SID 26681509

Modify Date: 2024-01-02 16:47:35

SID 26681509 Structure
SID 26681509 structure
Common Name SID 26681509
CAS Number 958772-66-2 Molecular Weight 539.64600
Density N/A Boiling Point N/A
Molecular Formula C27H33N5O5S Melting Point N/A
MSDS N/A Flash Point N/A

 Use of SID 26681509


SID 26681509 is a potent, reversible, competitive, and selective inhibitor of human cathepsin L with an IC50 of 56 nM. SID 26681509 inhibits in vitro propagation of malaria parasite Plasmodium falciparum and inhibits Leishmania major with IC50s of 15.4 μM and 12.5 μM, respectively. SID 26681509 shows no inhibitory activity against cathepsin G[1].

 Names

Name S-{2-[(2-Ethylphenyl)amino]-2-oxoethyl} 2-[(2S)-3-(1H-indol-3-yl) -2-({[(2-methyl-2-propanyl)oxy]carbonyl}amino)propanoyl]hydrazine carbothioate (non-preferred name)
Synonym More Synonyms

 SID 26681509 Biological Activity

Description SID 26681509 is a potent, reversible, competitive, and selective inhibitor of human cathepsin L with an IC50 of 56 nM. SID 26681509 inhibits in vitro propagation of malaria parasite Plasmodium falciparum and inhibits Leishmania major with IC50s of 15.4 μM and 12.5 μM, respectively. SID 26681509 shows no inhibitory activity against cathepsin G[1].
Related Catalog
Target

IC50: 56 nM (Human cathepsin L), 15.4 μM (Plasmodium falciparum), 12.5 μM (Leishmania major)[1]

In Vitro After a 4 hr preincubation with cathepsin L, SID 26681509 becomes more potent, demonstrating an IC50 of 1.0 nM. SID 26681509 is determined to be a slow-binding and slowly reversible competitive inhibitor. Through a transient kinetic analysis for single-step reversibility, inhibition rate constants are kon = 24,000 M-1s-1 and koff = 2.2 × 10-5 s-1 (Ki = 0.89 nM). Molecular docking studies are undertaken using the experimentally-derived X-ray crystal structure of papain/CLIK-148[1]. SID 26681509 inhibits papain and cathepsins B, K, S, and V with IC50 values determined after one hour ranging from 618 nM to 8.442 μM. SID 26681509 shows no inhibitory activity against the serine protease cathepsin G[1].
In Vivo SID 26681509 treatment significantly improves survival in murine models of sepsis and reduces liver damage following warm liver ischemia/reperfusion (I/R) models[2].
References

[1]. Shah PP, et al. Kinetic characterization and molecular docking of a novel, potent, and selective slow-binding inhibitor of human cathepsin L. Mol Pharmacol. 2008 Jul;74(1):34-41.

[2]. Pribis JP, et al. The HIV Protease Inhibitor Saquinavir Inhibits HMGB1-Driven Inflammation by Targeting the Interaction of Cathepsin V with TLR4/MyD88. Mol Med. 2015 Dec;21(1):749-757.

 Chemical & Physical Properties

Molecular Formula C27H33N5O5S
Molecular Weight 539.64600
Exact Mass 539.22000
PSA 180.68000
LogP 6.17740

 Safety Information

Hazard Codes Xi

 Synonyms

Sibutramina [Spanish]
Medaria
N,N-dimethyl-1-[1-(4-chlorophenyl)cyclobutyl]-3-methylbutylamine
Sibutramina
S-[2-[(2-ethylphenyl)amino]-2-oxoethyl] [2-[(2S)-3-(1H-indol-3-yl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoyl]hydrazinyl]methanethioate
Sibutraminum
Reductil
N-{1-[1-(4-chlorophenyl)cyclobutyl]-3-methylbutyl}-N,N-dimethylamine
Sibutraminum [Latin]
Butramin
Meridia
sibutramine