Rivastigmine (CHEM022215)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 18:24:11 UTC
Update Date2016-11-09 01:17:27 UTC
Accession NumberCHEM022215
Identification
Common NameRivastigmine
ClassSmall Molecule
DescriptionRivastigmine 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.
Contaminant Sources
  • HMDB Contaminants - Urine
  • STOFF IDENT Compounds
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
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
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot 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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-052r-9840000000-cebc171eeaabb1a4ede5Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0a4i-0090000000-cb0be842083fd5bb182cSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0a4i-1090000000-d7335c9ff57f34335d3cSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-052r-9050000000-2739573cc72accdb3593Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-052r-9010000000-827dd9cfa5e61c705617Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-052r-9000000000-42e62adc5ba35b92f991Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0a4i-9000000000-717721d4d1b05cfae7d9Spectrum
LC-MS/MSLC-MS/MS Spectrum - 90V, Positivesplash10-0a4i-9000000000-d949d05b6cd3e162d58bSpectrum
LC-MS/MSLC-MS/MS Spectrum - 60V, Positivesplash10-052r-9010000000-5760056676efca6eb257Spectrum
LC-MS/MSLC-MS/MS Spectrum - 75V, Positivesplash10-052r-9000000000-0cc3e59dc055ba7a49deSpectrum
LC-MS/MSLC-MS/MS Spectrum - 15V, Positivesplash10-0a4i-0090000000-eccfb54798ebb256c17eSpectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-0a4i-1090000000-83af86b4d3f98140da7cSpectrum
LC-MS/MSLC-MS/MS Spectrum - 45V, Positivesplash10-052r-9040000000-39192061d885ca8118afSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0w29-9260000000-46b0854527ea930e35faSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-9410000000-785b9236f8f0b1281f85Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-8a00f3235049f66a4167Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-4390000000-6ea86750e92d155bb821Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0bu1-8970000000-a0de50e5661aa48ce5cdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0abc-9400000000-d292860976870f17d3cdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-01ot-2790000000-3c3461bed40612c137d6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-02t9-0910000000-a4b0d892364ce28e19b8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00kg-4900000000-e5aed0404b2c0b81c20dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0090000000-2da391c5d5cca4059989Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-5890000000-2c9186f75040840f942eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-003r-9710000000-7f50e45efc1635cc59b7Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
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.
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