine
  • Amine
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Carbonyl group
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Biological location:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility2.04 g/LNot Available
LogP2.3Not Available
Predicted Properties
PropertyValueSource
Water Solubility2.04 g/LALOGPS
logP2.45ALOGPS
logP2.41ChemAxon
logS-2.1ALOGPS
pKa (Strongest Basic)8.89ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area32.78 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity73.37 m³·mol⁻¹ChemAxon
Polarizability28.53 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra

GC-MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-052r-9840000000-cebc171eeaabb1a4ede52017-09-01View Spectrum
MSMass Spectrum (Electron Ionization)splash10-052r-9840000000-cebc171eeaabb1a4ede52021-09-05View Spectrum

LC-MS/MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0a4i-0090000000-cb0be842083fd5bb182c2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0a4i-1090000000-d7335c9ff57f34335d3c2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-052r-9050000000-2739573cc72accdb35932017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-052r-9010000000-827dd9cfa5e61c7056172017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-052r-9000000000-42e62adc5ba35b92f9912017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0a4i-9000000000-717721d4d1b05cfae7d92017-09-14View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0w29-9260000000-46b0854527ea930e35fa2016-08-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-9410000000-785b9236f8f0b1281f852016-08-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-8a00f3235049f66a41672016-08-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-4390000000-6ea86750e92d155bb8212016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0bu1-8970000000-a0de50e5661aa48ce5cd2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0abc-9400000000-d292860976870f17d3cd2016-08-03View Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00989 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00989 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00989
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID70377
KEGG Compound IDC11766
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkRivastigmine
METLIN IDNot Available
PubChem Compound77991
PDB IDNot Available
ChEBI ID8874
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. 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 Alzheimer's disease: international randomised controlled trial. BMJ. 1999 Mar 6;318(7184):633-8. [PubMed:10066203 ]
  2. Rosler M, Retz W, Retz-Junginger P, Dennler HJ: Effects of two-year treatment with the cholinesterase inhibitor rivastigmine on behavioural symptoms in Alzheimer's disease. Behav Neurol. 1998;11(4):211-216. [PubMed:11568422 ]
  3. Camps P, Munoz-Torrero D: Cholinergic drugs in pharmacotherapy of Alzheimer's disease. Mini Rev Med Chem. 2002 Feb;2(1):11-25. [PubMed:12369954 ]
  4. Farlow MR: Update on rivastigmine. Neurologist. 2003 Sep;9(5):230-4. [PubMed:14587496 ]
  5. Finkel SI: Effects of rivastigmine on behavioral and psychological symptoms of dementia in Alzheimer's disease. Clin Ther. 2004 Jul;26(7):980-90. [PubMed:15336465 ]
  6. 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 Parkinson's disease. N Engl J Med. 2004 Dec 9;351(24):2509-18. [PubMed:15590953 ]
  7. Birks J, Grimley Evans J, Iakovidou V, Tsolaki M, Holt FE: Rivastigmine for Alzheimer's disease. Cochrane Database Syst Rev. 2009 Apr 15;(2):CD001191. doi: 10.1002/14651858.CD001191.pub2. [PubMed:19370562 ]

