Dienogest

Dienogest

Dienogest
Systematic (IUPAC) name
[(17β)-17-Hydroxy-3-oxoestra-4,9-dien-17-yl]acetonitrile
Clinical data
Trade names Visanne
AHFS/Drugs.com
Pregnancy
category
Legal status
Routes of
administration
Oral
Pharmacokinetic data
Bioavailability 90%[1]
Protein binding 90%[2]
Metabolism Hepatic (CYP3A4-mediated)[3]
Biological half-life 6-12 hours[4]
Excretion Renal
Identifiers
CAS Registry Number  YesY
ATC code G03
G03 G03 (combinations with estrogen)
PubChem CID:
IUPHAR/BPS
ChemSpider  N
UNII  N
KEGG  YesY
ChEBI  N
ChEMBL  N
Synonyms 17-hydroxy-3-oxo-19-nor-17α-pregna-4,9-diene-21-nitrile
17α-cyanomethyl-17β-hydroxy-estra-4,9(10)-dien-3-one
Chemical data
Formula C20H25NO2
Molecular mass 311.42 g/mol[1]
Physical data
Density 1.2 g/cm3
Boiling point 549 °C (1,020 °F)
 N   

Dienogest is an orally-active semisynthetic, steroidal progestogen (or progestin).[5] It is available for use as an oral contraceptive in combination with ethinylestradiol. It has antiandrogenic activity and as a result can improve androgenic symptoms.[1][6] It is a non-ethinylated progestin which is structurally related to testosterone.[3] Dienogest given in isolation is available for the treatment of endometriosis under the trade name Visanne.

History

Dienogest was synthesised in 1979 in [9] The first product on the market to contain dienogest as a contraceptive pill Valette in 1995 made by Jenapharm.[10] It has been little used outside of Germany.[11]

Indications

Contraception

Dienogest is used primarily as a contraceptive in combination with ethinylestradiol. It is given as a tablet containing 2 mg of dienogest and 30 μg of ethinylestradiol.[12] Dienogest is also available in a quadriphasic oral contraceptive pill combined with estradiol valerate, marketed as Natazia in the United States and Qlaira in some European countries and Russia. This formulation is also approved for the treatment of heavy menstrual bleeding.

The minimum dose required to inhibit ovulation has been found to be approximately 1 mg.[13]

Endometriosis

Dienogest is also approved in the European Union for the treatment of endometriosis.[14][15] It has been shown to be equally effective as leuprorelin,[16] which is a second line medication against endometriosis.

Pharmacodynamics

Progestational activity

Dienogest has moderate affinity for the progesterone receptor in human uterus tissue, in vitro, about 10% that of progesterone.[17]

Inhibition of ovulation

The minimum effective dose of oral dienogest required to inhibit ovulation is 1 mg/day.[18] The inhibition of ovulation by dienogest occurs mainly via peripheral action as opposed to central action on gonadotrophin secretion.[1] Oral treatment of dienogest 2 mg/day in cyclical women reduced serum progesterone levels to anovulatory levels, however serum levels of lutenising hormone and follicle-stimulating hormone are not significantly altered.[18]

Adverse effects

Adverse effects associated with dienogest are the same as those expected of a progestogen.[1] These include weight gain, increased blood pressure, breast tenderness and nausea.[19] It produces no androgenic side effects and has little effect on metabolic and lipid haemostatic parameters.[20]

References

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  10. ^ http://www.jenapharm.de/unternehmen/ueber-uns/geschichte/1965-1995/
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  18. ^ a b
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  20. ^