ADIPHENINE

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

Structure Search

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

HIDE SMILES / InChI

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

Description
Sources: Aronson, K. (2015) Meyler's Side Effects of Drugs, page 85, retrieved from: https://books.google.ru/books?id=NOKoBAAAQBAJ | http://www.rusmedserv.com/lekarstva/spazmolitin.html | https://www.ncbi.nlm.nih.gov/pubmed/14038458

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

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Nicotinic acetylcholine receptor alpha1/beta1/epsilon/delta 13 Target ID: CHEMBL3137264 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19422391	Inhibitor 8297
Muscarinic acetylcholine receptor 160 Target ID: CHEMBL1907609 Sources: https://www.ncbi.nlm.nih.gov/pubmed/3404446	Inhibitor 8297		198.0 nM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Spasm 18 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15435188 https://www.ncbi.nlm.nih.gov/pubmed/14353164 https://www.ncbi.nlm.nih.gov/pubmed/13977229	Primary		Withdrawn	Trasentine Approved Use Adiphenine is indicated for the treatment of spasms of smooth muscles of the digestive tract, bile ducts, bronchi.
Pain 614 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19422391	Primary		Withdrawn	Trasentine Approved Use Unknown

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 1587	inhibitor 1767	inhibitor 1852

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
BSEP 402 CYP1A2 1524 CYP2C19 1478 OATP1B1 788 OATP1B3 706

Drug as perpetrator

Target	Modality	Activity
CYP2C19 1553	inhibitor 3277 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwzNjIyIiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDM1Mzg0NiJ9fQ%3D%3D	no [Activation >10 uM]
CYP2C9 1819	inhibitor 3277 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwzMzk3IiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDM1Mzg0NiJ9fQ%3D%3D	no [Activation >10 uM]
CYP3A4 1925	inhibitor 3277 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwzNDAiLCJ1c2VfY3VzdG9tX3F1ZXJ5Ijp0cnVlLCJzZWFyY2hfdGVybSI6IiIsInRleHRfZmlsdGVyIjoiQ0hFTUJMMzUzODQ2In19	no [Activation >10 uM]
CYP1A2 1692	inhibitor 3277 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwzMzU2IiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDM1Mzg0NiJ9fQ%3D%3D	yes [Activation 5.01187 uM]
CYP2D6 1891	inhibitor 3277 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwyODkiLCJ1c2VfY3VzdG9tX3F1ZXJ5Ijp0cnVlLCJzZWFyY2hfdGVybSI6IiIsInRleHRfZmlsdGVyIjoiQ0hFTUJMMzUzODQ2In19	yes [Activation 5.01187 uM]
BSEP 403	inhibitor 3277 Sources: http://www.bindingdb.org/bind/chemsearch/marvin/MolStructure.jsp?monomerid=50395519, https://pubmed.ncbi.nlm.nih.gov/22961681/	yes [IC50 158.4 uM]
OATP1B1 803	inhibitor 3277 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwxNjk3NjY4IiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDU1NTY1NCJ9fQ%3D%3D, https://pubmed.ncbi.nlm.nih.gov/23571415/	yes [Inhibition 10 uM]
OATP1B3 715	inhibitor 3277 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwxNzQzMTIxIiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDU1NTY1NCJ9fQ%3D%3D, https://pubmed.ncbi.nlm.nih.gov/23571415/	yes [Inhibition 10 uM]

Sourcing

Vendor/Aggregator	ID	URL
001 Chemical	DY564988	https://www.001chemical.com/chem/64-95-9
Ambinter	Amb1866835	http://www.ambinter.com/reference/1866835
Aurora Fine Chemicals LLC	K02.237.239	http://online.aurorafinechemicals.com/info?ID=K02.237.239
BLD Pharm	BD01303012	http://www.bldpharm.com/products/64-95-9.html
BOC Sciences	64-95-9	https://www.bocsci.com/2-diethylaminoethyl-2-2-di-phenyl-acetate-cas-64-95-9-item-130836.html
ChemMol	49409913	http://www.chemmol.com/chemmol/49409913.html
Chemspace	CSSS00046194224	https://chem-space.com/CSSS00046194224
MolPort	MolPort-002-579-049	https://www.molport.com/shop/molecule-link/MolPort-002-579-049
Molcore	MC564988	https://www.molcore.com/product/64-95-9
Smolecule	S517271	http://www.smolecule.com/products/s517271
THE BioTek	bt-258061	https://www.thebiotek.com/product/inhibitors/bt-258061
Yuhao Chemical	XJ0042	http://www.chemyuhao.com/64-95-9.html
mcule	MCULE-6767246073	https://mcule.com/MCULE-6767246073/

