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Details

Stereochemistry MIXED
Molecular Formula 2C21H27NO2.C4H6O6
Molecular Weight 800.976
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 6
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of IFENPRODIL TARTRATE

SMILES

O[C@H]([C@@H](O)C(O)=O)C(O)=O.CC(C(O)C1=CC=C(O)C=C1)N2CCC(CC3=CC=CC=C3)CC2.CC(C(O)C4=CC=C(O)C=C4)N5CCC(CC6=CC=CC=C6)CC5

InChI

InChIKey=DMPRDSPPYMZQBT-CEAXSRTFSA-N
InChI=1S/2C21H27NO2.C4H6O6/c2*1-16(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;5-1(3(7)8)2(6)4(9)10/h2*2-10,16,18,21,23-24H,11-15H2,1H3;1-2,5-6H,(H,7,8)(H,9,10)/t;;1-,2-/m..1/s1

HIDE SMILES / InChI
Molecular Formula C21H27NO2
Molecular Weight 325.4446
Charge 0
Count
Stereochemistry MIXED
Additional Stereochemistry No
Defined Stereocenters 0 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED
Molecular Formula C4H6O6
Molecular Weight 150.0868
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/11554553 http://en.pharmacodia.com/web/drug/1_11124.html

Ifenprodil (marketed under the brands Vadilex; Dilvax; Creocral; Cerocral) is a selective NMDA receptor (glutamate) antagonist. Additionally, ifenprodil inhibits GIRK channels, and interacts with alpha1 adrenergic, serotonin, and sigma receptors. Ifenprodil acts as a vasodilator. Ifenprodil is a medicine available in a number of countries worldwide, but not in US.

CNS Activity

Originator

Approval Year

Unknown
149124
Targets

Targets

Primary TargetPharmacologyConditionPotency
Antagonist
2849
 190.0 nM [IC50]
Antagonist
2849
 47.0 nM [IC50]
Agonist
2752
 28.27 nM [IC50]
Antagonist
2849
 100.0 nM [IC50]
Inhibitor
8504
 7.01 µM [IC50]
Inhibitor
8504
 2.83 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Approved
8583
Ifenprodil

Approved Use

Peripheral vascular disease
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
10.13 ng/mL
EXPERIMENT
https://www.sciencedirect.com/science/article/pii/S2211383513000336
5 mg single, intravenous
dose: 5 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
IFENPRODIL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
19.1 ng/mL
EXPERIMENT
https://www.sciencedirect.com/science/article/pii/S2211383513000336
10 mg single, intravenous
dose: 10 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
IFENPRODIL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
28.9 ng/mL
EXPERIMENT
https://www.sciencedirect.com/science/article/pii/S2211383513000336
15 mg single, oral
dose: 15 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
IFENPRODIL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
20.4 ng/mL
EXPERIMENT
https://www.sciencedirect.com/science/article/pii/S2211383513000336
10 mg 1 times / day steady-state, intravenous
dose: 10 mg
route of administration: Intravenous
experiment type: STEADY-STATE
co-administered:
IFENPRODIL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
21.7 ng × h/mL
EXPERIMENT
https://www.sciencedirect.com/science/article/pii/S2211383513000336
5 mg single, intravenous
dose: 5 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
IFENPRODIL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
41.3 ng × h/mL
EXPERIMENT
https://www.sciencedirect.com/science/article/pii/S2211383513000336
10 mg single, intravenous
dose: 10 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
IFENPRODIL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
63.1 ng × h/mL
EXPERIMENT
https://www.sciencedirect.com/science/article/pii/S2211383513000336
15 mg single, oral
dose: 15 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
IFENPRODIL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
47 ng × h/mL
EXPERIMENT
https://www.sciencedirect.com/science/article/pii/S2211383513000336
10 mg 1 times / day steady-state, intravenous
dose: 10 mg
route of administration: Intravenous
experiment type: STEADY-STATE
co-administered:
IFENPRODIL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
3.87 h
EXPERIMENT
https://www.sciencedirect.com/science/article/pii/S2211383513000336
5 mg single, intravenous
dose: 5 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
IFENPRODIL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
3.61 h
EXPERIMENT
https://www.sciencedirect.com/science/article/pii/S2211383513000336
10 mg single, intravenous
dose: 10 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
IFENPRODIL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
4.07 h
EXPERIMENT
https://www.sciencedirect.com/science/article/pii/S2211383513000336
15 mg single, oral
dose: 15 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
IFENPRODIL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
4.25 h
EXPERIMENT
https://www.sciencedirect.com/science/article/pii/S2211383513000336
10 mg 1 times / day steady-state, intravenous
dose: 10 mg
route of administration: Intravenous
experiment type: STEADY-STATE
co-administered:
IFENPRODIL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
Doses

