Rivastigmine (CED0002862)

Record Information
Version1.0
Creation Date2016-05-25 18:24:11 UTC
Update Date2026-08-19 07:19:17 UTC
Accession NumberCHEM022215
Identification
Common NameRivastigmine
ClassSmall Molecule
Description
Rivastigmine is an organic compound with the formula C14H22N2O2 and an average molecular weight of 250.34 g/mol. Rivastigmine belongs to the phenoxy compounds, a subclass of benzene and substituted derivatives within the organic compounds. It is categorized within the superclass of benzenoids. This compound acts as an inhibitor of two protein targets: cholinesterase (BCHE) and acetylcholinesterase (ACHE). In terms of health effects, rivastigmine is used as a treatment for Alzheimer's disease (PMC4179059). The compound is found in or released from 11 recorded sources. Within healthcare, pharmaceuticals, and veterinary products, it is utilized as anti-dementia drugs. Other recorded sources include household cleaning and consumer products, such as soap dispensers, other smoking requisites, and non electric simulated smoking devices. It is also associated with electrical and electronic equipment, including television systems, video games, antennas, amplifiers, and radio transmission systems. Additionally, it is linked to food, food processing, and cookware, specifically the preparation of wine or sparkling wine and the preparation of vinegar. Recorded exposure routes for rivastigmine include transdermal, topical, and oral administration.
Contaminant Type
  • Human Neurotoxin
Chemical Structure
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 Mass250.337 g/mol
Monoisotopic Mass250.168 g/mol
CAS Registry Number123441-03-2
IUPAC Name3-[(1S)-1-(dimethylamino)ethyl]phenyl N-ethyl-N-methylcarbamate
Traditional Nameexelon
SMILESCCN(C)C(=O)OC1=CC=CC(=C1)[C@H](C)N(C)C
InChI IdentifierInChI=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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Organoleptic EffectsNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot 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
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrumsplash10-052r-9840000000-cebc171eeaabb1a4ede5Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4i-0090000000-cb0be842083fd5bb182cNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4i-1090000000-d7335c9ff57f34335d3cNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-052r-9050000000-2739573cc72accdb3593Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-052r-9010000000-827dd9cfa5e61c705617Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-052r-9000000000-42e62adc5ba35b92f991Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4i-9000000000-717721d4d1b05cfae7d9Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4i-9000000000-d949d05b6cd3e162d58bNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-052r-9010000000-5760056676efca6eb257Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-052r-9000000000-0cc3e59dc055ba7a49deNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4i-0090000000-eccfb54798ebb256c17eNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4i-1090000000-83af86b4d3f98140da7cNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-052r-9040000000-39192061d885ca8118afNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0w29-9260000000-46b0854527ea930e35faNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03di-9410000000-785b9236f8f0b1281f85Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-9000000000-8a00f3235049f66a4167Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0002-4390000000-6ea86750e92d155bb821Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0bu1-8970000000-a0de50e5661aa48ce5cdNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0abc-9400000000-d292860976870f17d3cdNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-01ot-2790000000-3c3461bed40612c137d6Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-02t9-0910000000-a4b0d892364ce28e19b8Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00kg-4900000000-e5aed0404b2c0b81c20dNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0udi-0090000000-2da391c5d5cca4059989Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0udi-5890000000-2c9186f75040840f942eNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-003r-9710000000-7f50e45efc1635cc59b7Not AvailableView Spectrum
Toxicity Profile
Mechanism of ToxicityNot Available
Carcinogenicity (IARC Classification)Not Available
Minimum Risk LevelNot Available
SymptomsNot Available
TreatmentNot Available
Toxicity Values
Toxicity ValueUnitValue RangeOrganismDose DescriptorRoute of ExposurePredicted or ExperimentalReference
222.0Log mg/kg[130:400]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
Alzheimer's diseaseis_treatment_forNot AvailablePMC4179059
Exposure Sources
Source IDSourceSectorReference
380Anti-dementia drugsHealthcare, pharmaceuticals & veterinary productsNot Available
505AmplifiersElectrical & Electronic EquipmentNot Available
506AntennasElectrical & Electronic EquipmentNot Available
530Radio Transmission SystemsElectrical & Electronic EquipmentNot Available
537Television SystemsElectrical & Electronic EquipmentNot Available
539Video GamesElectrical & Electronic EquipmentNot Available
548Preparation Of VinegarFood, food processing & cookwareNot Available
549Preparation Of Wine Or Sparkling WineFood, food processing & cookwareNot Available
559Non Electric Simulated Smoking DevicesHousehold cleaning & consumer productsNot Available
560Other Smoking RequisitesHousehold cleaning & consumer productsNot Available
