Dienogest (DNG) is a progestogen used in hormonal contraceptives and for the treatment of endometriosis.
Abbreviation
DNG
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Names
CASRN
65928-58-7
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PubChem CID
68861
ECHA InfoCard
IUPHAR/BPS
7654
DrugBank Accession Number
DB09123
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UNII
46M3EV8HHE
KEGG Entry Number
D03799
Wikipedia Entry Name
Dienogest
ChEBI ID
CHEBI:70708
ChEMBL ID
CHEMBL1201864
ChemSpider ID
62093
ATC Code(s)
Molecular Formula
C20H25NO2
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Molecular Weight
311.43 g/mol
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Appearance
White, almost white, or slightly yellow crystalline powder
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Melting Point
144-145
Solubility
Practically insoluble in water, sparingly soluble in methylene chloride, slightly soluble in methanol
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Specific Optical Rotation
-352 to -344, 0.125 g dried substance in methanol, diluted to 25.0 mL
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GHS Hazard Code(s)
Class | Category | Code | Description |
---|---|---|---|
Carcinogenicity | 2 | H351 | Suspected of causing cancer if inhaled |
Reproductive Toxicity | 1A | H360 | May damage fertility or the unborn child |
Reproductive Toxicity, Effects On or Via Lactation | H362 | May cause harm to breast-fed children |
Side Effects
In COCs with ethinyl estradiol: irregular vaginal bleeding, headache, breast pain, nausea/vomiting, depression, decreased libido
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Carcinogenicity
No evidence in vivo and in vitro.
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Mutagenicity
No evidence in vivo and in vitro.
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LD50
Progesterone Receptor Activity
Agonist. Some antagonist behavior.
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Androgen Receptor Activity
Antagonist (40% of CPA, the most potent anti-androgenic progestin)
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Estrogen Receptor Activity
Weak or no agonist and antagonist activity
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Glucocorticoid Receptor Activity
Low to no activity
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Mineralocorticoid Receptor Activity
No activity
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Target Pathways
Bioavailability
90-96.2%
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Elimination Half-Life (t1/2)
8-10 h
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Serum Protein Binding
90% bound to serum albumin, 10% free. No binding to SHBG or CBG.
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Metabolism
CYP3A4
Excretion
Mainly via kidneys.
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Apparent Volume of Distribution
40 L from 2 mg/day oral dose
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Tmax
2 h
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Clearance
Oettel et al: 75 mL/h/kg
Foster et al: 3 L/h from 2 mg/day oral dose
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Enzyme Interactions
3β-hydroxysteroid dehydrogenase-Δ5-4-isomerase: inhibitor
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Minimum Contraceptive Threshold
Oettel: 4.0 ng/mL
Foster: 1 mg/day oral dose for inhibition of ovulation in cyclical women
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Indications
Indicated for use by women for pregnancy prevention. Also indicated for the treatment of heavy menstrual bleeding in women without organic pathology who choose to use an oral contraceptive as their method of birth control. (PubChem) Menorrhagia, endometriosis (ChEMBL)
A number of other metabolites have been detected, including unspecified hydrogenation and hydroxylation products.
Prescription
022252
None (Tentative Approval)
202999
Prescription
202349