ADIPHENINE HYDROCHLORIDE

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

Structure Search

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

HIDE SMILES / InChI

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https://www.ncbi.nlm.nih.gov/pubmed/14353164 https://www.ncbi.nlm.nih.gov/pubmed/13977229	Primary		Withdrawn	Trasentine Approved Use Adiphenine is indicated for the treatment of spasms of smooth muscles of the digestive tract, bile ducts, bronchi.
Pain 614 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19422391	Primary		Withdrawn	Trasentine Approved Use Unknown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
[A case of a rare side effects of paxil therapy in a male patient with irritable colon syndrome].	2001	11641945
Adolescents searching for health information on the Internet: an observational study.	2003 Oct 17	14713653
Medicalization, markets and consumers.	2004	15779472
A taxpayer-funded clinical trials registry and results database.	2004 Dec	15562322
Environmental risk assessment of paroxetine.	2004 Jun 15	15260335
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
Medicine as a corporate enterprise, patient welfare centered profession, or patient welfare centered professional enterprise?	2005 Nov	22679354
What are the public health effects of direct-to-consumer drug advertising?	2006 Mar	16563041
Urticarial vasculitis secondary to paroxetine.	2006 Nov-Dec	17373154
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
Prevalence and predictors of antidepressant use in a cohort of pregnant women.	2007 Sep	17565615
[The anxyolytic effect of mild hypobaric hypoxia in a model of post-traumatic stress disorder in rats].	2008 Jul-Aug	18825947
Adverse drug effects in hospitalized elderly: data from the healthcare cost and utilization project.	2010	22291486
Desvenlafaxine in major depressive disorder: an evidence-based review of its place in therapy.	2010 Jun 15	20694066
Negotiating the boundary between medicine and consumer culture: online marketing of nutrigenetic tests.	2010 Mar	20022680
The haunting of medical journals: how ghostwriting sold "HRT".	2010 Sep 7	20838656
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)).

Name

Type

Language

ADIPHENINE HYDROCHLORIDE

Official Name

English

NSC-129224

Code

English

ADIPHENINE HYDROCHLORIDE [MI]

Common Name

English

2-(Diethylamino)ethyl diphenylacetate hydrochloride

Systematic Name

English

ADIPHENINE HYDROCHLORIDE [MART.]

Common Name

English

Adiphenine hydrochloride [WHO-DD]

Common Name

English

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

Common Name

English

ADIPHENINE HYDROCHLORIDE [USAN]

Common Name

English

ADIPHENINE HCL

Common Name

English

TRASENTINE

Brand Name

English

Classification Tree Code System Code

NCI_THESAURUS

C29704