BECAMPANEL

Details

Stereochemistry	ACHIRAL
Molecular Formula	C10H11N4O7P
Molecular Weight	330.1907
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

OP(O)(=O)CNCC1=CC(=CC2=C1NC(=O)C(=O)N2)[N+]([O-])=O

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	330.1907
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.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Glutamate receptor ionotropic AMPA 42 Target ID: CHEMBL2096670 Sources: DOI: 10.1016/B0-08-045044-X/00171-1	Antagonist 2737		11.0 nM [IC50]
Hydroxyapatite 20 Target ID: CHEMBL2363055 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26457482	Binding Agent 1037

Conditions

Condition	Modality	Targets	Highest Phase	Product
Epilepsy 122 Sources: DOI: 10.1016/B0-08-045044-X/00171-1 https://www.ncbi.nlm.nih.gov/pubmed/17874969	Primary		Phase II 1133	Unknown Approved Use Unknown

Sourcing

Vendor/Aggregator	ID	URL
AbovChem LLC	HY-15073
Chem Scene	CS-6819	http://www.chemscene.com/goproductList/searchProductList?productObj=CS-6819
MedChem Express	HY-15073	https://www.medchemexpress.com/search.html?q=HY-15073&ft=&fa=&fp=
Molnova	M12950	https://www.molnova.com/en/serch-list.html?keywords=M12950
MuseChem	I004102	https://www.musechem.com/product/I004102.html
eMolecules	106945322	https://orderbb.emolecules.com/search/#?query=106945322
mcule	MCULE-8996885077	https://mcule.com/MCULE-8996885077/

PubMed

Title	Date	PubMed
Genotoxicity assessment of the antiepileptic drug AMP397, an Ames-positive aromatic nitro compound.	2002 Jul 25	12113769
alpha-Amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid (AMPA) antagonists: from bench to bedside.	2010 Aug 12	20356304
Insights into the novel three 'D's of epilepsy treatment: drugs, delivery systems and devices.	2010 Sep	20603226
Targeting α-amino-3-hydroxyl-5-methyl-4-isoxazole-propionate receptors in epilepsy.	2014 Mar	24387310
A General Strategy for Targeting Drugs to Bone.	2015 Nov 23	26457482

Patents

Sample Use Guides

In Vivo Use Guide

Rat: 60 mg/kg single dose

Route of Administration: Oral

In Vitro Use Guide

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 `Fri Dec 16 22:05:11 UTC 2022` Edited by `admin` on `Fri Dec 16 22:05:11 UTC 2022`
Record UNII	X3D0O800AJ
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

BECAMPANEL

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