Details
Stereochemistry | ACHIRAL |
Molecular Formula | C20H25NO2 |
Molecular Weight | 311.418 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CCN(CC)CCOC(=O)C(C1=CC=CC=C1)C2=CC=CC=C2
InChI
InChIKey=JGOAIQNSOGZNBX-UHFFFAOYSA-N
InChI=1S/C20H25NO2/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
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 |
---|---|---|
Paxil and self-scratching. | 2001 Jan |
|
Serotonin and depression: a disconnect between the advertisements and the scientific literature. | 2005 Dec |
|
Paroxetine versus placebo and other agents for depressive disorders: a systematic review and meta-analysis. | 2007 Dec |
|
Prevalence and predictors of antidepressant use in a cohort of pregnant women. | 2007 Sep |
|
Nutritional therapies for mental disorders. | 2008 Jan 21 |
|
[The anxyolytic effect of mild hypobaric hypoxia in a model of post-traumatic stress disorder in rats]. | 2008 Jul-Aug |
|
The local anaesthetics proadifen and adiphenine inhibit nicotinic receptors by different molecular mechanisms. | 2009 Jul |
|
Improving introspection to inform free will regarding the choice by healthy individuals to use or not use cognitive enhancing drugs. | 2009 Jun 16 |
|
Planning Future Strategies for Domestic and International NeuroAIDS Research, July 24-25, 2008. | 2009 Sep |
|
Sequestered evidence and the distortion of clinical practice guidelines. | 2009 Spring |
|
Adverse drug effects in hospitalized elderly: data from the healthcare cost and utilization project. | 2010 |
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)).
Name | Type | Language | ||
---|---|---|---|---|
|
Official Name | English | ||
|
Systematic Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English |
Classification Tree | Code System | Code | ||
---|---|---|---|---|
|
NCI_THESAURUS |
C29698
Created by
admin on Sat Dec 16 16:55:53 GMT 2023 , Edited by admin on Sat Dec 16 16:55:53 GMT 2023
|
Code System | Code | Type | Description | ||
---|---|---|---|---|---|
|
m1419
Created by
admin on Sat Dec 16 16:55:53 GMT 2023 , Edited by admin on Sat Dec 16 16:55:53 GMT 2023
|
PRIMARY | Merck Index | ||
|
YKG6OR043Q
Created by
admin on Sat Dec 16 16:55:53 GMT 2023 , Edited by admin on Sat Dec 16 16:55:53 GMT 2023
|
PRIMARY | |||
|
3282
Created by
admin on Sat Dec 16 16:55:53 GMT 2023 , Edited by admin on Sat Dec 16 16:55:53 GMT 2023
|
PRIMARY | |||
|
333
Created by
admin on Sat Dec 16 16:55:53 GMT 2023 , Edited by admin on Sat Dec 16 16:55:53 GMT 2023
|
PRIMARY | RxNorm | ||
|
2031
Created by
admin on Sat Dec 16 16:55:53 GMT 2023 , Edited by admin on Sat Dec 16 16:55:53 GMT 2023
|
PRIMARY | |||
|
100000087702
Created by
admin on Sat Dec 16 16:55:53 GMT 2023 , Edited by admin on Sat Dec 16 16:55:53 GMT 2023
|
PRIMARY | |||
|
Adiphenine
Created by
admin on Sat Dec 16 16:55:53 GMT 2023 , Edited by admin on Sat Dec 16 16:55:53 GMT 2023
|
PRIMARY | |||
|
DTXSID0022561
Created by
admin on Sat Dec 16 16:55:53 GMT 2023 , Edited by admin on Sat Dec 16 16:55:53 GMT 2023
|
PRIMARY | |||
|
C76456
Created by
admin on Sat Dec 16 16:55:53 GMT 2023 , Edited by admin on Sat Dec 16 16:55:53 GMT 2023
|
PRIMARY | |||
|
C084829
Created by
admin on Sat Dec 16 16:55:53 GMT 2023 , Edited by admin on Sat Dec 16 16:55:53 GMT 2023
|
PRIMARY | |||
|
200-599-0
Created by
admin on Sat Dec 16 16:55:53 GMT 2023 , Edited by admin on Sat Dec 16 16:55:53 GMT 2023
|
PRIMARY | |||
|
CHEMBL353846
Created by
admin on Sat Dec 16 16:55:53 GMT 2023 , Edited by admin on Sat Dec 16 16:55:53 GMT 2023
|
PRIMARY | |||
|
94
Created by
admin on Sat Dec 16 16:55:53 GMT 2023 , Edited by admin on Sat Dec 16 16:55:53 GMT 2023
|
PRIMARY | |||
|
SUB05272MIG
Created by
admin on Sat Dec 16 16:55:53 GMT 2023 , Edited by admin on Sat Dec 16 16:55:53 GMT 2023
|
PRIMARY | |||
|
2715
Created by
admin on Sat Dec 16 16:55:53 GMT 2023 , Edited by admin on Sat Dec 16 16:55:53 GMT 2023
|
PRIMARY | |||
|
64-95-9
Created by
admin on Sat Dec 16 16:55:53 GMT 2023 , Edited by admin on Sat Dec 16 16:55:53 GMT 2023
|
PRIMARY |
ACTIVE MOIETY
SALT/SOLVATE (PARENT)