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MedKoo Cat#: 319724 | Name: Fosdevirine

Description:

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

Fosdevirine, also known as GSK2248761 and IDX899, a Highly Potent Anti-HIV Non-nucleoside Reverse Transcriptase Inhibitor having an EC50 of 11 nM against the Y181C/K103N double mutant. GSK2248761 is a novel, once-daily (QD), next-generation nonnucleoside reverse transcriptase inhibitor (NNRTI) with activity against efavirenz-resistant strains. GSK2248761 at 100 to 800 mg QD for 7 days was well tolerated, demonstrated potent antiviral activity in treatment-naive HIV-infected subjects, and had favorable PK and resistance profiles. GSK2248761 is no longer in clinical development.

Chemical Structure

Fosdevirine
Fosdevirine
CAS#1018450-26-4

Theoretical Analysis

MedKoo Cat#: 319724

Name: Fosdevirine

CAS#: 1018450-26-4

Chemical Formula: C20H17ClN3O3P

Exact Mass: 413.0696

Molecular Weight: 413.80

Elemental Analysis: C, 58.05; H, 4.14; Cl, 8.57; N, 10.15; O, 11.60; P, 7.49

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
GSK2248761; GSK-2248761; GSK 2248761; GSK2248761A; GSK-2248761A; GSK 2248761A; IDX899; IDX-899; IDX 899, Fosdevirine.
IUPAC/Chemical Name
methyl (E)-(2-carbamoyl-5-chloro-1H-indol-3-yl)(3-(2-cyanovinyl)-5-methylphenyl)phosphinate
InChi Key
CGBYTKOSZYQOPV-ONEGZZNKSA-N
InChi Code
InChI=1S/C20H17ClN3O3P/c1-12-8-13(4-3-7-22)10-15(9-12)28(26,27-2)19-16-11-14(21)5-6-17(16)24-18(19)20(23)25/h3-6,8-11,24H,1-2H3,(H2,23,25)/b4-3+
SMILES Code
O=P(C1=CC(C)=CC(/C=C/C#N)=C1)(C2=C(C(N)=O)NC3=C2C=C(Cl)C=C3)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
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 413.80 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: Dousson C, Alexandre FR, Amador A, Bonaric S, Bot S, Caillet C, Convard T, da Costa D, Lioure MP, Roland A, Rosinovsky E, Maldonado S, Parsy C, Trochet C, Storer R, Stewart A, Wang J, Mayes BA, Musiu C, Poddesu B, Vargiu L, Liuzzi M, Moussa A, Jakubik J, Hubbard L, Seifer M, Standring D. Discovery of the Aryl-phospho-indole IDX899, a Highly Potent Anti-HIV Non-nucleoside Reverse Transcriptase Inhibitor. J Med Chem. 2016 Feb 3. [Epub ahead of print] PubMed PMID: 26804933. 2: Margolis DA, Eron JJ, DeJesus E, White S, Wannamaker P, Stancil B, Johnson M. Unexpected finding of delayed-onset seizures in HIV-positive, treatment-experienced subjects in the Phase IIb evaluation of fosdevirine (GSK2248761). Antivir Ther. 2014;19(1):69-78. doi: 10.3851/IMP2689. Epub 2013 Oct 24. PubMed PMID: 24158593. 3: Ölgen S. Recent development of new substituted indole and azaindole derivatives as anti-HIV agents. Mini Rev Med Chem. 2013 Oct;13(12):1700-8. Review. PubMed PMID: 23895189. 4: Castellino S, Groseclose MR, Sigafoos J, Wagner D, de Serres M, Polli JW, Romach E, Myer J, Hamilton B. Central nervous system disposition and metabolism of Fosdevirine (GSK2248761), a non-nucleoside reverse transcriptase inhibitor: an LC-MS and Matrix-assisted laser desorption/ionization imaging MS investigation into central nervous system toxicity. Chem Res Toxicol. 2013 Feb 18;26(2):241-51. doi: 10.1021/tx3004196. Epub 2012 Dec 20. PubMed PMID: 23227887. 5: Zala C, St Clair M, Dudas K, Kim J, Lou Y, White S, Piscitelli S, Dumont E, Pietropaolo K, Zhou XJ, Mayers D. Safety and efficacy of GSK2248761, a next-generation nonnucleoside reverse transcriptase inhibitor, in treatment-naive HIV-1-infected subjects. Antimicrob Agents Chemother. 2012 May;56(5):2570-5. doi: 10.1128/AAC.05597-11. Epub 2012 Feb 6. PubMed PMID: 22314532; PubMed Central PMCID: PMC3346662. 6: Piscitelli S, Kim J, Gould E, Lou Y, White S, de Serres M, Johnson M, Zhou XJ, Pietropaolo K, Mayers D. Drug interaction profile for GSK2248761, a next generation non-nucleoside reverse transcriptase inhibitor. Br J Clin Pharmacol. 2012 Aug;74(2):336-45. doi: 10.1111/j.1365-2125.2012.04194.x. PubMed PMID: 22288567; PubMed Central PMCID: PMC3630753. 7: La Regina G, Coluccia A, Silvestri R. Looking for an active conformation of the future HIV type-1 non-nucleoside reverse transcriptase inhibitors. Antivir Chem Chemother. 2010 Aug 11;20(6):213-37. doi: 10.3851/IMP1607. Review. PubMed PMID: 20710063. 8: Klibanov OM, Kaczor RL. IDX-899, an aryl phosphinate-indole non-nucleoside reverse transcriptase inhibitor for the potential treatment of HIV infection. Curr Opin Investig Drugs. 2010 Feb;11(2):237-45. Review. PubMed PMID: 20112173. 9: Zhou XJ, Garner RC, Nicholson S, Kissling CJ, Mayers D. Microdose pharmacokinetics of IDX899 and IDX989, candidate HIV-1 non-nucleoside reverse transcriptase inhibitors, following oral and intravenous administration in healthy male subjects. J Clin Pharmacol. 2009 Dec;49(12):1408-16. doi: 10.1177/0091270009343698. Epub 2009 Sep 23. PubMed PMID: 19776293. 10: Zhou XJ, Pietropaolo K, Damphousse D, Belanger B, Chen J, Sullivan-Bólyai J, Mayers D. Single-dose escalation and multiple-dose safety, tolerability, and pharmacokinetics of IDX899, a candidate human immunodeficiency virus type 1 nonnucleoside reverse transcriptase inhibitor, in healthy subjects. Antimicrob Agents Chemother. 2009 May;53(5):1739-46. doi: 10.1128/AAC.01479-08. Epub 2009 Feb 17. PubMed PMID: 19223643; PubMed Central PMCID: PMC2681571. 11: Mascolini M, Larder BA, Boucher CA, Richman DD, Mellors JW. Broad advances in understanding HIV resistance to antiretrovirals: report on the XVII International HIV Drug Resistance Workshop. Antivir Ther. 2008;13(8):1097-113. PubMed PMID: 19195337. 12: Dalton P. Two new NNRTIs enter the pipeline. Proj Inf Perspect. 2008 Sep;(46):13. PubMed PMID: 19048672. 13: Sweeney ZK, Klumpp K. Improving non-nucleoside reverse transcriptase inhibitors for first-line treatment of HIV infection: the development pipeline and recent clinical data. Curr Opin Drug Discov Devel. 2008 Jul;11(4):458-70. Review. PubMed PMID: 18600563.

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