564Soap DispensersHousehold cleaning & consumer productsNot Available
584BuoysMarine, shipping & aquacultureNot Available
616Face Mask CosmeticsPersonal care & cosmeticsNot Available
663Sanitary EquipmentWastewater, sanitation & biosolidsNot Available
Pathways
3 pathways
Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Click to view 3D structureCholinesteraseP81908Equus caballusPredicted (SEA)2.88042
Acetylcholinesterase structureClick to view 3D structureAcetylcholinesteraseP22303HumansPredicted (SEA)7.70707
Cholinesterase structureClick to view 3D structureCholinesteraseP06276HumansPredicted (SEA)6.07224
Click to view 3D structureButyrylcholinesteraseQ9N1N9Equus caballusPredicted (SEA)3.97031
Click to view 3D structureAcetylcholine receptor subunit epsilonP09660Rattus norvegicusPredicted (SEA)0.0778492
Click to view 3D structureAmine oxidase [flavin-containing] BP19643Rattus norvegicusPredicted (SEA)4.98235
Click to view 3D structureCholinesteraseP32750Canis lupus familiarisPredicted (SEA)0.0778492
Click to view 3D structureAmine oxidase [flavin-containing] AP21396Rattus norvegicusPredicted (SEA)5.60514
Sodium-dependent serotonin transporter structureClick to view 3D structureSodium-dependent serotonin transporterP31645HumansPredicted (SEA)61.423
Amine oxidase [flavin-containing] B structureClick to view 3D structureAmine oxidase [flavin-containing] BP27338HumansPredicted (SEA)39.8588
Click to view 3D structureAcetylcholinesteraseP37136Rattus norvegicusPredicted (SEA)22.4206
Click to view 3D structureButyrylcholinesteraseQ9JKC1Rattus norvegicusPredicted (SEA)14.7135
Click to view 3D structureSodium-dependent serotonin transporterP31652Rattus norvegicusPredicted (SEA)44.4519
Click to view 3D structureAcetylcholinesteraseP23795Bos taurusPredicted (SEA)14.5578
Click to view 3D structureAcetylcholinesteraseO42275Electrophorus electricusPredicted (SEA)43.907
Click to view 3D structureAcetylcholinesteraseP21836Mus musculusPredicted (SEA)21.175
Click to view 3D structureCholinesteraseQ03311Mus musculusPredicted (SEA)13.0008
MAP/microtubule affinity-regulating kinase 4 structureClick to view 3D structureMAP/microtubule affinity-regulating kinase 4Q96L34HumansPredicted (SEA)120.9
Amine oxidase [flavin-containing] A structureClick to view 3D structureAmine oxidase [flavin-containing] AP21397HumansPredicted (SEA)145.5
Click to view 3D structureAcidic phospholipase A2 CM-IP00602Naja mossambicaPredicted (SEA)14.5578
Click to view 3D structureFatty-acid amide hydrolase 1P97612Rattus norvegicusPredicted (SEA)76.9929
Rho-associated protein kinase 1 structureClick to view 3D structureRho-associated protein kinase 1Q13464HumansPredicted (SEA)821.854
Fibroblast growth factor receptor 1 structureClick to view 3D structureFibroblast growth factor receptor 1P11362HumansPredicted (SEA)1001.53
cGMP-dependent protein kinase 1 structureClick to view 3D structurecGMP-dependent protein kinase 1Q13976HumansPredicted (SEA)564.018
Click to view 3D structureProstaglandin G/H synthase 1P05979Ovis ariesPredicted (SEA)65.1598
Concentrations
Not Available
External Links
DrugBank IDDB00989
HMDB IDHMDB0015124
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkRivastigmine
Chemspider ID70377
ChEBI ID8874
PubChem Compound ID77991
Kegg Compound IDC11766
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot 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.
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.
3. Camps P, Munoz-Torrero D: Cholinergic drugs in pharmacotherapy of Alzheimer's disease. Mini Rev Med Chem. 2002 Feb;2(1):11-25.
4. Farlow MR: Update on rivastigmine. Neurologist. 2003 Sep;9(5):230-4.
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.
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.
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.
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=19032006
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=19370562
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=19392927
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=19619073
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=19893314
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=20070789
14. https://www.ncbi.nlm.nih.gov/pubmed/?term=20370805
15. https://www.ncbi.nlm.nih.gov/pubmed/?term=20865460
16. https://www.ncbi.nlm.nih.gov/pubmed/?term=21131668
17. https://www.ncbi.nlm.nih.gov/pubmed/?term=21246897
18. https://www.ncbi.nlm.nih.gov/pubmed/?term=21977379
19. https://www.ncbi.nlm.nih.gov/pubmed/?term=21996001
20. https://www.ncbi.nlm.nih.gov/pubmed/?term=22009228
21. https://www.ncbi.nlm.nih.gov/pubmed/?term=22010358
22. https://www.ncbi.nlm.nih.gov/pubmed/?term=22044027
23. https://www.ncbi.nlm.nih.gov/pubmed/?term=22054233
24. https://www.ncbi.nlm.nih.gov/pubmed/?term=22068922
25. https://www.ncbi.nlm.nih.gov/pubmed/?term=22087207
26. https://www.ncbi.nlm.nih.gov/pubmed/?term=22163241
27. https://www.ncbi.nlm.nih.gov/pubmed/?term=22163242
28. https://www.ncbi.nlm.nih.gov/pubmed/?term=22163243
29. https://www.ncbi.nlm.nih.gov/pubmed/?term=22173266
30. https://www.ncbi.nlm.nih.gov/pubmed/?term=22195801
31. https://www.ncbi.nlm.nih.gov/pubmed/?term=22224039
32. https://www.ncbi.nlm.nih.gov/pubmed/?term=22230648
33. https://www.ncbi.nlm.nih.gov/pubmed/?term=22230878
34. https://www.ncbi.nlm.nih.gov/pubmed/?term=22290743
35. https://www.ncbi.nlm.nih.gov/pubmed/?term=22362231
36. https://www.ncbi.nlm.nih.gov/pubmed/?term=22409834
37. https://www.ncbi.nlm.nih.gov/pubmed/?term=22451057