Dienogest

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Dienogest
Systematic (IUPAC) name
17α-cyanomethyl-17β-hydroxy-estra-4,9-di-ene-3-one[1]
Identifiers
CAS number 65928-58-7
ATC code G03FA15
PubChem 68861
Chemical data
Formula C20H25NO2 
Mol. mass 311.42 g/mol[2]
Physical data
Density 1.2 g/cm³
Boiling point 549 °C (1020 °F)
Pharmacokinetic data
Bioavailability 90%[2]
Protein binding 90%[3]
Metabolism Hepatic[4]
Half life 6-12 hours[5]
Excretion Renal
Therapeutic considerations
Pregnancy cat.

?
Legal status
Routes Oral

Dienogest is an orally active synthetic progesterone (or progestin).[1] 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.[4]

Contents

History

Dienogest was synthesised in 1979 in Jena, Germany under the leadership of Prof. Kurt Ponsald, was initially referred to as STS 557.[6][7] It was found that its potency was 10 times that of levonorgestrel.[8]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. [9]

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.[10] The minimum dose required to inhibit ovulation has been found to be approximately 1 mg[11]

Pharmacodynamics

Progestational Activity

Dienogest has moderate affinity for the progesterone receptor in human uterus tissue, in vitro, about 10% that of progesterone.[12]

Inhibition of Ovulation

The minimum effective dose of oral dienogest required to inhibit ovulation is 1 mg/day. [13] 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.[13]

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.[14] It produces no androgenic side effects and has little effect on metabolic and lipid haemostatic parameters.[15]

References

  1. ^ a b 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. 
  2. ^ a b c d e Foster RH, Wilde MI (1998). "Dienogest". Drugs 56 (5): 825–33; discussion 834–5. PMID 9829156. 
  3. ^ de Lignieres B, Dennerstein L, Backstrom T (1995). "Influence of route of administration on progesterone metabolism". Maturitas 21 (3): 251–7. doi:10.1016/0378-5122(94)00882-8. PMID 7616875. 
  4. ^ a b Stanczyk FZ (2003). "All progestins are not created equal". Steroids 68 (10-13): 879–90. doi:10.1016/j.steroids.2003.08.003. PMID 14667980. 
  5. ^ Sitruk-Ware R (2004). "Pharmacological profile of progestins". Maturitas 47 (4): 277–83. doi:10.1016/j.maturitas.2004.01.001. PMID 15063480. 
  6. ^ Menzenbach B, Hübner M, K. Ponsold (1984). "Untersuchungen zur Bromierung/Dehydrobromierung von 17-Cyanmethyl-17-hydroxy-östr-5(10)-en-3-on". Journal für Praktische Chemie 326 (6): 893–898. doi:10.1002/prac.19843260606. 
  7. ^ Kaufmann G, Dautzenberg H, Henkel H, et al (August 1999). "Nitrile hydratase from Rhodococcus erythropolis: metabolization of steroidal compounds with a nitrile group". Steroids 64 (8): 535–40. PMID 10493599. 
  8. ^ Oettel M, Kurischko A (1980). "STS 557, a new orally active progestin with antiprogestational and contragestational properties in rabbits". Contraception 21 (1): 61–9. doi:10.1016/0010-7824(80)90140-7. PMID 7357870. 
  9. ^ Kuhl H (1998). "Dienogest. A Viewpoint by Herbert Kuhl". Drugs 56 (5): 834. 
  10. ^ Wiegratz I, Mittmann K, Dietrich H, Zimmermann T, Kuhl H (2006). "Fertility after discontinuation of treatment with an oral contraceptive containing 30 microg of ethinyl estradiol and 2 mg of dienogest". Fertil. Steril. 85 (6): 1812–9. doi:10.1016/j.fertnstert.2005.11.052. PMID 16759929. 
  11. ^ Moore C, Carol W, Gräser T, Mellinger U, Walter F (1999). "Influence of Dienogest on Ovulation in Young Fertile Women". Clinical Drug Investigation 18 (4): 271–278. doi:10.1016/j.fertnstert.2005.11.052. 
  12. ^ 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. 
  13. ^ a b 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. 
  14. ^ Galbraith, Alan; Shane Bullock, Elizabeth Manias, Barry Hunt, Ann Richards (2007). Fundamentals of Pharmacology: An Applied Approach for Nursing and Health. United Kingdom: Pearson Education LTD, 632. ISBN 978-0131869011. 
  15. ^ Wiegratz I, Lee JH, Kutschera E, Bauer HH, von Hayn C, Moore C, Mellinger U, Winkler UH, Gross W, Kuhl H (2002). "Effect of dienogest-containing oral contraceptives on lipid metabolism". Contraception 65 (3): 223–9. doi:10.1016/S0010-7824(01)00310-9. PMID 11929644. 
v • d • e
Sex hormones and related agents (primarily G03, also L02, H01C) – human endogenous in small caps
Progestogens:
(receptor)
Agonist
Antiprogestogen
Androgens:
(receptor)
Agonist
Estrogens:
(receptor)
Agonist
Antiestrogen
Gonadotropins:
(FSHR/LHCGR)
ovulation stim.
Antigonadotropin
GnRH:
(receptor)
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