Rovafovir etalafenamide explained
| Legal Status: | Investigational |
| Cas Number: | 912809-27-9 |
| Unii: | U8S0IC8DY7 |
| Chemspiderid: | 34553889 |
| Chembl: | 4594257 |
| Kegg: | D11721 |
| Pubchem: | 15958717 |
| Iupac Name: | Ethyl (2S)-2-(2R,5R)-5-(6-aminopurin-9-yl)-4-fluoro-2,5-dihydrofuran-2-yloxymethyl-phenoxyphosphoryl]amino]propanoate |
| C: | 21 |
| H: | 24 |
| F: | 1 |
| N: | 6 |
| O: | 6 |
| P: | 1 |
| Smiles: | CCOC(=O)[C@H](C)N[P@@](=O)(CO[C@H]1O[C@@H](N2C=NC3=C2N=CN=C3N)C(F)=C1)OC4=CC=CC=C4 |
| Stdinchikey: | OCJRRXHWPBXZSU-BJBBEUPESA-N |
| Stdinchi: | 1S/C21H24FN6O6P/c1-3-31-21(29)13(2)27-35(30,34-14-7-5-4-6-8-14)12-32-16-9-15(22)20(33-16)28-11-26-17-18(23)24-10-25-19(17)28/h4-11,13,16,20H,3,12H2,1-2H3,(H,27,30)(H2,23,24,25)/t13-,16-,20+,35+/m0/s1 |
Rovafovir etalafenamide (development code GS-9131) is an experimental drug for the treatment of HIV-1 infection.[1] Rovafovir etalafenamide is a nucleotide reverse transcriptase inhibitor and prodrug of GS-9148. Rovafovir etalafenamide itself has no antiviral activity, but once consumed it is metabolized through the hydrolysis of the phosphonoamidate group to generate the antiviral compound GS-9148.[1]
The drug is being developed by Gilead Sciences.[2]
Rovafovir etalafenamide shows antiviral activity against viruses containing major mutations associated with resistance to the nucleoside analog reverse-transcriptase inhibitors which are commonly used to treat HIV/AIDS infection.[1]
The methods by which the drug is synthesized has been published.[3] [4] [5]
Notes and References
- Berg M, Temesgen Z . 10.1358/DOF.2020.45.7.3123468 . Rovafovir etalafenamide. Nucleotide reverse transcriptase inhibitor, Treatment of HIV-1 infection . 2020 . Drugs of the Future . 45 . 7 . 459 . 226610697 .
- Web site: Rovafovir etalafenamide - Gilead Sciences . Adis Insight .
- 10.1021/acs.oprd.1c00059 . Synthesis of Rovafovir Etalafenamide (Part I): Active Pharmaceutical Ingredient Process Development, Scale-Up, and Impurity Control Strategy . 2021 . Standley EA, Bringley DA, Calimsiz S, Ng JD, Sarma K, Shen J, Siler DA, Ambrosi A, Chang WT, Chiu A, Davy JA, Doxsee IJ, Esanu MM, Garber AO, Kim Y, Kwong B, Lapina O, Leung E, Lin L, Marins A, Phoenix J, Pull F, Roberts BJ, She B, St-Jean O, Wang X, Wang L, Wright N, Yu G . 6 . Organic Process Research & Development . 25 . 5 . 1215–1236 . 236571091 .
- 10.1021/acs.oprd.0c00439 . Synthesis of Rovafovir Etalafenamide (Part II): Dynamic Control for Successful Scale-Up of an Oxygen-Releasing Elimination Reaction Mediated by Oxone . 2021 . Bringley DA, Roberts BJ, Calimsiz S, Brown BH, Davy JA, Kwong B, Gao D, Martins A, Sarma K, Shao E, Shen J, Smith MV, Sujino K, Triman AS, Wright N . 6 . Organic Process Research & Development . 25 . 5 . 1237–1246 . 234838465 .
- 10.1021/acs.oprd.0c00428 . Synthesis of Rovafovir Etalafenamide (Part III): Evolution of the Synthetic Process to the Phosphonamidate Fragment . 2021 . Ambrosi A, Bringley DA, Calimsiz S, Garber JA, Huynh H, Mohan S, Sarma K, Shen J, Curl J, Kwong B, Lapina O, Leung E, Lin L, Martins A, McGinitie T, Pull J, Roberts B, Rosario M, She B, Standley EA, Wang L, Wang X, Yu G . 6 . Organic Process Research & Development . 25 . 5 . 1247–1262 . 235569360 .
