PROADIFEN HYDROCHLORIDE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C23H31NO2.ClH
Molecular Weight	389.959
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

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

InChI

InChIKey=FHIKZROVIDCMJA-UHFFFAOYSA-N

InChI=1S/C23H31NO2.ClH/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;1H

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

Molecular Formula	ClH
Molecular Weight	36.461
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 36 Target ID: CHEMBL3401 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20966043	Activator 1447		25.1 µM [EC50]
Cytochrome P450 3A4 127 Target ID: CHEMBL340 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20966043	Modulator 846		12.6 µM [EC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Unknown 2596

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
Understanding channel blocking in the nicotinic acetylcholine receptor.	2001	11697233
Low-density lipoprotein induced actin cytoskeleton reorganization in endothelial cells: mechanisms of action.	2001	11577705
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
Local anesthetics noncompetitively inhibit function of four distinct nicotinic acetylcholine receptor subtypes.	2001 Dec	11714893
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
Cytochrome P-450 metabolite of arachidonic acid mediates bradykinin-induced negative inotropic effect.	2001 Jun	11356641
Site-specific charge interactions of alpha-conotoxin MI with the nicotinic acetylcholine receptor.	2001 Jun 29	11323431
[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
Possible mechanisms for the suppressing action of 17beta-estradiol on beta-adrenoceptor-mediated vasorelaxation in rat aorta.	2001 Sep 7	11553364
Toxicity of ethacrynic acid in isolated rat hepatocytes.	2002 Apr	11869877
Production of carbon monoxide by cytochrome P450 during iron-dependent lipid peroxidation.	2002 Feb	11812634
The influence of metabolism on the MAO-B inhibitory potency of selegiline.	2002 Jan	11860347
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
In vitro and in vivo formation of aminophenylnorharman from norharman and aniline.	2002 Sep 30	12351144
Antiandrogenic activities of diesel exhaust particle extracts in PC3/AR human prostate carcinoma cells.	2003 Dec	12970580
A role of aryl hydrocarbon receptor in the antiandrogenic effects of polycyclic aromatic hydrocarbons in LNCaP human prostate carcinoma cells.	2003 Jun	12799773
The effect of valproic acid on hepatic and plasma levels of 15-F2t-isoprostane in rats.	2003 Jun 1	12757854
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
In vivo identification of aflatoxin-induced free radicals in rat bile.	2003 Nov 15	14607532
Rapid stimulation of free glucuronate formation by non-glucuronidable xenobiotics in isolated rat hepatocytes.	2003 Sep 19	12865420
Effect of ketamine on cocaine-induced immunotoxicity in rats.	2003 Sep-Oct	14555406
In vitro proliferation of fibrosarcoma cells depends on intact functions of lipoxygenases and cytochrome P-450-monooxygenase.	2004	15199606
Microbial transformations of chalcones: hydroxylation, O-demethylation, and cyclization to flavanones.	2004 Apr	15104483
Hepatobiliary excretion of berberine.	2004 Apr	15039293
Lipoxygenase-dependent superoxide release in skeletal muscle.	2004 Aug	15107407
Chlorpropham induces mitochondrial dysfunction in rat hepatocytes.	2004 Aug 5	15212809
Activation and up-regulation of nitric oxide synthase in human umbilical vein endothelial cells by polycyclic aromatic hydrocarbons.	2004 Jul 15	15183461
Gas chromatographic determination of cocaine and its metabolites in blood and urine from cocaine users in northwestern Spain.	2004 Jul-Aug	15300716
Role of endothelium-derived hyperpolarizing factor in ACE inhibitor-induced renal vasodilation in vivo.	2004 Mar	14769805
Relaxant effect of oxime derivatives in isolated rat aorta: role of nitric oxide (NO) formation in smooth muscle.	2004 Mar 15	15006555
In vitro confirmation of selegiline N-oxidation by flavin-containing monooxygenase in rat microsome using LC-ESI MS.	2004 Oct	15467197
Mechanisms of hydroxyl radical-induced contraction of rat aorta.	2004 Sep 19	15363964
Connexin26 is responsible for anionic molecule permeability in the cochlea for intercellular signalling and metabolic communications.	2005 Apr	15869481
Essential role of singlet oxygen species in cytochrome P450-dependent substrate oxygenation by rat liver microsomes.	2005 Feb	15770071
Alteration in endothelial function and modulation by treatment with pioglitazone in rabbit renal artery from short-term hypercholesterolemia.	2005 Jun	15953770
Increased cell-cell adhesion, a novel effect of R-(-)-deprenyl.	2005 Nov	15785858
Effect of cytochrome P450 inhibitors and anticonvulsants on the acute toxicity of acrylonitrile.	2005 Oct	15864551
Hydroxyeicosatetraenoic acids released through the cytochrome P-450 pathway regulate 3T6 fibroblast growth.	2006 Dec	16980726
Enhancement of DMNQ-induced hepatocyte toxicity by cytochrome P450 inhibition.	2006 Jul 15	16430935
Metabolism of pyrene by aquatic crustacean, Daphnia magna.	2006 Nov 16	16973224

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 `Mon Mar 31 18:01:08 GMT 2025` Edited by `admin` on `Mon Mar 31 18:01:08 GMT 2025`
Record UNII	30624AA6X2
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

NSC-170997

Preferred Name

English

PROADIFEN HYDROCHLORIDE

Official Name

English

RP 5171

Code

English

SK&F-525-A

Code

English

2-(Diethylamino)ethyl-2,2-diphenylvalerate hydrochloride

Systematic Name

English

PROADIFEN HCL

Common Name

English

RP-5171

Code

English

PROADIFEN HYDROCHLORIDE [USAN]

Common Name

English

SK&F 525-A

Code

English

PROADIFEN HYDROCHLORIDE [MART.]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C29574