A nucleoside reverse transcriptase inhibitor
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EFdA

Item No. 33873

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
2′-deoxy-4′-C-ethynyl-2-fluoro-adenosine
CAS Number
865363-93-5
Synonyms
  • 4’Ed2FA
  • 4′-ethynyl-2-fluoro-2′-Deoxyadenosine
  • EFDA
  • MK-8591
Molecular Formula
C12H12FN5O3
Formula Weight
293.3
Purity
≥98%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMSO: soluble
λmax
263 nm
SMILES
FC1=NC(N)=C2C(N([C@@]3([H])C[C@H](O)[C@@](C#C)(CO)O3)C=N2)=N1
InChi Code
InChI=1S/C12H12FN5O3/c1-2-12(4-19)6(20)3-7(21-12)18-5-15-8-9(14)16-11(13)17-10(8)18/h1,5-7,19-20H,3-4H2,(H2,14,16,17)/t6-,7+,12+/m0/s1
InChi Key
IKKXOSBHLYMWAE-QRPMWFLTSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

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    Cayman Chemical
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    Product Description

    EFdA is a nucleoside reverse transcriptase inhibitor (NRTI).1 It inhibits HIV-1 reverse transcriptase via multiple mechanisms. EFdA inhibits replication of the HIV-1 strain HIV-1 IIIb, the laboratory isolate HIV NL4-3, and the clinical isolate HIV-2 EHO in MT-4 cells (EC50s = 73, 50, and 98 pM, respectively).2 It is also active against drug-resistant HIV with EC50 values ranging from 0.23 to 23 nM in a multinuclear activation of a galactosidase indicator (MAGI) assay.3 EFdA (1 and 10 mg/kg per day) prevents infection with HIV JR-CSF in humanized mice.4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Michailidis, E., Huber, A.D., Ryan, E.M., et al. 4'-Ethynyl-2-fluoro-2'-deoxyadenosine (EFdA) inhibits HIV-1 reverse transcriptase with multiple mechanisms. The Journal of Biological Chemisty 289(35), 24533-24548 (2014).

    2. Markowitz, M., and Sarafianos, S.G. 4'-Ethynyl-2-fluoro-2'-deoxyadenosine, MK-8591: A novel HIV-1 reverse transcriptase translocation inhibitor. Curr. Opin. HIV AIDS 13(4), 294-299 (2018).

    3. Kawamoto, A., Kodama, E., Sarafianos, S.G., et al. 2'-deoxy-4'-C-ethynyl-2-halo-adenosines active against drug-resistant human immunodeficiency virus type 1 variants. Int. J. Biochem. Cell Biol. 40(11), 2410-2420 (2008).

    4. Stoddart, C.A., Galkina, S.A., Joshi, P., et al. Oral administration of the nucleoside EFdA (4'-ethynyl-2-fluoro-2'-deoxyadenosine) provides rapid suppression of HIV viremia in humanized mice and favorable pharmacokinetic properties in mice and the rhesus macaque. Antimicrob. Agents Chemother. 59(7), 4190-4198 (2015).