You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on DrugBank.
Identification
NameRivastigmine
Accession NumberDB00989  (APRD00321)
TypeSmall Molecule
GroupsApproved, Investigational
Description

Rivastigmine 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.

Structure
Thumb
Synonyms
(S)-3-(1-(Dimethylamino)ethyl)phenyl ethylmethylcarbamate
Ena 713 Free Base
m-((S)-1-(Dimethylamino)ethyl)phenyl ethylmethylcarbamate
External Identifiers Not Available
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Auro-rivastigminecapsule1.5 mgoralAuro Pharma Inc2016-04-12Not applicableCanada
Auro-rivastigminecapsule6 mgoralAuro Pharma Inc2016-04-12Not applicableCanada
Auro-rivastigminecapsule4.5 mgoralAuro Pharma Inc2016-04-12Not applicableCanada
Auro-rivastigminecapsule3 mgoralAuro Pharma Inc2016-04-12Not applicableCanada
Dom-rivastigminecapsule6.0 mgoralDominion PharmacalNot applicableNot applicableCanada
Dom-rivastigminecapsule4.5 mgoralDominion PharmacalNot applicableNot applicableCanada
Dom-rivastigminecapsule3.0 mgoralDominion PharmacalNot applicableNot applicableCanada
Dom-rivastigminecapsule1.5 mgoralDominion PharmacalNot applicableNot applicableCanada
Exeloncapsule4.5 mg/1oralPhysicians Total Care, Inc.2005-03-03Not applicableUs
Exeloncapsule1.5 mg/1oralNovartis Pharmaceuticals Corporation2000-04-30Not applicableUs
Exelonsolution2 mgoralNovartis Pharmaceuticals Canada Inc2002-12-05Not applicableCanada
Exeloncapsule6 mg/1oralPhysicians Total Care, Inc.2005-06-17Not applicableUs
Exeloncapsule1.5 mg/1oralPhysicians Total Care, Inc.2002-04-12Not applicableUs
Exeloncapsule6 mgoralNovartis Pharmaceuticals Canada Inc2000-05-15Not applicableCanada
Exelonpatch, extended release4.6 mg/24[USP'U]transdermalRebel Distributors Corp2009-10-07Not applicableUs
Exelonpatch, extended release13.3 mg/24htransdermalNovartis Pharmaceuticals Corporation2007-07-06Not applicableUs
Exeloncapsule4.5 mgoralNovartis Pharmaceuticals Canada Inc2000-05-15Not applicableCanada
Exelonpatch, extended release9.5 mg/24htransdermalNovartis Pharmaceuticals Corporation2007-07-06Not applicableUs
Exeloncapsule3 mgoralNovartis Pharmaceuticals Canada Inc2000-05-15Not applicableCanada
Exelonpatch, extended release4.6 mg/24htransdermalNovartis Pharmaceuticals Corporation2007-07-06Not applicableUs
Exeloncapsule6 mg/1oralNovartis Pharmaceuticals Corporation2000-04-30Not applicableUs
Exelonpatch, extended release4.6 mg/24[USP'U]transdermalPhysicians Total Care, Inc.2009-10-07Not applicableUs
Exeloncapsule4.5 mg/1oralNovartis Pharmaceuticals Corporation2000-04-30Not applicableUs
Exelonpatch, extended release9.5 mg/24[USP'U]transdermalPhysicians Total Care, Inc.2008-10-14Not applicableUs
Exeloncapsule3 mg/1oralPhysicians Total Care, Inc.2007-12-04Not applicableUs
Exeloncapsule3 mg/1oralNovartis Pharmaceuticals Corporation2000-04-30Not applicableUs
Exelon 1.5 mgcapsule1.5 mgoralNovartis Pharmaceuticals Canada Inc2000-05-15Not applicableCanada
Exelon Patch 10patch18 mgtransdermalNovartis Pharmaceuticals Canada Inc2007-12-12Not applicableCanada
Exelon Patch 15patch27 mgtransdermalNovartis Pharmaceuticals Canada Inc2015-04-17Not applicableCanada
Exelon Patch 5patch9 mgtransdermalNovartis Pharmaceuticals Canada Inc2007-12-12Not applicableCanada
Med-rivastigminecapsule6 mgoralGeneric Medical Partners Inc2013-11-27Not applicableCanada
