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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 of PROADIFEN

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

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
Deciphering the plasma membrane hallmarks of apoptotic cells: phosphatidylserine transverse redistribution and calcium entry.
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
Toxicity of ethacrynic acid in isolated rat hepatocytes.
2002 Apr
Production of carbon monoxide by cytochrome P450 during iron-dependent lipid peroxidation.
2002 Feb
Paraquat detoxicative system in the mouse liver postmitochondrial fraction.
2002 Jun 1
Inhibition of vascular smooth muscle cell migration by cytochrome p450 epoxygenase-derived eicosanoids.
2002 May 17
Chemiluminescence associated with the oxidative metabolism of salicylic acid in rat liver microsomes.
2002 May 20
Effects of gap junction uncoupling in the gerbil cochlea.
2002 Sep
In vitro and in vivo formation of aminophenylnorharman from norharman and aniline.
2002 Sep 30
In vitro inhibitory effect of 1-aminobenzotriazole on drug oxidations catalyzed by human cytochrome P450 enzymes: a comparison with SKF-525A and ketoconazole.
2003
Cylindrospermopsin-induced protein synthesis inhibition and its dissociation from acute toxicity in mouse hepatocytes.
2003 Aug
Antiandrogenic activities of diesel exhaust particle extracts in PC3/AR human prostate carcinoma cells.
2003 Dec
Assessment of mazindane, a pro-drug form of mazindol, in assays used to define cocaine treatment agents.
2003 Jan 5
11,12-epoxyeicosatrienoic acid attenuates synthesis of prostaglandin E2 in rat monocytes stimulated with lipopolysaccharide.
2003 Jul
Cytochrome p-450 epoxygenase products contribute to attenuated vasoconstriction after chronic hypoxia.
2003 Jul
Effects of cytochrome P450 inhibitors on agonist-induced Ca2+ responses and production of NO and PGI2 in vascular endothelial cells.
2003 Jun
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
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
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
Biotransformation of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK) in peripheral human lung microsomes.
2003 Sep
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
Hepatobiliary excretion of berberine.
2004 Apr
Lipoxygenase-dependent superoxide release in skeletal muscle.
2004 Aug
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
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
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
Pharmacokinetics of baicalin in rats and its interactions with cyclosporin A, quinidine and SKF-525A: a microdialysis study.
2004 Nov
In vitro confirmation of selegiline N-oxidation by flavin-containing monooxygenase in rat microsome using LC-ESI MS.
2004 Oct
Essential role of singlet oxygen species in cytochrome P450-dependent substrate oxygenation by rat liver microsomes.
2005 Feb
Primary hepatocyte apoptosis is unlikely to relate to caspase-3 activity under sustained endogenous oxidative stress.
2005 Feb
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
Reductase-mediated metabolism of motexafin gadolinium (Xcytrin) in rat and human liver subcellular fractions and purified enzyme preparations.
2005 Mar
Excretion and metabolism of DA-7867, a new oxazolidinone, in rats.
2005 Mar
Effect of potassium channel and cytochrome P450 inhibition on transient hypotension and survival during lipopolysaccharide-induced endotoxic shock in the rat.
2005 Mar
Properties and regional expression of a CYP3A-like protein in channel catfish intestine.
2005 May 15
Augmentation of lipogenesis by 15-deoxy-Delta12,14-prostaglandin J2 in hamster sebaceous glands: identification of cytochrome P-450-mediated 15-deoxy-Delta12,14-prostaglandin J2 production.
2005 Nov
Increased cell-cell adhesion, a novel effect of R-(-)-deprenyl.
2005 Nov
In vitro inhibitory effect of 1-aminobenzotriazole on drug oxidations in human liver microsomes: a comparison with SKF-525A.
2005 Oct
Hydroxyeicosatetraenoic acids released through the cytochrome P-450 pathway regulate 3T6 fibroblast growth.
2006 Dec
[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
Inhibition of PGI2 signaling by miconazole in vascular smooth muscle cells.
2006 Jul
Effects of enzyme inducers and inhibitors on the pharmacokinetics of intravenous omeprazole in rats.
2006 Jul
Metabolism of pyrene by aquatic crustacean, Daphnia magna.
2006 Nov 16
Analytical approach to determine ticlopidine in post-mortem blood.
2006 Oct 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 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
  • Download
Name Type Language
PROADIFEN
INN  
INN  
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
Created by admin on Sat Jun 26 03:15:06 UTC 2021 , Edited by admin on Sat Jun 26 03:15:06 UTC 2021
Code System Code Type Description
EVMPD
SUB10051MIG
Created by admin on Sat Jun 26 03:15:06 UTC 2021 , Edited by admin on Sat Jun 26 03:15:06 UTC 2021
PRIMARY
MESH
D011335
Created by admin on Sat Jun 26 03:15:06 UTC 2021 , Edited by admin on Sat Jun 26 03:15:06 UTC 2021
PRIMARY
ChEMBL
CHEMBL282567
Created by admin on Sat Jun 26 03:15:06 UTC 2021 , Edited by admin on Sat Jun 26 03:15:06 UTC 2021
PRIMARY
INN
1911
Created by admin on Sat Jun 26 03:15:06 UTC 2021 , Edited by admin on Sat Jun 26 03:15:06 UTC 2021
PRIMARY
PUBCHEM
4910
Created by admin on Sat Jun 26 03:15:06 UTC 2021 , Edited by admin on Sat Jun 26 03:15:06 UTC 2021
PRIMARY
CAS
302-33-0
Created by admin on Sat Jun 26 03:15:06 UTC 2021 , Edited by admin on Sat Jun 26 03:15:06 UTC 2021
PRIMARY
EPA CompTox
302-33-0
Created by admin on Sat Jun 26 03:15:06 UTC 2021 , Edited by admin on Sat Jun 26 03:15:06 UTC 2021
PRIMARY
NCI_THESAURUS
C84107
Created by admin on Sat Jun 26 03:15:06 UTC 2021 , Edited by admin on Sat Jun 26 03:15:06 UTC 2021
PRIMARY
WIKIPEDIA
PROADIFEN
Created by admin on Sat Jun 26 03:15:06 UTC 2021 , Edited by admin on Sat Jun 26 03:15:06 UTC 2021
PRIMARY
FDA UNII
A510CA4CBT
Created by admin on Sat Jun 26 03:15:06 UTC 2021 , Edited by admin on Sat Jun 26 03:15:06 UTC 2021
PRIMARY
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