6543-77-7Doxycycline EP Impurity C

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Catalogue No.:	VL159001
CAS No.:	6543-77-7
Mol. Formula:	C22H24N2O8
Mol. Weight:	444.43 g/mol

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Additional information on CAS 6543-77-7

Parent drug

Doxycycline

IUPAC Name

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

Pharmacopoeial Synonyms

4-Epidoxycycline

Other Synonyms

6-Deoxy-4-epioxytetracycline; 2-Naphthacenecarboxamide, 4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,5,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-, (4R,4aR,5S,5aR,6R,12aS)-; 2-NAPHTHACENECARBOXAMIDE, 4-(DIMETHYLAMINO)-1,4,4A,5,5A,6,11,12A-OCTAHYDRO-3,5,10,12,12A-PENTAHYDROXY-6-METHYL-1,11-DIOXO-, 4-EPIMER

Smile

O=C(C(C1=O)=C(O)[C@H](N(C)C)[C@]2([H])[C@@H](O)[C@]3([H])[C@@H](C)C4=C(C(C3=C(O)[C@@]21O)=O)C(O)=CC=C4)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/h4-7,10,14-15,17,25-27,30,32H,1-3H3,(H2,23,31)/t7-,10+,14+,15+,17-,22-/m0/s1

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

Doxycycline EP Impurity C, also designated 4-epidoxycycline, is a stereochemical epimer of doxycycline arising primarily through epimerization at the C-4 dimethylamino center under acidic, thermal, or long-term storage conditions. This tetracycline-class degradant, CAS 6543-77-7, has molecular formula C22H24N2O8 and molecular weight 444.43 g/mol. Its formation is relevant to stability-indicating impurity profiling and pharmacopeial specification setting because epimeric conversion can alter antimicrobial potency. Quantification commonly requires reversed-phase LC with diode-array detection and confirmatory LC-MS/MS, with high-resolution MS or chiral separations used when resolving closely related tetracycline impurities.

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. «