Doses

DosePopulationAdverse events​
40 mg 3 times / day multiple, oral
Highest studied dose
Dose: 40 mg, 3 times / day
Route: oral
Route: multiple
Dose: 40 mg, 3 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/30756527/
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: FED
Sources:
https://pubmed.ncbi.nlm.nih.gov/30756527/
Sources:
https://pubmed.ncbi.nlm.nih.gov/30756527/
PubMed

PubMed

TitleDatePubMed
Chronic ethanol ingestion facilitates N-methyl-D-aspartate receptor function and expression in rat lateral/basolateral amygdala neurons.
2003-12
NMDA currents and receptor protein are downregulated in the amygdala during maintenance of fear memory.
2003-11-12
Fyn kinase and NR2B-containing NMDA receptors regulate acute ethanol sensitivity but not ethanol intake or conditioned reward.
2003-11
Acute dissociation for analyses of NMDA receptor function in cortical neurons during aging.
2003-10-15
Effect of the NR3 subunit on ethanol inhibition of recombinant NMDA receptors.
2003-10-10
Postsynaptic contributions to hippocampal network hyperexcitability induced by chronic activity blockade in vivo.
2003-10
Overexpression of spermidine/spermine N1-acetyltransferase elevates the threshold to pentylenetetrazol-induced seizure activity in transgenic mice.
2003-10
Effects of NMDA receptor antagonists on acute mu-opioid analgesia in the rat.
2003-09
The effect of (+/-)-CP-101,606, an NMDA receptor NR2B subunit selective antagonist, in the Morris watermaze.
2003-08-29
Polyamines in a genetic animal model of paroxysmal dyskinesia.
2003-08-15
Activation of NMDA receptors in rat dentate gyrus granule cells by spontaneous and evoked transmitter release.
2003-08
Development and subunit composition of synaptic NMDA receptors in the amygdala: NR2B synapses in the adult central amygdala.
2003-07-30
Enhanced GABA(A) receptor-mediated activity following activation of NMDA receptors in Cajal-Retzius cells in the developing mouse neocortex.
2003-07-01
Therapeutic N-methyl-D-aspartate receptor antagonists: will reality meet expectation?
2003-07
Polyamines contribute to ethanol withdrawal-induced neurotoxicity in rat hippocampal slice cultures through interactions with the NMDA receptor.
2003-07
Amphetamine-evoked c-fos mRNA expression in the caudate-putamen: the effects of DA and NMDA receptor antagonists vary as a function of neuronal phenotype and environmental context.
2003-07
Behavioral effects of NMDA receptor agonists and antagonists in combination with nitric oxide-related compounds.
2003-06-20
Lack of ifenprodil anxiolytic activity after its multiple treatment in chronically ethanol-treated rats.
2003-06-20
ATP inhibits NMDA receptors after heterologous expression and in cultured hippocampal neurons and attenuates NMDA-mediated neurotoxicity.
2003-06-15
NR2B and NR2D subunits coassemble in cerebellar Golgi cells to form a distinct NMDA receptor subtype restricted to extrasynaptic sites.
2003-06-15
N-Methyl-D-aspartate receptors contribute to the maintenance of dopaminergic neurons in rat midbrain slice cultures.
2003-05-01
NMDA-receptor antagonism via dextromethorphan and ifenprodil modulates graded anxiety test performance of C57BL/6 mice.
2003-05
Role of the NMDA receptor NR2B subunit in the discriminative stimulus effects of ketamine.
2003-05
Involvement of voltage- and ligand-gated Ca2+ channels in the neuroexcitatory and synergistic effects of putative uremic neurotoxins.
