N-Nitroso Azithromycin

● Under Development

Catalogue No.:	VE0010108
CAS No.:	N/A
Mol. Formula:	C37H69N3O13
Mol. Weight:	764 g/mol

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Additional information on N-Nitroso Azithromycin

Parent drug

Azithromycin

IUPAC Name

(2R,3S,4R,5R,8R,10R,11R,12S,13S,14R)-11-(((2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-2-ethyl-3,4,10-trihydroxy-13-(((2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyltetrahydro-2H-pyran-2-yl)oxy)-3,5,8,10,12,14-hexamethyl-6-nitroso-1-oxa-6-azacyclopentadecan-15-one

Pharmacopeial Synonyms

N/A

Synonyms

N-Nitroso Azithromycin EP impurity A

Smiles

O=C1[C@H](C)[C@@H](O[C@H]2C[C@@](C)(OC)[C@@H](O)[C@H](C)O2)[C@H](C)[C@@H](O[C@H]3[C@H](O)[C@@H](N(C)C)C[C@@H](C)O3)[C@](C)(O)C[C@@H](C)CN(N=O)[C@H](C)[C@@H](O)[C@](C)(O)[C@@H](CC)O1

InChI

InChI=1S/C37H69N3O13/c1-14-26-37(10,46)30(42)23(6)40(38-47)18-19(2)16-35(8,45)32(53-34-28(41)25(39(11)12)15-20(3)49-34)21(4)29(22(5)33(44)51-26)52-27-17-36(9,48-13)31(43)24(7)50-27/h19-32,34,41-43,45-46H,14-18H2,1-13H3/t19-,20-,21+,22-,23-,24+,25+,26-,27+,28-,29+,30-,31+,32-,34+,35-,36-,37-/m1/s1

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

N-Nitroso Azithromycin, also designated N-Nitroso Azithromycin EP Impurity A, is a nitrosamine-related azithromycin impurity with molecular formula C37H69N3O13 and molecular weight 764 g/mol. It arises plausibly through nitrosation of the tertiary amine functionality during manufacturing or from interaction with nitrosating agents under acidic or oxidative conditions. As a structural nitrosamine analog, it is relevant to genotoxic impurity assessment under ICH M7 and current nitrosamine control expectations. Trace determination generally requires LC-MS/MS with selective reaction monitoring, often supported by high-resolution mass spectrometry and orthogonal chromatographic resolution to distinguish it from closely related macrolide degradants.