Donepezil Hydrochloride

HCID 5741CAS 120011-70-3

Grundinformationen

Standard-SMILES
COc1cc2c(cc1OC)C(=O)C(CC1CCN(Cc3ccccc3)CC1)C2.Cl
InChIKey
XWAIAVWHZJNZQQ-UHFFFAOYSA-N
Summenformel
C24H30ClNO3
Durchschnittliche Molmasse
416 g/mol
Monoisotopische Masse
415,1914215

Namen und Bezeichner

Bevorzugter Name
Donepezil Hydrochloride
IUPAC
2-[(1-benzylpiperidin-4-yl)methyl]-5,6-dimethoxy-2,3-dihydroinden-1-one;hydrochloride
Englischer Name
Donepezil Hydrochloride
Summenformel
C24H30ClNO3
Molmasse
415.95

Namen und Synonyme

Donepezil hydrochloride120011-70-3Donepezil HClBNAGAricept ODTE-2020E2020ADLARITYDTXSID0046698Aricept EvessNSC-737535NSC-758882
Weitere Namen anzeigen
ARICEPTDonepeziDonepezil-d7 HydrochlorideAKOS 226-31DOPEZIL HCLDonepezil HCI6-diMethoxy-2
3O2T2PJ89D1-Benzyl-4-((5,6-dimethoxy-1-indanon)-2-yl)methylpiperidine hclDTXCID8026698NAMZARIC COMPONENT DONEPEZIL HYDROCHLORIDEDonepezil HyrochlorideRefChem:56499Donepezil Hyrochloride 5mgDonepezil Hydrochloride 10mg

Datenbank-Bezeichner

CAS
120011-70-3
PubChem CID
5741
DTXSID
DTXSID0046698
ChEMBL
CHEMBL1678
UNII
3O2T2PJ89D
EC Number
620-543-2

Eigenschaften

Berechnete Struktureigenschaften

Polarare Oberfläche (TPSA)
38,8 Ų
H-Brücken-Donoren
1
H-Brücken-Akzeptoren
4
Frei drehbare Bindungen
6
Schwere Atome
29

Experimentelle und physikochemische Eigenschaften

Collision Cross Section196.6 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

Physikochemische Eigenschaften

Schmelzpunkt
220 · 220-222°C
storage temp.
room temp
Wasserlöslichkeit
Soluble in water
Löslichkeit
10.4 mg/mL · insoluble in EtOH; insoluble in DMSO; ≥10.4 mg/mL in H2O
Aggregatzustand
powder
Farbe
white to off-white

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 5 Einträge

Danger

H300 (17.9%): Fatal if swallowed [Danger Acute toxicity, oral];H301 (76.2%): Toxic if swallowed [Danger Acute toxicity, oral];H319 (79.8%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]

P264, P264+P265, P270, P280, P301+P316, P305+P351+P338, P321, P330, P337+P317, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 84 reports by companies from 15 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.;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 (17.9%);Acute Tox. 3 (76.2%);Eye Irrit. 2 (79.8%)

Toxikologische Informationen

Treatment · 1 Eintrag

If the compound has been ingested, rapid gastric lavage should be performed using 5% sodium bicarbonate. For skin contact, the skin should be washed with soap and water. If the compound has entered the eyes, they should be washed with large quantities of isotonic saline or water. In serious cases, atropine and/or pralidoxime should be administered. Anti-cholinergic drugs work to counteract the effects of excess acetylcholine and reactivate AChE. Atropine can be used as an antidote in conjunction with pralidoxime or other pyridinium oximes (such as trimedoxime or obidoxime), though the use of '-oximes' has been found to be of no benefit, or possibly harmful, in at least two meta-analyses. Atropine is a muscarinic antagonist, and thus blocks the action of acetylcholine peripherally.

Health Effects · 1 Eintrag

Acute exposure to cholinesterase inhibitors can cause a cholinergic crisis characterized by severe nausea/vomiting, salivation, sweating, bradycardia, hypotension, collapse, and convulsions. Increasing muscle weakness is a possibility and may result in death if respiratory muscles are involved. Accumulation of ACh at motor nerves causes overstimulation of nicotinic expression at the neuromuscular junction. When this occurs symptoms such as muscle weakness, fatigue, muscle cramps, fasciculation, and paralysis can be seen. When there is an accumulation of ACh at autonomic ganglia this causes overstimulation of nicotinic expression in the sympathetic system. Symptoms associated with this are hypertension, and hypoglycemia. Overstimulation of nicotinic acetylcholine receptors in the central nervous system, due to accumulation of ACh, results in anxiety, headache, convulsions, ataxia, depression of respiration and circulation, tremor, general weakness, and potentially coma. When there is expression of muscarinic overstimulation due to excess acetylcholine at muscarinic acetylcholine receptors symptoms of visual disturbances, tightness in chest, wheezing due to bronchoconstriction, increased bronchial secretions, increased salivation, lacrimation, sweating, peristalsis, and urination can occur. Certain reproductive effects in fertility, growth, and development for males and females have been linked specifically to organophosphate pesticide exposure. Most of the research on reproductive effects has been conducted on farmers working with pesticides and insecticdes in rural areas. In females menstrual cycle disturbances, longer pregnancies, spontaneous abortions, stillbirths, and some developmental effects in offspring have been linked to organophosphate pesticide exposure. Prenatal exposure has been linked to impaired fetal growth and development. Neurotoxic effects have also been linked to poisoning with OP pesticides causing four neurotoxic effects in humans: cholinergi

