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Details

Stereochemistry ACHIRAL
Molecular Formula C10H11N4O7P
Molecular Weight 330.1911
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of BECAMPANEL

SMILES

c1c(CNCP(=O)(O)O)c2c(cc1N(=O)=O)[nH]c(=O)c(=O)[nH]2

InChI

InChIKey=ABFMMCZFKUIJGQ-UHFFFAOYSA-N
InChI=1S/C10H11N4O7P/c15-9-10(16)13-8-5(3-11-4-22(19,20)21)1-6(14(17)18)2-7(8)12-9/h1-2,11H,3-4H2,(H,12,15)(H,13,16)(H2,19,20,21)

HIDE SMILES / InChI

Molecular Formula C10H11N4O7P
Molecular Weight 330.1911
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Sources: DOI: 10.1016/B0-08-045044-X/00171-1
Curator's Comment:: description was created based on several sources, including: https://www.ncbi.nlm.nih.gov/pubmed/26457482 | https://www.ncbi.nlm.nih.gov/pubmed/12113769 | https://www.pharmacodia.com/yaodu/html/v1/chemicals/adefdb0c97ab92a9e8d1437a75d6e27e.html

Becampanel (AMP397) is an aminomethylquinoxalinedione AMPA receptor antagonist. Also, AMP397 demonstrates binding to hydroxyapatite. AMP397 has no genotoxic potential in vivo. In particular, no genotoxic metabolite is formed in mammalian cells, and, if formed by intestinal bacteria, is unable to exert any genotoxic activity in the adjacent intestinal tissue. AMP397 has a significant oral bioavailability of 22% in mice and approximately 50% in humans. It was under development for the potential treatment of status epilepticus and other types of seizures. However, this research has been discontinued. It is also being evaluated for use in the treatment of neuropathic pain and cerebrovascular ischemia.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: CHEMBL2096670
Sources: DOI: 10.1016/B0-08-045044-X/00171-1
11.0 nM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Sources: DOI: 10.1016/B0-08-045044-X/00171-1 https://www.ncbi.nlm.nih.gov/pubmed/17874969
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Genotoxicity assessment of the antiepileptic drug AMP397, an Ames-positive aromatic nitro compound.
2002 Jul 25
alpha-Amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid (AMPA) antagonists: from bench to bedside.
2010 Aug 12
Insights into the novel three 'D's of epilepsy treatment: drugs, delivery systems and devices.
2010 Sep
Targeting α-amino-3-hydroxyl-5-methyl-4-isoxazole-propionate receptors in epilepsy.
2014 Mar
A General Strategy for Targeting Drugs to Bone.
2015 Nov 23
Patents

Sample Use Guides

Rat: 60 mg/kg single dose
Route of Administration: Oral
Becampanel is one of the weakest nitroaromatic Salmonella typhimurium mutagens known. It induced 0.077 revertants/nmol, which lies at the lower end of the potency ranges found previously.
Substance Class Chemical
Created
by admin
on Sat Jun 26 16:40:11 UTC 2021
Edited
by admin
on Sat Jun 26 16:40:11 UTC 2021
Record UNII
X3D0O800AJ
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
BECAMPANEL
INN  
INN  
Official Name English
((7-NITRO-2,3-DIOXO-1,2,3,4-TETRAHYDROQUINOXALIN-5-YL)METHYLAMINO)METHYLPHOSPHONIC ACID
Systematic Name English
BECAMPANEL [INN]
Common Name English
AMP-397
Code English
Classification Tree Code System Code
NCI_THESAURUS C47795
Created by admin on Sat Jun 26 16:40:11 UTC 2021 , Edited by admin on Sat Jun 26 16:40:11 UTC 2021
Code System Code Type Description
FDA UNII
X3D0O800AJ
Created by admin on Sat Jun 26 16:40:11 UTC 2021 , Edited by admin on Sat Jun 26 16:40:11 UTC 2021
PRIMARY
NCI_THESAURUS
C79860
Created by admin on Sat Jun 26 16:40:11 UTC 2021 , Edited by admin on Sat Jun 26 16:40:11 UTC 2021
PRIMARY
EPA CompTox
188696-80-2
Created by admin on Sat Jun 26 16:40:11 UTC 2021 , Edited by admin on Sat Jun 26 16:40:11 UTC 2021
PRIMARY
PUBCHEM
5491960
Created by admin on Sat Jun 26 16:40:11 UTC 2021 , Edited by admin on Sat Jun 26 16:40:11 UTC 2021
PRIMARY
ChEMBL
CHEMBL2107735
Created by admin on Sat Jun 26 16:40:11 UTC 2021 , Edited by admin on Sat Jun 26 16:40:11 UTC 2021
PRIMARY
CAS
188696-80-2
Created by admin on Sat Jun 26 16:40:11 UTC 2021 , Edited by admin on Sat Jun 26 16:40:11 UTC 2021
PRIMARY
INN
8395
Created by admin on Sat Jun 26 16:40:11 UTC 2021 , Edited by admin on Sat Jun 26 16:40:11 UTC 2021
PRIMARY
Related Record Type Details
ACTIVE MOIETY