Fostemsavir
featured

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

MedKoo CAT#: 522484

CAS#: 864953-29-7(free base)

Description: Fostemsavir, also known as BMS-663068, is a oral, safe and effective HIV-1 attachment inhibitor. BMS-663068 is a prodrug of the small-molecule inhibitor BMS-626529, which inhibits human immunodeficiency virus type 1 (HIV-1) infection by binding to gp120 and interfering with the attachment of virus to CD4+ T-cells.


Chemical Structure

img
Fostemsavir
CAS# 864953-29-7(free base)

Theoretical Analysis

MedKoo Cat#: 522484
Name: Fostemsavir
CAS#: 864953-29-7(free base)
Chemical Formula: C25H26N7O8P
Exact Mass: 583.15805
Molecular Weight: 583.49776
Elemental Analysis: C, 51.46; H, 4.49; N, 16.80; O, 21.94; P, 5.31

Price and Availability

Size Price Availability Quantity
200.0mg USD 1850.0 2 Weeks
500.0mg USD 2650.0 2 Weeks
1.0g USD 3950.0 2 Weeks
2.0g USD 6250.0 2 Weeks
5.0g USD 10650.0 2 Weeks
Bulk inquiry

Related CAS #: 864953-29-7(free base)   864953-39-9 (tromethamine)    

Synonym: BMS-663068; BMS663068; BMS-663068 dihydrate; BMS 663068; Fostemsavir

IUPAC/Chemical Name: (3-(2-(4-benzoylpiperazin-1-yl)-2-oxoacetyl)-4-methoxy-7-(3-methyl-1H-1,2,4-triazol-1-yl)-1H-pyrrolo[2,3-c]pyridin-1-yl)methyl dihydrogen phosphate

InChi Key: SWMDAPWAQQTBOG-UHFFFAOYSA-N

InChi Code: InChI=1S/C25H26N7O8P/c1-16-27-14-32(28-16)23-21-20(19(39-2)12-26-23)18(13-31(21)15-40-41(36,37)38)22(33)25(35)30-10-8-29(9-11-30)24(34)17-6-4-3-5-7-17/h3-7,12-14H,8-11,15H2,1-2H3,(H2,36,37,38)

SMILES Code: CC1=NN(C=N1)C2=NC=C(C3=C2N(C=C3C(=O)C(=O)N4CCN(CC4)C(=O)C5=CC=CC=C5)COP(=O)(O)O)OC

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, not in water

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

Preparing Stock Solutions

The following data is based on the product molecular weight 583.49776 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

Molarity Calculator

Calculate the mass, volume, or concentration required for a solution.
=
x
x
g/mol

*When preparing stock solutions always use the batch-specific molecular weight of the product found on the vial label and SDS / CoA (available online).

Reconstitution Calculator

The reconstitution calculator allows you to quickly calculate the volume of a reagent to reconstitute your vial. Simply enter the mass of reagent and the target concentration and the calculator will determine the rest.

=
÷

Dilution Calculator

Calculate the dilution required to prepare a stock solution.
x
=
x

1: Lalezari JP, Latiff GH, Brinson C, Echevarría J, Treviño-Pérez S, Bogner JR, Thompson M, Fourie J, Sussmann Pena OA, Mendo Urbina FC, Martins M, Diaconescu IG, Stock DA, Joshi SR, Hanna GJ, Lataillade M; AI438011 study team. Safety and efficacy of the HIV-1 attachment inhibitor prodrug BMS-663068 in treatment-experienced individuals: 24 week results of AI438011, a phase 2b, randomised controlled trial. Lancet HIV. 2015 Oct;2(10):e427-37. doi: 10.1016/S2352-3018(15)00177-0. Epub 2015 Sep 1. PubMed PMID: 26423650.

2: Ballana E, Esté JA. BMS-663068, a safe and effective HIV-1 attachment inhibitor. Lancet HIV. 2015 Oct;2(10):e404-5. doi: 10.1016/S2352-3018(15)00160-5. Epub 2015 Sep 2. PubMed PMID: 26423643.

3: Zhang XQ. [The newest developments of the study on anti-HIV drugs]. Yao Xue Xue Bao. 2015 May;50(5):509-15. Review. Chinese. PubMed PMID: 26234128.

