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Details

Stereochemistry UNKNOWN
Molecular Formula C17H20N2O
Molecular Weight 268.3535
Optical Activity ( + )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of REMACEMIDE, (+)-

SMILES

CC(CC1=CC=CC=C1)(NC(=O)CN)C2=CC=CC=C2

InChI

InChIKey=YSGASDXSLKIKOD-UHFFFAOYSA-N
InChI=1S/C17H20N2O/c1-17(19-16(20)13-18,15-10-6-3-7-11-15)12-14-8-4-2-5-9-14/h2-11H,12-13,18H2,1H3,(H,19,20)

HIDE SMILES / InChI

Molecular Formula C17H20N2O
Molecular Weight 268.3535
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

Description
Curator's Comment: description was created based on several sources, including: https://www.ncbi.nlm.nih.gov/pubmed/11502903 | https://www.ncbi.nlm.nih.gov/pubmed/11391123

Remacemide is a low-affinity noncompetitive NMDA receptor antagonist with sodium channel blocking properties. It has been studied for a number of conditions including acute ischemic stroke, epilepsy, Parkinsons Disease, and Huntington's disease. It was concluded, that was unlikely that remacemide would be further developed as an antiepileptic drug. As for other conditions, there no any information in the literature, why remacemide is no longer being developed for them.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
86.8 ng/mL
600 mg 1 times / day multiple, oral
dose: 600 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
AR-R12495 plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
458 ng/mL
600 mg 1 times / day multiple, oral
dose: 600 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
REMACEMIDE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
439.5 ng × h/mL
600 mg 1 times / day multiple, oral
dose: 600 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
AR-R12495 plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
1288 ng × h/mL
600 mg 1 times / day multiple, oral
dose: 600 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
REMACEMIDE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
PubMed

PubMed

TitleDatePubMed
Preclinical evaluation of newly approved and potential antiepileptic drugs against cocaine-induced seizures.
1999 Sep
A randomized, double-blind, placebo-controlled, ascending-dose tolerability and safety study of remacemide as adjuvant therapy in Parkinson's disease with response fluctuations.
2001 May-Jun
Patents

Patents

Sample Use Guides

acute ischemic stroke: Groups of 8 patients (6 active, 2 placeboes) were planned to receive twice-daily treatment, with l00 mg, 200 mg, 300 mg, 400 mg, 500 mg, or 600 mg remacemide hydrochloride given as 2 intravenous infusions followed by 6 days' oral treatment. The maximum well-tolerated dose for remacemide hydrochloride in acute stroke is 400 mg BID. Epilepsy: Two parallel group trials were included representing 514 individuals. Daily doses of 300, 600, 800 and 1200 mg of remacemide were tested. Regression models did, however, suggest a significant effect for 800-1200mg remacemide per day
Route of Administration: Other
In Vitro Use Guide
remacemide and its anticonvulsant metabolite 1,2-diphenyl-2-propylamine monohydrochloride (desglycinyl remacemide; DGR) a low-affinity NMDA receptor antagonist, were investigated using primary rat cortical neuronal cultures. Exposure of cortical cultures to NMDA (100 microM) for 15 min killed 85% of the neurons during the next 24 h. This neurotoxicity was blocked in a concentration-dependent manner by adding DGR (5-20 microM), but not its remacemide precursor (10-100 microM), to the cultures during the time of NMDA exposure. This suggests that the neuroprotective, as well as the anticonvulsant, the activity of remacemide is mediated by DGR.
Substance Class Chemical
Created
by admin
on Sat Dec 16 11:53:30 GMT 2023
Edited
by admin
on Sat Dec 16 11:53:30 GMT 2023
Record UNII
SVE7VVM49X
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
REMACEMIDE, (+)-
Common Name English
PR-1032-644
Code English
ACETAMIDE, 2-AMINO-N-(1-METHYL-1,2-DIPHENYLETHYL)-, (+)-
Systematic Name English
FPL-14144
Code English
Code System Code Type Description
EPA CompTox
DTXSID601030460
Created by admin on Sat Dec 16 11:53:30 GMT 2023 , Edited by admin on Sat Dec 16 11:53:30 GMT 2023
PRIMARY
CAS
118754-12-4
Created by admin on Sat Dec 16 11:53:30 GMT 2023 , Edited by admin on Sat Dec 16 11:53:30 GMT 2023
PRIMARY
FDA UNII
SVE7VVM49X
Created by admin on Sat Dec 16 11:53:30 GMT 2023 , Edited by admin on Sat Dec 16 11:53:30 GMT 2023
PRIMARY
Related Record Type Details
ENANTIOMER -> ENANTIOMER
RACEMATE -> ENANTIOMER