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MedKoo Cat#: 584414 | Name: GS-9148

Description:

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

GS-9148, also known as Rovafovir, is a dAMP (2'-deoxyadenosine monophosphate) analog that maintains its antiviral activity against drug-resistant HIV.

Chemical Structure

GS-9148
GS-9148
CAS#875608-25-6

Theoretical Analysis

MedKoo Cat#: 584414

Name: GS-9148

CAS#: 875608-25-6

Chemical Formula: C10H11FN5O5P

Exact Mass: 331.0482

Molecular Weight: 331.20

Elemental Analysis: C, 36.27; H, 3.35; F, 5.74; N, 21.15; O, 24.15; P, 9.35

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.
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Related CAS #
No Data
Synonym
GS-9148; GS9148; GS 9148
IUPAC/Chemical Name
Phosphonic acid, P-((((2R,5R)-5-(6-amino-9H-purin-9-yl)-4-fluoro-2,5-dihydro-2-furanyl)oxy)methyl)-
InChi Key
MPSGQQOHTJUJKB-QUBYGPBYSA-N
InChi Code
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
SMILES Code
OP(O)(CO[C@H]1O[C@@H](N2C=NC3=C(N)N=CN=C23)C(F)=C1)=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

Preparing Stock Solutions

The following data is based on the product molecular weight 331.20 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.

Recalculate based on batch purity %
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: 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. 2: Scarth BJ, White KL, Chen JM, Lansdon EB, Swaminathan S, Miller MD, Götte M. Mechanism of resistance to GS-9148 conferred by the Q151L mutation in HIV-1 reverse transcriptase. Antimicrob Agents Chemother. 2011 Jun;55(6):2662-9. doi: 10.1128/AAC.01738-10. Epub 2011 Mar 14. PubMed PMID: 21402840; PubMed Central PMCID: PMC3101450. 3: 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. 4: Mackman RL, Lin KY, Boojamra CG, Hui H, Douglas J, Grant D, Petrakovsky O, Prasad V, Ray AS, Cihlar T. Synthesis and anti-HIV activity of 2'-fluorine modified nucleoside phosphonates: analogs of GS-9148. Bioorg Med Chem Lett. 2008 Feb 1;18(3):1116-9. Epub 2007 Dec 5. PubMed PMID: 18082402. 5: 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. 6: 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. 7: Boojamra CG, Mackman RL, Markevitch DY, Prasad V, Ray AS, Douglas J, Grant D, Kim CU, Cihlar T. Synthesis and anti-HIV activity of GS-9148 (2'-Fd4AP), a novel nucleoside phosphonate HIV reverse transcriptase inhibitor. Bioorg Med Chem Lett. 2008 Feb 1;18(3):1120-3. doi: 10.1016/j.bmcl.2007.11.125. Epub 2007 Dec 5. PubMed PMID: 18164198. 8: Lansdon EB, Samuel D, Lagpacan L, Brendza KM, White KL, Hung M, Liu X, Boojamra CG, Mackman RL, Cihlar T, Ray AS, McGrath ME, Swaminathan S. Visualizing the molecular interactions of a nucleotide analog, GS-9148, with HIV-1 reverse transcriptase-DNA complex. J Mol Biol. 2010 Apr 9;397(4):967-78. doi: 10.1016/j.jmb.2010.02.019. Epub 2010 Feb 13. PubMed PMID: 20156454. 9: 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. 10: Boojamra CG, Parrish JP, Sperandio D, Gao Y, Petrakovsky OV, Lee SK, Markevitch DY, Vela JE, Laflamme G, Chen JM, Ray AS, Barron AC, Sparacino ML, Desai MC, Kim CU, Cihlar T, Mackman RL. Design, synthesis, and anti-HIV activity of 4'-modified carbocyclic nucleoside phosphonate reverse transcriptase inhibitors. Bioorg Med Chem. 2009 Feb 15;17(4):1739-46. doi: 10.1016/j.bmc.2008.12.028. Epub 2008 Dec 24. PubMed PMID: 19179082. 11: 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. 12: Biswas H, Kar I, Chattopadhyaya R. Deoxyadenosine family: improved synthesis, DNA damage and repair, analogs as drugs. Biomol Concepts. 2013 Aug;4(4):401-10. doi: 10.1515/bmc-2013-0010. Review. PubMed PMID: 25436589. 13: 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. 14: Cihlar T. Nucleotide HIV reverse transcriptase inhibitors: tenofovir and beyond. Curr Opin HIV AIDS. 2006 Sep;1(5):373-9. doi: 10.1097/01.COH.0000239849.20828.09. PubMed PMID: 19372836.