Med-rivastigminecapsule3 mgoralGeneric Medical Partners Inc2013-11-27Not applicableCanada
Med-rivastigminecapsule4.5 mgoralGeneric Medical Partners Inc2014-11-12Not applicableCanada
Med-rivastigminecapsule1.5 mgoralGeneric Medical Partners Inc2013-11-27Not applicableCanada
Mint-rivastigminecapsule1.5 mgoralMint Pharmaceuticals Inc2013-07-02Not applicableCanada
Mint-rivastigminecapsule6 mgoralMint Pharmaceuticals Inc2013-07-02Not applicableCanada
Mint-rivastigminecapsule4.5 mgoralMint Pharmaceuticals Inc2013-07-02Not applicableCanada
Mint-rivastigminecapsule3 mgoralMint Pharmaceuticals Inc2013-07-02Not applicableCanada
Mylan-rivastigminecapsule6 mgoralMylan Pharmaceuticals Ulc2009-09-02Not applicableCanada
Mylan-rivastigminecapsule4.5 mgoralMylan Pharmaceuticals Ulc2009-09-02Not applicableCanada
Mylan-rivastigminecapsule3 mgoralMylan Pharmaceuticals Ulc2009-09-02Not applicableCanada
Mylan-rivastigminecapsule1.5 mgoralMylan Pharmaceuticals Ulc2009-09-02Not applicableCanada
Novo-rivastigminecapsule6 mgoralNovopharm Limited2009-09-02Not applicableCanada
Novo-rivastigminecapsule4.5 mgoralNovopharm Limited2009-09-02Not applicableCanada
Novo-rivastigminecapsule3 mgoralNovopharm Limited2009-09-02Not applicableCanada
Novo-rivastigminecapsule1.5 mgoralNovopharm Limited2009-09-02Not applicableCanada
Novo-rivastigminecapsule1.5 mgoralNovartis Pharmaceuticals Canada IncNot applicableNot applicableCanada
PHL-rivastigminecapsule6.0 mgoralPharmel IncNot applicableNot applicableCanada
PHL-rivastigminecapsule4.5 mgoralPharmel IncNot applicableNot applicableCanada
PHL-rivastigminecapsule3.0 mgoralPharmel IncNot applicableNot applicableCanada
PHL-rivastigminecapsule1.5 mgoralPharmel IncNot applicableNot applicableCanada
PMS-rivastigminecapsule4.5 mgoralPharmascience Inc2009-08-11Not applicableCanada
PMS-rivastigminecapsule3.0 mgoralPharmascience Inc2009-08-11Not applicableCanada
PMS-rivastigminecapsule1.5 mgoralPharmascience Inc2009-08-11Not applicableCanada
PMS-rivastigminecapsule6.0 mgoralPharmascience Inc2009-08-11Not applicableCanada
Ratio-rivastigminecapsule6 mgoralTeva Canada Limited2009-09-02Not applicableCanada
Ratio-rivastigminecapsule4.5 mgoralTeva Canada Limited2009-09-02Not applicableCanada
Ratio-rivastigminecapsule3 mgoralTeva Canada Limited2009-09-02Not applicableCanada
Ratio-rivastigminecapsule1.5 mgoralTeva Canada Limited2009-09-02Not applicableCanada
Rivastigminecapsule6 mgoralPro Doc Limitee2013-12-05Not applicableCanada
Rivastigminecapsule4.5 mgoralPro Doc Limitee2013-12-05Not applicableCanada
Rivastigminepatch, extended release13.3 mg/24htransdermalSandoz Inc2015-09-02Not applicableUs
Rivastigminecapsule3 mgoralPro Doc Limitee2013-12-05Not applicableCanada
Rivastigminepatch, extended release9.5 mg/24htransdermalSandoz Inc2015-09-02Not applicableUs
Rivastigminecapsule1.5 mgoralPro Doc Limitee2013-12-05Not applicableCanada
Rivastigminepatch, extended release4.6 mg/24htransdermalSandoz Inc2015-09-02Not applicableUs
Rivastigmine Tartratecapsule3 mg/1oralSandoz Inc2000-04-30Not applicableUs
Rivastigmine Tartratecapsule1.5 mg/1oralSandoz Inc2000-04-30Not applicableUs
Rivastigmine Tartratecapsule6 mg/1oralSandoz Inc2000-04-30Not applicableUs
Rivastigmine Tartratecapsule4.5 mg/1oralSandoz Inc2000-04-30Not applicableUs
Rivastigmine Tartrate Capsulescapsule6.0 mgoralDr Reddys Laboratories LtdNot applicableNot applicableCanada
