Details
Stereochemistry | ACHIRAL |
Molecular Formula | C21H27NO2 |
Molecular Weight | 325.4446 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CCN(CC)CCOC(=O)C(C)(C1=CC=CC=C1)C2=CC=CC=C2
InChI
InChIKey=DIDYGLSKVUKRRP-UHFFFAOYSA-N
InChI=1S/C21H27NO2/c1-4-22(5-2)16-17-24-20(23)21(3,18-12-8-6-9-13-18)19-14-10-7-11-15-19/h6-15H,4-5,16-17H2,1-3H3
Molecular Formula | C21H27NO2 |
Molecular Weight | 325.4446 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
Aprofene (widely known as aprophen or Апрофен (in Russia)), a Soviet drug, is an antagonist of muscarinic and nicotinic acetylcholine receptors. It had been used in Russia for the treatment of endarteritis (inflammation of the inner shell of the artery), peptic ulcer of the stomach and duodenum, spastic colitis (inflammation of the colon characterized by sharp contractions), cholecystitis (inflammation of the gallbladder) until was included in the list of psychotropic substances.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: CHEMBL2094109 Sources: https://www.ncbi.nlm.nih.gov/pubmed/3683366 |
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Target ID: nicotinic acetylcholine receptor Sources: https://www.ncbi.nlm.nih.gov/pubmed/3683366 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | Апрофен Approved UseUnknown |
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Primary | Апрофен Approved UseUnknown |
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Primary | Апрофен Approved UseUnknown |
PubMed
Title | Date | PubMed |
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[Pharmacology of a new spasmolytic drug aprophen]. | 1957 Jul-Aug |
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Diphasic action of 2,2-diphenylpropionic acid N,N-diethylaminoethyl ester hydrochloride on hepatic drug metabolism in the mouse. | 1982 Oct 15 |
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Aprophen: a substrate and inhibitor of butyrylcholinesterase and carboxylesterases. | 1985 Jun 15 |
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The muscarinic antagonists aprophen and benactyzine are noncompetitive inhibitors of the nicotinic acetylcholine receptor. | 1987 Nov |
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[The results of inducing labor with aprofen]. | 1988 |
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[Delivery in prolonged pregnancy following preparation and induction with aprofen and prednisolone]. | 1990 |
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Effects of selected anticholinergics on acoustic startle response in rats. | 2001 Dec |
Sample Use Guides
In Vivo Use Guide
Sources: https://www.piluli.kharkov.ua/drugs/drug/174/
oral: 0.025 g 2-4 times/day after the meal
intramuscular or subcutaneous: 0.5-1 mL of 1% solution
Route of Administration:
Other
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/3683366
It was studied the interaction of aprophen with nicotinic acetylcholine receptor (AChR) in BC3H-1 intact muscle cells and with receptor-enriched membranes of Torpedo californica. Aprophen diminished the maximal carbamylcholine-elicited sodium influx into muscle cells without shifting Kact (carbamylcholine concentration eliciting 50% of the maximal 22Na+ influx). Aprophen interacted with the AChR in its desensitized state in BC3H-1 cells without further enhancing agonist affinity. The affinity of aprophen for the allosterically coupled noncompetitive inhibitor site of the AChR in Torpedo was determined using [3H]phencyclidine as a probe. This compound was found to preferentially associate with the high affinity (desensitized) state rather than the resting state of Torpedo AChR. Thus, aprophen was the effective noncompetitive inhibitor of the AChR at concentrations of 1-50 microM, in either Torpedo or mammalian AChR.
Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Dec 16 15:57:30 GMT 2023
by
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on
Sat Dec 16 15:57:30 GMT 2023
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Record UNII |
PL791XXJ7B
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Record Status |
Validated (UNII)
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Record Version |
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C29707
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100000087163
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DTXSID8046294
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CHEMBL26505
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71128
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C006615
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C73106
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SALT/SOLVATE -> PARENT |
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ACTIVE MOIETY |