Dienogest
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| Systematic (IUPAC) name | |
| [(17β)-17-Hydroxy-3-oxoestra-4,9-dien-17-yl]acetonitrile | |
| Clinical data | |
| Trade names | Visanne |
| AHFS/Drugs.com | International Drug Names |
| Pregnancy cat. | B3 (AU) |
| Legal status | Prescription Only (S4) (AU) |
| Routes | Oral |
| Pharmacokinetic data | |
| Bioavailability | 90%[1] |
| Protein binding | 90%[2] |
| Metabolism | Hepatic (CYP3A4-mediated)[3] |
| Half-life | 6-12 hours[4] |
| Excretion | Renal |
| Identifiers | |
| CAS number | 65928-58-7  |
| ATC code | G03DB08 G03AB08 G03FA15 (combinations with estrogen) |
| PubChem | CID 68861 |
| ChemSpider | 62093  |
| UNII | 46M3EV8HHE |
| KEGG | D03799 |
| ChEBI | CHEBI:70708 |
| ChEMBL | CHEMBL1201864 |
| 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 |
| Mol. mass | 311.42 g/mol[1] |
| Physical data | |
| Density | 1.2 g/cm³ |
| Boiling point | 549 °C (1020 °F) |
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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.
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History [edit]
Dienogest was synthesised in 1979 in Jena, Germany under the leadership of Prof. Kurt Ponsold, was initially referred to as STS 557.[7][8] It was found that its potency was 10 times that of levonorgestrel.[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 [edit]
Contraception [edit]
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] The minimum dose required to inhibit ovulation has been found to be approximately 1 mg.[13]
Endometriosis [edit]
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 [edit]
Progestational activity [edit]
Dienogest has moderate affinity for the progesterone receptor in human uterus tissue, in vitro, about 10% that of progesterone.[17]
Inhibition of ovulation [edit]
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 [edit]
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 [edit]
- ^ a b c d e Foster RH, Wilde MI (1998). "Dienogest". Drugs 56 (5): 825–33; discussion 834–5. doi:10.2165/00003495-199856050-00007. PMID 9829156.
- ^ 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.
- ^ 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.
- ^ Sitruk-Ware R (2004). "Pharmacological profile of progestins". Maturitas 47 (4): 277–83. doi:10.1016/j.maturitas.2004.01.001. PMID 15063480.
- ^ 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.
- ^ Raudrant D, Rabe T (2003). "Progestogens with antiandrogenic properties". Drugs 63 (5): 463–92. doi:10.2165/00003495-200363050-00003. PMID 12600226.
- ^ 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.
- ^ 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. doi:10.1016/S0039-128X(99)00028-8. PMID 10493599.
- ^ 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.
- ^ http://www.jenapharm.de/unternehmen/ueber-uns/geschichte/1965-1995/
- ^ Kuhl H (1998). "Dienogest. A Viewpoint by Herbert Kuhl". Drugs 56 (5): 834.
- ^ 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.
- ^ 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.
- ^ "Dienogest for the treatment of endometriosis" (PDF). London New Drugs Group. Retrieved 2010-12-07.
- ^ "Visanne" (in German). Netdoctor.de.
- ^ Strowitzki, T; Marr, J; Gerlinger, C; Faustmann, T; Seitz, C (2010). "Dienogest is as effective as leuprolide acetate in treating the painful symptoms of endometriosis: a 24-week, randomized, multicentre, open-label trial". Human reproduction (Oxford, England) 25 (3): 633–41. doi:10.1093/humrep/dep469. PMID 20089522.
- ^ 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.
- ^ 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.
- ^ 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. p. 632. ISBN 978-0-13-186901-1.
- ^ 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.
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