Identification

Name
Ifenprodil
Accession Number
DB08954
Type
Small Molecule
Groups
Approved, Investigational, Withdrawn
Description

Ifenprodil is a selective NMDA receptor (glutamate) antagonist.

Structure
Thumb
Synonyms
Not Available
External IDs
RC 61-91 / RC 61-96
Product Ingredients
IngredientUNIICASInChI Key
Ifenprodil Tartrate89CTB4XUF723210-58-4DMPRDSPPYMZQBT-CEAXSRTFSA-N
International/Other Brands
Cerocral (Sanofi) / Furezanil (Tsuruhara Seiyaku) / Iburonol (Towa Yakuhin) / Linbulane (Tatsumi Kagaku) / Technis (Sawai Seiyaku) / Vadilex (Sanofi) / Vasculodil (Kyowa Yakuhin) / Youajyl (Yoshindo)
Categories
UNII
R8OE3P6O5S
CAS number
23210-56-2
Weight
Average: 325.4446
Monoisotopic: 325.204179113
Chemical Formula
C21H27NO2
InChI Key
UYNVMODNBIQBMV-UHFFFAOYSA-N
InChI
InChI=1S/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

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
AGlutamate receptor ionotropic, NMDA 1
antagonist
Human
AGlutamate receptor ionotropic, NMDA 2B
antagonist
Human
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not 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, Investigational
Acetylsalicylic acidThe risk or severity of adverse effects can be increased when Ifenprodil is combined with Acetylsalicylic acid.Approved, Vet Approved
AloxiprinThe risk or severity of adverse effects can be increased when Ifenprodil is combined with Aloxiprin.Experimental
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.Approved, Investigational
AndrographolideAndrographolide may increase the antiplatelet activities of Ifenprodil.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, Investigational, Withdrawn
ArgatrobanIfenprodil may increase the anticoagulant activities of Argatroban.Approved, Investigational
AstaxanthinIfenprodil may increase the anticoagulant activities of Astaxanthin.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
BatroxobinIfenprodil may increase the anticoagulant activities of Batroxobin.Experimental
BecaplerminIfenprodil may increase the anticoagulant activities of Becaplermin.Approved, Investigational
BemiparinIfenprodil may increase the anticoagulant activities of Bemiparin.Approved, Investigational
BeraprostIfenprodil may increase the anticoagulant activities of Beraprost.Investigational
BivalirudinIfenprodil may increase the anticoagulant activities of Bivalirudin.Approved, Investigational
BrinaseIfenprodil may increase the anticoagulant activities of Brinase.Experimental
BuflomedilIfenprodil may increase the antiplatelet activities of Buflomedil.Experimental
ButylphthalideIfenprodil may increase the antiplatelet activities of Butylphthalide.Investigational
CangrelorIfenprodil may increase the anticoagulant activities of Cangrelor.Approved
CaplacizumabIfenprodil may increase the anticoagulant activities of Caplacizumab.Investigational
Carbaspirin calciumThe risk or severity of adverse effects can be increased when Ifenprodil is combined with Carbaspirin calcium.Experimental, Investigational
CertoparinIfenprodil may increase the anticoagulant activities of Certoparin.Approved, Investigational
CilostazolIfenprodil may increase the anticoagulant activities of Cilostazol.Approved, Investigational
Citric AcidIfenprodil may increase the anticoagulant activities of Citric Acid.Approved, Nutraceutical, Vet Approved
ClopidogrelIfenprodil may increase the anticoagulant activities of Clopidogrel.Approved
CloricromenIfenprodil may increase the anticoagulant activities of Cloricromen.Experimental
ClorindioneIfenprodil may increase the anticoagulant activities of Clorindione.Experimental
Collagenase clostridium histolyticumThe risk or severity of adverse effects can be increased when Ifenprodil is combined with Collagenase clostridium histolyticum.Approved, Investigational
Dabigatran etexilateIfenprodil may increase the anticoagulant activities of Dabigatran etexilate.Approved
DalteparinIfenprodil may increase the anticoagulant activities of Dalteparin.Approved
DanaparoidIfenprodil may increase the anticoagulant activities of Danaparoid.Approved, Withdrawn
DarexabanIfenprodil may increase the anticoagulant activities of Darexaban.Investigational
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
DersalazineThe risk or severity of adverse effects can be increased when Ifenprodil is combined with Dersalazine.Investigational
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, Investigational, Vet 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, Investigational
DiphenadioneIfenprodil may increase the anticoagulant activities of Diphenadione.Experimental
DipyridamoleIfenprodil may increase the anticoagulant activities of Dipyridamole.Approved
DitazoleIfenprodil may increase the anticoagulant activities of Ditazole.Approved, Withdrawn
DoxofyllineThe serum concentration of Doxofylline can be decreased when it is combined with Ifenprodil.Approved, Investigational
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
EplivanserinIfenprodil may increase the anticoagulant activities of Eplivanserin.Investigational
eplivanserineIfenprodil may increase the anticoagulant activities of eplivanserine.Investigational
EpoprostenolIfenprodil may increase the anticoagulant activities of Epoprostenol.Approved
EptifibatideIfenprodil may increase the anticoagulant activities of Eptifibatide.Approved, Investigational
Ethyl biscoumacetateIfenprodil may increase the anticoagulant activities of Ethyl biscoumacetate.Withdrawn
Ferulic acidIfenprodil may increase the anticoagulant activities of Ferulic acid.Experimental
FibrinolysinIfenprodil may increase the anticoagulant activities of Fibrinolysin.Investigational
FluindioneIfenprodil may increase the anticoagulant activities of Fluindione.Approved, Investigational
FondaparinuxIfenprodil may increase the anticoagulant activities of Fondaparinux sodium.Approved, Investigational
GabexateIfenprodil may increase the anticoagulant activities of Gabexate.Investigational
GlucosamineGlucosamine may increase the antiplatelet activities of Ifenprodil.Approved, Investigational
GuacetisalThe risk or severity of adverse effects can be increased when Ifenprodil is combined with Guacetisal.Experimental
Hemoglobin crosfumarilThe risk or severity of adverse effects can be increased when Ifenprodil is combined with Hemoglobin crosfumaril.Experimental
HeparinIfenprodil may increase the anticoagulant activities of Heparin.Approved, Investigational
