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CHEBI:180900 - midafotel

ChEBI IDCHEBI:180900
ChEBI Namemidafotel
Stars
DefinitionA member of the class of piperazines that is piperazine substituted by a carboxy group at position 2R and a (1E)-1-phosphonoprop-1-en-3-yl group at position 4. It is an antagonist of N-methyl-D-aspartate receptors (NMDARs) and was in clinical development by Novartis for the treatment of cognition disorders and brain injuries (now discontinued).
Last Modified4 November 2021
Submitterslaulederkind
DownloadsMolfile
FormulaC8H15N2O5P
Net Charge0
Average Mass250.191
Monoisotopic Mass250.07186
SMILESO=C(O)[C@H]1CN(C/C=C/P(=O)(O)O)CCN1
InChIInChI=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
InChIKeyVZXMZMJSGLFKQI-ABVWVHJUSA-N
Wikipedia
Roles Classification
Chemical Roles:
Bronsted base  A molecular entity capable of accepting a hydron from a donor (Brønsted acid).
Bronsted acid  A molecular entity capable of donating a hydron to an acceptor (Brønsted base).
Biological Role:
NMDA receptor antagonist  Any substance that inhibits the action of N-methyl-D-aspartate (NMDA) receptors. They tend to induce a state known as dissociative anesthesia, marked by catalepsy, amnesia, and analgesia, while side effects can include hallucinations, nightmares, and confusion. Due to their psychotomimetic effects, many NMDA receptor antagonists are used as recreational drugs.
Applications:
neuroprotective agent  Any compound that can be used for the treatment of neurodegenerative disorders.
anticonvulsant  A drug used to prevent seizures or reduce their severity.
ChEBI Ontology
Outgoing Relation(s)
midafotel (CHEBI:180900) has role anticonvulsant (CHEBI:35623)
midafotel (CHEBI:180900) has role neuroprotective agent (CHEBI:63726)
midafotel (CHEBI:180900) has role NMDA receptor antagonist (CHEBI:60643)
midafotel (CHEBI:180900) is a monocarboxylic acid (CHEBI:25384)
midafotel (CHEBI:180900) is a olefinic compound (CHEBI:78840)
midafotel (CHEBI:180900) is a phosphonic acids (CHEBI:26069)
midafotel (CHEBI:180900) is a piperazinecarboxylic acid (CHEBI:48683)
midafotel (CHEBI:180900) is a tertiary amino compound (CHEBI:50996)
IUPAC Name 
(2R)-4-[(2E)-3-phosphonoprop-2-en-1-yl]piperazine-2-carboxylic acid
INNs  Source
midafotelWHO MedNet
midafotelumWHO MedNet
midafotelWHO MedNet
midafotelWHO MedNet
Synonyms  Source
D-CPPeneSUBMITTER
SDZ-EAA-494SUBMITTER
D-CPP-eneChemIDplus
SDZ-EAA 494ChemIDplus
SDZ EAA 494ChEBI
(2R)-4-[(2E)-3-phosphono-2-propenyl]-2-piperazinecarboxylic acidChEBI
Manual XrefsDatabases
MidafotelWikipedia
4940497ChemSpider
Registry NumbersSources
CAS:117414-74-1ChemIDplus
Citations