75128-73-3Acyclovir EP Impurity G

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Catalogue No.:	VL13011
CAS No.:	75128-73-3
Mol. Formula:	C12H15N5O5
Mol. Weight:	309.28 g/mol

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Additional information on CAS 75128-73-3

Parent drug

Acyclovir

IUPAC Name

2-[[2-(Acetylamino)-6-oxo-1,6-dihydro-9H-purin-9-yl]methoxy]ethyl acetate

Pharmacopeial Synonyms

Acyclovir Related Compound G

Synonyms

9-Acetyl Acyclovir; Acyclovir N,O-Diacetate; Diacetyl Acyclovir; N-[9-[[2-(Acetyloxy)ethoxy]methyl]-6, 9-dihydro-6-oxo-1H-purin-2-yl]acetamide; 9-[(2-Acetoxyethoxy)methyl]-N2-acetylguanine

Smiles

CC(=O)Nc2nc1c(ncn1COCCOC(C)=O)c(=O)[nH]2

InChI

InChI=1S/C12H15N5O5/c1-7(18)14-12-15-10-9(11(20)16-12)13-5-17(10)6-21-3-4-22-8(2)19/h5H,3-4,6H2,1-2H3,(H2,14,15,16,18,20)

Shipping Condition

Ambient Temperature

Characterization Data (Included)

HPLC, MASS/LC-MS, 1H NMR, FT-IR, Potency, and Structure Elucidation Report (SER).

Additional Characterization Data

QNMR, D2O Exchange, 13C NMR, 13C APT, COSY NMR, NOESY NMR, 15N NMR, HSQC NMR, HMQC NMR, and HMBC NMR. These are available upon request and may be free or subject to additional charges.

Description

Acyclovir EP Impurity G, also designated Acyclovir Related Compound G, 9-Acetyl Acyclovir, Acyclovir N,O-Diacetate, or Diacetyl Acyclovir, CAS 75128-73-3, is a diacetylated acyclic guanine nucleoside derivative with molecular formula C12H15N5O5 and molecular weight 309.28 g/mol. Structurally, it represents an N2- and O-acetylated acetylation product of acyclovir, typically arising from over-acetylation during synthesis or from acetyl-transfer mediated degradation under acylating conditions. Because it is a closely related process impurity rather than a classical mutagenic alert, characterization generally relies on LC-MS/MS, HPLC with diode-array detection, and, when needed, NMR confirmation.

References

Darville, J. M., et al. “Development, Evaluation and Application of an Isocratic High-Performance Liquid Chromatography (HPLC) Assay for the Simultaneous Determination of Aciclovir and Its Metabolite 9-Carboxymethoxymethylguanine in Human Serum and Cerebrospinal Fluid.” International Journal of Antimicrobial Agents, vol. 30, no. 1, July 2007, pp. 30–33, https://doi.org/10.1016/j.ijantimicag.2007.02.005. Huidobro, A. L., et al. “LC Methods for Acyclovir and Related Impurities Determination.” Jour