U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry MIXED
Molecular Formula C21H27NO2
Molecular Weight 325.4446
Optical Activity UNSPECIFIED
Defined Stereocenters 0 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of IFENPRODIL

SMILES

CC(C(O)C1=CC=C(O)C=C1)N2CCC(CC3=CC=CC=C3)CC2

InChI

InChIKey=UYNVMODNBIQBMV-UHFFFAOYSA-N
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

HIDE SMILES / InChI
Molecular Formula C21H27NO2
Molecular Weight 325.4446
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry MIXED
Additional Stereochemistry No
Defined Stereocenters 0 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

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

CNS Active
3,913

Originator

Sanofi-Synthelabo
26

Approval Year

Unknown
139,594

Targets

Primary TargetPharmacologyConditionPotency
Glutamate NMDA receptor; GRIN1/GRIN2B
6
Antagonist
2,778
 190.0 nM [IC50]
Glutamate [NMDA] receptor subunit epsilon 2
13
Antagonist
2,778
 47.0 nM [IC50]
Sigma opioid receptor
63
Agonist
2,678
 28.27 nM [IC50]
Adrenergic receptor alpha-1
169
Antagonist
2,778
 100.0 nM [IC50]
Kir3.1/Kir3.2
2
Inhibitor
8,297
 7.01 µM [IC50]
Kir3.1/Kir3.4
2
Inhibitor
8,297
 2.83 µM [IC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Peripheral vascular disorders
15
 Primary
Approved
8,429
Ifenprodil

Cmax

ValueDoseCo-administeredAnalytePopulation
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

ValueDoseCo-administeredAnalytePopulation
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

T1/2

ValueDoseCo-administeredAnalytePopulation
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

PubMed

Patents

JP2002517462A
7
JP2003515526A
462
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
Record UNII
R8OE3P6O5S
Record Status Validated (UNII)
Record Version
NIH
NCATS
PRIVACY ACT
ACCESSIBILITY
DISCLAIMER
HHS VULNERABILITY DISCLOSURE
For language access assistance, contact the NCATS Public Information Officer
National Center for Advancing Translational Sciences (NCATS),
6701 Democracy Boulevard, Bethesda MD 20892-4874 • 301-594-8966