2003-05
Expression of behavioral sensitization to ethanol by DBA/2J mice: the role of NMDA and non-NMDA glutamate receptors.
2003-05
Functional NMDA receptor subtype 2B is expressed in astrocytes after ischemia in vivo and anoxia in vitro.
2003-04-15
Contribution of NR2B subunits to synaptic transmission in amygdaloid interneurons.
2003-04-01
PSD-95 regulates NMDA receptors in developing cerebellar granule neurons of the rat.
2003-04-01
Excitatory synaptic transmission in the lateral and central amygdala.
2003-04
Lithium-induced inhibition of Src tyrosine kinase in rat cerebral cortical neurons: a role in neuroprotection against N-methyl-D-aspartate receptor-mediated excitotoxicity.
2003-03-13
Ionotropic glutamate receptors: still a target for neuroprotection in brain ischemia? Insights from in vitro studies.
2003-02
Excitatory amino acid receptors of the electrosensory system: the NR1/NR2B N-methyl-D-aspartate receptor.
2003-02
Evidence for functionally distinct synaptic NMDA receptors in ventromedial versus dorsolateral striatum.
2003-01
Comparison of effect of ethanol on N-methyl-D-aspartate- and GABA-gated currents from acutely dissociated neurons: absence of regional differences in sensitivity to ethanol.
2003-01
Differential alterations in the expression of NMDA receptor subunits following chronic ethanol treatment in primary cultures of rat cortical and hippocampal neurones.
2003-01
Ionotropic and metabotropic glutamate receptor mediation of glucocorticoid-induced apoptosis in hippocampal cells and the neuroprotective role of synaptic N-methyl-D-aspartate receptors.
2003
Studies on neuronal apoptosis in primary forebrain cultures: neuroprotective/anti-apoptotic action of NR2B NMDA antagonists.
2003
Developmental Pb2+ exposure alters NMDAR subtypes and reduces CREB phosphorylation in the rat brain.
2002-12-15
Expression of functional NR1/NR2B-type NMDA receptors in neuronally differentiated SK-N-SH human cell line.
2002-12
Ethanol sensitivity of NMDA receptors.
2002-12
Radioligand binding studies reveal agmatine is a more selective antagonist for a polyamine-site on the NMDA receptor than arcaine or ifenprodil.
2002-10-11
Intrathecally administered big dynorphin, a prodynorphin-derived peptide, produces nociceptive behavior through an N-methyl-D-aspartate receptor mechanism.
2002-10-11
Acamprosate, MK-801, and ifenprodil inhibit neurotoxicity and calcium entry induced by ethanol withdrawal in organotypic slice cultures from neonatal rat hippocampus.
2002-10
Changes in the effect of isoflurane on N-methyl-D-aspartic acid-gated currents in cultured cerebral cortical neurons with time in culture: evidence for subunit specificity.
2002-10
Resistance to alcohol withdrawal-induced behaviour in Fyn transgenic mice and its reversal by ifenprodil.
2002-09-30
Selective NR2B NMDA receptor antagonists are protective against staurosporine-induced apoptosis.
2002-09-27
Site-selective N-methyl-D-aspartate and alpha-amino-3-hydroxy-5-methyl-4-isoxazolepropionate antagonists produce distinct effects in rats performing complex discriminations.
2002-09
Differential regulation of synaptic and extra-synaptic NMDA receptors.
2002-09
Effects of acamprosate and some polyamine site ligands of NMDA receptor on short-term memory in rats.
2002-05-24
[Effects of 2-(4-benzyl-piperidino)-1-(4-hydroxyphenyl)-1-propanol (ifenprodil) on the cardiovascular system in vivo].
1975-09
Patents

