Dienogest

Dienogest
Clinical data
Routes of; administration	Oral
ATC code	G03FA15 (WHO) ;
Pharmacokinetic data
Bioavailability	90%
Protein binding	90%
Metabolism	Hepatic
Elimination half-life	6-12 hours
Excretion	Renal
Identifiers
	IUPAC name 17a-cyanomethyl-17b-hydroxy-estra-4,9-di-ene-3-one;
CAS Number	65928-58-7;
PubChem CID	68861;
E number	{{#property:P628}}
ECHA InfoCard	{{#property:P2566}}Lua error in Module:EditAtWikidata at line 36: attempt to index field 'wikibase' (a nil value).
Chemical and physical data
Formula	C20H25NO2
Molar mass	311.42 g/mol
Density	1.2 g/cm3
Boiling point	549 °C (1,020.2 °F)

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Dienogest is an orally active synthetic progesterone (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.^[2] It is a non-ethinylated progestin which is structurally related to testosterone.^[6]

History

Dienogest was discovered in 1979 in Jena, Germany and first named STS 557. It was found that its potency was 10 times that of levonorgestrel.^[7]The first product on the market to contain dienogest as a contraceptive pill Valette in 1995 made by Jenapharm. It has been little used outside of Germany. ^[8]

Indications

Contraception

Dienogest is used primarily as a contraceptive in combination with ethinylestradiol. It is given as a tablet containing 2mg of dienogest and 30μg of ethinylestradiol.^[9]

Pharmacodynamics

Progestational Activity

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

Inhibition of Ovulation

The minimum effective dose of oral dienogest required to inhibit ovulation is 1 mg/day. ^[11] The inhibition of ovulation by dienogest occurs mainly via peripheral action as opposed to central action on gonadotrophin secretion.^[2] Oral treatment of dienogest 2mg/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.^[11]

Adverse effects

Adverse effects associated with dienogest are the same as those expected of a progestogen.^[2] These include weight gain, increased blood pressure, breast tenderness and nausea.^[12] It produces no androgenic side effects and has little effect on metabolic and lipid haemostatic parameters.

References

↑ Nakamura M, Katsuki Y, Shibutani Y, Oikawa T (2003). "All progestins are not created equal". Steroids. 68 (10–13): 879–890. doi:10.1016/j.steroids.2003.08.003. PMID 14667980.
↑ ^2.0 ^2.1 ^2.2 ^2.3 ^2.4 Foster RH, Wilde MI (1998). "Dienogest". Drugs. 56 (5): 825–833. PMID 9829156.
↑ de Lignieres B, Dennerstein L, Backstrom T (1995). "Influence of route of administration on progesterone metabolism". Maturitas. 21 (3): 251–257. doi:10.1016/0378-5122(94)00882-8. PMID 7616875.
↑ Sitruk-Ware R (2004). "Pharmacological profile of progestins". Maturitas. 47 (4): 277–283. doi:10.1016/j.maturitas.2004.01.001. PMID 15063480.
↑ ^5.0 ^5.1 Nakamura M, Katsuki Y, Shibutani Y, Oikawa T (1999). "Dienogest, a synthetic steroid, suppresses both embryonic and tumor-cell-induced angiogenesis". European Journal of Pharmacology. 386 (1): 33–40. doi:10.1016/S0014-2999(99)00765-7. PMID 10611461. line feed character in |title= at position 62 (help)
↑ Nakamura M, Katsuki Y, Shibutani Y, Oikawa T (2003). "All progestins are not created equal". Steroids. 68 (10–13): 879–890. doi:10.1016/j.steroids.2003.08.003. PMID 14667980.
↑ Oettel M, Kurischko A (1980). "STS 557, a new orally active progestin with antiprogestational and contragestational properties in rabbits". Contraception. 21 (1): 61–75. doi:10.1016/0010-7824(80)90140-7. PMID 7357870.
↑ Kuhl H (1998). "Dienogest. A Viewpoint by Herbert Kuhl". Drugs. 56 (5): 834.
↑ Wiegratz I, Mittmann K, Dietrichb H, Zimmermann T, Kuhl H (2006). "Fertility after discontinuation of treatment with an oral contraceptive containing 30 μg of ethinyl estradiol and 2 mg of dienogest". Fertility and Sterility. 85 (6): 1812–1819. doi:10.1016/j.fertnstert.2005.11.052. PMID 16759929.
↑ Oettel M, Bervoas-Martin S, Elger W, Golbs S, Hobe G, Kaufmann G, Mathieu M, Moore C, Schneider B, Puri C, Ritter P, Reddersen G, Schon R, Strauch G, Zimmermann H (1995). "A 19-norprogestin without 17α-ethinyl group II: Dienogest from a pharmacokinetic point of view". Drugs of Today. 31 (7): 499–516.
↑ ^11.0 ^11.1 Oettel M, Carol W, Elger W, Kaufmann G, Moore C, Romer W, Klinger G, Schneider B, Schroder J, Sobek L, Walter F, Zimmermann H (1995). "A 19-norprogestin without 17α-ethinyl group II: Dienogest from a pharmacodynamic point of view". Drugs of Today. 31 (7): 517–536.
↑ Galbraith, Alan (2007). Fundamentals of Pharmacology: An Applied Approach for Nursing and Health. United Kingdom: Pearson Education LTD. p. 632. ISBN 978-0131869011. Unknown parameter |coauthors= ignored (help)

