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Aceclidin

Aceclidine

HCID 1979
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Grundinformationen

CAS
827-61-2
Standard-SMILES
CC(=O)OC1CN2CCC1CC2
InChIKey
WRJPSSPFHGNBMG-UHFFFAOYSA-N
Summenformel
C9H15NO2
Durchschnittliche Molmasse
169,22 g/mol
Monoisotopische Masse
169,11027872

Namen und Bezeichner

Bevorzugter Name
Aceclidine
IUPAC
1-azabicyclo[2.2.2]octan-3-yl acetate
Lokaler Name
Aceclidin
Englischer Name
Aceclidine
Summenformel
C9H15NO2
Molmasse
169.22

Namen und Synonyme

aceclidine827-61-23-Acetoxyquinuclidine3-Quinuclidinol acetate (ester)AceclidinaAceclidinum3-Quinuclidinol acetate1-Azabicyclo(2.2.2)octan-3-ol, acetate (ester)DTXSID2045658NSC-657843NSC-7582390578K3ELIO
Weitere Namen anzeigen
quinuclidin-3-yl acetateNSC657843NSC 6578433-Quinuclidinyl acetateQuinuclidine-3-ol acetate3-Quinuclidinol acetate ester
1-Azabicyclo(2.2.2)octan-3-ol, acetateacetic acid quinuclidin-3-yl esterDTXCID00256581-Azabicyclo[2.2.2]octan-3-ol, acetate (ester)aceclidin3-quinuclidinol dl-form acetate (ester)1-Azabicyclo[2.2.2]octan-3-ol, acetateRefChem:914942

Datenbank-Bezeichner

CAS
827-61-2
PubChem CID
1979
DTXSID
DTXSID2045658
ChEMBL
CHEMBL20835
ChEBI
CHEBI:93847
UNII
0578K3ELIO
EC Number
212-574-1
Nikkaji
J48.379F

Eigenschaften

Berechnete Struktureigenschaften

XLogP
0,7
Polarare Oberfläche (TPSA)
29,5 Ų
H-Brücken-Donoren
0
H-Brücken-Akzeptoren
3
Frei drehbare Bindungen
2
Schwere Atome
12
Formalladung
0
Komplexität
185

Experimentelle und physikochemische Eigenschaften

Collision Cross Section · 2 Einträge

135.39 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

136.2 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

Physikochemische Eigenschaften

Siedepunkt
298.52 °C · 298.52°C (rough estimate)
Dichte
1.0873 · 1.0873 (rough estimate)
Brechungsindex
1.478 · 1.4780 (estimate)
storage temp.
-20 °C · Sealed in dry,Store in freezer, under -20°C
Aggregatzustand
36 °C · 36°C Liquid
pka
9.22 · 9.22±0.33(Predicted)
Farbe
Off-white to light yellow
InChI
InChI=1S/C9H15NO2/c1-7(11)12-9-6-10-4-2-8(9)3-5-10/h8-9H,2-6H2,1H3
InChIKey
WRJPSSPFHGNBMG-UHFFFAOYSA-N
SMILES
N12CCC(CC1)C(OC(=O)C)C2

Sicherheit und Regulatorisches

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

Sicherheitsdaten

Toxizität
LD50 scu-rat: 225 mg/kg ARZNAD 18,320,68

Chemie und Industrie

Pharmakologische Informationen

ATC Code · 2 Einträge

S - Sensory organs;S01 - Ophthalmologicals;S01E - Antiglaucoma preparations and miotics;S01EB - Parasympathomimetics;S01EB08 - Aceclidine

QS - Sensory organs;QS01 - Ophthalmologicals;QS01E - Antiglaucoma preparations and miotics;QS01EB - Parasympathomimetics;QS01EB08 - Aceclidine

Pharmacodynamics · 1 Eintrag

Aceclidine is a cholinergic muscarinic agonist that stimulates miosis in order to extend the depth of focus to improve vision. Systemic exposure to aceclidine and its metabolites following topical ocular administration is low. The onset of effect for presbyopia treatment is observed within 30 minutes, and the effect can last up to 10 hours. Patients may experience temporary dim or dark vision and should exercise caution with night driving or other hazardous activities in poor illumination. Rare cases of retinal tears and detachments have been reported with miotics, and patients should be advised to seek immediate medical care for sudden onset of flashing lights, floaters, or vision loss. Caution is also advised in patients with a history of iritis, as miotics may exacerbate ocular inflammation.

Mechanism of Action · 1 Eintrag

Presbyopia is a common age-related condition characterized by the inability of the eye to accommodate and focus properly on objects at different distances, leading to near vision loss. Aceclidine is a selective cholinergic muscarinic agonist that treats presbyopia by stimulating muscarinic receptors located on smooth muscles. It is a predominately pupil-selective miotic, interacting primarily with the iris with minimal ciliary muscle stimulation. This interaction causes contraction of the iris sphincter muscle, which results in a pinhole effect that extends the depth of focus and improves vision.

Biological Half-LifeThe half-life of aceclidine could not be estimated at any timepoint due to the limited amount of quantifiable concentrations of drug product following ophthalmic dosing.
Metabolism/MetabolitesAceclidine undergoes hydrolysis in the eye to acetate and 3-quinuclidinol (3-Q), with one mole of aceclidine being hydrolyzed to one mole of 3-Q.
FDA Pharmacological Classification · 6 Einträge

0578K3ELIO

ACECLIDINE

Established Pharmacologic Class [EPC] - Cholinergic Receptor Agonist

Mechanisms of Action [MoA] - Cholinergic Muscarinic Agonists

Aceclidine is a Cholinergic Receptor Agonist. The mechanism of action of aceclidine is as a Cholinergic Muscarinic Agonist.

ACECLIDINE

MeSH Pharmacological Classification · 2 Einträge

Agents causing contraction of the pupil of the eye. Some sources use the term miotics only for the parasympathomimetics but any drug used to induce miosis is included here.

Drugs that mimic the effects of parasympathetic nervous system activity. Included here are drugs that directly stimulate muscarinic receptors and drugs that potentiate cholinergic activity, usually by slowing the breakdown of acetylcholine (CHOLINESTERASE INHIBITORS). Drugs that stimulate both sympathetic and parasympathetic postganglionic neurons (GANGLIONIC STIMULANTS) are not included here.

Absorption, Distribution and Excretion · 1 Eintrag

Systemic exposure of aceclidine was evaluated in 16 subjects with presbyopia following once daily administration for 8 days. The mean Cmax and AUC0-t values for 3-Q, the primary metabolite formed from the hydrolysis of aceclidine, after the 8-day interval were 2,114 ng/mL and 4,899 hr*ng/mL, respectively.

Anwendungen

Verwendenanalgesic (topical), depletes Substance P, neurotoxic

Vor- und nachgelagerte Produkte

Vorgelagerte Rohstoffe

KaliumWasserstoffEthyl-bromacetatMethylisonicotinatKaliumhydrogenphthalatChinuclidin-3-olWasserEssigsäureanhydridPyridin

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