Rivastigmine Tartrate Capsulescapsule4.5 mgoralDr Reddys Laboratories LtdNot applicableNot applicableCanada
Rivastigmine Tartrate Capsulescapsule3.0 mgoralDr Reddys Laboratories LtdNot applicableNot applicableCanada
Rivastigmine Tartrate Capsulescapsule1.5 mgoralDr Reddys Laboratories LtdNot applicableNot applicableCanada
Sandoz Rivastigminecapsule4.5 mgoralSandoz Canada Incorporated2009-07-21Not applicableCanada
Sandoz Rivastigminecapsule3 mgoralSandoz Canada Incorporated2009-07-21Not applicableCanada
Sandoz Rivastigminecapsule1.5 mgoralSandoz Canada Incorporated2009-07-21Not applicableCanada
Sandoz Rivastigminecapsule6 mgoralSandoz Canada Incorporated2009-07-21Not applicableCanada
Sandoz Rivastigmine Patch 10patch18 mgtransdermalSandoz Canada IncorporatedNot applicableNot applicableCanada
Sandoz Rivastigmine Patch 5patch9 mgtransdermalSandoz Canada IncorporatedNot applicableNot applicableCanada
Approved Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Apo-rivastigminecapsule1.5 mgoralApotex Inc2010-04-07Not applicableCanada
Apo-rivastigminecapsule6 mgoralApotex Inc2010-04-07Not applicableCanada
Apo-rivastigminecapsule4.5 mgoralApotex Inc2010-04-07Not applicableCanada
Apo-rivastigminecapsule3 mgoralApotex Inc2010-04-07Not applicableCanada
Rivastigmine Tartratecapsule3 mg/1oralBreckenridge Pharmaceutical, Inc2012-06-13Not applicableUs
Rivastigmine Tartratecapsule1.5 mg/1oralAlembic Pharmaceuticals Limited2012-06-13Not applicableUs
Rivastigmine Tartratecapsule1.5 mg/1oralWatson Laboratories, Inc.2010-07-01Not applicableUs
Rivastigmine Tartratecapsule6 mg/1oralAurobindo Pharma Limited2016-03-25Not applicableUs
Rivastigmine Tartratecapsule4.5 mg/1oralSun Pharmaceutical Industries Limited2010-07-01Not applicableUs
Rivastigmine Tartratecapsule3 mg/1oralSun Pharmaceutical Industries Limited2010-07-01Not applicableUs
Rivastigmine Tartratecapsule3 mg/1oralGolden State Medical Supply, Inc.2015-03-10Not applicableUs
Rivastigmine Tartratecapsule4.5 mg/1oralBreckenridge Pharmaceutical, Inc2012-06-13Not applicableUs
Rivastigmine Tartratecapsule4.5 mg/1oralAurobindo Pharma Limited2016-03-25Not applicableUs
Rivastigmine Tartratecapsule1.5 mg/1oralCarilion Materials Management2010-07-01Not applicableUs
Rivastigmine Tartratecapsule1.5 mg/1oralSun Pharmaceutical Industries Limited2010-07-01Not applicableUs
Rivastigmine Tartratecapsule1.5 mg/1oralGolden State Medical Supply, Inc.2015-03-10Not applicableUs
Rivastigmine Tartratecapsule1.5 mg/1oralBreckenridge Pharmaceutical, Inc2012-06-13Not applicableUs
Rivastigmine Tartratecapsule6 mg/1oralMacleods Pharmaceuticals Limited2014-09-02Not applicableUs
Rivastigmine Tartratecapsule3 mg/1oralAurobindo Pharma Limited2016-03-25Not applicableUs
Rivastigmine Tartratecapsule1.5 mg/1oralAmerican Health Packaging2012-01-06Not applicableUs
Rivastigmine Tartratecapsule6 mg/1oralApotex Corp.2013-02-20Not applicableUs
Rivastigmine Tartratecapsule6 mg/1oralDr. Reddy's Laboratories Limited2011-09-01Not applicableUs
Rivastigmine Tartratecapsule4.5 mg/1oralMacleods Pharmaceuticals Limited2014-09-02Not applicableUs
Rivastigmine Tartratecapsule1.5 mg/1oralAurobindo Pharma Limited2016-03-25Not applicableUs
Rivastigmine Tartratecapsule6 mg/1oralMc Kesson Packaging Services A Business Unit Of Mc Kesson Corporation2013-03-01Not applicableUs
