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Details

Stereochemistry ACHIRAL
Molecular Formula C25H38FN5O4
Molecular Weight 491.5987
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of BN-201

SMILES

CC(C)CN(CC(=O)N(CCCN1CCCC1=O)CC(N)=O)C(=O)CNCCC2=C(F)C=CC=C2

InChI

InChIKey=ODCKWAPNRBCXHV-UHFFFAOYSA-N
InChI=1S/C25H38FN5O4/c1-19(2)16-31(24(34)15-28-11-10-20-7-3-4-8-21(20)26)18-25(35)30(17-22(27)32)14-6-13-29-12-5-9-23(29)33/h3-4,7-8,19,28H,5-6,9-18H2,1-2H3,(H2,27,32)

HIDE SMILES / InChI
N-[2-[(2-amino-2-oxoethyl)-[3-(2-oxopyrrolidin-1-yl)propyl]amino]-2-oxoethyl]-2-[2-(2-fluorophenyl)ethylamino]-N-(2-methylpropyl)acetamide (BN201) is a small peptide molecule, a first-in-class neuroprotective compound. BN201 promotes the survival of cultured neural cells when subjected to oxidative stress or when deprived of trophic factors. BN201 promotes neuronal differentiation, the differentiation of precursor cells to mature oligodendrocytes in vitro, and the myelination of new axons. BN201 modulates several kinases participating in the insulin growth factor 1 pathway including serum-glucocorticoid kinase and midkine, inducing the phosphorylation of NDRG1 and the translocation of the transcription factor Foxo3 to the cytoplasm. In vivo, BN201 prevents axonal and neuronal loss, and it promotes remyelination in models of multiple sclerosis, chemically induced demyelination, and glaucoma. Bionure, a spin-off from Hospital Clínic de Barcelona that is based in California, is developing BN201 for multiple sclerosis, acute optic neuritis (AON) and glaucoma. BN201 was granted with orphan designation status for optic neuritis by the FDA. Optic neuritis is often an early sign of multiple sclerosis. The efficacy, safety, and capacity of the drug to cross the blood-brain barrier have been demonstrated in animal models, but the drug has not yet entered clinical testing.

CNS Activity

Curator's Comment: The capacity of the drug to cross the blood-brain barrier has been demonstrated in animal models

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: Neurotrophin
Sources: DOI: 10.1186/s40893-016-0004-0
PubMed

PubMed

TitleDatePubMed
Axonal and Myelin Neuroprotection by the Peptoid BN201 in Brain Inflammation.
2019 Jul

Sample Use Guides

Mice: Intraperitoneal administration of BN201 to animals after clinical onset of EAE (curative trial) ameliorated the clinical course and pathology in a dose-dependent manner, with clinical efficacy starting at 12.5 mg/kg, with the maximum benefit at 50 mg/kg, and with no further added benefit after this dose (up to 100 mg/kg)
Route of Administration: Intraperitoneal
The effects of BN201 on the differentiation of OPCs (Olig+ cells) to mature OLs (MBP+) in vitro and on promoting the myelin ensheathing of axons were evaluated. Primary RGCs from P8 mice were cultured and allowed to differentiate and to produce axons in culture. Then, OPCs were added in the presence of a positive control (the gamma-secretase inhibitor DAPT, 1 uM), placebo, or increasing concentrations of BN201 (from 50 nM to 100 uM). The number of MBP+ cells formed in the presence of BN201 increased in a dose-dependent manner, indicating differentiation of the OPCs to mature OLs (EC50 = 6.3 uM). The quantification of linear MBP+ structures indicative of the formation of myelin sheaths around axons showed enhanced axon myelination in cultures treated with BN201 or the positive control (EC50 = 16.6 uM).
Name Type Language
BN-201
Common Name English
BN201
Code English
GLYCINAMIDE, N-(2-(2-FLUOROPHENYL)ETHYL)GLYCYL-N-(2-METHYLPROPYL)GLYCYL-N2-(3-(2-OXO-1-PYRROLIDINYL)PROPYL)-
Systematic Name English
G-79
Code English
Classification Tree Code System Code
EU-Orphan Drug EU/3/14/1248
Created by admin on Sat Dec 16 11:17:21 GMT 2023 , Edited by admin on Sat Dec 16 11:17:21 GMT 2023
FDA ORPHAN DRUG 440014
Created by admin on Sat Dec 16 11:17:21 GMT 2023 , Edited by admin on Sat Dec 16 11:17:21 GMT 2023
Code System Code Type Description
CAS
1361200-34-1
Created by admin on Sat Dec 16 11:17:21 GMT 2023 , Edited by admin on Sat Dec 16 11:17:21 GMT 2023
PRIMARY
PUBCHEM
66610682
Created by admin on Sat Dec 16 11:17:21 GMT 2023 , Edited by admin on Sat Dec 16 11:17:21 GMT 2023
PRIMARY
SMS_ID
100000183618
Created by admin on Sat Dec 16 11:17:21 GMT 2023 , Edited by admin on Sat Dec 16 11:17:21 GMT 2023
PRIMARY
FDA UNII
KCN37L7EIH
Created by admin on Sat Dec 16 11:17:21 GMT 2023 , Edited by admin on Sat Dec 16 11:17:21 GMT 2023
PRIMARY