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Approved, Investigational, Withdrawn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
DrugInteraction
AlimemazineThe risk or severity of adverse effects can be increased when Ifenprodil is combined with Alimemazine.
AloxiprinThe risk or severity of adverse effects can be increased when Ifenprodil is combined with Aloxiprin.
AlprazolamThe risk or severity of adverse effects can be increased when Alprazolam is combined with Ifenprodil.
AlprostadilAlprostadil may increase the antiplatelet activities of Ifenprodil.
AmikacinThe risk or severity of adverse effects can be increased when Ifenprodil is combined with Amikacin.
AmitriptylineThe risk or severity of adverse effects can be increased when Amitriptyline is combined with Ifenprodil.
AmphetamineThe risk or severity of adverse effects can be increased when Amphetamine is combined with Ifenprodil.
AncrodIfenprodil may increase the anticoagulant activities of Ancrod.
AndrographolideAndrographolide may increase the antiplatelet activities of Ifenprodil.
AnistreplaseIfenprodil may increase the anticoagulant activities of Anistreplase.
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 August 02, 2018 07:48