HigenamineIfenprodil may increase the anticoagulant activities of Higenamine.Investigational
HydroxytyrosolIfenprodil may increase the antiplatelet activities of Hydroxytyrosol.Investigational
Ibritumomab tiuxetanThe risk or severity of adverse effects can be increased when Ifenprodil is combined with Ibritumomab tiuxetan.Approved, Investigational
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, Investigational, Nutraceutical
IdraparinuxIfenprodil may increase the anticoagulant activities of Idraparinux.Investigational
IfetrobanIfenprodil may increase the antiplatelet activities of Ifetroban.Investigational
IloprostIfenprodil may increase the anticoagulant activities of Iloprost.Approved, Investigational
IndobufenIfenprodil may increase the anticoagulant activities of Indobufen.Investigational
KetanserinIfenprodil may increase the antiplatelet activities of Ketanserin.Investigational
LepirudinIfenprodil may increase the anticoagulant activities of Lepirudin.Approved
LetaxabanIfenprodil may increase the anticoagulant activities of Letaxaban.Investigational
LimaprostLimaprost may increase the antiplatelet activities of Ifenprodil.Approved, Investigational
LinsidomineIfenprodil may increase the antiplatelet activities of Linsidomine.Experimental
MefloquineThe therapeutic efficacy of Ifenprodil can be decreased when used in combination with Mefloquine.Approved, Investigational
MelagatranIfenprodil may increase the anticoagulant activities of Melagatran.Experimental
MemantineThe risk or severity of adverse effects can be increased when Ifenprodil is combined with Memantine.Approved, Investigational
MesalazineThe risk or severity of adverse effects can be increased when Ifenprodil is combined with Mesalazine.Approved
Methyl salicylateThe risk or severity of adverse effects can be increased when Ifenprodil is combined with Methyl salicylate.Approved, Vet Approved
MianserinThe therapeutic efficacy of Ifenprodil can be decreased when used in combination with Mianserin.Approved, Investigational
MilrinoneMilrinone may increase the antiplatelet activities of Ifenprodil.Approved
NadroparinIfenprodil may increase the anticoagulant activities of Nadroparin.Approved, Investigational
NafamostatIfenprodil may increase the anticoagulant activities of Nafamostat.Approved, Investigational
NaftopidilIfenprodil may increase the antiplatelet activities of Naftopidil.Investigational
NimesulideNimesulide may increase the antiplatelet activities of Ifenprodil.Approved, Investigational, Withdrawn
NitroaspirinThe risk or severity of adverse effects can be increased when Ifenprodil is combined with Nitroaspirin.Investigational
ObinutuzumabThe risk or severity of adverse effects can be increased when Ifenprodil is combined with Obinutuzumab.Approved, Investigational
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
OtamixabanIfenprodil may increase the anticoagulant activities of Otamixaban.Investigational
OzagrelIfenprodil may increase the anticoagulant activities of Ozagrel.Investigational
ParnaparinIfenprodil may increase the anticoagulant activities of Parnaparin.Approved, Investigational
Pentaerythritol TetranitrateIfenprodil may increase the anticoagulant activities of Pentaerythritol Tetranitrate.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, Investigational
PhenprocoumonIfenprodil may increase the anticoagulant activities of Phenprocoumon.Approved, Investigational
Phenyl aminosalicylateThe risk or severity of adverse effects can be increased when Ifenprodil is combined with Phenyl aminosalicylate.Approved
PicotamideIfenprodil may increase the anticoagulant activities of Picotamide.Experimental
Potassium CitrateIfenprodil may increase the anticoagulant activities of Potassium Citrate.Approved, Investigational, Vet Approved
PrasugrelIfenprodil may increase the anticoagulant activities of Prasugrel.Approved
PregabalinThe therapeutic efficacy of Ifenprodil can be decreased when used in combination with Pregabalin.Approved, Illicit, Investigational
Protein CIfenprodil may increase the anticoagulant activities of Protein C.Approved
Protein S humanIfenprodil may increase the anticoagulant activities of Protein S human.Approved
ProtocatechualdehydeIfenprodil may increase the anticoagulant activities of Protocatechualdehyde.Approved
RamatrobanIfenprodil may increase the antiplatelet activities of Ramatroban.Investigational
RelcovaptanIfenprodil may increase the antiplatelet activities of Relcovaptan.Investigational
ResveratrolResveratrol may increase the antiplatelet activities of Ifenprodil.Approved, Experimental, Investigational
ReteplaseIfenprodil may increase the anticoagulant activities of Reteplase.Approved, Investigational
ReviparinIfenprodil may increase the anticoagulant activities of Reviparin.Approved, Investigational
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, Investigational, Vet Approved
SarpogrelateIfenprodil may increase the anticoagulant activities of Sarpogrelate.Investigational
SaruplaseIfenprodil may increase the anticoagulant activities of Saruplase.Experimental
SelexipagIfenprodil may increase the anticoagulant activities of Selexipag.Approved
SevofluraneSevoflurane may increase the antiplatelet activities of Ifenprodil.Approved, Vet Approved
Sodium CitrateIfenprodil may increase the anticoagulant activities of Sodium Citrate.Approved, Investigational
SRT501SRT501 may increase the antiplatelet activities of Ifenprodil.Investigational
StreptokinaseIfenprodil may increase the anticoagulant activities of Streptokinase.Approved, Investigational
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
TioclomarolIfenprodil may increase the anticoagulant activities of Tioclomarol.Experimental
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, Investigational
TranilastTranilast may increase the antiplatelet activities of Ifenprodil.Approved, Investigational
TrapidilIfenprodil may increase the antiplatelet activities of Trapidil.Approved
TreprostinilIfenprodil may increase the anticoagulant activities of Treprostinil.Approved, Investigational
TriflusalIfenprodil may increase the anticoagulant activities of Triflusal.Approved, Investigational
Trolamine salicylateThe risk or severity of adverse effects can be increased when Ifenprodil is combined with Trolamine salicylate.Approved
TroxerutinIfenprodil may increase the anticoagulant activities of Troxerutin.Investigational
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 Interactions
Not Available

