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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
[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
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
Bradykinin attenuates the [Ca(2+)](i) response to angiotensin II of renal juxtamedullary efferent arterioles via an EDHF.
2001 Feb
A conformational intermediate between the resting and desensitized states of the nicotinic acetylcholine receptor.
2001 Feb 16
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
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
Site-specific charge interactions of alpha-conotoxin MI with the nicotinic acetylcholine receptor.
2001 Jun 29
The role of desensitisation in decay time of miniature endplate currents in frogs Rana ridibunda and Rana temporaria.
2001 Mar
Phosphoinositide 3-kinase regulates crosstalk between Trk A tyrosine kinase and p75(NTR)-dependent sphingolipid signaling pathways.
2001 Mar
Cytochrome p450-dependent metabolism of trichloroethylene in rat kidney.
2001 Mar
[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
Toxicity of ethacrynic acid in isolated rat hepatocytes.
2002 Apr
The influence of metabolism on the MAO-B inhibitory potency of selegiline.
2002 Jan
Paraquat detoxicative system in the mouse liver postmitochondrial fraction.
2002 Jun 1
Chemiluminescence associated with the oxidative metabolism of salicylic acid in rat liver microsomes.
2002 May 20
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
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
Inhibition of cocaine oxidative metabolism attenuates endotoxin potentiation of cocaine mediated hepatotoxicity.
2002 Sep 30
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
Effects of cytochrome P450 inhibitors on agonist-induced Ca2+ responses and production of NO and PGI2 in vascular endothelial cells.
2003 Jun
Concurrent corticosteroid and phenanthrene transformation by filamentous fungus Cunninghamella elegans.
2003 May
Biotransformation of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK) in peripheral human lung microsomes.
2003 Sep
Microbial transformations of chalcones: hydroxylation, O-demethylation, and cyclization to flavanones.
2004 Apr
Chlorpropham induces mitochondrial dysfunction in rat hepatocytes.
2004 Aug 5
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
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
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
Alteration in endothelial function and modulation by treatment with pioglitazone in rabbit renal artery from short-term hypercholesterolemia.
2005 Jun
Excretion and metabolism of DA-7867, a new oxazolidinone, in rats.
2005 Mar
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
Endothelium-dependent and direct relaxation induced by ethyl acetate extract from Flos Chrysanthemi in rat thoracic aorta.
2005 Oct 3
Hydroxyeicosatetraenoic acids released through the cytochrome P-450 pathway regulate 3T6 fibroblast growth.
2006 Dec
Site specificity of agonist-induced opening and desensitization of the Torpedo californica nicotinic acetylcholine receptor.
2006 Jan 10
Participation of epoxygenase activation in saikogenin D-induced inhibition of prostaglandin E(2) synthesis.
2006 Jun
GC-FID determination of cocaine and its metabolites in human bile and vitreous humor.
2006 May-Jun
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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