PubMed

Title	Date	PubMed
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	11175469
Receptor protection studies to characterize neuronal nicotinic receptors: tubocurarine prevents alkylation of adrenal nicotinic receptors.	2001 Feb 9	11164821
Paxil and self-scratching.	2001 Jan	11195562
New use for Paxil approved.	2001 Jul-Aug	11692882
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	12234955
Concerns about Paxil for children.	2003 Sep-Oct	14666887
A taxpayer-funded clinical trials registry and results database.	2004 Dec	15562322
Antidepressant medication use among First Nations peoples residing within British Columbia.	2004 Nov 5	15536588
Acute and chronic toxicity of five selective serotonin reuptake inhibitors in Ceriodaphnia dubia.	2004 Sep	15379001
[Clinical effects of paxil in poststroke rehabilitation].	2005	15704483
Serotonin and depression: a disconnect between the advertisements and the scientific literature.	2005 Dec	16268734
Medicine as a corporate enterprise, patient welfare centered profession, or patient welfare centered professional enterprise?	2005 Nov	22679354
Paxil: part of the process.	2006 Apr	16628835
Disease mongering in drug promotion: do governments have a regulatory role?	2006 Apr	16597181
Rare case of serotonin syndrome with therapeutic doses of paroxetine.	2006 Nov-Dec	17122538
Effect of generic-only drug benefits on seniors' medication use and financial burden.	2006 Sep	16961441
The SSRI trials in children: disturbing implications for academic medicine.	2006 Spring	16862717
Patterns of prescription and self-medication for treating primary dysmenorrhea in a Mexican population.	2007	18605257
Paroxetine versus placebo and other agents for depressive disorders: a systematic review and meta-analysis.	2007 Dec	18162015
Generic entry, reformulations and promotion of SSRIs in the US.	2008	18563951
Paroxetine.	2008 Apr	18345955
Trial registration for public trust: making the case for medical devices.	2008 Jan	18095047
Nutritional therapies for mental disorders.	2008 Jan 21	18208598
[The anxyolytic effect of mild hypobaric hypoxia in a model of post-traumatic stress disorder in rats].	2008 Jul-Aug	18825947
Sequestered evidence and the distortion of clinical practice guidelines.	2009 Spring	19395820
Adverse drug effects in hospitalized elderly: data from the healthcare cost and utilization project.	2010	22291486
Legal remedies for medical ghostwriting: imposing fraud liability on guest authors of ghostwritten articles.	2010 Aug	21829331
The chemical basis of pharmacology.	2010 Dec 7	21058655
Of sophists and spin-doctors: industry-sponsored ghostwriting and the crisis of academic medicine.	2010 Jan	21327175
Could chiropractors screen for adverse drug events in the community? Survey of US chiropractors.	2010 Nov 17	21083911
Screening of a chemical library reveals novel PXR-activating pharmacologic compounds.	2015 Jan 5	25455453

Patents

Sample Use Guides

In Vivo Use Guide

50-100 mg 2-3-4 times per day. Course of treatment - 3-4 weeks.

Route of Administration: Oral

In Vitro Use Guide

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 `Sat Dec 16 16:55:52 GMT 2023` Edited by `admin` on `Sat Dec 16 16:55:52 GMT 2023`
Record UNII	YKG6OR043Q
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ADIPHENINE

Official Name

English

2-(DIETHYLAMINO)ETHYL DIPHENYLACETATE

Systematic Name

English

ADIPHENINE [MART.]

Common Name

English

BENZENEACETIC ACID, .ALPHA.-PHENYL-2-(DIETHYLAMINO)ETHYL ESTER

Common Name

English

ADIPHENINE [MI]

Common Name

English

Adiphenine [WHO-DD]

Common Name

English

ADIPHENINE [HSDB]

Common Name

English

adiphenine [INN]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C29698