PROADIFEN

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 Search

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

Description
Sources: https://www.ncbi.nlm.nih.gov/mesh/68011335 | https://www.ncbi.nlm.nih.gov/pubmed/3532206

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

Primary Target	Pharmacology	Condition	Potency
Pregnane X receptor 36 Target ID: CHEMBL3401 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20966043	Activator 1447		25.1 µM [EC50]
Cytochrome P450 3A4 127 Target ID: CHEMBL340 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20966043	Modulator 846		12.6 µM [EC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Unknown 2596

PubMed

Title	Date	PubMed
Hydroxyeicosatetraenoic acids released through the cytochrome P-450 pathway regulate 3T6 fibroblast growth.	2006-12	16980726
Metabolism of pyrene by aquatic crustacean, Daphnia magna.	2006-11-16	16973224
Analytical approach to determine ticlopidine in post-mortem blood.	2006-10-16	16859849
Clozapine bioactivation induces dose-dependent, drug-specific toxicity of human bone marrow stromal cells: a potential in vitro system for the study of agranulocytosis.	2006-09-14	16844094
Enhancement of DMNQ-induced hepatocyte toxicity by cytochrome P450 inhibition.	2006-07-15	16430935
Inhibition of PGI2 signaling by miconazole in vascular smooth muscle cells.	2006-07	16846784
Effects of enzyme inducers and inhibitors on the pharmacokinetics of intravenous omeprazole in rats.	2006-07	16586464
Participation of epoxygenase activation in saikogenin D-induced inhibition of prostaglandin E(2) synthesis.	2006-06	16734988
Glial cells dilate and constrict blood vessels: a mechanism of neurovascular coupling.	2006-03-15	16540563
[Analysis of the interaction between nicotinic acetylcholine receptor and Na+,K(+)-ATPase in the rat skeletal muscle and the Torpedo electric organ membrane preparation].	2006-02	16739652
Site specificity of agonist-induced opening and desensitization of the Torpedo californica nicotinic acetylcholine receptor.	2006-01-10	16388595
GC-FID determination of cocaine and its metabolites in human bile and vitreous humor.	2006-01-04	16389661
Involvement of phenobarbital and SKF 525A in the hepatotoxicity of antifungal drugs itraconazole and fluconazole in rats.	2006	16777703
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.	2005-11	16297182
Increased cell-cell adhesion, a novel effect of R-(-)-deprenyl.	2005-11	15785858
Endothelium-dependent and direct relaxation induced by ethyl acetate extract from Flos Chrysanthemi in rat thoracic aorta.	2005-10-03	15950416
In vitro inhibitory effect of 1-aminobenzotriazole on drug oxidations in human liver microsomes: a comparison with SKF-525A.	2005-10	16272753
In-vitro cytotoxicity of ET-743 (Trabectedin, Yondelis), a marine anti-cancer drug, in the Hep G2 cell line: influence of cytochrome P450 and phase II inhibition, and cytochrome P450 induction.	2005-10	16162970
Effect of cytochrome P450 inhibitors and anticonvulsants on the acute toxicity of acrylonitrile.	2005-10	15864551
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.	2005-08	15863696
Identification of cytochrome P450 forms involved in the 4-hydroxylation of valsartan, a potent and specific angiotensin II receptor antagonist, in human liver microsomes.	2005-06	16192110
[Role of endothelium-derived hyperpolarizing factor in shear stress-induced endothelium-dependent relaxations of rats].	2005-06	16144311
Alteration in endothelial function and modulation by treatment with pioglitazone in rabbit renal artery from short-term hypercholesterolemia.	2005-06	15953770
Role of nitric oxide during coronary endothelial dysfunction after myocardial infarction.	2005-05-23	15923002
Properties and regional expression of a CYP3A-like protein in channel catfish intestine.	2005-05-15	15848255
Connexin26 is responsible for anionic molecule permeability in the cochlea for intercellular signalling and metabolic communications.	2005-04	15869481
Reductase-mediated metabolism of motexafin gadolinium (Xcytrin) in rat and human liver subcellular fractions and purified enzyme preparations.	2005-03	15666291
Excretion and metabolism of DA-7867, a new oxazolidinone, in rats.	2005-03	15617136
Effect of potassium channel and cytochrome P450 inhibition on transient hypotension and survival during lipopolysaccharide-induced endotoxic shock in the rat.	2005-03	15499226
Essential role of singlet oxygen species in cytochrome P450-dependent substrate oxygenation by rat liver microsomes.	2005-02	15770071
Primary hepatocyte apoptosis is unlikely to relate to caspase-3 activity under sustained endogenous oxidative stress.	2005-02	15763964
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.	2004-12	15513895
Pharmacokinetics of baicalin in rats and its interactions with cyclosporin A, quinidine and SKF-525A: a microdialysis study.	2004-11	15549664
In vitro confirmation of selegiline N-oxidation by flavin-containing monooxygenase in rat microsome using LC-ESI MS.	2004-10	15467197
Pharmacokinetic factors in sex differences in Delta 9-tetrahydrocannabinol-induced behavioral effects in rats.	2004-09-23	15302113
Mechanisms of hydroxyl radical-induced contraction of rat aorta.	2004-09-19	15363964
Characterization of endothelium-dependent relaxation and modulation by treatment with pioglitazone in the hypercholesterolemic rabbit renal artery.	2004-08-30	15336950
Gas chromatographic determination of cocaine and its metabolites in blood and urine from cocaine users in northwestern Spain.	2004-08-10	15300716
Chlorpropham induces mitochondrial dysfunction in rat hepatocytes.	2004-08-05	15212809
Lipoxygenase-dependent superoxide release in skeletal muscle.	2004-08	15107407
Activation and up-regulation of nitric oxide synthase in human umbilical vein endothelial cells by polycyclic aromatic hydrocarbons.	2004-07-15	15183461
Microbial transformations of chalcones: hydroxylation, O-demethylation, and cyclization to flavanones.	2004-04	15104483
Hepatobiliary excretion of berberine.	2004-04	15039293
Relaxant effect of oxime derivatives in isolated rat aorta: role of nitric oxide (NO) formation in smooth muscle.	2004-03-15	15006555
Ca2+ influx is not involved in acute cytotoxicity of arachidonic acid.	2004-03-01	15104243
Role of endothelium-derived hyperpolarizing factor in ACE inhibitor-induced renal vasodilation in vivo.	2004-03	14769805
Hyperosmolar solution effects in guinea pig airways. III. Studies on the identity of epithelium-derived relaxing factor in isolated perfused trachea using pharmacological agents.	2004-01	14566001
In vitro proliferation of fibrosarcoma cells depends on intact functions of lipoxygenases and cytochrome P-450-monooxygenase.	2004	15199606
In vivo identification of aflatoxin-induced free radicals in rat bile.	2003-11-15	14607532
In vitro inhibitory effect of 1-aminobenzotriazole on drug oxidations catalyzed by human cytochrome P450 enzymes: a comparison with SKF-525A and ketoconazole.	2003	15618748

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 18:25:19 GMT 2025` Edited by `admin` on `Mon Mar 31 18:25:19 GMT 2025`
Record UNII	A510CA4CBT
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

BENZENEACETIC ACID, .ALPHA.-PHENYL-.ALPHA.-PROPYL-, 2-(DIETHYLAMINO)ETHYL ESTER

Preferred Name

English

PROADIFEN

Official Name

English

2-(DIETHYLAMINO)ETHYL-2,2-DIPHENYLVALERATE

Systematic Name

English

proadifen [INN]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C29574