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Aceclidine

HCID 1979
NotesReactions

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Basic informationNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
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Basic information

CAS
827-61-2
Standard SMILES
CC(=O)OC1CN2CCC1CC2
InChIKey
WRJPSSPFHGNBMG-UHFFFAOYSA-N
Molecular formula
C9H15NO2
Average molar mass
169.22 g/mol
Monoisotopic mass
169.11027872

Names & identifiers

Preferred name
Aceclidine
IUPAC
1-azabicyclo[2.2.2]octan-3-yl acetate
English name
Aceclidine
Molecular formula
C9H15NO2
Molecular weight
169.22

Names & synonyms

aceclidine827-61-23-Acetoxyquinuclidine3-Quinuclidinol acetate (ester)AceclidinaAceclidinum3-Quinuclidinol acetate1-Azabicyclo(2.2.2)octan-3-ol, acetate (ester)DTXSID2045658NSC-657843NSC-7582390578K3ELIO
Show more names
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

Database identifiers

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

Properties

Computed structural propertiesFilling in

XLogP
0.7
Topological polar surface area
29.5 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
3
Rotatable bonds
2
Heavy atoms
12
Formal charge
0
Complexity
185

Experimental & physicochemical properties

Collision Cross Section · 2 items

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]

Physicochemical properties

Boiling point
298.52 °C · 298.52°C (rough estimate)
Density
1.0873 · 1.0873 (rough estimate)
refractive index
1.478 · 1.4780 (estimate)
storage temp.
-20 °C · Sealed in dry,Store in freezer, under -20°C
form
36 °C · 36°C Liquid
pka
9.22 · 9.22±0.33(Predicted)
color
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

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

Safety data

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

Chemistry & industry

Pharmacology

ATC Code · 2 items

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 item

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 item

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.

Related reactions

5 records
New reaction record
HRID 152867 reaction equation
HRID 152867As productTraining data from https://doi.org/10.1039/C8SC04228D (9/10)
HRID 273676 reaction equation
HRID 273676As productuspto-grants-1995_02
HRID 865902 reaction equation
HRID 865902As productuspto-grants-1996_10
HRID 937483 reaction equation
HRID 937483As productValidation data from https://doi.org/10.1039/C8SC04228D
HRID 1973356 reaction equation
HRID 1973356As productuspto-grants-1976_12

Compound notes

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On this pageBasic informationNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
FDA UNII
578 K3ELIO · 0578K3ELIO
ATC code
1 EB08,S01EB58 · S01EB08,S01EB58
Toxicity
50 scu-rat: · LD50 scu-rat: 225 mg/kg ARZNAD 18,320,68
FDA Pharmacological Classification · 6 items

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 items

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 item

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.

Applications

Usesanalgesic (topical), depletes Substance P, neurotoxic

Upstream & downstream products

Upstream raw materials

PotassiumHydrogenEthyl bromoacetateMethyl isonicotinatePotassium hydrogen phthalate3-QuinuclidinolWaterAcetic anhydridePyridine

Suppliers61 total

上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
上海凌富药物研究有限公司+86(21)5895 0110 19945755304 · [email protected]
Hebei Chuanghai Biotechnology Co., Ltd+86-17732866630 · [email protected]
上海策嵘生物科技有限公司[email protected]
上海麦克林生化科技股份有限公司021-50706066 15221275939 · [email protected]
广州佳途科技股份有限公司81960175-877 18933936954 · [email protected]
普善实业(陕西)有限公司029-81310890 18165209495 · [email protected]
Aladdin Scientific[email protected]
韶远科技(上海)有限公司4000665055 · [email protected]
北京索莱宝科技有限公司010-50973130 17801761073 · [email protected]
安耐吉化学&3A(安徽泽升科技有限公司)021-58432009 400-005-6266 · [email protected]
安耐吉化学&3A(安徽泽升科技股份有限公司)400-0056266 · [email protected]
梯希爱(上海)化工贸易有限公司021-61109150 · [email protected]
北京博奥森生物技术有限公司400-901-9800 18611424007 · [email protected]
湖北扬信医药科技有限公司0714-3999001 19171453112 · [email protected]
上海陶素生化科技有限公司021-33632979 · [email protected]
上海高蹈医药科技有限公司021-15001867143 15001867143 · [email protected]
武汉德拜技术有限公司18086626237 18086626237 · [email protected]
上海陶术生物科技股份有限公司+1-781-999-5354; +1-00000000000 · [email protected]
HANGZHOU LEAP CHEM CO., LTD.+86-571-87711850 +86-15355479329 · [email protected]
西安乐纯化工有限责任公司029-15596886083 15596886083 · [email protected]
广州维奥康药业科技有限公司+86-13424074264; 13726739909 · [email protected]
淄博航宇生物科技发展有限公司13053322091 13053322091 · [email protected]
上海歆硕科技有限公司021-62165619 13917231399 · [email protected]
上海炎泽化工有限公司15345144255 19901447308 · [email protected]
南京熠康达医药科技有限公司18118984557; 18118984557 · [email protected]
山东西亚化学有限公司4009903999 13395398332 · [email protected]
北京硕齐科技有限公司18610542700;18701499489 · [email protected]
上海贤鼎生物科技有限公司021-021-52271985 17721149837 · [email protected]
Shaanxi Dideu New Materials Co. Ltd18192503167 · [email protected]
Shanghai Acmec Biochemical Technology Co., Ltd.+86-18621343501 · [email protected]
江苏艾康生物医药研发有限公司025-58859352 15955137747 · [email protected]
天津希恩思生化科技有限公司400-6387771-6039 18920764717 · [email protected]
ATK CHEMICAL COMPANY LIMITED+undefined-21-51877795 · [email protected]
上海吉至生化科技有限公司021-4009004166/18616739031 18616739031 · [email protected]
上海丝帆医药科技有限公司18916696128 · [email protected]
career henan chemical co+86-0371-86658258 · [email protected]
上海珂华生物科技有限公司021-58581007 18019463053 · [email protected]
上海蓝乐鸟实业有限公司15021845385 · [email protected]
广州同信医药技术有限公司13660719760 · [email protected]
爆牛贸易重庆有限公司+86-023-6139-8061 +86-86-13650506873 · [email protected]
陕西缔都医药化工有限公司029-029-029-81148696 18161915376 · [email protected]
上海皓鸿生物医药科技有限公司400-8210725 4008210725 · [email protected]
TargetMol中国(陶术生物)4008200310 15002144251 · [email protected]
上海凯为化学科技有限公司021-58461859 15821823057 · [email protected]
上海迈瑞尔生化科技有限公司18621169109 · [email protected]
SHANGHAI KEAN TECHNOLOGY CO., LTD.+8613817748580 · [email protected]
上海瀚鸿科技股份有限公司021-54306202 18917919676 · [email protected]
TLC梯尔希(南京)药物研发有限公司18012923235 18012923235 · [email protected]
BOC Sciences+1-631-485-4226 · [email protected]

Additional notes

DefinitionChEBI: Acetic acid 1-azabicyclo[2.2.2]octan-3-yl ester is a member of quinuclidines.