RIVASTIGMINE

Search structure
Trade Names:
Synonyms:
Status: Approved (2000)
Entry Type: Small molecule
Molecule Category: Parent
ATC: N06DA03
UNII: PKI06M3IW0

Structure
InChI Key XSVMFMHYUFZWBK-NSHDSACASA-N
Smile CCN(C)C(=O)Oc1cccc([C@H](C)N(C)C)c1
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

Physicochemical Descriptors

Property Name Value
Molecular Formula C14H22N2O2
Molecular Weight 250.34
AlogP 2.76
Hydrogen Bond Acceptor 3.0
Hydrogen Bond Donor 0.0
Number of Rotational Bond 4.0
Polar Surface Area 32.78
Molecular species BASE
Aromatic Rings 1.0
Heavy Atoms 18.0

Pharmacology

Action Mechanism of Action Reference
INHIBITOR Cholinesterases; ACHE & BCHE inhibitor FDA
Primary Target
acetylcholinesterase (Cartwright blood group)
butyrylcholinesterase
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Enzyme Hydrolase
- 37-48000 - 5680 25-100
Ion channel Ligand-gated ion channel Nicotinic acetylcholine receptor Nicotinic acetylcholine receptor epsilon subunit
- 9000 - - 2
Membrane receptor
- - - - 18

Indications

Mesh Heading Maximum Phase Mesh ID Reference
Dementia 4 D003704 ClinicalTrials
Depressive Disorder 3 D003866 ClinicalTrials
Cognitive Dysfunction 3 D060825 ClinicalTrials
Supranuclear Palsy, Progressive 3 D013494 ClinicalTrials
Neurobehavioral Manifestations 3 D019954 ClinicalTrials
Dementia, Vascular 3 D015140 ClinicalTrials
Anxiety 3 D001007 ClinicalTrials
Delirium 3 D003693 ClinicalTrials
Brain Injuries 3 D001930 ClinicalTrials
Schizophrenia 3 D012559 ClinicalTrials
Amphetamine-Related Disorders 1 D019969 ClinicalTrials
Substance-Related Disorders 1 D019966 ClinicalTrials
Substance-Related Disorders 1 D019966 ClinicalTrials
Cocaine-Related Disorders 1 D019970 ClinicalTrials
Down Syndrome 1 D004314 ClinicalTrials