References

Synthesis Reference

U.S. Patent 3,509,164.

General References
Not Available
External Links
KEGG Drug
D08064
PubChem Compound
3689
PubChem Substance
310264919
ChemSpider
3561
BindingDB
50083351
ChEBI
93829
ChEMBL
CHEMBL305187
Drugs.com
Drugs.com Drug Page
Wikipedia
Ifenprodil
ATC Codes
C04AX28 — Ifenprodil

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1, 2RecruitingTreatmentPosttraumatic Stress Disorders1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not 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 RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
MS/MS Spectrum - , positiveLC-MS/MSsplash10-004i-0319000000-a8642bda70c1638039bd

Taxonomy

Description
This compound belongs to the class of organic compounds known as 4-benzylpiperidines. These are organic compounds containing a benzyl group attached to the 4-position of a piperidine.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Piperidines
Sub Class
Benzylpiperidines
Direct Parent
4-benzylpiperidines
Alternative Parents
Phenylpropanes / Aralkylamines / 1-hydroxy-2-unsubstituted benzenoids / Trialkylamines / Secondary alcohols / 1,2-aminoalcohols / Azacyclic compounds / Organopnictogen compounds / Hydrocarbon derivatives / Aromatic alcohols
Substituents
4-benzylpiperidine / Phenylpropane / 1-hydroxy-2-unsubstituted benzenoid / Phenol / Aralkylamine / Monocyclic benzene moiety / Benzenoid / 1,2-aminoalcohol / Secondary alcohol / Tertiary amine
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
Not 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 p...
Gene Name
GRIN1
Uniprot ID
Q05586
Uniprot Name
Glutamate receptor ionotropic, NMDA 1
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 site...
Gene Name
GRIN2B
Uniprot ID
Q13224
Uniprot Name
Glutamate receptor ionotropic, NMDA 2B
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]

Drug created on May 28, 2014 11:48 / Updated on July 02, 2018 20:41