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[1] Nakamura M, Katsuki Y, Shibutani Y, Oikawa T (2003). "All progestins are not created equal". Steroids. 68 (10–13): 879–890. doi:10.1016/j.steroids.2003.08.003. PMID 14667980.

[Dienogest-2] 2.0 ^2.1 ^2.2 ^2.3 ^2.4 Foster RH, Wilde MI (1998). "Dienogest". Drugs. 56 (5): 825–833. PMID 9829156.

[metabolism_of_progestins-3] Lignieres B, Dennerstein L, Backstrom T (1995). "Influence of route of administration on progesterone metabolism". Maturitas. 21 (3): 251–257. doi:10.1016/0378-5122(94)00882-8. PMID 7616875.

[Pharmacological_profile_of_progestins-4] Sitruk-Ware R (2004). "Pharmacological profile of progestins". Maturitas. 47 (4): 277–283. doi:10.1016/j.maturitas.2004.01.001. PMID 15063480.

[Dienogest0antitumour-5] 5.0 ^5.1 Nakamura M, Katsuki Y, Shibutani Y, Oikawa T (1999). "Dienogest, a synthetic steroid, suppresses both embryonic and tumor-cell-induced angiogenesis". European Journal of Pharmacology. 386 (1): 33–40. doi:10.1016/S0014-2999(99)00765-7. PMID 10611461. line feed character in |title= at position 62 (help)

[6] Nakamura M, Katsuki Y, Shibutani Y, Oikawa T (2003). "All progestins are not created equal". Steroids. 68 (10–13): 879–890. doi:10.1016/j.steroids.2003.08.003. PMID 14667980.

[STS_556-7] Oettel M, Kurischko A (1980). "STS 557, a new orally active progestin with antiprogestational and contragestational properties in rabbits". Contraception. 21 (1): 61–75. doi:10.1016/0010-7824(80)90140-7. PMID 7357870.

[DienogestcommentarybyHK-8] Kuhl H (1998). "Dienogest. A Viewpoint by Herbert Kuhl". Drugs. 56 (5): 834.

[Fertility_after_treatment_with_valette-9] Wiegratz I, Mittmann K, Dietrichb H, Zimmermann T, Kuhl H (2006). "Fertility after discontinuation of treatment with an oral contraceptive containing 30 μg of ethinyl estradiol and 2 mg of dienogest". Fertility and Sterility. 85 (6): 1812–1819. doi:10.1016/j.fertnstert.2005.11.052. PMID 16759929.

[Dienogest_pharmacokinetics-10] Oettel M, Bervoas-Martin S, Elger W, Golbs S, Hobe G, Kaufmann G, Mathieu M, Moore C, Schneider B, Puri C, Ritter P, Reddersen G, Schon R, Strauch G, Zimmermann H (1995). "A 19-norprogestin without 17α-ethinyl group II: Dienogest from a pharmacokinetic point of view". Drugs of Today. 31 (7): 499–516.

[Dienogest_pharmacodynamics-11] 11.0 ^11.1 Oettel M, Carol W, Elger W, Kaufmann G, Moore C, Romer W, Klinger G, Schneider B, Schroder J, Sobek L, Walter F, Zimmermann H (1995). "A 19-norprogestin without 17α-ethinyl group II: Dienogest from a pharmacodynamic point of view". Drugs of Today. 31 (7): 517–536.

[12] Galbraith, Alan (2007). Fundamentals of Pharmacology: An Applied Approach for Nursing and Health. United Kingdom: Pearson Education LTD. p. 632. ISBN 978-0131869011. Unknown parameter |coauthors= ignored (help)

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