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Rovafovir etalafenamide

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]

Rovafovir etalafenamide
Legal status
Legal status
  • Investigational
Identifiers
  • Ethyl (2S)-2-[[[(2R,5R)-5-(6-aminopurin-9-yl)-4-fluoro-2,5-dihydrofuran-2-yl]oxymethyl-phenoxyphosphoryl]amino]propanoate
CAS Number
  • 912809-27-9 Y
PubChem CID
  • 15958717
ChemSpider
  • 34553889
UNII
  • U8S0IC8DY7
KEGG
  • D11721
ChEMBL
  • ChEMBL4594257
Chemical and physical data
FormulaC21H24FN6O6P
Molar mass506.431 g·mol−1
3D model (JSmol)
  • Interactive image
  • 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
  • InChI=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
  • Key:OCJRRXHWPBXZSU-BJBBEUPESA-N
Chemical strucuture of GS-9148, the active antiviral agent

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 by been published.[3][4][5]

References Edit

  1. ^ a b c Berg M, Temesgen Z (2020). "Rovafovir etalafenamide. Nucleotide reverse transcriptase inhibitor, Treatment of HIV-1 infection". Drugs of the Future. 45 (7): 459. doi:10.1358/DOF.2020.45.7.3123468. S2CID 226610697.
  2. ^ "Rovafovir etalafenamide - Gilead Sciences". Adis Insight.
  3. ^ Standley EA, Bringley DA, Calimsiz S, Ng JD, Sarma K, Shen J, et al. (2021). "Synthesis of Rovafovir Etalafenamide (Part I): Active Pharmaceutical Ingredient Process Development, Scale-Up, and Impurity Control Strategy". Organic Process Research & Development. 25 (5): 1215–1236. doi:10.1021/acs.oprd.1c00059.
  4. ^ Bringley DA, Roberts BJ, Calimsiz S, Brown BH, Davy JA, Kwong B, et al. (2021). "Synthesis of Rovafovir Etalafenamide (Part II): Dynamic Control for Successful Scale-Up of an Oxygen-Releasing Elimination Reaction Mediated by Oxone". Organic Process Research & Development. 25 (5): 1237–1246. doi:10.1021/acs.oprd.0c00439. S2CID 234838465.
  5. ^ Ambrosi A, Bringley DA, Calimsiz S, Garber JA, Huynh H, Mohan S, et al. (2021). "Synthesis of Rovafovir Etalafenamide (Part III): Evolution of the Synthetic Process to the Phosphonamidate Fragment". Organic Process Research & Development. 25 (5): 1247–1262. doi:10.1021/acs.oprd.0c00428. S2CID 235569360.

rovafovir, etalafenamide, development, code, 9131, experimental, drug, treatment, infection, nucleotide, reverse, transcriptase, inhibitor, prodrug, 9148, itself, antiviral, activity, once, consumed, metabolized, through, hydrolysis, phosphonoamidate, group, g. 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 Rovafovir etalafenamideLegal statusLegal statusInvestigationalIdentifiersIUPAC name Ethyl 2S 2 2R 5R 5 6 aminopurin 9 yl 4 fluoro 2 5 dihydrofuran 2 yl oxymethyl phenoxyphosphoryl amino propanoateCAS Number912809 27 9 YPubChem CID15958717ChemSpider34553889UNIIU8S0IC8DY7KEGGD11721ChEMBLChEMBL4594257Chemical and physical dataFormulaC 21H 24F N 6O 6PMolar mass506 431 g mol 13D model JSmol Interactive imageSMILES 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 C4InChI InChI 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 s1Key OCJRRXHWPBXZSU BJBBEUPESA N Chemical strucuture of GS 9148 the active antiviral agentThe 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 by been published 3 4 5 References Edit a b c Berg M Temesgen Z 2020 Rovafovir etalafenamide Nucleotide reverse transcriptase inhibitor Treatment of HIV 1 infection Drugs of the Future 45 7 459 doi 10 1358 DOF 2020 45 7 3123468 S2CID 226610697 Rovafovir etalafenamide Gilead Sciences Adis Insight Standley EA Bringley DA Calimsiz S Ng JD Sarma K Shen J et al 2021 Synthesis of Rovafovir Etalafenamide Part I Active Pharmaceutical Ingredient Process Development Scale Up and Impurity Control Strategy Organic Process Research amp Development 25 5 1215 1236 doi 10 1021 acs oprd 1c00059 Bringley DA Roberts BJ Calimsiz S Brown BH Davy JA Kwong B et al 2021 Synthesis of Rovafovir Etalafenamide Part II Dynamic Control for Successful Scale Up of an Oxygen Releasing Elimination Reaction Mediated by Oxone Organic Process Research amp Development 25 5 1237 1246 doi 10 1021 acs oprd 0c00439 S2CID 234838465 Ambrosi A Bringley DA Calimsiz S Garber JA Huynh H Mohan S et al 2021 Synthesis of Rovafovir Etalafenamide Part III Evolution of the Synthetic Process to the Phosphonamidate Fragment Organic Process Research amp Development 25 5 1247 1262 doi 10 1021 acs oprd 0c00428 S2CID 235569360 This pharmacology related article is a stub You can help Wikipedia by expanding it vte Retrieved from https en wikipedia org w index php title Rovafovir etalafenamide amp oldid 1171067312, wikipedia, wiki, book, books, library,

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