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Rivastigmine

HCID 77991
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GrundinformationenNamen und BezeichnerEigenschaftenSicherheit und RegulatorischesChemie und IndustrieZugehörige ReaktionenNotizen zur Verbindung
TeilstruktursucheÄhnliche Strukturen suchen

Grundinformationen

CAS
123441-03-2
Standard-SMILES
CCN(C)C(=O)Oc1cccc([C@H](C)N(C)C)c1
InChIKey
XSVMFMHYUFZWBK-NSHDSACASA-N
Summenformel
C14H22N2O2
Durchschnittliche Molmasse
250,34 g/mol
Monoisotopische Masse
250,16812795

Namen und Bezeichner

Bevorzugter Name
Rivastigmine
IUPAC
[3-[(1S)-1-(dimethylamino)ethyl]phenyl] N-ethyl-N-methylcarbamate
Englischer Name
Rivastigmine
Summenformel
C14H22N2O2
Molmasse
250.34

Namen und Synonyme

rivastigmine123441-03-2PrometaxENA 713 free baseNimvastidRivastigmine Tevarivastigmine hexalSDZ-ENA-713RivastigminaSDZ-212-713Rivastigmine sandozPKI06M3IW0
Weitere Namen anzeigen
RIVASTIGMINE HYDROGEN TARTRATEmineEXELONRivastigmine baseRivastigKabaratincabalatineRevastigmineRivastigiMine
m-((S)-1-(Dimethylamino)ethyl)phenyl ethylmethylcarbamate(S)-3-(1-(Dimethylamino)ethyl)phenyl ethylmethylcarbamateRivastigmine Transdermal SystemSDZ 212-713ENA-713D3-[(1S)-1-(dimethylamino)ethyl]phenyl N-ethyl-N-methylcarbamateONO-2540SDZ-212713

Datenbank-Bezeichner

CAS
123441-03-2
PubChem CID
77991
DTXSID
DTXSID7023564
ChEMBL
CHEMBL636
ChEBI
CHEBI:8874
UNII
PKI06M3IW0
EC Number
602-936-0
Nikkaji

Eigenschaften

Berechnete Struktureigenschaften

XLogP
2,3
Polarare Oberfläche (TPSA)
32,8 Ų
H-Brücken-Donoren
0
H-Brücken-Akzeptoren
3
Frei drehbare Bindungen
5
Schwere Atome
18
Formalladung
0
Komplexität
269

Experimentelle und physikochemische Eigenschaften

LogP · 2 Einträge

2.3

2.3

Solubility2.04e+00 g/L
Physical DescriptionSolid
Dissociation Constants · 2 Einträge

8.8

8.99

Collision Cross Section165 Ų [M+H]+ [CCS Type: TW; Method: Major Mix IMS/Tof Calibration Kit (Waters)]

Physikochemische Eigenschaften

Siedepunkt
316.2 · 316.2±34.0 °C(Predicted)
Dichte
1.038 · 1.038±0.06 g/cm3(Predicted)
Flammpunkt
145 ℃ · 145℃
storage temp.
-20 °C · Sealed in dry,Store in freezer, under -20°C
Löslichkeit
Chloroform (Sparingly), Ethyl Acetate (Slightly)
Aggregatzustand
Powder

Sicherheit und Regulatorisches

Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.

GHS-Klassifizierung

GHS Classification · 6 Einträge

This chemical does not meet GHS hazard criteria for 6.2% (1 of 16) of reports.

Danger

H300 (31.2%): Fatal if swallowed [Danger Acute toxicity, oral];H301 (62.5%): Toxic if swallowed [Danger Acute toxicity, oral];H312 (56.2%): Harmful in contact with skin [Warning Acute toxicity, dermal];H332 (56.2%): Harmful if inhaled [Warning Acute toxicity, inhalation];H411 (62.5%): Toxic to aquatic life with long lasting effects [Hazardous to the aquatic environment, long-term hazard]

P261, P264, P270, P271, P273, P280, P301+P316, P302+P352, P304+P340, P317, P321, P330, P362+P364, P391, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 16 reports by companies from 6 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.;Reported as not meeting GHS hazard criteria per 1 of 16 reports by companies.;There are 5 notifications provided by 15 of 16 reports by companies with hazard statement code(s).;Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.

