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3219-99-6Doxycycline EP Impurity A (Free Base)

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Catalogue No.:	VL159004
CAS No.:	3219-99-6
Mol. Formula:	C22H24N2O8
Mol. Weight:	444.43 g/mol

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Additional information on CAS 3219-99-6

Parent drug

Doxycycline

IUPAC Name

(4S,4aR,5S,5aR,6S,12aS)-4-(Dimethylamino)-3,5,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydrotetracene-2-carboxamide

Pharmacopoeial Synonyms

Doxycycline Related Compound A; 6-Epi Doxycycline

Other Synonyms

6-Deoxy-6-epioxytetracycline

Smiles

O=C(C1=C(O)[C@@H](N(C)C)[C@@]([C@@H](O)[C@@]2([H])C(C(C3=C(O)C=CC=C3[C@H]2C)=O)=C4O)([H])[C@@]4(O)C1=O)N

InChI

InChI=1S/C22H24N2O8/c1-7-8-5-4-6-9(25)11(8)16(26)12-10(7)17(27)14-15(24(2)3)18(28)13(21(23)31)20(30)22(14,32)19(12)29/h4-7,10,14-15,17,25,27-29,32H,1-3H3,(H2,23,31)/t7-,10-,14-,15+,17+,22+/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

Doxycycline EP Impurity A, also designated Doxycycline Related Compound A or 6-Epi Doxycycline (free base), CAS 3219-99-6, is a stereoisomeric tetracycline impurity arising mainly from epimerization at C-6 during manufacture or storage. Its molecular formula, C22H24N2O8, and molecular weight, 444.43 g/mol, correspond to a polyoxygenated, amphoteric scaffold with the characteristic tetracyclic naphthacene core. The impurity is relevant to pharmacopeial identity and related-substance profiling because configurational inversion can alter chromatographic behavior and antimicrobial activity. Quantification typically requires reversed-phase LC with photodiode array detection and confirmation by LC-MS or LC-MS/MS, often with chiral or high-resolution methods to resolve closely related tetracycline degradants.

References

“Smith, Kelly, and James J. Leyden. “Safety of Doxycycline and Minocycline: A Systematic Review.” Clinical Therapeutics, vol. 27, no. 9, Sept. 2005, pp. 1329–42, https://doi.org/10.1016/j.clinthera.2005.09.005. ?Saivin, S., and G. Houin. “Clinical Pharmacokinetics of Doxycycline and Minocycline.” Clinical Pharmacokinetics, vol. 15, no. 6, Dec. 1988, pp. 355–66, https://doi.org/10.2165/00003088-198815060-00001. ?”