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Details

Stereochemistry ABSOLUTE
Molecular Formula C8H15N2O5P
Molecular Weight 250.1889
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of MIDAFOTEL

SMILES

OC(=O)[C@H]1CN(C\C=C\P(O)(O)=O)CCN1

InChI

InChIKey=VZXMZMJSGLFKQI-ABVWVHJUSA-N
InChI=1S/C8H15N2O5P/c11-8(12)7-6-10(4-2-9-7)3-1-5-16(13,14)15/h1,5,7,9H,2-4,6H2,(H,11,12)(H2,13,14,15)/b5-1+/t7-/m1/s1

HIDE SMILES / InChI

Molecular Formula C8H15N2O5P
Molecular Weight 250.1889
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 1
Optical Activity UNSPECIFIED

Midafotel (CPPene; SDZ EAA 494) is a selective competitive antagonist at the N-methyl-D-aspartate (NMDA) subtype of glutamate receptor. It was originally designed as a potential therapy for excitotoxicity, epilepsy or neuropathic pain. Midafotel had been in phase III clinical trials by Novartis for the treatment of brain injury. However, this research has been discontinued.

Originator

Curator's Comment: # Novartis

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
199 ng/mL
1000 mg 2 times / day multiple, oral
dose: 1000 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
MIDAFOTEL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
20 h
1000 mg 2 times / day multiple, oral
dose: 1000 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
MIDAFOTEL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
50 mg single, intravenous (unknown)
Highest studied dose
Dose: 50 mg
Route: intravenous
Route: single
Dose: 50 mg
Sources:
healthy
n = 9
Health Status: healthy
Sex: M
Food Status: UNKNOWN
Population Size: 9
Sources:
25 mg 2 times / day multiple, intravenous (unknown)
Overdose
Dose: 25 mg, 2 times / day
Route: intravenous
Route: multiple
Dose: 25 mg, 2 times / day
Sources:
healthy
n = 9
Health Status: healthy
Sex: M
Food Status: UNKNOWN
Population Size: 9
Sources:
PubMed

PubMed

TitleDatePubMed
Patents

Sample Use Guides

Midafotel was administered either as single doses at a dose range of 1-50 mg, or as multiple doses over the course of 1 week at doses of 25 mg once or twice daily.
Route of Administration: Oral
Midafotel (d-CPPene) strongly inhibited the frequency of spontaneous epileptiform discharges. This effect was concentration-dependent. Epileptiform discharges were reduced up to 70% at a concentration of 0.1 uM and were completely blocked at a concentration of 0.3 uM in the rat cortical wedge preparation. d-CPPene inhibited in concentration-dependent manner NMDA-induced depolarisations. A concentration of 0.1 uM that blocked 70% of spontaneous discharges inhibited 60% of depolarisations induced by NMDA. A concentration of 1 uM completely blocked NMDA-induced depolarisations.
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:57:15 UTC 2023
Edited
by admin
on Fri Dec 15 15:57:15 UTC 2023
Record UNII
7LYU6ZF84G
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
MIDAFOTEL
INN   WHO-DD  
INN  
Official Name English
SDZ-EAA-494
Code English
(R)-4-((E)-3-PHOSPHONOPROP-2-ENYL)PIPERAZINE-2-CARBOXYLIC ACID
Systematic Name English
4-(3-PHOSPHONO-2-PROPENYL)-2-PIPERAZINECARBOXYLIC ACID, (R-(E))
Common Name English
SDZ EAA 494
Code English
midafotel [INN]
Common Name English
Midafotel [WHO-DD]
Common Name English
Classification Tree Code System Code
WIKIPEDIA NMDA receptor antagonist
Created by admin on Fri Dec 15 15:57:16 UTC 2023 , Edited by admin on Fri Dec 15 15:57:16 UTC 2023
Code System Code Type Description
INN
7736
Created by admin on Fri Dec 15 15:57:15 UTC 2023 , Edited by admin on Fri Dec 15 15:57:15 UTC 2023
PRIMARY
NCI_THESAURUS
C167034
Created by admin on Fri Dec 15 15:57:15 UTC 2023 , Edited by admin on Fri Dec 15 15:57:15 UTC 2023
PRIMARY
CAS
117414-74-1
Created by admin on Fri Dec 15 15:57:15 UTC 2023 , Edited by admin on Fri Dec 15 15:57:15 UTC 2023
PRIMARY
PUBCHEM
6435801
Created by admin on Fri Dec 15 15:57:15 UTC 2023 , Edited by admin on Fri Dec 15 15:57:15 UTC 2023
PRIMARY
EVMPD
SUB03287MIG
Created by admin on Fri Dec 15 15:57:15 UTC 2023 , Edited by admin on Fri Dec 15 15:57:15 UTC 2023
PRIMARY
WIKIPEDIA
MIDAFOTEL
Created by admin on Fri Dec 15 15:57:15 UTC 2023 , Edited by admin on Fri Dec 15 15:57:15 UTC 2023
PRIMARY
SMS_ID
100000085981
Created by admin on Fri Dec 15 15:57:15 UTC 2023 , Edited by admin on Fri Dec 15 15:57:15 UTC 2023
PRIMARY
FDA UNII
7LYU6ZF84G
Created by admin on Fri Dec 15 15:57:15 UTC 2023 , Edited by admin on Fri Dec 15 15:57:15 UTC 2023
PRIMARY
ChEMBL
CHEMBL90564
Created by admin on Fri Dec 15 15:57:15 UTC 2023 , Edited by admin on Fri Dec 15 15:57:15 UTC 2023
PRIMARY
EPA CompTox
DTXSID1045740
Created by admin on Fri Dec 15 15:57:15 UTC 2023 , Edited by admin on Fri Dec 15 15:57:15 UTC 2023
PRIMARY
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