Gefahrenhinweise

Hazard Classes and CategoriesAcute Tox. 2 (31.2%);Acute Tox. 3 (62.5%);Acute Tox. 4 (56.2%);Acute Tox. 4 (56.2%);Aquatic Chronic 2 (62.5%)

Toxikologische Informationen

Hepatotoxicity · 1 Eintrag

In large placebo controlled trials, rivastigmine therapy was not associated with an increased rate of serum enzyme elevations compared to placebo treatment and no instances of clinically apparent liver injury with jaundice were reported. Nevertheless, since its introduction into clinical use, rivastigmine (administered by transdermal patch) has been implicated in at least one report of clinically apparent hepatotoxicity with mild jaundice. The time to onset was 2 months and the serum enzyme elevations had a mildly hepatocellular pattern. Mild rash and eosinophilia were also present, but autoimmune features were not. Recovery was complete within 5 weeks of drug discontinuation.;Likelihood score: D (possible, rare cause of clinically apparent drug-induced liver injury).

Chemie und Industrie

Pharmakologische Informationen

ATC Code · 3 Einträge

N06DA03

N - Nervous system;N06 - Psychoanaleptics;N06D - Anti-dementia drugs;N06DA - Anticholinesterases;N06DA03 - Rivastigmine

QN - Nervous system;QN06 - Psychoanaleptics;QN06D - Anti-dementia drugs;QN06DA - Anticholinesterases;QN06DA03 - Rivastigmine

Protein Binding40%
Pharmacodynamics · 1 Eintrag

Rivastigmine 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 Action · 1 Eintrag

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.

Biological Half-Life1.5 hours
Metabolism/MetabolitesRivastigmine is rapidly metabolized by cholinesterase-mediated hydrolysis.

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Auf dieser SeiteGrundinformationenNamen und BezeichnerEigenschaftenSicherheit und RegulatorischesChemie und IndustrieZugehörige ReaktionenNotizen zur Verbindung
J982.502I
pka
8.99 · pKa 8.99 (Uncertain)
Farbe
Colorless to light yellow
Major Application
pharmaceutical (small molecule)
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
InChIKey
XSVMFMHYUFZWBK-NSHDSACASA-N
SMILES
C(OC1=CC=CC([C@@H](N(C)C)C)=C1)(=O)N(CC)C
CAS Datenbank
123441 · 123441-03-2(CAS DataBase Reference)
Adverse Effects · 1 Eintrag

Adverse effects of rivastigmine have received thorough study as it has been on the market for some time. The main adverse effects associated with the use of rivastigmine are gastrointestinal. The primary symptoms are nausea and vomiting. These acute effects primarily occur during the initial dose-escalation phase of therapy with upward dose titration of the drug to achieve a therapeutic dose. These events can be minimized using a slow titration schedule and taking the medication with food if prescribing an oral formulation. In a study done to analyze the safety and tolerability of cholinesterase inhibitors used to treat Alzheimer dementia, researchers found rivastigmine to be the drug to have the highest rate of gastrointestinal side effects.;Common adverse effects include extrapyramidal symptoms, sleep disturbances, muscle cramps, and weakness. These issues are less frequent during the maintenance phase of therapy when the dose is not adjusted, but when the drug is being taken for an extended period, central nervous system effects can occur. However, these central nervous system effects are rather rare in rivastigmine and are more common with its counterpart drug, donepezil.;Studies have shown that using the transdermal patch to deliver rivastigmine is associated with fewer reports of nausea and vomiting. Rivastigmine also has a rare case of angioedema related to its use, although overall very uncommon. While the transdermal route offers decreased rates of gastrointestinal effects, reactions like contact dermatitis are prevalent. Also, allergic reactions to the transdermal patch can manifest as vesicles and edema beyond the boundaries of the patch.;Long-term use of rivastigmine has also been associated with an increased risk of death compared to patients treated with donepezil.

