1. APIs
  2. Levonorgestrel
  3. Impurities
  4. Δ5(10)-8β-Levonorgestrel

Δ5(10)-8β-Levonorgestrel

Structure

MOL SDF CML

Other Names & Identifiers

  • BP Levonorgestrel Impurity B
  • 13-ethyl-17-hydroxy-18,19-dinor-17α-pregn-5(10)-en-20-yn-3-one

CASRN

19914-67-1

Reaxys ID Number

2626494

References

Molecular Formula

C21H28O2

References

Molecular Weight

312.45 g/mol

References

Infrared Spectra Available

see references

library_books

References

  1. Smith HP, P. C.; Smith, L. L.; Gadsby, B.; Hartley, D.; Ledig, K.; Herbst, D.; Wendt, G. R.; Fisher, J.; Pattison, T. W.; Watson, D. H. P.; Siddall, J.; McLoughlin, B. J.; Tokolics, J.; Siuda, J.; Rees, R.; McMenamin, J.; Douglas, G. H.; Foell, T.; Edgren, R. A.; Buzby, G. C.; Jansen, A. B. A.; Hughes, G. A. Totally synthetic steroid hormones. 2. 13β-alkylgona-1,3,5(10)-trienes 13β-alkylgon-4-en-3-ones + related compounds. Journal of the Chemical Society. 1964:4472-&.
    2. (View all citations for this reference)
  2. Cessac, James W., Rao, Pemmaraju N., Blye Richard P., Kim, Hyun K., 11 beta-substituted 13 beta-ethyl gonane derivatives exhibit reversal of antiprogestational activity; Steroids 1998; 63 (50-57)
    3. (View all citations for this reference)

Structural Difference from API

no double bond between C4 & C5; additional double bond between C5 & C10

References

Source of Impurity

Synthetic side product formed during the Birch Reduction/hydrolysis

library_books

References

  1. Görög, S.; Babják, M.; Balogh, G.; Brlik, J.; Dravecz, F.; Gazdag, M.; Horváth, P.; Laukó, A.; Varga, K. Estimation of impurity profiles of drugs and related materials Part 19: Theme with variations. Identification of impurities in 3-oxosteroids. Journal of Pharmaceutical and Biomedical Analysis.1998, 18 (4), 511–525. 1998; 18:511-25.
    2. (View all citations for this reference)

Melting Point

169-171° C in acetonitile; water; 182-190° C in petroleum ether; ethyl acetate

library_books

References

  1. Online Subscription Database. Reed Elsevier Properties SA. (View all citations for this reference)
  2. Cessac, James W., Rao, Pemmaraju N., Blye Richard P., Kim, Hyun K., 11 beta-substituted 13 beta-ethyl gonane derivatives exhibit reversal of antiprogestational activity; Steroids 1998; 63 (50-57)
    3. (View all citations for this reference)
  3. Smith H, Phillips PC, Smith LL, Gadsby B, Hartley D, Ledig K, Herbst D, Wendt GR, Fisher J, Pattison TW, Watson DHP, Siddall J, McLoughlin BJ, Tokolics J, Siuda, J Rees R, McMenamin J, Douglas GH, Foell T, Edgren RA, Buzby GC, Jansen ABA, Hughes GA; Totally synthetic steroid hormones. 2. 13β-alkylgona-1,3,5(10)-trienes 13β-alkylgon-4-en-3-ones + related compounds. Journal of the Chemical Society, 1964 (4472-4481)
    4. (View all citations for this reference)

NMR Spectra Available

see references

library_books

References

  1. Cessac, James W., Rao, Pemmaraju N., Blye Richard P., Kim, Hyun K., 11 beta-substituted 13 beta-ethyl gonane derivatives exhibit reversal of antiprogestational activity; Steroids 1998; 63 (50-57)
    2. (View all citations for this reference)

Limits

0.3%

References

  1. British Pharmacopoeia 2017: Levonorgestrel monograph.
    2. (View all citations for this reference)