PROADIFEN

Details

Stereochemistry	ACHIRAL
Molecular Formula	C23H31NO2
Molecular Weight	353.4977
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CCCC(C(=O)OCCN(CC)CC)(C1=CC=CC=C1)C2=CC=CC=C2

InChI

InChIKey=SNTQPLDRUZOSDP-UHFFFAOYSA-N

InChI=1S/C23H31NO2/c1-4-17-23(20-13-9-7-10-14-20,21-15-11-8-12-16-21)22(25)26-19-18-24(5-2)6-3/h7-16H,4-6,17-19H2,1-3H3

HIDE SMILES / InChI

Molecular Formula	C23H31NO2
Molecular Weight	353.4977
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.ncbi.nlm.nih.gov/mesh/68011335 | https://www.ncbi.nlm.nih.gov/pubmed/3532206

Proadifen is an inhibitor of drug metabolism and cytochrome P450 enzyme system activity. It stimulated the release of prostacyclin (PGI2) from the rabbit aorta, bovine aorta and human umbilical vein in vitro, but had no effect on cultured smooth muscle from the bovine aortic media. In human platelets, proadifen inhibited prostaglandin and thromboxane production induced by A23187, thrombin, and ADP. Proadifen might thus constitute the prototype of a new class of antiplatelet drugs.

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Pregnane X receptor 35 Target ID: CHEMBL3401 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20966043	Activator 1430		25.1 µM [EC50]
Cytochrome P450 3A4 127 Target ID: CHEMBL340 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20966043	Modulator 828		12.6 µM [EC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Unknown 2578

PubMed

Title	Date	PubMed
The role of enzyme induction and inhibition on cypermethrin hepatotoxicity.	2001 Jul	11428908
Production of carbon monoxide by cytochrome P450 during iron-dependent lipid peroxidation.	2002 Feb	11812634
In vitro inhibitory effect of 1-aminobenzotriazole on drug oxidations catalyzed by human cytochrome P450 enzymes: a comparison with SKF-525A and ketoconazole.	2003	15618748
Assessment of mazindane, a pro-drug form of mazindol, in assays used to define cocaine treatment agents.	2003 Jan 5	12504782
Involvement of cytochrome P450 and the flavin-containing monooxygenase(s) in the sulphoxidation of simple sulphides in human liver microsomes.	2003 Jun 6	12757843
Concurrent corticosteroid and phenanthrene transformation by filamentous fungus Cunninghamella elegans.	2003 May	12798358
Metabolism of medroxyprogesterone acetate (MPA) via CYP enzymes in vitro and effect of MPA on bleeding time in female rats in dependence on CYP activity in vivo.	2003 Nov 7	14561525
Characterization of endothelium-dependent relaxation and modulation by treatment with pioglitazone in the hypercholesterolemic rabbit renal artery.	2004 Aug 30	15336950
Skf 525-A induces cocaine N-demethylase, ethoxyresorufin O-deethylase, and pentoxyresorufin O-dealkylase activities by induction of cytochrome p-450 2B in female B6C3F1 mice.	2004 Dec	15513895
Hyperosmolar solution effects in guinea pig airways. III. Studies on the identity of epithelium-derived relaxing factor in isolated perfused trachea using pharmacological agents.	2004 Jan	14566001
Pharmacokinetics of baicalin in rats and its interactions with cyclosporin A, quinidine and SKF-525A: a microdialysis study.	2004 Nov	15549664
In vitro confirmation of selegiline N-oxidation by flavin-containing monooxygenase in rat microsome using LC-ESI MS.	2004 Oct	15467197
Essential role of singlet oxygen species in cytochrome P450-dependent substrate oxygenation by rat liver microsomes.	2005 Feb	15770071
Primary hepatocyte apoptosis is unlikely to relate to caspase-3 activity under sustained endogenous oxidative stress.	2005 Feb	15763964
Reductase-mediated metabolism of motexafin gadolinium (Xcytrin) in rat and human liver subcellular fractions and purified enzyme preparations.	2005 Mar	15666291
Increased cell-cell adhesion, a novel effect of R-(-)-deprenyl.	2005 Nov	15785858
In-vitro cytotoxicity of ET-743 (Trabectedin, Yondelis), a marine anti-cancer drug, in the Hep G2 cell line: influence of cytochrome P450 and phase II inhibition, and cytochrome P450 induction.	2005 Oct	16162970
Hydroxyeicosatetraenoic acids released through the cytochrome P-450 pathway regulate 3T6 fibroblast growth.	2006 Dec	16980726
[Analysis of the interaction between nicotinic acetylcholine receptor and Na+,K(+)-ATPase in the rat skeletal muscle and the Torpedo electric organ membrane preparation].	2006 Feb	16739652
Participation of epoxygenase activation in saikogenin D-induced inhibition of prostaglandin E(2) synthesis.	2006 Jun	16734988

Patents

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Unknown

In Vitro Use Guide

Effects of local anesthetics-related drugs, proadifen, and quinacrine, on glibenclamide-sensitive K+ currents, were investigated using native Xenopus oocytes. Proadifen and quinacrine suppressed cromakalim-induced/glibenclamide-sensitive K+ currents with IC50 values of 9.8 microM and 4.4 microM, respectively. Inhibitors of either cytochrome P450 or phospholipase A2, which are structurally unrelated to local anesthetics, however, did not affect the K+ currents. Similar results were obtained for Y-26763-induced/glibenclamide-sensitive K+ currents. Proadifen and quinacrine block the glibenclamide-sensitive K+ currents by a mechanism irrelevant to the inhibition of cytochrome P450 or phospholipase A2 in oocytes.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 16:20:02 GMT 2023` Edited by `admin` on `Fri Dec 15 16:20:02 GMT 2023`
Record UNII	A510CA4CBT
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

PROADIFEN

Official Name

English

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

Common Name

English

2-(DIETHYLAMINO)ETHYL-2,2-DIPHENYLVALERATE

Systematic Name

English

proadifen [INN]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C29574