PROADIFEN

Details

Stereochemistry	ACHIRAL
Molecular Formula	C23H31NO2
Molecular Weight	353.4986
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CCCC(c1ccccc1)(c2ccccc2)C(=O)OCCN(CC)CC

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	353.4986
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 34 Target ID: CHEMBL3401 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20966043	Activator 1343		25.1 µM [EC50]
Cytochrome P450 3A4 116 Target ID: CHEMBL340 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20966043	Modulator 780		12.6 µM [EC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Unknown 2502

PubMed

Title	Date	PubMed
Acute cytogenetic effect of benzene on rat bone marrow cells in vivo and the effect of inducers or inhibitors of drug-metabolizing enzymes.	1992 Dec	1282215
[Effect of arachidonic and other fatty acids on the intracellular calcium concentration and calcium signaling in peritoneal macrophages].	2001	11840781
Deciphering the plasma membrane hallmarks of apoptotic cells: phosphatidylserine transverse redistribution and calcium entry.	2001	11701087
Anti-apoptotic and apoptotic action of (-)-deprenyl and its metabolites.	2001	11261744
Sex-dependent toxicity of a novel acyl-CoA:cholesterol acyltransferase inhibitor, YIC-C8-434, in relation to sex-specific forms of cytochrome P450 in rats.	2001 Dec	11719709
Bradykinin attenuates the [Ca(2+)](i) response to angiotensin II of renal juxtamedullary efferent arterioles via an EDHF.	2001 Feb	11159728
A conformational intermediate between the resting and desensitized states of the nicotinic acetylcholine receptor.	2001 Feb 16	11083863
Role of copper ions and cytochrome P450 in the vasodilator actions of the nitroxyl anion generator, Angeli's salt, on rat aorta.	2001 Feb 2	11166292
The role of enzyme induction and inhibition on cypermethrin hepatotoxicity.	2001 Jul	11428908
Perinatal development influences mechanisms of bradykinin-induced relaxations in pulmonary resistance and conduit arteries differently.	2001 Jul	11399256
Site-specific charge interactions of alpha-conotoxin MI with the nicotinic acetylcholine receptor.	2001 Jun 29	11323431
The role of desensitisation in decay time of miniature endplate currents in frogs Rana ridibunda and Rana temporaria.	2001 Mar	11248368
Phosphoinositide 3-kinase regulates crosstalk between Trk A tyrosine kinase and p75(NTR)-dependent sphingolipid signaling pathways.	2001 Mar	11238738
Cytochrome p450-dependent metabolism of trichloroethylene in rat kidney.	2001 Mar	11222868
[Role of phospholipase A2 and epoxygenase in inhibition of respiration burst in neutrophils by low intensity radiation of extremely high frequency].	2001 Mar-Apr	11357344
Activation of Galpha s mediates induction of tissue-type plasminogen activator gene transcription by epoxyeicosatrienoic acids.	2001 May 11	11279071
Microsomal metabolism of ciprofloxacin generates free radicals.	2001 May 15	11369501
Toxicity of ethacrynic acid in isolated rat hepatocytes.	2002 Apr	11869877
The influence of metabolism on the MAO-B inhibitory potency of selegiline.	2002 Jan	11860347
Paraquat detoxicative system in the mouse liver postmitochondrial fraction.	2002 Jun 1	12051692
Chemiluminescence associated with the oxidative metabolism of salicylic acid in rat liver microsomes.	2002 May 20	12076519
Involvement of NO in the endothelium-independent relaxing effects of N(omega)-hydroxy-L-arginine and other compounds bearing a C=NOH function in the rat aorta.	2002 Nov	12388669
The critical role of mitochondrial energetic impairment in the toxicity of nimesulide to hepatocytes.	2002 Nov	12388641
In vivo detection of aflatoxin-induced lipid free radicals in rat bile.	2002 Oct 10	12383942
Effects of gap junction uncoupling in the gerbil cochlea.	2002 Sep	12352678
In vitro and in vivo formation of aminophenylnorharman from norharman and aniline.	2002 Sep 30	12351144
Inhibition of cocaine oxidative metabolism attenuates endotoxin potentiation of cocaine mediated hepatotoxicity.	2002 Sep 30	12204538
Cylindrospermopsin-induced protein synthesis inhibition and its dissociation from acute toxicity in mouse hepatocytes.	2003 Aug	12900943
Antiandrogenic activities of diesel exhaust particle extracts in PC3/AR human prostate carcinoma cells.	2003 Dec	12970580
Effects of cytochrome P450 inhibitors on agonist-induced Ca2+ responses and production of NO and PGI2 in vascular endothelial cells.	2003 Jun	12870664
Concurrent corticosteroid and phenanthrene transformation by filamentous fungus Cunninghamella elegans.	2003 May	12798358
Biotransformation of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK) in peripheral human lung microsomes.	2003 Sep	12920169
Microbial transformations of chalcones: hydroxylation, O-demethylation, and cyclization to flavanones.	2004 Apr	15104483
Chlorpropham induces mitochondrial dysfunction in rat hepatocytes.	2004 Aug 5	15212809
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
Metabolism of the alpha,beta-unsaturated ketones, chalcone and trans-4-phenyl-3-buten-2-one, by rat liver microsomes and estrogenic activity of the metabolites.	2005 Aug	15863696
Primary hepatocyte apoptosis is unlikely to relate to caspase-3 activity under sustained endogenous oxidative stress.	2005 Feb	15763964
Identification of cytochrome P450 forms involved in the 4-hydroxylation of valsartan, a potent and specific angiotensin II receptor antagonist, in human liver microsomes.	2005 Jun	16192110
Alteration in endothelial function and modulation by treatment with pioglitazone in rabbit renal artery from short-term hypercholesterolemia.	2005 Jun	15953770
Excretion and metabolism of DA-7867, a new oxazolidinone, in rats.	2005 Mar	15617136
Increased cell-cell adhesion, a novel effect of R-(-)-deprenyl.	2005 Nov	15785858
In vitro inhibitory effect of 1-aminobenzotriazole on drug oxidations in human liver microsomes: a comparison with SKF-525A.	2005 Oct	16272753
Endothelium-dependent and direct relaxation induced by ethyl acetate extract from Flos Chrysanthemi in rat thoracic aorta.	2005 Oct 3	15950416
Hydroxyeicosatetraenoic acids released through the cytochrome P-450 pathway regulate 3T6 fibroblast growth.	2006 Dec	16980726
Site specificity of agonist-induced opening and desensitization of the Torpedo californica nicotinic acetylcholine receptor.	2006 Jan 10	16388595
Participation of epoxygenase activation in saikogenin D-induced inhibition of prostaglandin E(2) synthesis.	2006 Jun	16734988
GC-FID determination of cocaine and its metabolites in human bile and vitreous humor.	2006 May-Jun	16389661
Metabolism of pyrene by aquatic crustacean, Daphnia magna.	2006 Nov 16	16973224
Analytical approach to determine ticlopidine in post-mortem blood.	2006 Oct 16	16859849

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 `Sat Jun 26 03:15:06 UTC 2021` Edited by `admin` on `Sat Jun 26 03:15:06 UTC 2021`
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