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Identification
NameIfenprodil
Accession NumberDB08954
TypeSmall Molecule
GroupsApproved, Withdrawn
DescriptionIfenprodil is a selective NMDA receptor (glutamate) antagonist.
Structure
Thumb
SynonymsNot Available
External IDs RC 61-91 / RC 61-96
Product Ingredients
IngredientUNIICASInChI KeyDetails
Ifenprodil Tartrate89CTB4XUF7 23210-58-4DMPRDSPPYMZQBT-CEAXSRTFSA-NDetails
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
CerocralSanofi
FurezanilTsuruhara Seiyaku
IburonolTowa Yakuhin
LinbulaneTatsumi Kagaku
TechnisSawai Seiyaku
VadilexSanofi
VasculodilKyowa Yakuhin
YouajylYoshindo
Brand mixturesNot Available
Categories
UNIIR8OE3P6O5S
CAS number23210-56-2
WeightAverage: 325.4446
Monoisotopic: 325.204179113
Chemical FormulaC21H27NO2
InChI KeyUYNVMODNBIQBMV-UHFFFAOYNA-N
InChI
InChI=1/C21H27NO2/c1-16(21(24)19-7-9-20(23)10-8-19)22-13-11-18(12-14-22)15-17-5-3-2-4-6-17/h2-10,16,18,21,23-24H,11-15H2,1H3
IUPAC Name
4-[2-(4-benzylpiperidin-1-yl)-1-hydroxypropyl]phenol
SMILES
CC(C(O)C1=CC=C(O)C=C1)N1CCC(CC2=CC=CC=C2)CC1
Pharmacology
IndicationNot Available
Structured Indications Not Available
PharmacodynamicsNot Available
Mechanism of action
TargetKindPharmacological actionActionsOrganismUniProt ID
Glutamate receptor ionotropic, NMDA 1Proteinyes
antagonist
HumanQ05586 details
Glutamate receptor ionotropic, NMDA 2BProteinyes
antagonist
HumanQ13224 details
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organismsNot Available
PathwaysNot Available
Pharmacogenomic Effects/ADRs Not Available
Interactions
Drug Interactions
DrugInteractionDrug group
AbciximabIfenprodil may increase the anticoagulant activities of Abciximab.Approved
AcenocoumarolIfenprodil may increase the anticoagulant activities of Acenocoumarol.Approved
Acetylsalicylic acidThe risk or severity of adverse effects can be increased when Ifenprodil is combined with Acetylsalicylic acid.Approved, Vet Approved
AlprostadilAlprostadil may increase the antiplatelet activities of Ifenprodil.Approved, Investigational
AlteplaseIfenprodil may increase the anticoagulant activities of Alteplase.Approved
Aminosalicylic AcidThe risk or severity of adverse effects can be increased when Ifenprodil is combined with Aminosalicylic Acid.Approved
AnagrelideIfenprodil may increase the anticoagulant activities of Anagrelide.Approved
AncrodIfenprodil may increase the anticoagulant activities of Ancrod.Investigational
AnistreplaseIfenprodil may increase the anticoagulant activities of Anistreplase.Approved
Antithrombin III humanIfenprodil may increase the anticoagulant activities of Antithrombin III human.Approved
ApixabanThe risk or severity of adverse effects can be increased when Ifenprodil is combined with Apixaban.Approved
ArdeparinIfenprodil may increase the anticoagulant activities of Ardeparin.Approved, Withdrawn
ArgatrobanIfenprodil may increase the anticoagulant activities of Argatroban.Approved, Investigational
AzelastineAzelastine may increase the antiplatelet activities of Ifenprodil.Approved
BalsalazideThe risk or severity of adverse effects can be increased when Ifenprodil is combined with Balsalazide.Approved, Investigational
BecaplerminIfenprodil may increase the anticoagulant activities of Becaplermin.Approved, Investigational
BemiparinIfenprodil may increase the anticoagulant activities of Bemiparin.Approved
BeraprostIfenprodil may increase the anticoagulant activities of Beraprost.Investigational
BivalirudinIfenprodil may increase the anticoagulant activities of Bivalirudin.Approved, Investigational
CangrelorIfenprodil may increase the anticoagulant activities of Cangrelor.Approved
CertoparinIfenprodil may increase the anticoagulant activities of Certoparin.Approved
CilostazolIfenprodil may increase the anticoagulant activities of Cilostazol.Approved
Citric AcidIfenprodil may increase the anticoagulant activities of Citric Acid.Nutraceutical, Vet Approved
ClopidogrelIfenprodil may increase the anticoagulant activities of Clopidogrel.Approved, Nutraceutical
Dabigatran etexilateIfenprodil may increase the anticoagulant activities of Dabigatran etexilate.Approved
