A degradation product and potential impurity of minocycline
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4-epi Minocycline

Item No. 90001066

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(4R,4aS,5aR,12aS)-4,7-bis(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-1,11-dioxo-2-naphthacenecarboxamide
CAS Number
43168-51-0
Synonyms
  • 4-EMC
  • Minocycline Impurity A
Molecular Formula
C23H27N3O7
Formula Weight
457.5
Purity
≥80%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
Aqueous acid: soluble
SMILES
NC(C1=C(O)[C@H](N(C)C)[C@@]2([H])[C@](C1=O)(O)C(O)=C3C(C4=C(O)C=CC(N(C)C)=C4C[C@@]3([H])C2)=O)=O
InChi Code
InChI=1S/C23H27N3O7/c1-25(2)12-5-6-13(27)15-10(12)7-9-8-11-17(26(3)4)19(29)16(22(24)32)21(31)23(11,33)20(30)14(9)18(15)28/h5-6,9,11,17,27,29-30,33H,7-8H2,1-4H3,(H2,24,32)/t9-,11-,17+,23-/m0/s1
InChi Key
DYKFCLLONBREIL-MJPDVNATSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    4-epi Minocycline is the main degradation product of and a potential impurity in commercial preparations of minocycline.1,2 Minocycline (Item No. 14454) is a broad spectrum tetracycline antibiotic that has a particularly long half-life in serum. Formulations containing minocycline have been used in the treatment of acne in older patients.3 Minocycline also has both anti-inflammatory and neuroprotective actions.4,5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Zbinovsky, V., and Chrekian, G. Minocycline. Analytical profiles of drug substances 6, 324-339 (1977).

    2. Zawilla, N.H., Diana, J., Hoogmartens, J., et al. Improved LC of minocycline drug substance. J. Pharm. Biomed. Anal. 40(4), 815-821 (2006).

    3. Strauss, J.S., Krowchuk, D.P., Leyden, J.J., et al. Guidelines of care for acne vulgaris management. J. Am. Acad. Dermatol. 56(4), 651-663 (2007).

    4. Giuliani, F., Hader, W., and Yong, V.W. Minocyline attenuates T cell and microglia activity to impair cytokine production in T cell-microglia interaction. J. Leukoc. Biol. 78(1), 135-143 (2005).

    5. Maier, K., Merkler, D., Gerber, J., et al. Multiple neuroprotective mechanisms of minocycline in autoimmune CNS inflammation. Neurobiol. Dis. 25(3), 514-525 (2007).