Rivastigmine Tartratecapsule4.5 mg/1oralApotex Corp.2013-02-20Not applicableUs
Rivastigmine Tartratecapsule4.5 mg/1oralDr. Reddy's Laboratories Limited2011-09-01Not applicableUs
Rivastigmine Tartratecapsule3 mg/1oralMacleods Pharmaceuticals Limited2014-09-02Not applicableUs
Rivastigmine Tartratecapsule1.5 mg/1oralAvera Mc Kennan Hospital2015-11-19Not applicableUs
Rivastigmine Tartratecapsule4.5 mg/1oralMc Kesson Packaging Services A Business Unit Of Mc Kesson Corporation2013-03-01Not applicableUs
Rivastigmine Tartratecapsule3 mg/1oralApotex Corp.2013-02-20Not applicableUs
Rivastigmine Tartratecapsule3 mg/1oralDr. Reddy's Laboratories Limited2011-09-01Not applicableUs
Rivastigmine Tartratecapsule1.5 mg/1oralMacleods Pharmaceuticals Limited2014-09-02Not applicableUs
Rivastigmine Tartratecapsule3 mg/1oralMc Kesson Packaging Services A Business Unit Of Mc Kesson Corporation2013-02-01Not applicableUs
Rivastigmine Tartratecapsule1.5 mg/1oralApotex Corp.2013-02-20Not applicableUs
Rivastigmine Tartratecapsule1.5 mg/1oralDr. Reddy's Laboratories Limited2011-09-01Not applicableUs
Rivastigmine Tartratecapsule6 mg/1oralAlembic Pharmaceuticals Limited2012-06-13Not applicableUs
Rivastigmine Tartratecapsule6 mg/1oralWatson Laboratories, Inc.2010-07-01Not applicableUs
Rivastigmine Tartratecapsule6 mg/1oralGolden State Medical Supply, Inc.2015-03-10Not applicableUs
Rivastigmine Tartratecapsule6 mg/1oralPhysicians Total Care, Inc.2010-09-15Not applicableUs
Rivastigmine Tartratecapsule4.5 mg/1oralAlembic Pharmaceuticals Limited2012-06-13Not applicableUs
Rivastigmine Tartratecapsule4.5 mg/1oralWatson Laboratories, Inc.2010-07-01Not applicableUs
Rivastigmine Tartratecapsule1.5 mg/1oralMc Kesson Packaging Services A Business Unit Of Mc Kesson Corporation2013-03-01Not applicableUs
Rivastigmine Tartratecapsule6 mg/1oralBreckenridge Pharmaceutical, Inc2012-06-13Not applicableUs
Rivastigmine Tartratecapsule3 mg/1oralAlembic Pharmaceuticals Limited2012-06-13Not applicableUs
Rivastigmine Tartratecapsule3 mg/1oralWatson Laboratories, Inc.2010-07-01Not applicableUs
Rivastigmine Tartratecapsule6 mg/1oralSun Pharmaceutical Industries Limited2010-07-01Not applicableUs
Rivastigmine Tartratecapsule4.5 mg/1oralGolden State Medical Supply, Inc.2015-03-10Not applicableUs
Rivastigmine Transdermal Systempatch, extended release13.3 mg/1transdermalAlvogen Inc.2015-09-02Not applicableUs
Rivastigmine Transdermal Systempatch, extended release9.5 mg/1transdermalAlvogen Inc.2015-09-04Not applicableUs
Rivastigmine Transdermal Systempatch, extended release4.6 mg/1transdermalAlvogen Inc.2015-09-04Not applicableUs
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
Exelon PatchNot Available
Brand mixturesNot Available
Salts
Name/CASStructureProperties
Rivastigmine tartrate
ThumbNot applicableDBSALT001252
Categories
UNIIPKI06M3IW0
CAS number123441-03-2
WeightAverage: 250.3367
Monoisotopic: 250.168127958
Chemical FormulaC14H22N2O2
InChI KeyInChIKey=XSVMFMHYUFZWBK-NSHDSACASA-N
InChI
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
IUPAC Name
3-[(1S)-1-(dimethylamino)ethyl]phenyl N-ethyl-N-methylcarbamate
SMILES
CCN(C)C(=O)OC1=CC=CC(=C1)[[email protected]](C)N(C)C
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as aralkylamines. These are alkylamines in which the alkyl group is substituted at one carbon atom by an aromatic hydrocarbyl group.