DalteparinIfenprodil may increase the anticoagulant activities of Dalteparin.Approved
DasatinibDasatinib may increase the anticoagulant activities of Ifenprodil.Approved, Investigational
DefibrotideIfenprodil may increase the anticoagulant activities of Defibrotide.Approved, Investigational
Deoxycholic AcidThe risk or severity of adverse effects can be increased when Ifenprodil is combined with Deoxycholic Acid.Approved
DesirudinIfenprodil may increase the anticoagulant activities of Desirudin.Approved
DesmoteplaseIfenprodil may increase the anticoagulant activities of Desmoteplase.Investigational
DextranIfenprodil may increase the anticoagulant activities of Dextran.Approved, Vet Approved
Dextran 40Ifenprodil may increase the anticoagulant activities of Dextran 40.Approved
DicoumarolIfenprodil may increase the anticoagulant activities of Dicoumarol.Approved
DiflunisalThe risk or severity of adverse effects can be increased when Ifenprodil is combined with Diflunisal.Approved
DipyridamoleIfenprodil may increase the anticoagulant activities of Dipyridamole.Approved
DitazoleIfenprodil may increase the anticoagulant activities of Ditazole.Approved, Withdrawn
Drotrecogin alfaIfenprodil may increase the anticoagulant activities of Drotrecogin alfa.Approved, Investigational, Withdrawn
Edetic AcidIfenprodil may increase the anticoagulant activities of Edetic Acid.Approved, Vet Approved
EdoxabanIfenprodil may increase the anticoagulant activities of Edoxaban.Approved
EnoxaparinIfenprodil may increase the anticoagulant activities of Enoxaparin.Approved
EpinastineEpinastine may increase the antiplatelet activities of Ifenprodil.Approved, Investigational
EpoprostenolEpoprostenol may increase the antiplatelet activities of Ifenprodil.Approved
EptifibatideIfenprodil may increase the anticoagulant activities of Eptifibatide.Approved, Investigational
Ethyl biscoumacetateIfenprodil may increase the anticoagulant activities of Ethyl biscoumacetate.Withdrawn
FibrinolysinIfenprodil may increase the anticoagulant activities of Fibrinolysin.Approved
Fondaparinux sodiumIfenprodil may increase the anticoagulant activities of Fondaparinux sodium.Approved, Investigational
GabexateIfenprodil may increase the anticoagulant activities of Gabexate.Approved, Investigational
GlucosamineGlucosamine may increase the antiplatelet activities of Ifenprodil.Approved
HeparinIfenprodil may increase the anticoagulant activities of Heparin.Approved, Investigational
Ibritumomab tiuxetanThe risk or severity of adverse effects can be increased when Ifenprodil is combined with Ibritumomab tiuxetan.Approved
IbrutinibThe risk or severity of adverse effects can be increased when Ibrutinib is combined with Ifenprodil.Approved
IbudilastIbudilast may increase the antiplatelet activities of Ifenprodil.Approved, Investigational
Icosapent ethylIcosapent ethyl may increase the antiplatelet activities of Ifenprodil.Approved, Nutraceutical
IloprostIloprost may increase the antiplatelet activities of Ifenprodil.Approved, Investigational
LepirudinIfenprodil may increase the anticoagulant activities of Lepirudin.Approved
LimaprostLimaprost may increase the antiplatelet activities of Ifenprodil.Approved
MefloquineThe therapeutic efficacy of Ifenprodil can be decreased when used in combination with Mefloquine.Approved
MesalazineThe risk or severity of adverse effects can be increased when Ifenprodil is combined with Mesalazine.Approved
MianserinThe therapeutic efficacy of Ifenprodil can be decreased when used in combination with Mianserin.Approved
MilrinoneMilrinone may increase the antiplatelet activities of Ifenprodil.Approved
NadroparinIfenprodil may increase the anticoagulant activities of Nadroparin.Approved
NafamostatIfenprodil may increase the anticoagulant activities of Nafamostat.Approved, Investigational
NCX 4016The risk or severity of adverse effects can be increased when Ifenprodil is combined with NCX 4016.Investigational
NimesulideNimesulide may increase the antiplatelet activities of Ifenprodil.Approved, Withdrawn
ObinutuzumabThe risk or severity of adverse effects can be increased when Ifenprodil is combined with Obinutuzumab.Approved
