Norethindrone Acetate

Norethindrone acetate (NETA), or norethisterone acetate, is an ester prodrug of norethindrone. It is a synthetic progestogen used in place of norethindrone in some hormonal contraceptives.

Tags
Approvals
US FDA-Approved
Related Compounds
Norethindrone
norethisterone acetate

Identifiers

Abbreviation

NETA

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References

Names

  • norethisterone acetate
  • 3-oxo-19-nor-17α-pregn-4-en-20-yn-17-yl acetate
  • 17α-ethynyl-19-nortestosterone 17β-acetate
  • 17α-ethynylestra-4-en-17β-ol-3-one 17β-acetate
  • SH-420

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References

CASRN

38673-38-0

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References

PubChem CID

5832

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Wikipedia Entry Name

Norethisterone Acetate

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ChEBI ID

CHEBI:7628

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ChEMBL ID

CHEMBL1201146

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Physical & Chemical Properties

Molecular Formula

C22H28O3

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References

Molecular Weight

340.5 g/mol

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References

Solubility

Practically insoluble in water (1 g in > 10 L). Soluble in chloroform (1 part in <1), ethanol (1 part in 10), dioxane (1 part in 2), and diethyl ether (1 part in 18).

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Polymorphism

Polymorphism identified

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References

  1. European Pharmacopoeia 8.2 Norethisterone Acetate.
  2. (View all citations for this reference)

Toxicology

Biochemistry & Pharmacology

Pharmacology

See norethindrone

References

Indications

Lymphoma, hyperplasia, endometriosis.

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Metabolites

Name
Structure
Notes
structure

Norethindrone acetate, norethindrone enanthate, lynestrenol, and ethynodiol diacetate (and to a very small extent, norethynodrel) are prodrugs of norethindrone. Conversion of lynestrenol to ethynodiol to norethindrone facilitated by CYP2C9, CYP2C19, and CYP3A4. Conversion of norethynodrel to norethindrone is accomplished by either non-enzymatic or enzymatic ketosteroid isomerization.

Impurities

Name
Structure
CASRN
Other Names & Identifiers
structure

  • BP Norethisterone Acetate Impurity I

structure

  • BP Norethisterone Acetate Impurity G
  • 3,6-dioxo-19-nor-17α-pregn-4-en-20-yn-17-yl acetate

structure

  • BP Norethisterone Acetate Impurity F
  • 6β-hydroxy-3-oxo-19-nor-17α-pregn-4-en-20-yn-17-yl Acetate

structure

  • BP Norethisterone Acetate Impurity E

US FDA-Approved Products

Name
Formulation
Status
ANDA #

Prescription

206597

Prescription

207505

Prescription

207580

Prescription

207506

Prescription

207581