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Details

Stereochemistry ACHIRAL
Molecular Formula C23H31NO2
Molecular Weight 353.4977
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PROADIFEN

SMILES

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

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 353.4977
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
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
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
Phosphoinositide 3-kinase regulates crosstalk between Trk A tyrosine kinase and p75(NTR)-dependent sphingolipid signaling pathways.
2001 Mar
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
Inhibition of vascular smooth muscle cell migration by cytochrome p450 epoxygenase-derived eicosanoids.
2002 May 17
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
Antiandrogenic activities of diesel exhaust particle extracts in PC3/AR human prostate carcinoma cells.
2003 Dec
Role of metabolism by flavin-containing monooxygenase in thioacetamide-induced immunosuppression.
2003 Jan 13
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
A role of aryl hydrocarbon receptor in the antiandrogenic effects of polycyclic aromatic hydrocarbons in LNCaP human prostate carcinoma cells.
2003 Jun
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
Effect of ketamine on cocaine-induced immunotoxicity in rats.
2003 Sep-Oct
Lipoxygenase-dependent superoxide release in skeletal muscle.
2004 Aug
Chlorpropham induces mitochondrial dysfunction in rat hepatocytes.
2004 Aug 5
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
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
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
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
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
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
Role of nitric oxide during coronary endothelial dysfunction after myocardial infarction.
2005 May 23
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
Involvement of phenobarbital and SKF 525A in the hepatotoxicity of antifungal drugs itraconazole and fluconazole in rats.
2006
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
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
Glial cells dilate and constrict blood vessels: a mechanism of neurovascular coupling.
2006 Mar 15
Metabolism of pyrene by aquatic crustacean, Daphnia magna.
2006 Nov 16
Analytical approach to determine ticlopidine in post-mortem blood.
2006 Oct 16
Clozapine bioactivation induces dose-dependent, drug-specific toxicity of human bone marrow stromal cells: a potential in vitro system for the study of agranulocytosis.
2006 Sep 14
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 Wed Jul 05 23:46:46 UTC 2023
Edited
by admin
on Wed Jul 05 23:46:46 UTC 2023
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 Wed Jul 05 23:46:46 UTC 2023 , Edited by admin on Wed Jul 05 23:46:46 UTC 2023
Code System Code Type Description
EVMPD
SUB10051MIG
Created by admin on Wed Jul 05 23:46:46 UTC 2023 , Edited by admin on Wed Jul 05 23:46:46 UTC 2023
PRIMARY
MESH
D011335
Created by admin on Wed Jul 05 23:46:46 UTC 2023 , Edited by admin on Wed Jul 05 23:46:46 UTC 2023
PRIMARY
ChEMBL
CHEMBL282567
Created by admin on Wed Jul 05 23:46:46 UTC 2023 , Edited by admin on Wed Jul 05 23:46:46 UTC 2023
PRIMARY
INN
1911
Created by admin on Wed Jul 05 23:46:46 UTC 2023 , Edited by admin on Wed Jul 05 23:46:46 UTC 2023
PRIMARY
PUBCHEM
4910
Created by admin on Wed Jul 05 23:46:46 UTC 2023 , Edited by admin on Wed Jul 05 23:46:46 UTC 2023
PRIMARY
CAS
302-33-0
Created by admin on Wed Jul 05 23:46:46 UTC 2023 , Edited by admin on Wed Jul 05 23:46:46 UTC 2023
PRIMARY
EPA CompTox
DTXSID2048452
Created by admin on Wed Jul 05 23:46:46 UTC 2023 , Edited by admin on Wed Jul 05 23:46:46 UTC 2023
PRIMARY
NCI_THESAURUS
C84107
Created by admin on Wed Jul 05 23:46:46 UTC 2023 , Edited by admin on Wed Jul 05 23:46:46 UTC 2023
PRIMARY
WIKIPEDIA
PROADIFEN
Created by admin on Wed Jul 05 23:46:46 UTC 2023 , Edited by admin on Wed Jul 05 23:46:46 UTC 2023
PRIMARY
FDA UNII
A510CA4CBT
Created by admin on Wed Jul 05 23:46:46 UTC 2023 , Edited by admin on Wed Jul 05 23:46:46 UTC 2023
PRIMARY
SMS_ID
100000081090
Created by admin on Wed Jul 05 23:46:46 UTC 2023 , Edited by admin on Wed Jul 05 23:46:46 UTC 2023
PRIMARY
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