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Details

Stereochemistry RACEMIC
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 Fri Dec 15 19:08:50 GMT 2023
Edited
by admin
on Fri Dec 15 19:08:50 GMT 2023
Record UNII
EH6763C1IC
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
REMACEMIDE
INN   MI   WHO-DD  
INN  
Official Name English
2-AMINO-N-(1,2-DI(PHENYL)PROPAN-2-YL)ACETAMIDE
Systematic Name English
FPL-12924
Code English
ACETAMIDE, 2-AMINO-N-(1-METHYL-1,2-DIPHENYLETHYL)-
Systematic Name English
PR-934423A
Code English
N-(1-METHYL-1,2-DIPHENYLETHYL)GLYCINAMIDE
Systematic Name English
ACETAMIDE, 2-AMINO-N-(1-METHYL-1,2-DIPHENYLETHYL)-, (±)-
Systematic Name English
(±)-REMACEMIDE
Common Name English
remacemide [INN]
Common Name English
AR-R-12924
Code English
(±)-2-AMINO-N-(1-METHYL-1,2-DIPHENYLETHYL)ACETAMIDE
Systematic Name English
REMACEMIDE [MI]
Common Name English
Remacemide [WHO-DD]
Common Name English
PR-934-423
Code English
Classification Tree Code System Code
FDA ORPHAN DRUG 130599
Created by admin on Fri Dec 15 19:08:50 GMT 2023 , Edited by admin on Fri Dec 15 19:08:50 GMT 2023
NCI_THESAURUS C78272
Created by admin on Fri Dec 15 19:08:50 GMT 2023 , Edited by admin on Fri Dec 15 19:08:50 GMT 2023
Code System Code Type Description
EPA CompTox
DTXSID6048250
Created by admin on Fri Dec 15 19:08:50 GMT 2023 , Edited by admin on Fri Dec 15 19:08:50 GMT 2023
PRIMARY
WIKIPEDIA
REMACEMIDE
Created by admin on Fri Dec 15 19:08:50 GMT 2023 , Edited by admin on Fri Dec 15 19:08:50 GMT 2023
PRIMARY
CAS
135252-01-6
Created by admin on Fri Dec 15 19:08:50 GMT 2023 , Edited by admin on Fri Dec 15 19:08:50 GMT 2023
SUPERSEDED
MESH
C067553
Created by admin on Fri Dec 15 19:08:50 GMT 2023 , Edited by admin on Fri Dec 15 19:08:50 GMT 2023
PRIMARY
INN
6589
Created by admin on Fri Dec 15 19:08:50 GMT 2023 , Edited by admin on Fri Dec 15 19:08:50 GMT 2023
PRIMARY
SMS_ID
100000080805
Created by admin on Fri Dec 15 19:08:50 GMT 2023 , Edited by admin on Fri Dec 15 19:08:50 GMT 2023
PRIMARY
MERCK INDEX
m9520
Created by admin on Fri Dec 15 19:08:50 GMT 2023 , Edited by admin on Fri Dec 15 19:08:50 GMT 2023
PRIMARY Merck Index
EVMPD
SUB10271MIG
Created by admin on Fri Dec 15 19:08:50 GMT 2023 , Edited by admin on Fri Dec 15 19:08:50 GMT 2023
PRIMARY
FDA UNII
EH6763C1IC
Created by admin on Fri Dec 15 19:08:50 GMT 2023 , Edited by admin on Fri Dec 15 19:08:50 GMT 2023
PRIMARY
CAS
128298-28-2
Created by admin on Fri Dec 15 19:08:50 GMT 2023 , Edited by admin on Fri Dec 15 19:08:50 GMT 2023
PRIMARY
NCI_THESAURUS
C152183
Created by admin on Fri Dec 15 19:08:50 GMT 2023 , Edited by admin on Fri Dec 15 19:08:50 GMT 2023
PRIMARY
DRUG BANK
DB06458
Created by admin on Fri Dec 15 19:08:50 GMT 2023 , Edited by admin on Fri Dec 15 19:08:50 GMT 2023
PRIMARY
ChEMBL
CHEMBL25843
Created by admin on Fri Dec 15 19:08:50 GMT 2023 , Edited by admin on Fri Dec 15 19:08:50 GMT 2023
PRIMARY
PUBCHEM
60511
Created by admin on Fri Dec 15 19:08:50 GMT 2023 , Edited by admin on Fri Dec 15 19:08:50 GMT 2023
PRIMARY
Related Record Type Details
ENANTIOMER -> RACEMATE
SALT/SOLVATE -> PARENT
ENANTIOMER -> RACEMATE
Related Record Type Details
METABOLITE ACTIVE -> PARENT
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ACTIVE MOIETY