Enzymes

General function:
Involved in carboxylesterase activity
Specific function:
Terminates signal transduction at the neuromuscular junction by rapid hydrolysis of the acetylcholine released into the synaptic cleft. Role in neuronal apoptosis.
Gene Name:
ACHE
Uniprot ID:
P22303
Molecular weight:
67795.525
References
  1. Kennedy JS, Polinsky RJ, Johnson B, Loosen P, Enz A, Laplanche R, Schmidt D, Mancione LC, Parris WC, Ebert MH: Preferential cerebrospinal fluid acetylcholinesterase inhibition by rivastigmine in humans. J Clin Psychopharmacol. 1999 Dec;19(6):513-21. [PubMed:10587286 ]
  2. Goldblum D, Garweg JG, Bohnke M: Topical rivastigmine, a selective acetylcholinesterase inhibitor, lowers intraocular pressure in rabbits. J Ocul Pharmacol Ther. 2000 Feb;16(1):29-35. [PubMed:10673128 ]
  3. Grossberg GT, Stahelin HB, Messina JC, Anand R, Veach J: Lack of adverse pharmacodynamic drug interactions with rivastigmine and twenty-two classes of medications. Int J Geriatr Psychiatry. 2000 Mar;15(3):242-7. [PubMed:10713582 ]
  4. Stahl SM: The new cholinesterase inhibitors for Alzheimer's disease, Part 1: their similarities are different. J Clin Psychiatry. 2000 Oct;61(10):710-1. [PubMed:11078030 ]
  5. Gottwald MD, Rozanski RI: Rivastigmine, a brain-region selective acetylcholinesterase inhibitor for treating Alzheimer's disease: review and current status. Expert Opin Investig Drugs. 1999 Oct;8(10):1673-1682. [PubMed:11139819 ]
  6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
  7. Birks J, Grimley Evans J, Iakovidou V, Tsolaki M, Holt FE: Rivastigmine for Alzheimer's disease. Cochrane Database Syst Rev. 2009 Apr 15;(2):CD001191. doi: 10.1002/14651858.CD001191.pub2. [PubMed:19370562 ]
  8. 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:19470293 ]
  9. Lalli S, Albanese A: Rivastigmine in Parkinson's disease dementia. Expert Rev Neurother. 2008 Aug;8(8):1181-8. doi: 10.1586/14737175.8.8.1181. [PubMed:18671661 ]
  10. Onor ML, Trevisiol M, Aguglia E: Rivastigmine in the treatment of Alzheimer's disease: an update. Clin Interv Aging. 2007;2(1):17-32. [PubMed:18044073 ]
  11. Farlow MR: Update on rivastigmine. Neurologist. 2003 Sep;9(5):230-4. [PubMed:14587496 ]
  12. Greig NH, Lahiri DK, Sambamurti K: Butyrylcholinesterase: an important new target in Alzheimer's disease therapy. Int Psychogeriatr. 2002;14 Suppl 1:77-91. [PubMed:12636181 ]
General function:
Involved in carboxylesterase activity
Specific function:
Esterase with broad substrate specificity. Contributes to the inactivation of the neurotransmitter acetylcholine. Can degrade neurotoxic organophosphate esters.
Gene Name:
BCHE
Uniprot ID:
P06276
Molecular weight:
68417.575
References
  1. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
  2. Stahl SM: The new cholinesterase inhibitors for Alzheimer's disease, Part 1: their similarities are different. J Clin Psychiatry. 2000 Oct;61(10):710-1. [PubMed:11078030 ]
  3. Gottwald MD, Rozanski RI: Rivastigmine, a brain-region selective acetylcholinesterase inhibitor for treating Alzheimer's disease: review and current status. Expert Opin Investig Drugs. 1999 Oct;8(10):1673-1682. [PubMed:11139819 ]
  4. Birks J, Grimley Evans J, Iakovidou V, Tsolaki M, Holt FE: Rivastigmine for Alzheimer's disease. Cochrane Database Syst Rev. 2009 Apr 15;(2):CD001191. doi: 10.1002/14651858.CD001191.pub2. [PubMed:19370562 ]
  5. Birks J: Cholinesterase inhibitors for Alzheimer's disease. Cochrane Database Syst Rev. 2006 Jan 25;(1):CD005593. [PubMed:16437532 ]
  6. 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:19470293 ]
  7. Smith DA: Treatment of Alzheimer's disease in the long-term-care setting. Am J Health Syst Pharm. 2009 May 15;66(10):899-907. doi: 10.2146/ajhp070622. [PubMed:19420308 ]
  8. Bassil N, Grossberg GT: Novel regimens and delivery systems in the pharmacological treatment of Alzheimer's disease. CNS Drugs. 2009;23(4):293-307. [PubMed:19374459 ]
  9. Lalli S, Albanese A: Rivastigmine in Parkinson's disease dementia. Expert Rev Neurother. 2008 Aug;8(8):1181-8. doi: 10.1586/14737175.8.8.1181. [PubMed:18671661 ]
  10. Onor ML, Trevisiol M, Aguglia E: Rivastigmine in the treatment of Alzheimer's disease: an update. Clin Interv Aging. 2007;2(1):17-32. [PubMed:18044073 ]
  11. Farlow MR: Update on rivastigmine. Neurologist. 2003 Sep;9(5):230-4. [PubMed:14587496 ]
  12. Greig NH, Lahiri DK, Sambamurti K: Butyrylcholinesterase: an important new target in Alzheimer's disease therapy. Int Psychogeriatr. 2002;14 Suppl 1:77-91. [PubMed:12636181 ]
General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:
CYP3A4
Uniprot ID:
P08684
Molecular weight:
57255.585
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
General function:
Involved in monooxygenase 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 antidepressants.
Gene Name:
CYP2D6
Uniprot ID:
P10635
Molecular weight:
55768.94
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]