KingdomOrganic compounds
Super ClassOrganonitrogen compounds
ClassAmines
Sub ClassAralkylamines
Direct ParentAralkylamines
Alternative Parents
Substituents
  • Aralkylamine
  • Benzenoid
  • Monocyclic benzene moiety
  • Tertiary aliphatic amine
  • Tertiary amine
  • Monocarboxylic acid or derivatives
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Pharmacology
IndicationFor the treatment of mild to moderate dementia associated with Parkinson's disease or of the Alzheimer's type.
PharmacodynamicsRivastigmine 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.
Mechanism of actionRivastigmine 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.
Related Articles
AbsorptionNot Available
Volume of distribution
  • 1.8 to 2.7 L/kg
Protein binding40%
Metabolism

Rivastigmine is rapidly metabolized by cholinesterase-mediated hydrolysis.

Route of eliminationRivastigmine is extensively metabolized primarily via cholinesterase-mediated hydrolysis to the decarbamylated metabolite NAP226-90. Renal excretion of the metabolites is the major route of elimination. Less than 1% of the administered dose is excreted in the feces.
Half life1.5 hours
Clearance
  • renal cl=2.1-2.8 L/hr
ToxicityNot Available
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.9853
Caco-2 permeable+0.7001
P-glycoprotein substrateNon-substrate0.6571
P-glycoprotein inhibitor INon-inhibitor0.7919
P-glycoprotein inhibitor IINon-inhibitor0.8756
Renal organic cation transporterNon-inhibitor0.8406
CYP450 2C9 substrateNon-substrate0.7993
CYP450 2D6 substrateNon-substrate0.6659
CYP450 3A4 substrateSubstrate0.5932
CYP450 1A2 substrateNon-inhibitor0.609
CYP450 2C9 inhibitorNon-inhibitor0.8928
CYP450 2D6 inhibitorNon-inhibitor0.8384
CYP450 2C19 inhibitorNon-inhibitor0.8734
CYP450 3A4 inhibitorNon-inhibitor0.9545
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8062
Ames testNon AMES toxic0.5279
CarcinogenicityNon-carcinogens0.5858
BiodegradationNot ready biodegradable0.9463
Rat acute toxicity3.4167 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9355
hERG inhibition (predictor II)Non-inhibitor0.8986
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
Manufacturers
  • Novartis pharmaceuticals corp
  • Dr reddys laboratories inc
  • Sun pharmaceutical industries ltd
  • Watson laboratories inc
Packagers
Dosage forms
FormRouteStrength
Capsuleoral1.5 mg/1
Capsuleoral3 mg
Capsuleoral3 mg/1
Capsuleoral4.5 mg
Capsuleoral4.5 mg/1
Capsuleoral6 mg/1
Capsuleoral6 mg
Patch, extended releasetransdermal13.3 mg/24h
Patch, extended releasetransdermal4.6 mg/24[USP'U]
Patch, extended releasetransdermal4.6 mg/24h
Patch, extended releasetransdermal9.5 mg/24h
Patch, extended releasetransdermal9.5 mg/24[USP'U]
Solutionoral2 mg
Capsuleoral1.5 mg
Patchtransdermal18 mg
Patchtransdermal27 mg
Patchtransdermal9 mg
Capsuleoral3.0 mg
Capsuleoral6.0 mg
Patch, extended releasetransdermal13.3 mg/1
Patch, extended releasetransdermal4.6 mg/1
Patch, extended releasetransdermal9.5 mg/1
Prices
Unit descriptionCostUnit
Exelon 30 4.6 mg/24hr Patches Box252.18USD box
Exelon 30 9.5 mg/24hr Patches Box252.18USD box
Exelon 4.6 mg/24hr patch8.08USD patch
Exelon 9.5 mg/24hr patch8.08USD patch
Exelon 1.5 mg capsule4.81USD capsule
Exelon 3 mg capsule4.81USD capsule
Exelon 4.5 mg capsule4.81USD capsule
Exelon 6 mg capsule4.81USD capsule
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
CA2315784 No2006-06-272019-01-08Canada
US4948807 No1992-08-142012-08-14Us
US6316023 No1999-01-082019-01-08Us
US6335031 No1999-01-082019-01-08Us
Properties
StateSolid
Experimental Properties
PropertyValueSource
logP2.3Not Available
Predicted Properties
PropertyValueSource
Water Solubility2.04 mg/mLALOGPS
logP2.45ALOGPS
logP2.41ChemAxon
logS-2.1ALOGPS
pKa (Strongest Basic)8.89ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area32.78 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity73.37 m3·mol-1ChemAxon
Polarizability28.53 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
References
Synthesis Reference

Venkata Naga Brahmeswara Rao Mandava, Venkata Reddy Vajrala, Ganesh Varanasi, Vijay Kumar Adla, Mukund Reddy Jambula, Vijaypal Reddy Kanumathi Reddy, “PREPARATION OF RIVASTIGMINE AND ITS SALTS.” U.S. Patent US20080255383, issued October 16, 2008.

