| Identification | Back Directory | [Name]
IFENPRODIL HEMITARTRATE | [CAS]
23210-58-4 | [Synonyms]
Dilvax
Vadilex
Cerocral
RC-61-91
IFENPRODIL TARTRATE
IFENPRODIL TARTARATE
IFENPRODIL HEMITARTRATE
IFENPRODIL TARTRATE SALT
Ifenprodil L-(+)-Tartrate
2-(4-BENZYLPIPERIDINO)-1-(4-HYDROXYPHENYL)-1-PROPANOL HEMITARTRATE
α-(4-hydroxyphenyl)-β-methyl-4-benzyl-1-piperidineethanol tartrate salt
ALPHA-[4-HYDROXYPHENYL]-BETA-METHYL-4-BENZYL-1-PIPERIDINEETHANOL TARTRATE SALT
α-(4-Hydroxyphenyl)-β-methyl-4-benzyl-1-piperidineethanol/L-tartaric acid,(2:1)
4-benzyl-1-[beta,4-dihydroxy-alpha-methylphenethyl]piperidinium hydrogen tartrate
4-Benzyl-1-[beta,4-dihydroxy-alpha-methylphenethyl]piperidinium hydrogen tartrate (2:1)
a-(4-Hydroxyphenyl)--methyl-4-(phenylmethyl)-1-piperidineethanol (2R,3R)-2,3-Dihydroxybutanedioate
Ifenprodil (+)-tartrate salt,α-(4-Hydroxyphenyl)-β-methyl-4-benzyl-1-piperidineethanol (+)-tartrate salt
1-Piperidineethanol, α-(4-hydroxyphenyl)-β-methyl-4-(phenylmethyl)-, (2R,3R)-2,3-dihydroxybutanedioate (2:1) | [EINECS(EC#)]
245-493-5 | [Molecular Formula]
C25H33NO8 | [MDL Number]
MFCD00078585 | [MOL File]
23210-58-4.mol | [Molecular Weight]
475.53 |
| Chemical Properties | Back Directory | [Appearance]
Crystalline Solid | [Melting point ]
178-180°C | [storage temp. ]
Refrigerator | [solubility ]
DMSO (Slightly), Methanol (Slightly), Water (Slightly) | [form ]
White solid | [color ]
White | [Water Solubility ]
Soluble in water (15mM, gentle warming) | [Stability:]
Hygroscopic |
| Hazard Information | Back Directory | [Chemical Properties]
Crystalline Solid | [Uses]
Vasodilatator;Adrenergic antagonist | [Uses]
Vasodilator (cerebral and peripheral) | [Originator]
Vadilex,Carriere,France,1972 | [Definition]
ChEBI: Ifenprodil tartrate is a member of piperidines. | [Manufacturing Process]
The initial steps involve reacting benzyl chloride with 4-
hydroxypropiophenone. The benzyloxypropiophene thus obtained is first
brominated and then reacted with 4-benzylpiperidine to give 1-(pbenzyloxyphenyl)-2-(4-benzyl-piperidino)propan-1-one.
The neutral tartrate may be prepared directly by reduction of 1-(pbenzyloxyphenyl)-2-(4-benzyl-piperidino)propan-1-one. For the reduction, a
mixture of 175 g of ketone (0.425 mol) and 32 g of tartaric acid (0.213 mol)
is hydrogenated at 50°C under pressure of 50 kg/cm2 in 440 ml of methanol
in the presence of 12 g of palladium on charcoal.
The catalyst is filtered off at elevated temperature, and the filtrate is
concentrated by evaporation under reduced pressure to a volume of 300 ml
and added in a thin stream to 2.5 liters of diethyl ether with mechanical
agitation. The precipitate is separated, washed with diethyl ether and dried in
vacuo at 80° to 85°C for several hours. 325 g (96% yield) of the neutral
tartrate of 1-(p-hydroxyphenyl)-2-(4-benzyl-piperidino)propan-1-ol are
obtained. | [Therapeutic Function]
Vasodilator | [General Description]
Ifenprodil is a phenylethanolamine, which stimulates blood circulation. It has anticonvulsant and antinociceptive properties. Ifenprodil is used to treat posttraumatic stress disorder, cerebrovascular diseases and peripheral arterial obliterative disease. It blocks G protein-coupled inwardly-rectifying potassium channels (GIRKs) and interacts with α1 adrenergic, N-methyl-D-aspartate and serotonin receptors. | [Biological Activity]
Ifenprodil hemitartrate is a NMDA receptor antagonist, acting at the polyamine site. Also an α-adrenergic vasodilator. σ2 ligand displaying about 3-fold selectivity over σ1 sites. | [Biochem/physiol Actions]
NMDA antagonist acting at the polyamine site; neuroprotective agent; α-adrenergic central and peripheral vasodilator; α2 adrenergic receptor ligand. | [in vitro]
Ifenprodil treatment of oocytes, at NR1A/NR2B and NR1A/NR2A receptors, inhibited NMDA-induced currents with IC50 of 0.34 μM and 146 μM, respectively, and voltage-clamped at -70 mV. Ifenprodil acts as a weak open channel blocker of NR1A/NR2A receptors, the degree of inhibition of NR1A/NR2A receptors by 100 μM fenprodil is not affected by extracellular glycine concentration. Increasing glycine concentration decreased the inhibitory effect of 1mMIfenprodil on NR1A/NR2B receptors. Ifenprodil (10 μM) acts on young rat cortical neurons, a single population of receptors with high affinity for glycine, inhibits almost all NMDA receptor-evoked currents. Ifenprodil (10 μM) inhibited a significant proportion of high- and low-affinity components in aged rat cortical neurons, revealing three pharmacologically distinct distribution populations of NMDA receptors in a single neuron. Ifenprodil antagonizes NMDA receptors in an activity-dependent manner and also enhances the receptor's affinity for glutamate recognition site agonists. In the inhibition curves of Ifenprodil on 10μM and 100μM NMDA-evoked currents, IC50 was 0.88μM and 0.17μM, respectively. Ifenprodil (3μM) can enhance the control level of cultured rat cortical neurons. Enhanced by about 200%. Ifenprodil has a 39- and 50-fold enhanced affinity for NMDA receptors in the agonist-bound activated and desensitized states compared to the resting, agonist-unbound state. Ifenprodil binds to NMDA receptors with a 6-fold increased affinity for glutamate receptor agonists. | [storage]
Room temperature |
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