OlsalazineThe risk or severity of adverse effects can be increased when Ifenprodil is combined with Olsalazine.Approved
Omega-3 fatty acidsOmega-3 fatty acids may increase the antiplatelet activities of Ifenprodil.Approved, Nutraceutical
OrlistatThe serum concentration of Ifenprodil can be decreased when it is combined with Orlistat.Approved, Investigational
ParnaparinIfenprodil may increase the anticoagulant activities of Parnaparin.Approved
Pentosan PolysulfateThe risk or severity of adverse effects can be increased when Pentosan Polysulfate is combined with Ifenprodil.Approved
PentoxifyllinePentoxifylline may increase the antiplatelet activities of Ifenprodil.Approved, Investigational
PhenindioneIfenprodil may increase the anticoagulant activities of Phenindione.Approved
PhenprocoumonIfenprodil may increase the anticoagulant activities of Phenprocoumon.Approved
PlasminIfenprodil may increase the anticoagulant activities of Plasmin.Investigational
PrasugrelIfenprodil may increase the anticoagulant activities of Prasugrel.Approved
Protein S humanIfenprodil may increase the anticoagulant activities of Protein S human.Approved
ResveratrolResveratrol may increase the antiplatelet activities of Ifenprodil.Experimental, Investigational
ReteplaseIfenprodil may increase the anticoagulant activities of Reteplase.Approved
ReviparinIfenprodil may increase the anticoagulant activities of Reviparin.Approved
RidogrelRidogrel may increase the antiplatelet activities of Ifenprodil.Approved
RivaroxabanIfenprodil may increase the anticoagulant activities of Rivaroxaban.Approved
RosiglitazoneIfenprodil may increase the anticoagulant activities of Rosiglitazone.Approved, Investigational
Salicylic acidThe risk or severity of adverse effects can be increased when Ifenprodil is combined with Salicylic acid.Approved, Vet Approved
SCH-530348SCH-530348 may increase the antiplatelet activities of Ifenprodil.Investigational
SelexipagIfenprodil may increase the anticoagulant activities of Selexipag.Approved
SevofluraneSevoflurane may increase the antiplatelet activities of Ifenprodil.Approved, Vet Approved
SRT501SRT501 may increase the antiplatelet activities of Ifenprodil.Investigational
StreptokinaseIfenprodil may increase the anticoagulant activities of Streptokinase.Approved
SulodexideIfenprodil may increase the anticoagulant activities of Sulodexide.Approved, Investigational
TenecteplaseIfenprodil may increase the anticoagulant activities of Tenecteplase.Approved
TesmilifeneTesmilifene may increase the antiplatelet activities of Ifenprodil.Investigational
TicagrelorIfenprodil may increase the anticoagulant activities of Ticagrelor.Approved
TiclopidineIfenprodil may increase the anticoagulant activities of Ticlopidine.Approved
TinzaparinIfenprodil may increase the anticoagulant activities of Tinzaparin.Approved
TipranavirTipranavir may increase the antiplatelet activities of Ifenprodil.Approved, Investigational
TirofibanIfenprodil may increase the anticoagulant activities of Tirofiban.Approved
TositumomabThe risk or severity of adverse effects can be increased when Ifenprodil is combined with Tositumomab.Approved
TranilastTranilast may increase the antiplatelet activities of Ifenprodil.Approved, Investigational
TrapidilIfenprodil may increase the antiplatelet activities of Trapidil.Approved
TreprostinilTreprostinil may increase the antiplatelet activities of Ifenprodil.Approved, Investigational
TriflusalIfenprodil may increase the anticoagulant activities of Triflusal.Approved
UrokinaseIfenprodil may increase the anticoagulant activities of Urokinase.Approved, Investigational, Withdrawn
Vitamin EVitamin E may increase the antiplatelet activities of Ifenprodil.Approved, Nutraceutical, Vet Approved
VorapaxarIfenprodil may increase the anticoagulant activities of Vorapaxar.Approved
WarfarinIfenprodil may increase the anticoagulant activities of Warfarin.Approved
XimelagatranIfenprodil may increase the anticoagulant activities of Ximelagatran.Approved, Investigational, Withdrawn
Food InteractionsNot Available
References
Synthesis Reference

U.S. Patent 3,509,164.

