A nucleoside reverse transcriptase inhibitor
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Isomer(s)
18514Lamivudine
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Apricitabine

Item No. 36037

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
4-amino-1-[(2R,4R)-2-(hydroxymethyl)-1,3-oxathiolan-4-yl]-2(1H)-pyrimidinone
CAS Number
160707-69-7
Synonyms
  • AVX754
  • BCH 10618
  • (–)-BCH 10652
  • (–)-dOTC
  • SPD-754
Molecular Formula
C8H11N3O3S
Formula Weight
229.3
Purity
≥95%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMSO: soluble
λmax
277 nm
SMILES
O=C1N(C=CC(N)=N1)[C@]2([H])S[C@H](CO)OC2
InChi Code
InChI=1S/C8H11N3O3S/c9-5-1-2-11(8(13)10-5)6-4-14-7(3-12)15-6/h1-2,6-7,12H,3-4H2,(H2,9,10,13)/t6-,7-/m1/s1
InChi Key
RYMCFYKJDVMSIR-RNFRBKRXSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    5 mg

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    25 mg

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    Cayman Chemical
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    Product Description

    Apricitabine is a nucleoside reverse transcriptase inhibitor (NRTI) and derivative of 2’-deoxycytidine (Item Nos. 34708 | 30125).1 It is phosphorylated intracellularly to its active form, apricitabine-5’-triphosphate, which competes with a monophosphate form for binding to HIV-1 reverse transcriptase and incorporation into the nascent viral DNA, inducing chain termination and HIV-1 replication. Apricitabine reduces HIV-1 infectivity in MT-4 and U937 cells (IC50s = 2.8 and 0.4 µM, respectively), as well as in isolated human cord blood mononuclear cells (CBMCs; IC50 = 0.4 µM).2

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Cox, S., and Southby, J. Apricitabine--a novel nucleoside reverse transcriptase inhibitor for the treatment of HIV infection that is refractory to existing drugs. Expert Opin. Investig. Drugs 18(2), 199-209 (2009).

    2. Mansour, T.S., Jin, H., Wang, W., et al. Structure-activity relationships among a new class of antiviral heterosubstituted 2′,3′-dideoxynucleoside analogues. Nucleos. Nucleot. 14(3-5), 627-635 (1995).