US20080255383
General References
  1. 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 ]
  2. 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 ]
  3. 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 ]
  4. 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 ]
  5. 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 ]
  6. 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 ]
  7. 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 ]
  8. Farlow MR: Update on rivastigmine. Neurologist. 2003 Sep;9(5):230-4. [PubMed:14587496 ]
External Links
ATC CodesN06DA03
AHFS Codes
  • 12:04.00
PDB Entries
FDA labelDownload (74 KB)
MSDSNot Available
Interactions
Drug Interactions
Drug
AcebutololRivastigmine may increase the bradycardic activities of Acebutolol.
AcepromazineRivastigmine may increase the central neurotoxic activities of Acepromazine.
AcetophenazineRivastigmine may increase the central neurotoxic activities of Acetophenazine.
AcetylcholineThe risk or severity of adverse effects can be increased when Rivastigmine is combined with Acetylcholine.
AmisulprideRivastigmine may increase the central neurotoxic activities of Amisulpride.
AripiprazoleRivastigmine may increase the central neurotoxic activities of Aripiprazole.
AtenololRivastigmine may increase the bradycardic activities of Atenolol.
Atracurium besylateRivastigmine may decrease the neuromuscular blocking activities of Atracurium besylate.
BenzquinamideRivastigmine may increase the central neurotoxic activities of Benzquinamide.
BetaxololRivastigmine may increase the bradycardic activities of Betaxolol.
BisoprololRivastigmine may increase the bradycardic activities of Bisoprolol.
BretyliumBretylium may increase the bradycardic activities of Rivastigmine.
CarbacholThe risk or severity of adverse effects can be increased when Rivastigmine is combined with Carbachol.
CarphenazineRivastigmine may increase the central neurotoxic activities of Carphenazine.
CarteololRivastigmine may increase the bradycardic activities of Carteolol.
CarvedilolRivastigmine may increase the bradycardic activities of Carvedilol.
CeritinibRivastigmine may increase the bradycardic activities of Ceritinib.
ChlormezanoneRivastigmine may increase the central neurotoxic activities of Chlormezanone.
ChlorpromazineRivastigmine may increase the central neurotoxic activities of Chlorpromazine.
ChlorprothixeneRivastigmine may increase the central neurotoxic activities of Chlorprothixene.
ClozapineRivastigmine may increase the central neurotoxic activities of Clozapine.
DipyridamoleThe therapeutic efficacy of Rivastigmine can be decreased when used in combination with Dipyridamole.
DroperidolRivastigmine may increase the central neurotoxic activities of Droperidol.
EsmololRivastigmine may increase the bradycardic activities of Esmolol.
FencamfamineRivastigmine may increase the central neurotoxic activities of Fencamfamine.
FludrocortisoneThe risk or severity of adverse effects can be increased when Fludrocortisone is combined with Rivastigmine.
FlupentixolRivastigmine may increase the central neurotoxic activities of Flupentixol.
FluphenazineRivastigmine may increase the central neurotoxic activities of Fluphenazine.
FluspirileneRivastigmine may increase the central neurotoxic activities of Fluspirilene.
