Nomegestrol acetate (NOMAC) is a synthetic progestogen used in hormonal contraceptives, hormone replacement therapy, and for the treatment of gynecological disorders. It is available internationally, but not in the US.
Abbreviation
NOMAC
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Names
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CASRN
58652-20-3
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PubChem CID
91668
ECHA InfoCard
UNII
83J78V5W05
KEGG Entry Number
D08281
Wikipedia Entry Name
Nomegestrol Acetate
ChEBI ID
CHEBI:135564
ChEMBL ID
CHEMBL1476022
ChemSpider ID
82771
ATC Code(s)
Molecular Formula
C23H30O4
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Molecular Weight
370.4819 g/mol
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Appearance
White or almost white crystalline powder
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Melting Point
214-215° C
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Solubility
Practically insoluble in water, freely soluble in acetone, soluble in ethanol (96%)
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logP
3.46
Specific Optical Rotation
-62.6 in absolute ethanol at 22° C; -60 to -64 in absolute ethanol at 25° C
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GHS Hazard Code(s)
Class | Category | Code | Description |
---|---|---|---|
Reproductive Toxicity | 2 | H361 | Suspected of damaging fertility or the unborn child |
Reproductive Toxicity | 1B | H360 | May damage fertility or the unborn child |
Side Effects
Abnormal bleeding/spotting, headache, hot flushes
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LD50
LD50, mouse intraperitoneal: > 2 g/kg
LD50, mouse oral: > 2 g/kg
LD50, rat intraperitoneal: > 2 g/kg
LD50, rat oral: >2 g/kg
(TDLo), women oral: 1.05 mg/kg
Safety Profile Overview
Generally very well tolerated, positive safety profile
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Progesterone Receptor Activity
Agonist
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Androgen Receptor Activity
Binds but no agonist activity. "Weak," "partial" or "moderate" antagonist.
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Estrogen Receptor Activity
Antagonist
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Glucocorticoid Receptor Activity
No activity
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Mineralocorticoid Receptor Activity
No activity
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Target Pathways
Bioavailability
63-65%
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Elimination Half-Life (t1/2)
45-50 h
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Serum Protein Binding
98% bound to serum albumin
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Metabolism
CYP3A3, CYP3A4, CYP2A6
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Cmax
12.3 +/- 3.5 ng/mL
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Tmax
1.5-2 h, 2-3 h regardless of dose
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Enzyme Interactions
Estrone sulfatase inhibitor
6 main metabolites, all of which are basically inactive. Metabolized in the liver through hydroxylation by CYP3A3, CYP3A4, CYP2A6.