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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 of PROADIFEN HYDROCHLORIDE

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

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

Targets

Primary TargetPharmacologyConditionPotency
25.1 µM [EC50]
12.6 µM [EC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
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
[Effect of arachidonic and other fatty acids on the intracellular calcium concentration and calcium signaling in peritoneal macrophages].
2001
Deciphering the plasma membrane hallmarks of apoptotic cells: phosphatidylserine transverse redistribution and calcium entry.
2001
Understanding channel blocking in the nicotinic acetylcholine receptor.
2001
Low-density lipoprotein induced actin cytoskeleton reorganization in endothelial cells: mechanisms of action.
2001
Anti-apoptotic and apoptotic action of (-)-deprenyl and its metabolites.
2001
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
Local anesthetics noncompetitively inhibit function of four distinct nicotinic acetylcholine receptor subtypes.
2001 Dec
The role of enzyme induction and inhibition on cypermethrin hepatotoxicity.
2001 Jul
Perinatal development influences mechanisms of bradykinin-induced relaxations in pulmonary resistance and conduit arteries differently.
2001 Jul
Cytochrome P-450 metabolite of arachidonic acid mediates bradykinin-induced negative inotropic effect.
2001 Jun
Site-specific charge interactions of alpha-conotoxin MI with the nicotinic acetylcholine receptor.
2001 Jun 29
[Role of phospholipase A2 and epoxygenase in inhibition of respiration burst in neutrophils by low intensity radiation of extremely high frequency].
2001 Mar-Apr
Activation of Galpha s mediates induction of tissue-type plasminogen activator gene transcription by epoxyeicosatrienoic acids.
2001 May 11
Microsomal metabolism of ciprofloxacin generates free radicals.
2001 May 15
Possible mechanisms for the suppressing action of 17beta-estradiol on beta-adrenoceptor-mediated vasorelaxation in rat aorta.
2001 Sep 7
Toxicity of ethacrynic acid in isolated rat hepatocytes.
2002 Apr
Production of carbon monoxide by cytochrome P450 during iron-dependent lipid peroxidation.
2002 Feb
The influence of metabolism on the MAO-B inhibitory potency of selegiline.
2002 Jan
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
The critical role of mitochondrial energetic impairment in the toxicity of nimesulide to hepatocytes.
2002 Nov
In vivo detection of aflatoxin-induced lipid free radicals in rat bile.
2002 Oct 10
In vitro and in vivo formation of aminophenylnorharman from norharman and aniline.
2002 Sep 30
Antiandrogenic activities of diesel exhaust particle extracts in PC3/AR human prostate carcinoma cells.
2003 Dec
A role of aryl hydrocarbon receptor in the antiandrogenic effects of polycyclic aromatic hydrocarbons in LNCaP human prostate carcinoma cells.
2003 Jun
The effect of valproic acid on hepatic and plasma levels of 15-F2t-isoprostane in rats.
2003 Jun 1
Involvement of cytochrome P450 and the flavin-containing monooxygenase(s) in the sulphoxidation of simple sulphides in human liver microsomes.
2003 Jun 6
Concurrent corticosteroid and phenanthrene transformation by filamentous fungus Cunninghamella elegans.
2003 May
In vivo identification of aflatoxin-induced free radicals in rat bile.
2003 Nov 15
Rapid stimulation of free glucuronate formation by non-glucuronidable xenobiotics in isolated rat hepatocytes.
2003 Sep 19
Effect of ketamine on cocaine-induced immunotoxicity in rats.
2003 Sep-Oct
In vitro proliferation of fibrosarcoma cells depends on intact functions of lipoxygenases and cytochrome P-450-monooxygenase.
2004
Microbial transformations of chalcones: hydroxylation, O-demethylation, and cyclization to flavanones.
2004 Apr
Hepatobiliary excretion of berberine.
2004 Apr
Lipoxygenase-dependent superoxide release in skeletal muscle.
2004 Aug
Chlorpropham induces mitochondrial dysfunction in rat hepatocytes.
2004 Aug 5
Activation and up-regulation of nitric oxide synthase in human umbilical vein endothelial cells by polycyclic aromatic hydrocarbons.
2004 Jul 15
Gas chromatographic determination of cocaine and its metabolites in blood and urine from cocaine users in northwestern Spain.
2004 Jul-Aug
Role of endothelium-derived hyperpolarizing factor in ACE inhibitor-induced renal vasodilation in vivo.
2004 Mar
Relaxant effect of oxime derivatives in isolated rat aorta: role of nitric oxide (NO) formation in smooth muscle.
2004 Mar 15
In vitro confirmation of selegiline N-oxidation by flavin-containing monooxygenase in rat microsome using LC-ESI MS.
2004 Oct
Mechanisms of hydroxyl radical-induced contraction of rat aorta.
2004 Sep 19
Connexin26 is responsible for anionic molecule permeability in the cochlea for intercellular signalling and metabolic communications.
2005 Apr
Essential role of singlet oxygen species in cytochrome P450-dependent substrate oxygenation by rat liver microsomes.
2005 Feb
Alteration in endothelial function and modulation by treatment with pioglitazone in rabbit renal artery from short-term hypercholesterolemia.
2005 Jun
Increased cell-cell adhesion, a novel effect of R-(-)-deprenyl.
2005 Nov
Effect of cytochrome P450 inhibitors and anticonvulsants on the acute toxicity of acrylonitrile.
2005 Oct
Hydroxyeicosatetraenoic acids released through the cytochrome P-450 pathway regulate 3T6 fibroblast growth.
2006 Dec
Enhancement of DMNQ-induced hepatocyte toxicity by cytochrome P450 inhibition.
2006 Jul 15
Metabolism of pyrene by aquatic crustacean, Daphnia magna.
2006 Nov 16
Patents