4: Patel RV, Park SW. Pyrroloaryls and pyrroloheteroaryls: Inhibitors of the HIV fusion/attachment, reverse transcriptase and integrase. Bioorg Med Chem. 2015 Sep 1;23(17):5247-63. doi: 10.1016/j.bmc.2015.06.016. Epub 2015 Jun 14. Review. PubMed PMID: 26116177.

5: Zhu L, Hruska M, Hwang C, Shah V, Furlong M, Hanna GJ, Bertz R, Landry IS. Pharmacokinetic interactions between BMS-626529, the active moiety of the HIV-1 attachment inhibitor prodrug BMS-663068, and ritonavir or ritonavir-boosted atazanavir in healthy subjects. Antimicrob Agents Chemother. 2015 Jul;59(7):3816-22. doi: 10.1128/AAC.04914-14. Epub 2015 Apr 13. PubMed PMID: 25870057; PubMed Central PMCID: PMC4468697.

6: Majewska A, Mlynarczyk-Bonikowska B, Malejczyk M, Mlynarczyk G, Majewski S. Antiviral medication in sexually transmitted diseases. Part II: HIV. Mini Rev Med Chem. 2015;15(2):93-103. PubMed PMID: 25751258.

7: Langley DR, Kimura SR, Sivaprakasam P, Zhou N, Dicker I, McAuliffe B, Wang T, Kadow JF, Meanwell NA, Krystal M. Homology models of the HIV-1 attachment inhibitor BMS-626529 bound to gp120 suggest a unique mechanism of action. Proteins. 2015 Feb;83(2):331-50. doi: 10.1002/prot.24726. Epub 2014 Dec 23. PubMed PMID: 25401969.

8: Lalezari J, Latiff GH, Brinson C, Echevarria J, Treviño-Pérez S, Bogner JR, Stock D, Joshi SR, Hanna GJ, Lataillade M. Safety profile of HIV-1 attachment inhibitor prodrug BMS-663068 in antiretroviral-experienced subjects: week 24 analysis. J Int AIDS Soc. 2014 Nov 2;17(4 Suppl 3):19530. doi: 10.7448/IAS.17.4.19530. eCollection 2014. PubMed PMID: 25394039; PubMed Central PMCID: PMC4224850.

9: Brinson C, Lalezari J, Gulam LH, Thompson M, Echevarria J, Treviño-Pérez S, Stock D, Samit JR, George HJ, Lataillade M. HIV-1 attachment inhibitor prodrug BMS-663068 in antiretroviral-experienced subjects: week 24 sub-group analysis. J Int AIDS Soc. 2014 Nov 2;17(4 Suppl 3):19529. doi: 10.7448/IAS.17.4.19529. eCollection 2014. PubMed PMID: 25394038; PubMed Central PMCID: PMC4224901.

10: Gulick R. HIV treatment 2020: what will it look like? J Int AIDS Soc. 2014 Nov 2;17(4 Suppl 3):19528. doi: 10.7448/IAS.17.4.19528. eCollection 2014. PubMed PMID: 25394037; PubMed Central PMCID: PMC4224796.

11: Chen K, Risatti C, Bultman M, Soumeillant M, Simpson J, Zheng B, Fanfair D, Mahoney M, Mudryk B, Fox RJ, Hsaio Y, Murugesan S, Conlon DA, Buono FG, Eastgate MD. Synthesis of the 6-azaindole containing HIV-1 attachment inhibitor pro-drug, BMS-663068. J Org Chem. 2014 Sep 19;79(18):8757-67. doi: 10.1021/jo5016008. Epub 2014 Sep 5. PubMed PMID: 25144249.

12: Leane MM, Gamble JF, Brown J, Hughes H, Crull G, Engstrom J, Gao Q, Bunker M, Rutherford S, Parker A, Roberts CJ, Tobyn M. Imaging dehydration kinetics of a channel hydrate form of the HIV-1 attachment inhibitor prodrug BMS-663068. J Pharm Sci. 2013 Dec;102(12):4375-83. doi: 10.1002/jps.23747. Epub 2013 Oct 15. PubMed PMID: 24129913.

