1. APIs
  2. Medroxy­progesterone Acetate
  3. Impurities
  4. 6-Hydroxymedroxyprogesterone Acetate

6-Hydroxymedroxyprogesterone Acetate

Structure

MOL SDF CML

Other Names & Identifiers

  • BP MPA Impurity A
  • BP Medroxyprogesterone Injection Impurity A
  • BP Medroxyprogesterone Tablets Impurity A
  • 17α-acetoxy-6β-hydroxy-6α-methyl-pregn-4-en-3,20-dione
  • 6β-hydroxy-6-methyl-3,20-dioxopregn-4-en-17-yl acetate

Notes

Also a metabolite

Molecular Formula

C24H34O5

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References

  1. Online Subscription Database. Reed Elsevier Properties SA. (View all citations for this reference)

Molecular Weight

402.53 g/mol

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References

  1. Online Subscription Database. Reed Elsevier Properties SA. (View all citations for this reference)

Structural Difference from API

the hydrogen on the C6 of MPA is replaced with an -OH

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References

  1. British Pharmacopea 2015; Volume II pages 179 through 199; pertains to MPA and its impurities
    2. (View all citations for this reference)

Source of Impurity

Formed from the oxidation of medroxyprogesterone acetate; produced as a major metabolite from the P450 catalyzed degradation of medroxyprogesterone acetate

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References

  1. Title: Structure elucidation of major metabolites from medroxyprogesterone acetate by P450  Contains 2D NMR and MS spectra of MPA and some of its impurities
    2. (View all citations for this reference)

Reaxys ID #

7365607

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References

  1. Online Subscription Database. Reed Elsevier Properties SA. (View all citations for this reference)

NMR

See reference

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References

  1. Chen, J.; Zhang, J.-W.; Yang, L.; Li, W. Structure Elucidation of Major Metabolites from Medroxyprogesterone Acetate by P450. Chem. Pharm. Bull. (Tokyo). 2009, 57 (8), 835–839.
    2. (View all citations for this reference)

Limits

0.3%

References

  1. European Pharmacopoeia 8.0 Medroxyprogesterone Acetate API
    2. (View all citations for this reference)
  2. British Pharmacopoeia 2017: Medroxyprogesterone Acetate monograph
    3. (View all citations for this reference)
  3. British Pharmacopoeia 2017: Medroxyprogesterone Injection monograph
    4. (View all citations for this reference)
  4. British Pharmacopoeia 2017: Medroxyprogesterone Tablets monograph
    5. (View all citations for this reference)
  5. Chen, J.; Zhang, J.-W.; Yang, L.; Li, W. Structure Elucidation of Major Metabolites from Medroxyprogesterone Acetate by P450. Chem. Pharm. Bull. (Tokyo). 2009, 57 (8), 835–839.
    6. (View all citations for this reference)