Related Entries

Salt

Side Effects from Label

Side effects Relative Frequency (%) Labels
Gastrointestinal disorders Nausea 47.0
Gastrointestinal disorders Nausea 40.0
Gastrointestinal disorders Nausea 38.0
Gastrointestinal disorders Nausea 37.0
Gastrointestinal disorders Vomiting 31.0
Gastrointestinal disorders Nausea 29.0
Gastrointestinal disorders Nausea 27.0
Gastrointestinal disorders Nausea 23.0
Nervous system disorders Tremor 23.0
Gastrointestinal disorders Vomiting 23.0
Cardiac disorders Dizziness 21.0
Gastrointestinal disorders Nausea 21.0
Gastrointestinal disorders Diarrhoea 19.0
Cardiac disorders Dizziness 19.0
Gastrointestinal disorders Vomiting 19.0
General disorders and administration site conditions Decreased appetite 17.0
Nervous system disorders Headache 17.0
Gastrointestinal disorders Nausea 17.0
Gastrointestinal disorders Vomiting 17.0
Gastrointestinal disorders Diarrhoea 16.0
Nervous system disorders Headache 15.0
Gastrointestinal disorders Nausea 15.0
Gastrointestinal disorders Vomiting 15.0
Nervous system disorders Agitation 14.0
Gastrointestinal disorders Vomiting 14.0
Gastrointestinal disorders Abdominal pain 13.0
General disorders and administration site conditions Application site erythema 13.0
General disorders and administration site conditions Decreased appetite 13.0
Gastrointestinal disorders Gastrointestinal pain 13.0
Gastrointestinal disorders Vomiting 13.0
Nervous system disorders Agitation 12.0
General disorders and administration site conditions Application site erythema 12.0
Nervous system disorders Headache
Nervous system disorders Headache 12.0
Gastrointestinal disorders Nausea
Gastrointestinal disorders Nausea 12.0
Gastrointestinal disorders Abdominal pain 11.0
General disorders and administration site conditions Application site erythema 11.0
Gastrointestinal disorders Diarrhoea
Cardiac disorders Dizziness
Gastrointestinal disorders Gastrointestinal pain 11.0
Gastrointestinal disorders Nausea
Gastrointestinal disorders Abdominal pain 10.0
Gastrointestinal disorders Diarrhoea 10.0
Cardiac disorders Dizziness
Cardiac disorders Dizziness 10.0
Gastrointestinal disorders Gastrointestinal pain 10.0
Injury, poisoning and procedural complications Injury 10.0
Gastrointestinal disorders Nausea 10.0
Nervous system disorders Tremor 10.0
Infections and infestations Urinary tract infection 10.0
Gastrointestinal disorders Vomiting 10.0
General disorders and administration site conditions Asthenia 9.0
General disorders and administration site conditions Decreased appetite 9.0
Gastrointestinal disorders Diarrhoea
Gastrointestinal disorders Diarrhoea 9.0
Gastrointestinal disorders Dyspepsia 9.0
General disorders and administration site conditions Fatigue 9.0
Injury, poisoning and procedural complications Injury
Nervous system disorders Insomnia 9.0
Gastrointestinal disorders Nausea
Nervous system disorders Tremor 9.0
Gastrointestinal disorders Vomiting 9.0
General disorders and administration site conditions Asthenia 8.0
Nervous system disorders Confusional state 8.0
Gastrointestinal disorders Diarrhoea 8.0
Cardiac disorders Dizziness 8.0
Gastrointestinal disorders Dyspepsia 8.0
General disorders and administration site conditions Fatigue 8.0
General disorders and administration site conditions Feeling abnormal 8.0
Nervous system disorders Insomnia 8.0
Gastrointestinal disorders Nausea 8.0
Infections and infestations Urinary tract infection 8.0
Gastrointestinal disorders Vomiting 8.0
Investigations Weight decreased 8.0
General disorders and administration site conditions Asthenia 7.0
Nervous system disorders Confusional state
Gastrointestinal disorders Diarrhoea 7.0
Cardiac disorders Dizziness 7.0
General disorders and administration site conditions Fatigue 7.0
General disorders and administration site conditions Feeling abnormal
Nervous system disorders Insomnia
Nervous system disorders Insomnia 7.0
Gastrointestinal disorders Nausea 7.0
Nervous system disorders Tremor 7.0
Infections and infestations Urinary tract infection 7.0
Gastrointestinal disorders Vomiting 7.0
Investigations Weight decreased 7.0
Gastrointestinal disorders Abdominal pain
General disorders and administration site conditions Application site erythema 6.0