Patents

JP2002517462A
7
JP2003515526A
470
JPH02221222A
5
JPH02255612A
2
JPH0840902A
2

Sample Use Guides

In Vivo Use Guide
Oral Peripheral vascular disease Adult: As tartrate: 40-60 mg daily. Injection Peripheral vascular disease Adult: As tartrate: Up to 15 mg daily by deep IM or slow IV Inj or IV infusion.
Route of Administration: Other
In Vitro Use Guide
Ifenprodil (10 uM) reduced whole-cell NMDA-evoked currents by approximately 80 % in Golgi cells of the rat cerebellum..
Substance Class Chemical
Created
by admin
on Mon Mar 31 19:40:32 GMT 2025
Edited
by admin
on Mon Mar 31 19:40:32 GMT 2025
Record UNII
89CTB4XUF7
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
4-BENZYL-1-(.BETA.,4-DIHYDROXY-.ALPHA.-METHYLPHENETHYL PIPERIDINIUM HYDROGEN TARTRATE
Preferred Name English
IFENPRODIL TARTRATE
MART.   WHO-DD  
Common Name English
1-PIPERIDINEETHANOL, .ALPHA.-(4-HYDROXYPHENYL)-.BETA.-METHYL-4-(PHENYLMETHYL)-, (2R,3R)-2,3-DIHYDROXYBUTANEDIOATE (2:1)
Systematic Name English
IFENPRODIL TARTRATE [MART.]
Common Name English
Ifenprodil tartrate [WHO-DD]
Common Name English
IFENPRODIL TARTRATE [JAN]
Common Name English
IFENPRODIL HEMITARTRATE
Common Name English
Code System Code Type Description
EVMPD
SUB02636MIG
Created by admin on Mon Mar 31 19:40:32 GMT 2025 , Edited by admin on Mon Mar 31 19:40:32 GMT 2025
PRIMARY
ECHA (EC/EINECS)
245-493-5
Created by admin on Mon Mar 31 19:40:32 GMT 2025 , Edited by admin on Mon Mar 31 19:40:32 GMT 2025
PRIMARY
CAS
23210-58-4
Created by admin on Mon Mar 31 19:40:32 GMT 2025 , Edited by admin on Mon Mar 31 19:40:32 GMT 2025
PRIMARY
DRUG BANK
DBSALT001078
Created by admin on Mon Mar 31 19:40:32 GMT 2025 , Edited by admin on Mon Mar 31 19:40:32 GMT 2025
PRIMARY
EPA CompTox
DTXSID50945896
Created by admin on Mon Mar 31 19:40:32 GMT 2025 , Edited by admin on Mon Mar 31 19:40:32 GMT 2025
PRIMARY
SMS_ID
100000086980
Created by admin on Mon Mar 31 19:40:32 GMT 2025 , Edited by admin on Mon Mar 31 19:40:32 GMT 2025
PRIMARY
ChEMBL
CHEMBL305187
Created by admin on Mon Mar 31 19:40:32 GMT 2025 , Edited by admin on Mon Mar 31 19:40:32 GMT 2025
PRIMARY
PUBCHEM
656586
Created by admin on Mon Mar 31 19:40:32 GMT 2025 , Edited by admin on Mon Mar 31 19:40:32 GMT 2025
PRIMARY
MESH
C010739
Created by admin on Mon Mar 31 19:40:32 GMT 2025 , Edited by admin on Mon Mar 31 19:40:32 GMT 2025
PRIMARY
FDA UNII
89CTB4XUF7
Created by admin on Mon Mar 31 19:40:32 GMT 2025 , Edited by admin on Mon Mar 31 19:40:32 GMT 2025
PRIMARY
RXCUI
289912
Created by admin on Mon Mar 31 19:40:32 GMT 2025 , Edited by admin on Mon Mar 31 19:40:32 GMT 2025
PRIMARY RxNorm
Related Record Type Details
Structure of IFENPRODIL
PARENT -> SALT/SOLVATE
Related Record Type Details
Structure of IFENPRODIL
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