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
  • Download
Name Type Language
NSC-170997
Preferred Name English
PROADIFEN HYDROCHLORIDE
MART.   USAN  
USAN  
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
Created by admin on Mon Mar 31 18:01:08 GMT 2025 , Edited by admin on Mon Mar 31 18:01:08 GMT 2025
Code System Code Type Description
NCI_THESAURUS
C66468
Created by admin on Mon Mar 31 18:01:08 GMT 2025 , Edited by admin on Mon Mar 31 18:01:08 GMT 2025
PRIMARY
ChEMBL
CHEMBL282567
Created by admin on Mon Mar 31 18:01:08 GMT 2025 , Edited by admin on Mon Mar 31 18:01:08 GMT 2025
PRIMARY
NSC
170997
Created by admin on Mon Mar 31 18:01:08 GMT 2025 , Edited by admin on Mon Mar 31 18:01:08 GMT 2025
PRIMARY
CAS
62-68-0
Created by admin on Mon Mar 31 18:01:08 GMT 2025 , Edited by admin on Mon Mar 31 18:01:08 GMT 2025
PRIMARY
PUBCHEM
65341
Created by admin on Mon Mar 31 18:01:08 GMT 2025 , Edited by admin on Mon Mar 31 18:01:08 GMT 2025
PRIMARY
SMS_ID
300000055018
Created by admin on Mon Mar 31 18:01:08 GMT 2025 , Edited by admin on Mon Mar 31 18:01:08 GMT 2025
PRIMARY
EPA CompTox
DTXSID1045792
Created by admin on Mon Mar 31 18:01:08 GMT 2025 , Edited by admin on Mon Mar 31 18:01:08 GMT 2025
PRIMARY
NSC
39690
Created by admin on Mon Mar 31 18:01:08 GMT 2025 , Edited by admin on Mon Mar 31 18:01:08 GMT 2025
PRIMARY
FDA UNII
30624AA6X2
Created by admin on Mon Mar 31 18:01:08 GMT 2025 , Edited by admin on Mon Mar 31 18:01:08 GMT 2025
PRIMARY
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