General ReferencesNot Available
External Links
ATC CodesC04AX28
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Clinical Trials
Clinical Trials
PhaseStatusPurposeConditionsCount
1, 2RecruitingTreatmentPosttraumatic Stress Disorders1
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental PropertiesNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.105 mg/mLALOGPS
logP3.98ALOGPS
logP3.57ChemAxon
logS-3.5ALOGPS
pKa (Strongest Acidic)9.67ChemAxon
pKa (Strongest Basic)9.03ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area43.7 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity98.35 m3·mol-1ChemAxon
Polarizability37.52 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET featuresNot Available
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-004i-0319000000-a8642bda70c1638039bdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as 4-benzylpiperidines. These are organic compounds containing a benzyl group attached to the 4-position of a piperidine.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganoheterocyclic compounds
Sub ClassPiperidines
Direct Parent4-benzylpiperidines
Alternative Parents
Substituents
  • 4-benzylpiperidine
  • Phenylpropane
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Aralkylamine
  • Monocyclic benzene moiety
  • Benzenoid
  • 1,2-aminoalcohol
  • Secondary alcohol
  • Tertiary amine
  • Tertiary aliphatic amine
  • Azacycle
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Amine
  • Alcohol
  • Aromatic alcohol
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
antagonist
General Function:
Voltage-gated cation channel activity
Specific Function:
NMDA receptor subtype of glutamate-gated ion channels with high calcium permeability and voltage-dependent sensitivity to magnesium. Mediated by glycine. This protein plays a key role in synaptic plasticity, synaptogenesis, excitotoxicity, memory acquisition and learning. It mediates neuronal functions in glutamate neurotransmission. Is involved in the cell surface targeting of NMDA receptors (...
Gene Name:
GRIN1
Uniprot ID:
Q05586
Molecular Weight:
105371.945 Da
References
  1. Seppala T, Stromberg C, Mattila MJ: Effects of the novel 5-hydroxytryptamine reuptake inhibitor indalpine and ethanol on psychomotor performance. Arzneimittelforschung. 1988 Jan;38(1):98-102. [PubMed:3365283 ]
Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
antagonist
General Function:
Zinc ion binding
Specific Function:
NMDA receptor subtype of glutamate-gated ion channels with high calcium permeability and voltage-dependent sensitivity to magnesium. Mediated by glycine. In concert with DAPK1 at extrasynaptic sites, acts as a central mediator for stroke damage. Its phosphorylation at Ser-1303 by DAPK1 enhances synaptic NMDA receptor channel activity inducing injurious Ca2+ influx through them, resulting in an ...
Gene Name:
GRIN2B
Uniprot ID:
Q13224
Molecular Weight:
166365.885 Da
References
  1. Seppala T, Stromberg C, Mattila MJ: Effects of the novel 5-hydroxytryptamine reuptake inhibitor indalpine and ethanol on psychomotor performance. Arzneimittelforschung. 1988 Jan;38(1):98-102. [PubMed:3365283 ]
Comments
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Drug created on May 28, 2014 11:48 / Updated on December 08, 2016 11:46