Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C23H17Cl2N3O5S |
| Molecular Weight | 518.369 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CC1=CC(=CC=C1NC(=O)COC2=CC=C(Cl)C=C2C(=O)C3=CC(Cl)=CC(=C3)C#N)S(N)(=O)=O
InChI
InChIKey=BTOMIMSUTLPSHA-UHFFFAOYSA-N
InChI=1S/C23H17Cl2N3O5S/c1-13-6-18(34(27,31)32)3-4-20(13)28-22(29)12-33-21-5-2-16(24)10-19(21)23(30)15-7-14(11-26)8-17(25)9-15/h2-10H,12H2,1H3,(H,28,29)(H2,27,31,32)
| Molecular Formula | C23H17Cl2N3O5S |
| Molecular Weight | 518.369 |
| 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
Edited
Sat Dec 16 11:29:08 GMT 2023
by
admin
on
Sat Dec 16 11:29:08 GMT 2023
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| Record UNII |
C932C98SNY
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| Record Status |
Validated (UNII)
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| Record Version |
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-
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486532
Created by
admin on Sat Dec 16 11:29:08 GMT 2023 , Edited by admin on Sat Dec 16 11:29:08 GMT 2023
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329939-64-2
Created by
admin on Sat Dec 16 11:29:08 GMT 2023 , Edited by admin on Sat Dec 16 11:29:08 GMT 2023
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DTXSID00333148
Created by
admin on Sat Dec 16 11:29:08 GMT 2023 , Edited by admin on Sat Dec 16 11:29:08 GMT 2023
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C932C98SNY
Created by
admin on Sat Dec 16 11:29:08 GMT 2023 , Edited by admin on Sat Dec 16 11:29:08 GMT 2023
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| Related Record | Type | Details | ||
|---|---|---|---|---|
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TARGET -> INHIBITOR |
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TARGET ORGANISM->INHIBITOR |
Preclinical assessment of GW678248 indicates that this compound potently inhibits wild-type (WT) and mutant human immunodeficiency virus type 1 (HIV-1) reverse transcriptase in biochemical assays, with 50% inhibitory concentrations (IC50s) between 0.8 and 6.8 nM. In HeLa CD4 MAGI cell culture virus replication assays, GW678248 has an IC50 of 21 nM against HIV-1 isogenic strains with single or double mutations known to be associated with NNRTI resistance, including L100I, K101E, K103N, V106A/I/M, V108I, E138K, Y181C, Y188C, Y188L, G190A/E, P225H, and P236L and various combinations. An IC50 of 86 nM was obtained with a mutant virus having V106I, E138K, and P236L mutations that resulted from serial passage of WT virus in the presence of GW678248.
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| Related Record | Type | Details | ||
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PRODRUG -> METABOLITE ACTIVE |
Class: Antiretroviral; Mechanism of Action: Non-nucleoside reverse transcriptase inhibitor; Highest Development Phase: Discontinued for HIV-1 infections; Most Recent Events: 31 Dec 2005 Discontinued - Phase-II for HIV-1 infections in USA (PO), 22 Aug 2005 Data presented at the 3rd Conference on HIV Pathogenesis and Treatment have been added to the Viral infections therapeutic trials section
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| Related Record | Type | Details | ||
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ACTIVE MOIETY |
GW-678248: Inhibition of HIV replication in vitro EC50 (nM): 0.84 +/- 0.25, Enhancement of Gag processing(Fig. 2): ++, Cytotoxicity on MT4-CMV-EGFP control cells CC50: > 10, Cytotoxicity on MT4-LTR-EGFP-IIIB HIV-1 producing cells CC50(.MU.M): 0.68 +/- 0.29, Ctotoxicity on MT4-LTREGFP-
IIIB cells in presence of 0.1 .MU.M DRV CC50 (.MU.M): > 10, Enhancement of RT-Dimerization EC50 (.MU.M): 0.0032
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