Toxicity Summary · 1 Eintrag

Toxicity to the drug, while rare, should be carefully monitored. Common toxicity manifestations include severe gastrointestinal reactions, allergic cutaneous reactions, and central nervous system effects. All cutaneous reactions due to usage of the patch should prompt immediate removal of the patch for at least 48 hours before reapplying in a new area. Therapy should be discontinued if symptoms last longer than 48 hours or a severe cutaneous reaction occurs.;In addition to serious manifestations of common side effects, clinical staff members should always look for cholinergic crises whenever prescribing anticholinergic medications. Classic manifestations of a patient in crisis can be remembered by the mnemonic DUMBELS - diarrhea, urination, miosis, bradycardia, excitability, lacrimation, salivation/excessive sweating before treatment. Patients experiencing a cholinergic crisis should have atropine followed by pralidoxime to reverse the anticholinergic effects of rivastigmine. While the usual treatment of the crisis involves giving atropine before pralidoxime, a case study done in 2009 showed a successful reversal of cholinergic crisis with just pralidoxime without atropine pretreatment.

Drug Induced Liver Injury · 5 Einträge

Drug-Induced Liver Injury Severity and Toxicity (DILIst)

rivastigmine

DILI Positive

Oral

DOI:10.1016/j.drudis.2019.09.022

Sicherheitsdaten

wgk
WGK 3
ridadr
UN 2810 6.1 / PGIII
hs_code
2924296000
Speicherklasse
6.1A - Combustible acute toxic Cat. 1 and 2very toxic hazardous materials
Hazard Classifications
Acute Tox. 2 OralAquatic Chronic 2
FDA Pharmacological Classification · 6 Einträge

PKI06M3IW0

RIVASTIGMINE

Established Pharmacologic Class [EPC] - Cholinesterase Inhibitor

Mechanisms of Action [MoA] - Cholinesterase Inhibitors

Rivastigmine is a Cholinesterase Inhibitor. The mechanism of action of rivastigmine is as a Cholinesterase Inhibitor.

RIVASTIGMINE

MeSH Pharmacological Classification · 2 Einträge

Drugs that inhibit cholinesterases. The neurotransmitter ACETYLCHOLINE is rapidly hydrolyzed, and thereby inactivated, by cholinesterases. When cholinesterases are inhibited, the action of endogenously released acetylcholine at cholinergic synapses is potentiated. Cholinesterase inhibitors are widely used clinically for their potentiation of cholinergic inputs to the gastrointestinal tract and urinary bladder, the eye, and skeletal muscles; they are also used for their effects on the heart and the central nervous system.

Drugs intended to prevent damage to the brain or spinal cord from ischemia, stroke, convulsions, or trauma. Some must be administered before the event, but others may be effective for some time after. They act by a variety of mechanisms, but often directly or indirectly minimize the damage produced by endogenous excitatory amino acids.

Absorption, Distribution and Excretion · 3 Einträge

Rivastigmine 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.

1.8 to 2.7 L/kg

renal cl=2.1-2.8 L/hr

Cellular LocationsCytoplasm;Membrane

Verwendung und Herstellung

UsesUse (kg; approx.) in Germany (2009): >100;Consumption (g per capita; approx.) in Germany (2009): 0.00122;Calculated removal (%): 23.6
Anwendungen · 2 Einträge

HistoryRivastigmine was discovered by Marta Weinstock-Rosin of the Department of Pharmacology at the Hebrew University of Jerusalem and sold to Novartis by Yissum for commercial development. Rivastigmine, sold under the brand name Exelon among others, is an acetylcholinesterase inhibitor used for the treatment of dementia associated with Alzheimer's disease and with Parkinson's disease.

VerwendenAntidepressant

Vor- und nachgelagerte Produkte

Vorgelagerte Rohstoffe

(S)-1-(3-(ethyl(methyl)carbamoyloxy)phenyl)-N,N-dimethyl-N-((S)-1-phenylethyl)ethanaminium iodideRivastigmine hydrochlorideCarbamic acid, N-ethyl-N-methyl-, 3-[(1S)-1-aminoethyl]phenyl ester1257519-35-9Methanamine, N-(benzoyloxy)-N-methyl-3-(1-(Dimethylamino)ethyl]phenol3-[(1S)-1-(Dimethylaminoethyl)]phenolEthylmethyl-carbamic chlorideRivastigmine EP Impurity E3-(1-hydroxyethyl)phenyl ethyl(methyl)carbamate(R)-3-(1-hydroxyethyl)phenylethyl(methyl)carbamate

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Ergänzende Hinweise

DefinitionChEBI: A carbamate ester obtained by formal condensation of the carboxy group of ethyl(methyl)carbamic acid with the phenolic OH group of 3-[(1S)-1-(dimethylamino)ethyl]phenol. A reversible cholinesterase inhibitor.