Details
Stereochemistry | ACHIRAL |
Molecular Formula | C20H25NO2.ClH |
Molecular Weight | 347.879 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
Cl.CCN(CC)CCOC(=O)C(C1=CC=CC=C1)C2=CC=CC=C2
InChI
InChIKey=LKPINBXAWIMZCG-UHFFFAOYSA-N
InChI=1S/C20H25NO2.ClH/c1-3-21(4-2)15-16-23-20(22)19(17-11-7-5-8-12-17)18-13-9-6-10-14-18;/h5-14,19H,3-4,15-16H2,1-2H3;1H
Molecular Formula | ClH |
Molecular Weight | 36.461 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
Molecular Formula | C20H25NO2 |
Molecular Weight | 311.418 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
Adiphenine is a ternary amino ligand. It is used as a local anesthetic that reduces the frequency of acetylcholine-induced single-channel currents. It was originally introduced as a spasmolytic agent. Adiphenine reduced the muscle tone of the gastrointestinal tract, bile duct and gallbladder, bronchi, bladder. It affects the tone of the muscles of the eye, causing the pupil dilated (mydriasis), increased intraocular pressure, and paralysis of accommodation. Influences on the cardiovascular system, causing tachycardia and improving AV-conduction. Adiphenine side effects are: nausea, vomiting, heartburn, dizziness, headache. Adiphenine has not been widely used clinically.
CNS Activity
Sources: https://www.ncbi.nlm.nih.gov/pubmed/6112821
Curator's Comment: Known to be CNS penetrant in mice and rats. Human data not available.
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL3137264 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19422391 |
|||
Target ID: CHEMBL1907609 Sources: https://www.ncbi.nlm.nih.gov/pubmed/3404446 |
198.0 nM [Ki] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | Trasentine Approved UseAdiphenine is indicated for the treatment of spasms of smooth muscles of the digestive tract, bile ducts, bronchi. |
|||
Sources: https://www.ncbi.nlm.nih.gov/pubmed/19422391 |
Primary | Trasentine Approved UseUnknown |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as perpetrator​
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
no [Activation >10 uM] | ||||
no [Activation >10 uM] | ||||
no [Activation >10 uM] | ||||
yes [Activation 5.01187 uM] | ||||
yes [Activation 5.01187 uM] | ||||
yes [IC50 158.4 uM] | ||||
yes [Inhibition 10 uM] | ||||
yes [Inhibition 10 uM] |
PubMed
Title | Date | PubMed |
---|---|---|
[Effect of several neuroleptic, adreno-, sympatho- and cholinolytic substances on the development of experimental cerebral edema induced by nicotine]. | 1977 May-Jun |
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[A case of a rare side effects of paxil therapy in a male patient with irritable colon syndrome]. | 2001 |
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By the way, doctor. I've been taking Paxil for depression for about six months. Although it's helped my symptoms of depression, I've lost interest in sex. Aside from stopping the medication, is there any way to regain my sexual function? | 2001 Feb |
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Receptor protection studies to characterize neuronal nicotinic receptors: tubocurarine prevents alkylation of adrenal nicotinic receptors. | 2001 Feb 9 |
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New use for Paxil approved. | 2001 Jul-Aug |
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Serotonin reuptake inhibitor (Paxil) does not prevent the vasovagal reaction associated with carotid sinus massage and/or lower body negative pressure in healthy volunteers. | 2002 Sep 17 |
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Causality and collateral estoppel: process and content of recent SSRI litigation. | 2003 |
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Adolescents searching for health information on the Internet: an observational study. | 2003 Oct 17 |
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A taxpayer-funded clinical trials registry and results database. | 2004 Dec |
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Environmental risk assessment of paroxetine. | 2004 Jun 15 |
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Acute and chronic toxicity of five selective serotonin reuptake inhibitors in Ceriodaphnia dubia. | 2004 Sep |
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Manufacturing violations prompt seizure of Paxil CR, Avandamet. | 2005 May-Jun |
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Medicine as a corporate enterprise, patient welfare centered profession, or patient welfare centered professional enterprise? | 2005 Nov |
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Damming the flow of drugs into drinking water. | 2005 Oct |
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Disease mongering in drug promotion: do governments have a regulatory role? | 2006 Apr |
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[Selective serotonin reuptake inhibitors (SSRIs) in pregnancy]. | 2006 Apr 12 |
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There is no such thing as a psychiatric disorder/disease/chemical imbalance. | 2006 Jul |
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Paxil and the risk of birth defects. | 2006 Mar-Apr |
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Urticarial vasculitis secondary to paroxetine. | 2006 Nov-Dec |
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Effect of generic-only drug benefits on seniors' medication use and financial burden. | 2006 Sep |
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Paroxetine versus placebo and other agents for depressive disorders: a systematic review and meta-analysis. | 2007 Dec |
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Paroxetine and congenital malformations: meta-Analysis and consideration of potential confounding factors. | 2007 May |
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Prevalence and predictors of antidepressant use in a cohort of pregnant women. | 2007 Sep |
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(3S,4R)-4-(4-Fluoro-phen-yl)-3-(hydroxy-meth-yl)piperidinium chloride. | 2008 Apr 4 |
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Trial registration for public trust: making the case for medical devices. | 2008 Jan |
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Nutritional therapies for mental disorders. | 2008 Jan 21 |
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The local anaesthetics proadifen and adiphenine inhibit nicotinic receptors by different molecular mechanisms. | 2009 Jul |
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Planning Future Strategies for Domestic and International NeuroAIDS Research, July 24-25, 2008. | 2009 Sep |
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Adverse drug effects in hospitalized elderly: data from the healthcare cost and utilization project. | 2010 |
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Legal remedies for medical ghostwriting: imposing fraud liability on guest authors of ghostwritten articles. | 2010 Aug |
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The chemical basis of pharmacology. | 2010 Dec 7 |
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Of sophists and spin-doctors: industry-sponsored ghostwriting and the crisis of academic medicine. | 2010 Jan |
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Desvenlafaxine in major depressive disorder: an evidence-based review of its place in therapy. | 2010 Jun 15 |
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Negotiating the boundary between medicine and consumer culture: online marketing of nutrigenetic tests. | 2010 Mar |
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Could chiropractors screen for adverse drug events in the community? Survey of US chiropractors. | 2010 Nov 17 |
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The haunting of medical journals: how ghostwriting sold "HRT". | 2010 Sep 7 |
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Screening of a chemical library reveals novel PXR-activating pharmacologic compounds. | 2015 Jan 5 |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.piluli.kharkov.ua/drugs/drug/195/
50-100 mg 2-3-4 times per day. Course of treatment - 3-4 weeks.
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/19422391
Adiphenine decreased the frequency of ACh-induced single-channel currents. Adiphenine decreased cluster duration (36-fold at 100 uM x L(-1)). Preincubation with adiphenine did not change amplitude but increased the decay rate (IC(50)= 15 uM x L(-1)).
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 15:16:05 UTC 2023
by
admin
on
Fri Dec 15 15:16:05 UTC 2023
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Record UNII |
42B4PDY0AV
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Record Status |
Validated (UNII)
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Record Version |
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C29704
Created by
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200-036-9
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5763
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100000078855
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C75271
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50-42-0
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SUB00305MIG
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129224
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m1419
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DTXSID0045880
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CHEMBL353846
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235433
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42B4PDY0AV
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