54617-39-9Neomycin Sulfate EP Impurity B

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Catalogue No.:	VE006928
CAS No.:	54617-39-9
Mol. Formula:	C14H28N4O7
Mol. Weight:	364.39 g/mol

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Additional information on CAS 54617-39-9

Parent drug

Neomycin

IUPAC Name

3-N-acetyl-2-deoxy-4-O-(2,6-diamino-2,6-dideoxy-α-D -glucopyranosyl)-D -streptamine

Pharmacopoeial Synonyms

N/A

Other Synonyms

3-Acetylneamine; 3-N-Acetyl-2-deoxy-4-O-(2,6-diamino-2,6-dideoxy-alpha-D-glucopyranosyl)-D-streptamine; N2-Acetyl Neamine

Smiles

CC(N[C@@H]1[C@@H](O[C@@H]2[C@H](N)[C@@H](O)[C@H](O)[C@@H](CN)O2)[C@H](O)[C@@H](O)[C@H](N)C1)=O

InChI

InChI=1S/C14H28N4O7/c1-4(19)18-6-2-5(16)9(20)12(23)13(6)25-14-8(17)11(22)10(21)7(3-15)24-14/h5-14,20-23H,2-3,15-17H2,1H3,(H,18,19)/t5-,6+,7-,8-,9+,10-,11-,12-,13-,14-/m1/s1

Description

Neomycin Sulfate EP Impurity B, identified as 3-Acetylneamine (CAS 54617-39-9), is an acetylated aminoglycoside-related process impurity formed by partial modification of the neamine nucleus during synthesis or stress-induced degradation. The molecular formula is C14H28N4O7 and the molecular weight is 364.39 g/mol. Structurally, it retains the deoxystreptamine-derived polyhydroxylated aminocyclitol framework with one N-acetyl substituent, which can alter polarity, ionization behavior, and chromatographic retention. Trace-level determination typically requires LC-MS/MS or high-resolution LC-MS, with hydrophilic interaction or ion-pair LC often used to resolve closely related aminoglycoside species.

References

Clarot, I., et al. â€œAnalysis of Neomycin Sulfate and Framycetin Sulfate by High-Performance Liquid Chromatography Using Evaporative Light Scattering Detection.â€ Journal of Chromatography A, vol. 1087, no. 1-2, Sept. 2005, pp. 236â€“44, https://doi.org/10.1016/j.chroma.2005.05.054.?Sasseville, Denis. â€œNeomycin.â€ Dermatitis, vol. 21, no. 1, Jan. 2010, pp. 3â€“7, https://doi.org/10.2310/6620.2009.09073.?