Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C10H11FN5O5P |
| Molecular Weight | 331.197 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 2 / 2 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
NC1=NC=NC2=C1N=CN2[C@@H]3O[C@H](OCP(O)(O)=O)C=C3F
InChI
InChIKey=MPSGQQOHTJUJKB-QUBYGPBYSA-N
InChI=1S/C10H11FN5O5P/c11-5-1-6(20-4-22(17,18)19)21-10(5)16-3-15-7-8(12)13-2-14-9(7)16/h1-3,6,10H,4H2,(H2,12,13,14)(H2,17,18,19)/t6-,10+/m0/s1
| Molecular Formula | C10H11FN5O5P |
| Molecular Weight | 331.197 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 2 / 2 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
Approval Year
| Substance Class |
Chemical
Created
by
admin
on
Edited
Tue Apr 01 16:31:00 GMT 2025
by
admin
on
Tue Apr 01 16:31:00 GMT 2025
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| Record UNII |
A8OH1KW2TZ
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| Record Status |
Validated (UNII)
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| Record Version |
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-
Download
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Code | English | ||
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Systematic Name | English |
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875608-25-6
Created by
admin on Tue Apr 01 16:31:00 GMT 2025 , Edited by admin on Tue Apr 01 16:31:00 GMT 2025
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A8OH1KW2TZ
Created by
admin on Tue Apr 01 16:31:00 GMT 2025 , Edited by admin on Tue Apr 01 16:31:00 GMT 2025
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PRIMARY | |||
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15958718
Created by
admin on Tue Apr 01 16:31:00 GMT 2025 , Edited by admin on Tue Apr 01 16:31:00 GMT 2025
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PRIMARY |
| Related Record | Type | Details | ||
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TARGET ORGANISM->INHIBITOR |
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TARGET -> INHIBITOR |
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| Related Record | Type | Details | ||
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PRODRUG -> METABOLITE ACTIVE |
In another program, a novel nucleotide analog, phosphonomethoxy-2'-fluoro-2', 3'-dideoxydidehydroadenosine (GS-9148), was selected as an NRTI with an improved pharmacological and resistance profile. The prodrug of GS-9148 (GS-9131) exhibits potent antiretroviral activity both in primary cells and T-cell lines (EC50 = 25-200 nM), low cytotoxicity (CC50 > 50 iM) in multiple cell types, and shows no effect on mitochondrial DNA or lactate production in HepG2 cells. In phenotypic assays, the activity of GS-9148 was not affected by the K65R, L74V, or M184V mutations in RT (EC50 fold change <1). Viruses with 4 or more thymidine analog mutations showed 0.74 to 2.0-fold change in the susceptibility, a shift that was smaller than that of any other tested NRTI. Passage of HIV-1 in the presence of GS-9148 selected for a primary K70E mutation and two other RT mutations that together conferred <3-fold resistance to GS-9148.
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ACTIVE MOIETY |
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