HaloperidolRivastigmine may increase the central neurotoxic activities of Haloperidol.
IvabradineRivastigmine may increase the bradycardic activities of Ivabradine.
LabetalolRivastigmine may increase the bradycardic activities of Labetalol.
LacosamideRivastigmine may increase the atrioventricular blocking (AV block) activities of Lacosamide.
LevobunololRivastigmine may increase the bradycardic activities of Levobunolol.
LoxapineRivastigmine may increase the central neurotoxic activities of Loxapine.
MesoridazineRivastigmine may increase the central neurotoxic activities of Mesoridazine.
MethotrimeprazineRivastigmine may increase the central neurotoxic activities of Methotrimeprazine.
MetipranololRivastigmine may increase the bradycardic activities of Metipranolol.
MetoclopramideThe risk or severity of adverse effects can be increased when Rivastigmine is combined with Metoclopramide.
MetoprololRivastigmine may increase the bradycardic activities of Metoprolol.
MolindoneRivastigmine may increase the central neurotoxic activities of Molindone.
NadololRivastigmine may increase the bradycardic activities of Nadolol.
NebivololRivastigmine may increase the bradycardic activities of Nebivolol.
OctreotideOctreotide may increase the bradycardic activities of Rivastigmine.
OlanzapineRivastigmine may increase the central neurotoxic activities of Olanzapine.
OndansetronRivastigmine may increase the central neurotoxic activities of Ondansetron.
PaliperidoneRivastigmine may increase the central neurotoxic activities of Paliperidone.
PenbutololRivastigmine may increase the bradycardic activities of Penbutolol.
PerphenazineRivastigmine may increase the central neurotoxic activities of Perphenazine.
PimozideRivastigmine may increase the central neurotoxic activities of Pimozide.
PindololRivastigmine may increase the bradycardic activities of Pindolol.
PiperacetazineRivastigmine may increase the central neurotoxic activities of Piperacetazine.
ProchlorperazineRivastigmine may increase the central neurotoxic activities of Prochlorperazine.
ProcyclidineThe therapeutic efficacy of Procyclidine can be decreased when used in combination with Rivastigmine.
PromazineRivastigmine may increase the central neurotoxic activities of Promazine.
PropranololRivastigmine may increase the bradycardic activities of Propranolol.
QuetiapineRivastigmine may increase the central neurotoxic activities of Quetiapine.
RemoxiprideRivastigmine may increase the central neurotoxic activities of Remoxipride.
ReserpineRivastigmine may increase the central neurotoxic activities of Reserpine.
RisperidoneRivastigmine may increase the central neurotoxic activities of Risperidone.
RuxolitinibRuxolitinib may increase the bradycardic activities of Rivastigmine.
SertindoleRivastigmine may increase the central neurotoxic activities of Sertindole.
SotalolRivastigmine may increase the bradycardic activities of Sotalol.
SuccinylcholineThe serum concentration of Succinylcholine can be increased when it is combined with Rivastigmine.
SulpirideRivastigmine may increase the central neurotoxic activities of Sulpiride.
ThioridazineRivastigmine may increase the central neurotoxic activities of Thioridazine.
ThiothixeneRivastigmine may increase the central neurotoxic activities of Thiothixene.
TimololRivastigmine may increase the bradycardic activities of Timolol.
TofacitinibTofacitinib may increase the bradycardic activities of Rivastigmine.
TrifluoperazineRivastigmine may increase the central neurotoxic activities of Trifluoperazine.
TriflupromazineRivastigmine may increase the central neurotoxic activities of Triflupromazine.
ZiprasidoneRivastigmine may increase the central neurotoxic activities of Ziprasidone.
ZuclopenthixolRivastigmine may increase the central neurotoxic activities of Zuclopenthixol.
Food InteractionsNot Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
inhibitor
General Function:
Serine hydrolase 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 Da
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 ]
Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
inhibitor
General Function:
Identical protein binding
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 Da
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 ]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Steroid hydroxylase 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 Da
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 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Vitamin d3 25-hydroxylase 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 xenobiot...
Gene Name:
CYP3A4
Uniprot ID:
P08684
Molecular Weight:
57342.67 Da
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 ]
Comments
comments powered by Disqus
Drug created on June 13, 2005 07:24 / Updated on May 28, 2016 02:11