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.
Abbreviation
NETA
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Names
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CASRN
38673-38-0
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PubChem CID
5832
Wikipedia Entry Name
Norethisterone Acetate
ChEBI ID
CHEBI:7628
ChEMBL ID
CHEMBL1201146
Molecular Formula
C22H28O3
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Molecular Weight
340.5 g/mol
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Appearance
white or yellowish-white, odorless, crystalline powder
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Melting Point
161-163 °C
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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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Specific Optical Rotation
-32° to -28°
Polymorphism
Polymorphism identified
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Toxicology
See Norethindrone.
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Mutagenicity
Not found to be mutagenic in the Ames Salmonella/microsome direct plate incorporation protocol.
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Genotoxicity
Clastogenic to human lymphocytes as determined chromosome aberrations and sister chromatid exchanges. The Ames Salmonella assay did not indicate genotoxicity.
MRTD
0.0167 mg/kg/day
Pharmacology
See norethindrone
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Indications
Lymphoma, hyperplasia, endometriosis.
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.