13: Zhou N, Nowicka-Sans B, McAuliffe B, Ray N, Eggers B, Fang H, Fan L, Healy M, Langley DR, Hwang C, Lataillade M, Hanna GJ, Krystal M. Genotypic correlates of susceptibility to HIV-1 attachment inhibitor BMS-626529, the active agent of the prodrug BMS-663068. J Antimicrob Chemother. 2014 Mar;69(3):573-81. doi: 10.1093/jac/dkt412. Epub 2013 Oct 14. PubMed PMID: 24128669.

14: Flexner C, Saag M. The antiretroviral drug pipeline: prospects and implications for future treatment research. Curr Opin HIV AIDS. 2013 Nov;8(6):572-8. doi: 10.1097/COH.0000000000000011. Review. PubMed PMID: 24100879.

15: Li Z, Zhou N, Sun Y, Ray N, Lataillade M, Hanna GJ, Krystal M. Activity of the HIV-1 attachment inhibitor BMS-626529, the active component of the prodrug BMS-663068, against CD4-independent viruses and HIV-1 envelopes resistant to other entry inhibitors. Antimicrob Agents Chemother. 2013 Sep;57(9):4172-80. doi: 10.1128/AAC.00513-13. Epub 2013 Jun 17. PubMed PMID: 23774428; PubMed Central PMCID: PMC3754311.

16: Brown J, Chien C, Timmins P, Dennis A, Doll W, Sandefer E, Page R, Nettles RE, Zhu L, Grasela D. Compartmental absorption modeling and site of absorption studies to determine feasibility of an extended-release formulation of an HIV-1 attachment inhibitor phosphate ester prodrug. J Pharm Sci. 2013 Jun;102(6):1742-51. doi: 10.1002/jps.23476. Epub 2013 Apr 5. PubMed PMID: 23681563.

17: Ray N, Hwang C, Healy MD, Whitcomb J, Lataillade M, Wind-Rotolo M, Krystal M, Hanna GJ. Prediction of virological response and assessment of resistance emergence to the HIV-1 attachment inhibitor BMS-626529 during 8-day monotherapy with its prodrug BMS-663068. J Acquir Immune Defic Syndr. 2013 Sep 1;64(1):7-15. doi: 10.1097/QAI.0b013e31829726f3. PubMed PMID: 23614999.

18: Henrich TJ, Kuritzkes DR. HIV-1 entry inhibitors: recent development and clinical use. Curr Opin Virol. 2013 Feb;3(1):51-7. doi: 10.1016/j.coviro.2012.12.002. Epub 2013 Jan 3. Review. PubMed PMID: 23290628; PubMed Central PMCID: PMC4213740.

19: Nettles RE, Schürmann D, Zhu L, Stonier M, Huang SP, Chang I, Chien C, Krystal M, Wind-Rotolo M, Ray N, Hanna GJ, Bertz R, Grasela D. Pharmacodynamics, safety, and pharmacokinetics of BMS-663068, an oral HIV-1 attachment inhibitor in HIV-1-infected subjects. J Infect Dis. 2012 Oct 1;206(7):1002-11. doi: 10.1093/infdis/jis432. Epub 2012 Aug 14. PubMed PMID: 22896665.

20: Nowicka-Sans B, Gong YF, McAuliffe B, Dicker I, Ho HT, Zhou N, Eggers B, Lin PF, Ray N, Wind-Rotolo M, Zhu L, Majumdar A, Stock D, Lataillade M, Hanna GJ, Matiskella JD, Ueda Y, Wang T, Kadow JF, Meanwell NA, Krystal M. In vitro antiviral characteristics of HIV-1 attachment inhibitor BMS-626529, the active component of the prodrug BMS-663068. Antimicrob Agents Chemother. 2012 Jul;56(7):3498-507. doi: 10.1128/AAC.00426-12. Epub 2012 Apr 30. PubMed PMID: 22547625; PubMed Central PMCID: PMC3393465.

Fostemsavir

200.0mg / USD 1850.0


Additional Information

Related CAS#
864953-29-7(Fostemsavir free base).
942117-71-7(Fostemsavir dihydrate);
864953-31-1(Fostemsavir disodium);
864953-39-9 (Fostemsavir tris salt).