General disorders and administration site conditions Asthenia 6.0
General disorders and administration site conditions Decreased appetite 6.0
Psychiatric disorders Depression 6.0
Gastrointestinal disorders Diarrhoea 6.0
Cardiac disorders Dizziness 6.0
Gastrointestinal disorders Gastrointestinal pain
Nervous system disorders Headache 6.0
Nervous system disorders Insomnia 6.0
Gastrointestinal disorders Nausea 6.0
Nervous system disorders Somnolence 6.0
Infections and infestations Urinary tract infection
Gastrointestinal disorders Vomiting
Gastrointestinal disorders Vomiting 6.0
Gastrointestinal disorders Abdominal pain 5.0
Nervous system disorders Agitation 5.0
Psychiatric disorders Anxiety 5.0
General disorders and administration site conditions Application site erythema 5.0
General disorders and administration site conditions Asthenia
General disorders and administration site conditions Asthenia 5.0
Gastrointestinal disorders Constipation 5.0
General disorders and administration site conditions Decreased appetite
General disorders and administration site conditions Decreased appetite 5.0
Psychiatric disorders Depression 5.0
Gastrointestinal disorders Diarrhoea 5.0
General disorders and administration site conditions Discomfort 5.0
General disorders and administration site conditions Fatigue
General disorders and administration site conditions Fatigue 5.0
General disorders and administration site conditions Feeling abnormal 5.0
Gastrointestinal disorders Gastrointestinal pain 5.0
Psychiatric disorders Hallucination 5.0
General disorders and administration site conditions Ill-defined disorder 5.0
General disorders and administration site conditions Malaise 5.0
Gastrointestinal disorders Nausea
Gastrointestinal disorders Nausea 5.0
Nervous system disorders Somnolence 5.0
Infections and infestations Urinary tract infection 5.0
Gastrointestinal disorders Vomiting 5.0
Investigations Weight decreased 5.0
Gastrointestinal disorders Abdominal pain
Gastrointestinal disorders Abdominal pain 4.0
Gastrointestinal disorders Abdominal pain upper 4.0
Nervous system disorders Agitation 4.0
Psychiatric disorders Anxiety 4.0
General disorders and administration site conditions Application site pruritus 4.0
General disorders and administration site conditions Asthenia
General disorders and administration site conditions Asthenia 4.0
Nervous system disorders Bradykinesia 4.0
Gastrointestinal disorders Constipation
General disorders and administration site conditions Decreased appetite 4.0
Psychiatric disorders Depression
Psychiatric disorders Depression 4.0
Gastrointestinal disorders Diarrhoea
Gastrointestinal disorders Diarrhoea 4.0
General disorders and administration site conditions Discomfort 4.0
Cardiac disorders Dizziness
Cardiac disorders Dizziness 4.0
Gastrointestinal disorders Dyspepsia
General disorders and administration site conditions Fatigue
General disorders and administration site conditions Fatigue 4.0
General disorders and administration site conditions Feeling abnormal 4.0
Gastrointestinal disorders Flatulence 4.0
General disorders and administration site conditions Gait disturbance 4.0
Gastrointestinal disorders Gastrointestinal pain
Gastrointestinal disorders Gastrointestinal pain 4.0
Psychiatric disorders Hallucination 4.0
Nervous system disorders Headache 4.0
General disorders and administration site conditions Hyperhidrosis 4.0
Nervous system disorders Hypokinesia 4.0
General disorders and administration site conditions Ill-defined disorder 4.0
Nervous system disorders Insomnia 4.0
General disorders and administration site conditions Malaise 4.0
Gastrointestinal disorders Nausea
Gastrointestinal disorders Nausea 4.0
Psychiatric disorders Nervousness 4.0
Infections and infestations Rhinitis 4.0
Nervous system disorders Somnolence 4.0
Psychiatric disorders Tension 4.0
Nervous system disorders Tremor
Nervous system disorders Tremor 4.0
Infections and infestations Urinary tract infection 4.0
Gastrointestinal disorders Vomiting 4.0
Gastrointestinal disorders Abdominal pain
Gastrointestinal disorders Abdominal pain 3.0
Gastrointestinal disorders Abdominal pain upper 3.0
