Rovafovir etalafenamide

Rovafovir etalafenamide
Legal status
Legal status	Investigational;
Identifiers
	IUPAC name 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 ;
PubChem CID	15958717;
ChemSpider	34553889;
UNII	U8S0IC8DY7;
KEGG	D11721;
ChEMBL	ChEMBL4594257;
Chemical and physical data
Formula	C21H24FN6O6P
Molar mass	506.431 g·mol−1
3D model (JSmol)	Interactive image;
	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;
	InChI 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;

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]

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 has been published.^[3]^[4]^[5]

References

^ ^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 & Development. 25 (5): 1215–1236. doi:10.1021/acs.oprd.1c00059. S2CID 236571091.
^ 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.
^ 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.

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[Berg-1] 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. S2CID 236571091.

[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.

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References

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