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
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
DescriptionCurator'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
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
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL1907603 |
190.0 nM [IC50] | ||
Target ID: CHEMBL1904 |
47.0 nM [IC50] | ||
Target ID: CHEMBL3465 |
28.27 nM [IC50] | ||
Target ID: CHEMBL2094251 |
100.0 nM [IC50] | ||
Target ID: CHEMBL3038489 |
7.01 µM [IC50] | ||
Target ID: CHEMBL3038488 |
2.83 µM [IC50] |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | Ifenprodil Approved UsePeripheral vascular disease |
PubMed
| Title | Date | PubMed |
|---|---|---|
| [Effects of 2-(4-benzyl-piperidino)-1-(4-hydroxyphenyl)-1-propanol (ifenprodil) on the cardiovascular system in vivo]. | 1975 Sep |
|
| Expression of functional NR1/NR2B-type NMDA receptors in neuronally differentiated SK-N-SH human cell line. | 2002 Dec |
|
| Ethanol sensitivity of NMDA receptors. | 2002 Dec |
|
| Developmental Pb2+ exposure alters NMDAR subtypes and reduces CREB phosphorylation in the rat brain. | 2002 Dec 15 |
|
| Effects of acamprosate and some polyamine site ligands of NMDA receptor on short-term memory in rats. | 2002 May 24 |
|
| Acamprosate, MK-801, and ifenprodil inhibit neurotoxicity and calcium entry induced by ethanol withdrawal in organotypic slice cultures from neonatal rat hippocampus. | 2002 Oct |
|
| 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 Oct |
|
| Radioligand binding studies reveal agmatine is a more selective antagonist for a polyamine-site on the NMDA receptor than arcaine or ifenprodil. | 2002 Oct 11 |
|
| Intrathecally administered big dynorphin, a prodynorphin-derived peptide, produces nociceptive behavior through an N-methyl-D-aspartate receptor mechanism. | 2002 Oct 11 |
|
| 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 Sep |
|
| Differential regulation of synaptic and extra-synaptic NMDA receptors. | 2002 Sep |
|
| Selective NR2B NMDA receptor antagonists are protective against staurosporine-induced apoptosis. | 2002 Sep 27 |
|
| Resistance to alcohol withdrawal-induced behaviour in Fyn transgenic mice and its reversal by ifenprodil. | 2002 Sep 30 |
|
| 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 |
|
| Excitatory synaptic transmission in the lateral and central amygdala. | 2003 Apr |
|
| Contribution of NR2B subunits to synaptic transmission in amygdaloid interneurons. | 2003 Apr 1 |
|
| PSD-95 regulates NMDA receptors in developing cerebellar granule neurons of the rat. | 2003 Apr 1 |
|
| Functional NMDA receptor subtype 2B is expressed in astrocytes after ischemia in vivo and anoxia in vitro. | 2003 Apr 15 |
|
| Activation of NMDA receptors in rat dentate gyrus granule cells by spontaneous and evoked transmitter release. | 2003 Aug |
|
| Polyamines in a genetic animal model of paroxysmal dyskinesia. | 2003 Aug 15 |
|
| The effect of (+/-)-CP-101,606, an NMDA receptor NR2B subunit selective antagonist, in the Morris watermaze. | 2003 Aug 29 |
|
| Chronic ethanol ingestion facilitates N-methyl-D-aspartate receptor function and expression in rat lateral/basolateral amygdala neurons. | 2003 Dec |
|
| Ionotropic glutamate receptors: still a target for neuroprotection in brain ischemia? Insights from in vitro studies. | 2003 Feb |
|
| Excitatory amino acid receptors of the electrosensory system: the NR1/NR2B N-methyl-D-aspartate receptor. | 2003 Feb |
|
| Evidence for functionally distinct synaptic NMDA receptors in ventromedial versus dorsolateral striatum. | 2003 Jan |
|
| 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 Jan |
|
| Differential alterations in the expression of NMDA receptor subunits following chronic ethanol treatment in primary cultures of rat cortical and hippocampal neurones. | 2003 Jan |
|
| Therapeutic N-methyl-D-aspartate receptor antagonists: will reality meet expectation? | 2003 Jul |
|
| Polyamines contribute to ethanol withdrawal-induced neurotoxicity in rat hippocampal slice cultures through interactions with the NMDA receptor. | 2003 Jul |
|
| 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 Jul |
|
| Enhanced GABA(A) receptor-mediated activity following activation of NMDA receptors in Cajal-Retzius cells in the developing mouse neocortex. | 2003 Jul 1 |
|
| Development and subunit composition of synaptic NMDA receptors in the amygdala: NR2B synapses in the adult central amygdala. | 2003 Jul 30 |
|
| Lack of ifenprodil anxiolytic activity after its multiple treatment in chronically ethanol-treated rats. | 2003 Jul-Aug |
|
| ATP inhibits NMDA receptors after heterologous expression and in cultured hippocampal neurons and attenuates NMDA-mediated neurotoxicity. | 2003 Jun 15 |
|
| NR2B and NR2D subunits coassemble in cerebellar Golgi cells to form a distinct NMDA receptor subtype restricted to extrasynaptic sites. | 2003 Jun 15 |
|
| Behavioral effects of NMDA receptor agonists and antagonists in combination with nitric oxide-related compounds. | 2003 Jun 20 |
|
| 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 Mar 13 |
|
| NMDA-receptor antagonism via dextromethorphan and ifenprodil modulates graded anxiety test performance of C57BL/6 mice. | 2003 May |
|
| Role of the NMDA receptor NR2B subunit in the discriminative stimulus effects of ketamine. | 2003 May |
|
| Involvement of voltage- and ligand-gated Ca2+ channels in the neuroexcitatory and synergistic effects of putative uremic neurotoxins. | 2003 May |
|
| Expression of behavioral sensitization to ethanol by DBA/2J mice: the role of NMDA and non-NMDA glutamate receptors. | 2003 May |
|
| N-Methyl-D-aspartate receptors contribute to the maintenance of dopaminergic neurons in rat midbrain slice cultures. | 2003 May 1 |
|
| Fyn kinase and NR2B-containing NMDA receptors regulate acute ethanol sensitivity but not ethanol intake or conditioned reward. | 2003 Nov |
|
| NMDA currents and receptor protein are downregulated in the amygdala during maintenance of fear memory. | 2003 Nov 12 |
|
| Postsynaptic contributions to hippocampal network hyperexcitability induced by chronic activity blockade in vivo. | 2003 Oct |
|
| Overexpression of spermidine/spermine N1-acetyltransferase elevates the threshold to pentylenetetrazol-induced seizure activity in transgenic mice. | 2003 Oct |
|
| Effect of the NR3 subunit on ethanol inhibition of recombinant NMDA receptors. | 2003 Oct 10 |
|
| Acute dissociation for analyses of NMDA receptor function in cortical neurons during aging. | 2003 Oct 15 |
|
| Effects of NMDA receptor antagonists on acute mu-opioid analgesia in the rat. | 2003 Sep |
Sample Use Guides
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
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SUB02636MIG
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245-493-5
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23210-58-4
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DBSALT001078
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DTXSID50945896
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100000086980
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CHEMBL305187
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656586
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C010739
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89CTB4XUF7
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289912
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ACTIVE MOIETY
SUBSTANCE RECORD
