U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C23H31NO2.ClH
Molecular Weight 389.959
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PROADIFEN HYDROCHLORIDE

SMILES

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

InChI

InChIKey=FHIKZROVIDCMJA-UHFFFAOYSA-N
InChI=1S/C23H31NO2.ClH/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;1H

HIDE SMILES / InChI

Molecular Formula ClH
Molecular Weight 36.461
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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
Deciphering the plasma membrane hallmarks of apoptotic cells: phosphatidylserine transverse redistribution and calcium entry.
2001
Understanding channel blocking in the nicotinic acetylcholine receptor.
2001
Anti-apoptotic and apoptotic action of (-)-deprenyl and its metabolites.
2001
Local anesthetics noncompetitively inhibit function of four distinct nicotinic acetylcholine receptor subtypes.
2001 Dec
Perinatal development influences mechanisms of bradykinin-induced relaxations in pulmonary resistance and conduit arteries differently.
2001 Jul
The role of desensitisation in decay time of miniature endplate currents in frogs Rana ridibunda and Rana temporaria.
2001 Mar
Possible mechanisms for the suppressing action of 17beta-estradiol on beta-adrenoceptor-mediated vasorelaxation in rat aorta.
2001 Sep 7
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
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
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
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
Involvement of cytochrome P450 and the flavin-containing monooxygenase(s) in the sulphoxidation of simple sulphides in human liver microsomes.
2003 Jun 6
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
Rapid stimulation of free glucuronate formation by non-glucuronidable xenobiotics in isolated rat hepatocytes.
2003 Sep 19
Microbial transformations of chalcones: hydroxylation, O-demethylation, and cyclization to flavanones.
2004 Apr
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
Ca2+ influx is not involved in acute cytotoxicity of arachidonic acid.
2004 Mar 1
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
Essential role of singlet oxygen species in cytochrome P450-dependent substrate oxygenation by rat liver microsomes.
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
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
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
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 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 Fri Dec 16 17:26:41 UTC 2022
Edited
by admin
on Fri Dec 16 17:26:41 UTC 2022
Record UNII
30624AA6X2
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
PROADIFEN HYDROCHLORIDE
MART.   USAN  
USAN  
Official Name English
NSC-170997
Code English
RP 5171
Code English
SK&F-525-A
Code English
2-(Diethylamino)ethyl-2,2-diphenylvalerate hydrochloride
Systematic Name English
PROADIFEN HCL
Common Name English
RP-5171
Code English
PROADIFEN HYDROCHLORIDE [USAN]
Common Name English
SK&F 525-A
Code English
PROADIFEN HYDROCHLORIDE [MART.]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C29574
Created by admin on Fri Dec 16 17:26:41 UTC 2022 , Edited by admin on Fri Dec 16 17:26:41 UTC 2022
Code System Code Type Description
NCI_THESAURUS
C66468
Created by admin on Fri Dec 16 17:26:41 UTC 2022 , Edited by admin on Fri Dec 16 17:26:41 UTC 2022
PRIMARY
ChEMBL
CHEMBL282567
Created by admin on Fri Dec 16 17:26:41 UTC 2022 , Edited by admin on Fri Dec 16 17:26:41 UTC 2022
PRIMARY
NSC
170997
Created by admin on Fri Dec 16 17:26:41 UTC 2022 , Edited by admin on Fri Dec 16 17:26:41 UTC 2022
PRIMARY
CAS
62-68-0
Created by admin on Fri Dec 16 17:26:41 UTC 2022 , Edited by admin on Fri Dec 16 17:26:41 UTC 2022
PRIMARY
PUBCHEM
65341
Created by admin on Fri Dec 16 17:26:41 UTC 2022 , Edited by admin on Fri Dec 16 17:26:41 UTC 2022
PRIMARY
EPA CompTox
DTXSID1045792
Created by admin on Fri Dec 16 17:26:41 UTC 2022 , Edited by admin on Fri Dec 16 17:26:41 UTC 2022
PRIMARY
NSC
39690
Created by admin on Fri Dec 16 17:26:41 UTC 2022 , Edited by admin on Fri Dec 16 17:26:41 UTC 2022
PRIMARY
FDA UNII
30624AA6X2
Created by admin on Fri Dec 16 17:26:41 UTC 2022 , Edited by admin on Fri Dec 16 17:26:41 UTC 2022
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY