IFENPRODIL TARTRATE

Possibly Marketed Outside US

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

HIDE SMILES / InChI

Description

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	Potency
Glutamate NMDA receptor; GRIN1/GRIN2B 6	Antagonist 2,849	190.0 nM [IC50]
Glutamate [NMDA] receptor subunit epsilon 2 13	Antagonist 2,849	47.0 nM [IC50]
Sigma opioid receptor 64	Agonist 2,752	28.27 nM [IC50]
Adrenergic receptor alpha-1 171	Antagonist 2,849	100.0 nM [IC50]
Kir3.1/Kir3.2 2	Inhibitor 8,504	7.01 µM [IC50]
Kir3.1/Kir3.4 2	Inhibitor 8,504	2.83 µM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Peripheral vascular disorders 15	Primary		Approved 8,583	Ifenprodil

C_max

Value	Dose	Analyte	Population
10.13 ng/mL	5 mg single, intravenous	IFENPRODIL plasma	Homo sapiens
19.1 ng/mL	10 mg single, intravenous	IFENPRODIL plasma	Homo sapiens
28.9 ng/mL	15 mg single, oral	IFENPRODIL plasma	Homo sapiens
20.4 ng/mL	10 mg 1 times / day steady-state, intravenous	IFENPRODIL plasma	Homo sapiens

AUC

Value	Dose	Analyte	Population
21.7 ng × h/mL	5 mg single, intravenous	IFENPRODIL plasma	Homo sapiens
41.3 ng × h/mL	10 mg single, intravenous	IFENPRODIL plasma	Homo sapiens
63.1 ng × h/mL	15 mg single, oral	IFENPRODIL plasma	Homo sapiens
47 ng × h/mL	10 mg 1 times / day steady-state, intravenous	IFENPRODIL plasma	Homo sapiens

T_1/2

Value	Dose	Analyte	Population
3.87 h	5 mg single, intravenous	IFENPRODIL plasma	Homo sapiens
3.61 h	10 mg single, intravenous	IFENPRODIL plasma	Homo sapiens
4.07 h	15 mg single, oral	IFENPRODIL plasma	Homo sapiens
4.25 h	10 mg 1 times / day steady-state, intravenous	IFENPRODIL plasma	Homo sapiens

Doses

Doses

Show entries

Dose	Population	Adverse events
40 mg 3 times / day multiple, oral Highest studied dose	unhealthy, ADULT

Showing 1 to 1 of 1 entries

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PubMed

Show entries

Title	Date	PubMed
Prevention of cocaine-induced convulsions and lethality in mice: effectiveness of targeting different sites on the NMDA receptor complex.	2000 Jan 28	10698007
Supraspinal vs spinal sites of the antinociceptive action of the subtype-selective NMDA antagonist ifenprodil.	2001	11114400
Developmental depression of glutamate neurotransmission by chronic low-level activation of NMDA receptors.	2001 Aug 15	11487646
Use of trifluoroperazine isolates a [(3)H]Ifenprodil binding site in rat brain membranes with the pharmacology of the voltage-independent ifenprodil site on N-methyl-D-aspartate receptors containing NR2B subunits.	2001 Jan	11123375
Polyamine and redox modulation of [3H]MK-801 binding to N-methyl-D-aspartate receptors in the spinal cord and cerebral cortex.	2001 Jun	11453375

Showing 1 to 5 of 30 entries

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Patents

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..

Show entries

Name

Type

Language

4-BENZYL-1-(.BETA.,4-DIHYDROXY-.ALPHA.-METHYLPHENETHYL PIPERIDINIUM HYDROGEN TARTRATE

Preferred Name

English

IFENPRODIL TARTRATE

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

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Code System

Code

Type

Description

EVMPD

SUB02636MIG

PRIMARY

ECHA (EC/EINECS)

245-493-5

PRIMARY

CAS

23210-58-4

PRIMARY

DRUG BANK

DBSALT001078

PRIMARY

EPA CompTox

DTXSID50945896

PRIMARY

Showing 1 to 5 of 11 entries

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ACTIVE MOIETY


					R8OE3P6O5S

IFENPRODIL

SUBSTANCE RECORD


					89CTB4XUF7

IFENPRODIL TARTRATE

SMILES

InChI

CNS Activity

Originator

Approval Year

Targets

Conditions

Cmax

AUC

T1/2

Doses

PubMed

Patents

Sample Use Guides

C_max

T_1/2