Psychiatric disorders Aggression 3.0
Nervous system disorders Agitation 3.0
Psychiatric disorders Anxiety
Psychiatric disorders Anxiety 3.0
General disorders and administration site conditions Application site pruritus 3.0
General disorders and administration site conditions Asthenia
General disorders and administration site conditions Asthenia 3.0
Nervous system disorders Bradykinesia 3.0
Cardiac disorders Cardiovascular disorder 3.0
Musculoskeletal and connective tissue disorders Cogwheel rigidity 3.0
General disorders and administration site conditions Decreased appetite
General disorders and administration site conditions Decreased appetite 3.0
Psychiatric disorders Depression 3.0
Gastrointestinal disorders Diarrhoea
Cardiac disorders Dizziness 3.0
Nervous system disorders Dyskinesia 3.0
General disorders and administration site conditions Fatigue
General disorders and administration site conditions Fatigue 3.0
Gastrointestinal disorders Gastrointestinal pain
Gastrointestinal disorders Gastrointestinal pain 3.0
Psychiatric disorders Hallucination
Nervous system disorders Headache
Nervous system disorders Headache 3.0
General disorders and administration site conditions Hyperhidrosis 3.0
Vascular disorders Hypertension 3.0
General disorders and administration site conditions Influenza like illness 3.0
Nervous system disorders Insomnia 3.0
Nervous system disorders Loss of consciousness 3.0
Gastrointestinal disorders Nausea 3.0
Psychiatric disorders Nervousness
Nervous system disorders Parkinsonism 3.0
Nervous system disorders Parkinson's disease 3.0
Infections and infestations Rhinitis
Vascular disorders Shock 3.0
Nervous system disorders Somnolence
Nervous system disorders Somnolence 3.0
Cardiac disorders Syncope 3.0
Psychiatric disorders Tension
Nervous system disorders Tremor
Nervous system disorders Tremor 3.0
Nervous system disorders Urinary incontinence 3.0
Infections and infestations Urinary tract infection 3.0
Gastrointestinal disorders Vomiting
Gastrointestinal disorders Vomiting 3.0
Investigations Weight decreased 3.0
Gastrointestinal disorders Abdominal pain 2.0
Gastrointestinal disorders Abdominal pain upper
Gastrointestinal disorders Abdominal pain upper 2.0
Psychiatric disorders Aggression
Psychiatric disorders Aggression 2.0
Nervous system disorders Agitation
Nervous system disorders Agitation 2.0
Psychiatric disorders Anxiety 2.0
General disorders and administration site conditions Application site erythema 2.0
General disorders and administration site conditions Asthenia
General disorders and administration site conditions Asthenia 2.0
Nervous system disorders Bradykinesia
Nervous system disorders Bradykinesia 2.0
Cardiac disorders Cardiovascular disorder
General disorders and administration site conditions Decreased appetite
General disorders and administration site conditions Decreased appetite 2.0
Metabolism and nutrition disorders Dehydration 2.0
Psychiatric disorders Depression 2.0
Gastrointestinal disorders Diarrhoea 2.0
General disorders and administration site conditions Discomfort
Cardiac disorders Dizziness
Cardiac disorders Dizziness 2.0
Cardiac disorders Dyspnoea 2.0
Gastrointestinal disorders Eructation 2.0
General disorders and administration site conditions Fatigue 2.0
General disorders and administration site conditions Feeling abnormal
Gastrointestinal disorders Flatulence
Gastrointestinal disorders Gastrointestinal pain 2.0
Psychiatric disorders Hallucination 2.0
Nervous system disorders Headache
General disorders and administration site conditions Hyperhidrosis 2.0
Vascular disorders Hypertension
Vascular disorders Hypertension 2.0
Nervous system disorders Hypokinesia 2.0
General disorders and administration site conditions Ill-defined disorder
General disorders and administration site conditions Influenza like illness
Nervous system disorders Insomnia
Nervous system disorders Insomnia 2.0
Nervous system disorders Loss of consciousness
General disorders and administration site conditions Malaise
Gastrointestinal disorders Nausea 2.0
Nervous system disorders Parkinsonism 2.0
Renal and urinary disorders Pollakiuria 2.0
Skin and subcutaneous tissue disorders Pruritus 2.0
Gastrointestinal disorders Salivary hypersecretion 2.0
