Chemical Information
Antiviral agent ID	DrugRepV_6372
Antiviral agent name	(2S)-N-[(5S,8S)-1-amino-11-carbamimidamido-8-({4-[(1E)-2-carbamoyleth-1-en-1-yl]phenyl}formamido)-6,7-dioxoundecan-5-yl]-2-hydrazinylhexanamide
IUPAC Name	(2S)-N-[(5S,8S)-1-amino-11-carbamimidamido-8-({4-[(1E)-2-carbamoyleth-1-en-1-yl]phenyl}formamido)-6,7-dioxoundecan-5-yl]-2-hydrazinylhexanamide
SMILES (isomeric)	CCCC[C@H](NN)C(=O)N[C@@H](CCCCN)C(=O)C(=O)[C@H](CCCNC(N)=N)NC(=O)C1=CC=C(\C=C\C(N)=O)C=C1
Molecular Formula	C28H45N9O5
Molecular Weight (g/mol)	587.726
InChl	InChI=1/C28H45N9O5/c1-2-3-7-22(37-33)27(42)36-20(8-4-5-16-29)24(39)25(40)21(9-6-17-34-28(31)32)35-26(41)19-13-10-18(11-14-19)12-15-23(30)38/h10-15,20-22,37H,2-9,16-17,29,33H2,1H3,(H2,30,38)(H,35,41)(H,36,42)(H4,31,32,34)/b15-12+/t20-,21-,22-/s2
Structural Information
Clinical Information
Biological Information
Secondary Indication	Dengue virus (DENV) 2 NA
Secondary Indication (Approaches)	Experimental
Secondary Indication (Methods)	In-vitro
Secondary Indication (Mode of viral infection)	Adsorption
Secondary Indication (Mode of drug delivery)	Culture
Secondary Indication (Drug concentration)	6.4 ± 0.2 μM
Secondary Indication (Cell based assay)	Protease Assay
Secondary Indication (Change)	Decrease
Secondary Indication (Type of Inhibition)	IC50 [ 50 % ]
Reference	Nitsche C, Schreier VN, Behnam MA, Kumar A, Bartenschlager R, Klein CD..Thiazolidinone-peptide hybrids as dengue virus protease inhibitors with antiviral activity in cell culture..J Med Chem. 2013 Nov 14;56(21):8389-403. doi: 10.1021/jm400828u. Epub 2013 Oct 22. PMID:24083834
Comment	The most promising in vitro affinities were observed for thiazolidinedione-based peptide hybrids containing hydrophobic groups with Ki values between 1.5 and 1.8 μM and competitive inhibition mechanisms. Rhodanine-capped peptide hybrids with hydrophobic substituents have, in correlation with their membrane permeability, a more pronounced antiviral activity in cell culture than the thiazolidinediones.