Norelgestromin (NGMN) is a synthetic progestogen used in combined oral contraceptives and in menopausal hormonal therapy. It is the primary metabolite of norgestimate.
Abbreviation
NGMN
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Names
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CASRN
53016-31-2
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PubChem CID
62930
DrugBank Accession Number
DB06713
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UNII
R0TAY3X631
KEGG Entry Number
D05205
Wikipedia Entry Name
Norelgestromin
ChEBI ID
CHEBI:135398
ChEMBL ID
CHEMBL1200807
ChemSpider ID
56648
ATC Code(s)
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Molecular Formula
C21H29NO2
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Molecular Weight
327.46 g/mol
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Specific Optical Rotation
+35° to +41 °, 5 mg/mL in 75:25 alcohol:water
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Ratio of (E)- to (Z)- Isomer
Between 1.3 and 1.6
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Progesterone Receptor Activity
Partial agonist
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Androgen Receptor Activity
Partial agonist
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Estrogen Receptor Activity
Selective agonist for ERα
Glucocorticoid Receptor Activity
Antagonist with low affinity
Mineralocorticoid Receptor Activity
Antagonist with moderate affinity
Elimination Half-Life (t1/2)
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Serum Protein Binding
>97% bound, primarily to albumin. No binding to SHBG, except as metabolite norgestrel.
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Metabolism
CYP3A4
Excretion
Via renal and fecal pathways.
Clearance
7.89 +/- 1.63 L/h from IV injection of 252 μg norelgestromin and 25 μg ethinyl estradiol.
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Enzyme Interactions
Inhibits estrone sulfatase
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Position of hydroxyl group not specified. Referred to as Met6 in source.
Position of hydroxyl group not specified. Referred to as Met5 in source.
Position of hydroxyl group not specified. Referred to as Met4 in source.
Position of hydroxyl group not specified. Referred to as Met3 in source.
Position of hydroxyl group not specified. Referred to as Met1 in source.
Prescription
200910
Discontinued
021180