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Details

Stereochemistry ACHIRAL
Molecular Formula C19H12Cl2F2N4O2
Molecular Weight 437.2276
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of AIC-292

SMILES

c1cc(c(cc1-n2c(cc(C(=O)N3CC(=NC3)O)n2)-c4cc(cc(c4)F)Cl)Cl)F

InChI

InChIKey=JPOJKNJIKXMZRB-UHFFFAOYSA-N
InChI=1S/C19H12Cl2F2N4O2/c20-11-3-10(4-12(22)5-11)17-7-16(19(29)26-8-18(28)24-9-26)25-27(17)13-1-2-15(23)14(21)6-13/h1-7H,8-9H2,(H,24,28)

HIDE SMILES / InChI

Molecular Formula C19H12Cl2F2N4O2
Molecular Weight 437.2276
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Approval Year

Substance Class Chemical
Created
by admin
on Sat Jun 26 10:14:59 UTC 2021
Edited
by admin
on Sat Jun 26 10:14:59 UTC 2021
Record UNII
LE2GYT0UFH
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
AIC-292
Common Name English
1-((1-(3-CHLORO-4-FLUOROPHENYL)-5-(3-CHLORO-5-FLUOROPHENYL)-1H-PYRAZOL-3-YL)CARBONYL)-4-IMIDAZOLIDINONE
Systematic Name English
4-IMIDAZOLIDINONE, 1-((1-(3-CHLORO-4-FLUOROPHENYL)-5-(3-CHLORO-5-FLUOROPHENYL)-1H-PYRAZOL-3-YL)CARBONYL)-
Systematic Name English
AIC 292
Code English
Code System Code Type Description
PUBCHEM
44230181
Created by admin on Sat Jun 26 10:14:59 UTC 2021 , Edited by admin on Sat Jun 26 10:14:59 UTC 2021
PRIMARY
CAS
1187917-12-9
Created by admin on Sat Jun 26 10:14:59 UTC 2021 , Edited by admin on Sat Jun 26 10:14:59 UTC 2021
PRIMARY
FDA UNII
LE2GYT0UFH
Created by admin on Sat Jun 26 10:14:59 UTC 2021 , Edited by admin on Sat Jun 26 10:14:59 UTC 2021
PRIMARY
Related Record Type Details
TARGET -> INHIBITOR
AIC292 inhibited the HIV-1 RT at an IC50 of 38 nM, similar to that observed for EFV, at 36 nM. In contrast, ETR and RPV showed IC50s of 219 and 122 nM, respectively. The anti-HIV activities of these compounds were also assessed against three different strains of HIV-1 (LAI, NL4-3, and D117III) and one strain of HIV-2 in cell-based assays (Table 1). The EC50s for AIC292 against HIV-1 LAI and NL4-3 determined in MT-4 cells and PBMCs were in the nanomolar range (0.9 to 1.9 nM). EFV, ETR, and RPV inhibited HIV in these assays with EC50s in the ranges of 0.1 to 0.8 nM, 0.1 to 1.4 nM, and 0.1 to 0.4 nM, respectively. In macrophages infected with HIV-1 D117III, all EC50s were generally higher than in the other cell assays. In this assay, AIC292 showed an EC50 of 49 nM compared to 20 to 22 nM for the other NNRTIs. Unsurprisingly, none of the tested NNRTIs was active against the HIV-2 isolate (EC50s > 33 .MU.M). Regarding cytotoxicity, AIC292 was well tolerated in a broad panel of cells from different tissues and species with CC50 values of 15 .MU.M, and the calculated selectivity indices (the ratios of the CC50s to the EC50s) were 7,900 and >20,000 for MT-4 cells and PBMCs, respectively (data not shown). The selectivity of AIC292 for HIV-1 RT was further confirmed using a Panlabs lead profiling screen. In this screen, none of the 68 investigated target proteins/receptors were significantly modulated by concentrations of AIC292 (data not shown).
IC50
Related Record Type Details
ACTIVE MOIETY
Originator: AiCuris; Class: Antiretroviral; Mechanism of Action: Non-nucleoside reverse tanscriptase inhibitor; Orphan Drug Status: No; On Fast track: No; New Molecular Entity: Yes; Highest Development Phase: No development reported for HIV infections; Most Recent Events: 16 Mar 2016 No recent reports on development identified - Phase-I for HIV infections in Germany (PO), 01 Jul 2010 Phase-I clinical trials in HIV infections in Germany (PO)