Exposure RoutesDonepezil is well absorbed with a relative oral bioavailability of 100% and reaches peak plasma concentrations in 3 to 4 hours.
Toxicity Summary · 1 Eintrag

Donepezil is a cholinesterase or acetylcholinesterase (AChE) inhibitor. A cholinesterase inhibitor (or 'anticholinesterase') suppresses the action of acetylcholinesterase. Because of its essential function, chemicals that interfere with the action of acetylcholinesterase are potent neurotoxins, causing excessive salivation and eye-watering in low doses, followed by muscle spasms and ultimately death. Nerve gases and many substances used in insecticides have been shown to act by binding a serine in the active site of acetylcholine esterase, inhibiting the enzyme completely. Acetylcholine esterase breaks down the neurotransmitter acetylcholine, which is released at nerve and muscle junctions, in order to allow the muscle or organ to relax. The result of acetylcholine esterase inhibition is that acetylcholine builds up and continues to act so that any nerve impulses are continually transmitted and muscle contractions do not stop. Among the most common acetylcholinesterase inhibitors are phosphorus-based compounds, which are designed to bind to the active site of the enzyme. The structural requirements are a phosphorus atom bearing two lipophilic groups, a leaving group (such as a halide or thiocyanate), and a terminal oxygen.

Signs and Symptoms · 1 Eintrag

Symptoms of overdose include severe nausea, vomiting, salivation, sweating, bradycardia, hypotension, respiratory depression, collapse and convulsions. Increasing muscle weakness is a possibility and may result in death if respiratory muscles are involved.

Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).

Sicherheitsdaten

wgk
1
ridadr
UN 2811
hs_code
2933.39.9200
RTECS-Nr.
NK8927885
risk_code
36/37/38
hazard_code
Xi

Chemie und Industrie

Pharmakologische Informationen

Metabolism/Metabolites · 1 Eintrag

Donepezil is metabolized by CYP 450 isoenzymes 2D6 and 3A4 in the liver and also undergoes glucuronidation. The main metabolite, 6-O-desmethyl donepezil, has been reported to inhibit AChE to the same extent as donepezil in vitro. Route of Elimination: Donepezil is both excreted in the urine intact and extensively metabolized to four major metabolites, two of which are known to be active, and a number of minor metabolites, not all of which have been identified. Half Life: 70 hours

FDA Pharmacological Classification · 2 Einträge

DONEPEZIL HYDROCHLORIDE

Cholinesterase Inhibitors [MoA]; Cholinesterase Inhibitor [EPC]

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 used to specifically facilitate learning or memory, particularly to prevent the cognitive deficits associated with dementias. These drugs act by a variety of mechanisms.

Verwendung und Herstellung

UsesFor the palliative treatment of mild to moderate dementia of the Alzheimer's type.
Anwendungen · 1 Eintrag

VerwendenDonepezil hydrochloride is an inhibitor of acetylcholinesterase with a labelled nootropic. It has been used in dose-response experiment to study its efficacy in ameliorating nicotine withdrawal-induced deficits in contextual conditioning in mice. It has also been intraperitoneally injected into rats to study its ability to improve social behavioral deficits, repetitive behavior and hyperactivity. Labeled Donepezil, intended for use as an internal standard for the quantification of Donepezilby GC- or LC-mass spectrometry.

Darstellung · 1 Eintrag

synthetischeDonepezil Hydrochloride is being synthesized from alkylidene or arylidene-2-indanone formed by Aldol condensation chemistry as key intermediates (Sugimoto and co-workers)) followed by catalytic reduction affording donepezil hydrochloride with an overall yield of 27%.Benzyl chloride (1.92 g, 0.0156 mol), potassium carbonate (2.28 g, 0.0165 mol) and PEG-200 (80 mg, 2% by weight) were added to a clear biphasic solution of 2-[(4-piperidyl)methyl]-5,6-dimethoxyindan-1-one 6 (4 g, 0.0138 mol) in 9 : 1 EtOAc–H2O (40 ml). The reaction mixture was heated to 50—55 °C and monitored on TLC. After completion of reaction (14 h), the solid was filtered and the filtrate was washed with water (4 ml). The EtOAc layer was separated, added water (8 ml) and acidified with conc. HCl till a pH 2. EtOAc layer was discarded and the acidic aqueous layer was extracted with CH2Cl2 (2*16 ml). The CH2Cl2 layer was separated, dried over anhydrous Na2SO4, filtered and evaporated under vacuum to yield the crude salt as a residue. The residue was dissolved in methanol (20 ml) followed by the addition of isopropyl ether (40 ml) and stirred for a further 1 h. The precipitated solid was filtered and dried under vacuum to yield pure donepezil hydrochloride.A New Commercially Viable Synthetic Route for Donepezil Hydrochloride

Vor- und nachgelagerte Produkte

Anbieter50 Anbieter

国药集团化学试剂有限公司86-21-63210123 · [email protected]
北京华美互利生物化工010-56205725 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
南京云志欣合生物科技有限公司18115209001 · [email protected]

Ergänzende Hinweise

DefinitionChEBI: Donepezil hydrochloride is a centrally acting reversible acetyl cholinesterase inhibitor. Its main therapeutic use is in the treatment of Alzheimer's disease where it is used to increase cortical acetylcholine.

Zugehörige Reaktionen

59

Verknüpfte Notizen

Wird geladen…