Vascular disorders Shock
Nervous system disorders Somnolence
Cardiac disorders Syncope
Nervous system disorders Urinary incontinence
Nervous system disorders Urinary incontinence 2.0
Infections and infestations Urinary tract infection 2.0
Ear and labyrinth disorders Vertigo 2.0
Eye disorders Visual impairment 2.0
Gastrointestinal disorders Vomiting
Gastrointestinal disorders Vomiting 2.0
Investigations Weight decreased 2.0
Skin and subcutaneous tissue disorders Pruritus 1.7
Gastrointestinal disorders Vomiting 1.4
Psychiatric disorders Aggression 1.1
General disorders and administration site conditions Application site pruritus 1.1
Skin and subcutaneous tissue disorders Erythema 1.1
Gastrointestinal disorders Abdominal pain
Gastrointestinal disorders Abdominal pain 1.0
Gastrointestinal disorders Abdominal pain upper
Gastrointestinal disorders Abdominal pain upper 1.0
Psychiatric disorders Aggression 1.0
Nervous system disorders Agitation 1.0
Psychiatric disorders Anxiety
Psychiatric disorders Anxiety 1.0
General disorders and administration site conditions Application site erythema 1.0
General disorders and administration site conditions Application site pruritus 1.0
General disorders and administration site conditions Asthenia
General disorders and administration site conditions Asthenia 1.0
General disorders and administration site conditions Decreased appetite
General disorders and administration site conditions Decreased appetite 1.0
Metabolism and nutrition disorders Dehydration
Metabolism and nutrition disorders Dehydration 1.0
Psychiatric disorders Depression
Gastrointestinal disorders Diarrhoea
Gastrointestinal disorders Diarrhoea 1.0
Cardiac disorders Dizziness
Cardiac disorders Dizziness 1.0
Nervous system disorders Dyskinesia
Cardiac disorders Dyspnoea
Gastrointestinal disorders Eructation
General disorders and administration site conditions Fatigue
General disorders and administration site conditions Fatigue 1.0
Gastrointestinal disorders Gastrointestinal pain
Gastrointestinal disorders Gastrointestinal pain 1.0
Nervous system disorders Headache 1.0
General disorders and administration site conditions Hyperhidrosis
Vascular disorders Hypertension 1.0
Nervous system disorders Insomnia 1.0
Gastrointestinal disorders Nausea
Gastrointestinal disorders Nausea 1.0
Nervous system disorders Parkinsonism
Nervous system disorders Parkinson's disease
Renal and urinary disorders Pollakiuria
Skin and subcutaneous tissue disorders Pruritus
Nervous system disorders Somnolence
Nervous system disorders Somnolence 1.0
Nervous system disorders Tremor
Nervous system disorders Tremor 1.0
Nervous system disorders Urinary incontinence 1.0
Infections and infestations Urinary tract infection
Infections and infestations Urinary tract infection 1.0
Ear and labyrinth disorders Vertigo
Ear and labyrinth disorders Vertigo 1.0
Eye disorders Visual impairment
Gastrointestinal disorders Vomiting
Gastrointestinal disorders Vomiting 1.0
Investigations Weight decreased
Investigations Weight decreased 1.0
Gastrointestinal disorders Vomiting 0.9
Psychiatric disorders Aggression 0.7
Psychiatric disorders Aggression 0.4
Gastrointestinal disorders Vomiting 0.4

Adverse Reactions

SOC By Demographic Distribution
System Organ Classification (SOC)
Relative Frequency (%)
Nervous system disorders
15.95
General disorders and administration site conditions
14.87
Psychiatric disorders
13.24
Injury, poisoning and procedural complications
9.46
Gastrointestinal disorders
5.57
Skin and subcutaneous tissue disorders
5.26
Vascular disorders
5.08
Respiratory, thoracic and mediastinal disorders
4.84
Cardiac disorders
4.26
Musculoskeletal and connective tissue disorders
4.05
Investigations
3.72
Infections and infestations
3.33
Metabolism and nutrition disorders
2.81

Cross References

Resources Reference
CAS NUMBER 123441-03-2
ChEBI 8874
ChEMBL CHEMBL636
DrugBank DB00989
DrugCentral 2392
EPA CompTox DTXSID7023564
FDA SRS PKI06M3IW0
Human Metabolome Database HMDB0015124
Guide to Pharmacology 6602
KEGG C11766
PharmGKB PA451262
PubChem 77991
SureChEMBL SCHEMBL2764
ZINC ZINC000000004413
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