Rovafovir Etalafenamide | GS-9131 | CAS#912809-27-9 | Anti-HIV Nucleoside Phosphonate Prodrug

MedKoo Cat#: 596782 | Name: Rovafovir Etalafenamide

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Rovafovir Etalafenamide, also known as GS-9131, is an anti-HIV Nucleoside Phosphonate prodrug.

Chemical Structure

Rovafovir Etalafenamide

CAS#912809-27-9

Theoretical Analysis

MedKoo Cat#: 596782

Name: Rovafovir Etalafenamide

CAS#: 912809-27-9

Chemical Formula: C21H24FN6O6P

Exact Mass: 506.1479

Molecular Weight: 506.43

Elemental Analysis: C, 49.81; H, 4.78; F, 3.75; N, 16.59; O, 18.95; P, 6.12

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.

Bulk Inquiry

Related CAS #

912809-27-9 1034559-30-2 (citrate)

Synonym

GS-9131; GS 9131; GS9131; Rovafovir Etalafenamide

IUPAC/Chemical Name

ethyl ((S)-((((2R,5R)-5-(6-amino-9H-purin-9-yl)-4-fluoro-2,5-dihydrofuran-2-yl)oxy)methyl)(phenoxy)phosphoryl)-L-alaninate

InChi Key

OCJRRXHWPBXZSU-BNCZGPJRSA-N

InChi Code

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

SMILES Code

C[C@@H](C(OCC)=O)N[P@@](OC1=CC=CC=C1)(CO[C@H]2O[C@@H](N3C=NC4=C(N)N=CN=C34)C(F)=C2)=O

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO

Shelf Life

>2 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 506.43 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

1: Rai MA, Pannek S, Fichtenbaum CJ. Emerging reverse transcriptase inhibitors for HIV-1 infection. Expert Opin Emerg Drugs. 2018 May 10:1-9. doi: 10.1080/14728214.2018.1474202. [Epub ahead of print] PubMed PMID: 29737220. 2: Mackman RL. Anti-HIV Nucleoside Phosphonate GS-9148 and Its Prodrug GS-9131: Scale Up of a 2'-F Modified Cyclic Nucleoside Phosphonate and Synthesis of Selected Amidate Prodrugs. Curr Protoc Nucleic Acid Chem. 2014 Mar 26;56:14.10.1-21. doi: 10.1002/0471142700.nc1410s56. Review. PubMed PMID: 25606977. 3: De Clercq E. The clinical potential of the acyclic (and cyclic) nucleoside phosphonates: the magic of the phosphonate bond. Biochem Pharmacol. 2011 Jul 15;82(2):99-109. doi: 10.1016/j.bcp.2011.03.027. Epub 2011 Apr 8. Review. PubMed PMID: 21501598. 4: Mackman RL, Ray AS, Hui HC, Zhang L, Birkus G, Boojamra CG, Desai MC, Douglas JL, Gao Y, Grant D, Laflamme G, Lin KY, Markevitch DY, Mishra R, McDermott M, Pakdaman R, Petrakovsky OV, Vela JE, Cihlar T. Discovery of GS-9131: Design, synthesis and optimization of amidate prodrugs of the novel nucleoside phosphonate HIV reverse transcriptase (RT) inhibitor GS-9148. Bioorg Med Chem. 2010 May 15;18(10):3606-17. doi: 10.1016/j.bmc.2010.03.041. Epub 2010 Mar 27. PubMed PMID: 20409721. 5: Cihlar T, Laflamme G, Fisher R, Carey AC, Vela JE, Mackman R, Ray AS. Novel nucleotide human immunodeficiency virus reverse transcriptase inhibitor GS-9148 with a low nephrotoxic potential: characterization of renal transport and accumulation. Antimicrob Agents Chemother. 2009 Jan;53(1):150-6. doi: 10.1128/AAC.01183-08. Epub 2008 Nov 10. PubMed PMID: 19001108; PubMed Central PMCID: PMC2612154. 6: Cihlar T, Ray AS, Boojamra CG, Zhang L, Hui H, Laflamme G, Vela JE, Grant D, Chen J, Myrick F, White KL, Gao Y, Lin KY, Douglas JL, Parkin NT, Carey A, Pakdaman R, Mackman RL. Design and profiling of GS-9148, a novel nucleotide analog active against nucleoside-resistant variants of human immunodeficiency virus type 1, and its orally bioavailable phosphonoamidate prodrug, GS-9131. Antimicrob Agents Chemother. 2008 Feb;52(2):655-65. Epub 2007 Dec 3. PubMed PMID: 18056282; PubMed Central PMCID: PMC2224772. 7: Ray AS, Vela JE, Boojamra CG, Zhang L, Hui H, Callebaut C, Stray K, Lin KY, Gao Y, Mackman RL, Cihlar T. Intracellular metabolism of the nucleotide prodrug GS-9131, a potent anti-human immunodeficiency virus agent. Antimicrob Agents Chemother. 2008 Feb;52(2):648-54. Epub 2007 Dec 3. PubMed PMID: 18056281; PubMed Central PMCID: PMC2224749. 8: Birkus G, Wang R, Liu X, Kutty N, MacArthur H, Cihlar T, Gibbs C, Swaminathan S, Lee W, McDermott M. Cathepsin A is the major hydrolase catalyzing the intracellular hydrolysis of the antiretroviral nucleotide phosphonoamidate prodrugs GS-7340 and GS-9131. Antimicrob Agents Chemother. 2007 Feb;51(2):543-50. Epub 2006 Dec 4. PubMed PMID: 17145787; PubMed Central PMCID: PMC1797775.