1. APIs
  2. Levonorgestrel
  3. Impurities
  4. 13-Ethylgon-5(10)-ene-3,17-dione

13-Ethylgon-5(10)-ene-3,17-dione

Structure

MOL SDF CML

Other Names & Identifiers

  • BP Levonorgestrel Impurity N
  • Δ5(10)-levodione

CASRN

4222-96-2

Notes

Although referred to as Δ5(10)-levodione in BP/EP and levodion in Berta et al., levodione describes a different chemical in other sources.

Molecular Formula

C19H26O2

References

Molecular Weight

286.41 g/mol

References

Reaxys ID Number

7302588

References

Structural Difference from API

hydroxy and ethynyl groups on C17 replaced by carbonyl; double bond between C5 & C10 instead of C4 & C5

References

Source of Impurity

Synthetic side product formed during the ethinylation step

library_books

References

  1. Horvath PB, G.; Brlik, J.; Csehi, A.; Dravecz, F.; Halmos, Z.; Lauko, A.; Renyei, M.; Varga, K.; Gorog, S. Estimation of impurity profiles of drugs and related materials .16. Identification of the side-products of the ethinylation step in the synthesis of contraceptive gestogens. Journal of Pharmaceutical and Biomedical Analysis. 1997; 15:1343-9.
    2. (View all citations for this reference)

Spectra

IR

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References

  1. Liu LGS, X. D.; Li, Z. S. A novel and efficient process to 13β-ethyl-gon-4-ene-3,11,17-trione. Synthetic Communications. 1995; 25:3113-24.
    2. (View all citations for this reference)
  2. Liu LGZ, T.; Li, Z. S. Silica gel promoted selective hydrolysis of 3-methoxy-2,5(10)-diene steroids. Synthetic Communications. 1996; 26:2999-3006.
    3. (View all citations for this reference)

Limits

0.1%

References

  1. British Pharmacopoeia 2017: Levonorgestrel monograph.
    2. (View all citations for this reference)
  2. Berta, R.; Babjak, M.; Gazdag, M. A Study of Some Practical Aspects of High Temperature Liquid Chromatography in Pharmaceutical Applications. J. Pharm. Biomed. Anal. 2011, 54 (3), 458–462.
    3. (View all citations for this reference)