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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
25.1000000000000014 µM [EC50]
12.5999999999999996 µM [EC50]
PubMed

PubMed

TitleDatePubMed
In vitro inhibitory effect of 1-aminobenzotriazole on drug oxidations catalyzed by human cytochrome P450 enzymes: a comparison with SKF-525A and ketoconazole.
2003
Antiandrogenic activities of diesel exhaust particle extracts in PC3/AR human prostate carcinoma cells.
2003 Dec
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
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
Characterization of endothelium-dependent relaxation and modulation by treatment with pioglitazone in the hypercholesterolemic rabbit renal artery.
2004 Aug 30
Chlorpropham induces mitochondrial dysfunction in rat hepatocytes.
2004 Aug 5
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
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
Ca2+ influx is not involved in acute cytotoxicity of arachidonic acid.
2004 Mar 1
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
Pharmacokinetic factors in sex differences in Delta 9-tetrahydrocannabinol-induced behavioral effects in rats.
2004 Sep 23
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
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
[Role of endothelium-derived hyperpolarizing factor in shear stress-induced endothelium-dependent relaxations of rats].
2005 Jun
Alteration in endothelial function and modulation by treatment with pioglitazone in rabbit renal artery from short-term hypercholesterolemia.
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
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
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
Effect of cytochrome P450 inhibitors and anticonvulsants on the acute toxicity of acrylonitrile.
2005 Oct
Endothelium-dependent and direct relaxation induced by ethyl acetate extract from Flos Chrysanthemi in rat thoracic aorta.
2005 Oct 3
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
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
Enhancement of DMNQ-induced hepatocyte toxicity by cytochrome P450 inhibition.
2006 Jul 15
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
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
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 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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