Gestodene

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Gestodene
Gestodene.svg
Gestodeno3D.png
Systematic (IUPAC) name
(17α)-13-Ethyl-17-hydroxy-18,19-dinorpregna-4,15-dien-20-yn-3-one
Clinical data
AHFS/Drugs.com International Drug Names
Pregnancy
category
  • X
Routes of
administration
oral administration
Legal status
Legal status
  • ℞ (Prescription only)
Pharmacokinetic data
Bioavailability in vitro 99% using 3H=R5020 / in vivo similar to progesterone
Biological half-life 16 to 18 hrs.
Excretion urinary tract mainly
Identifiers
CAS Number 60282-87-3 YesY
ATC code G03AA10 (WHO) G03AB06 (WHO) (only combinations with estrogens)
PubChem CID 3033968
DrugBank DB06730 YesY
ChemSpider 2298532 YesY
UNII 1664P6E6MI YesY
KEGG D04316 YesY
ChEMBL CHEMBL1213583 YesY
Chemical data
Formula C21H26O2
Molar mass 310.430 g/mol
  (verify)

Gestodene is a steroidal progestin of the 19-nortestosterone group that is used as a hormonal contraceptive. Products containing gestodene include:

  • Melodene-15, Mirelle, and Minesse which contain 15 μg of ethinylestradiol and 60 μg of gestodene;
  • Meliane, Sunya, Femodette, and Millinette 20/75 which contain 20 μg of ethinylestradiol and 75 μg of gestodene; and
  • Gynera, Minulet, Femoden, Femodene, Katya and Millinette 30/75 which contain 30 μg of ethinylestradiol and 75 μg of gestodene.[1]

Benefits[edit]

Gestodene is androgenically neutral, meaning that contraceptive pills containing gestodene do not exhibit the androgenic side effects (e.g. acne, hirsutism, weight gain) often associated with second-generation contraceptive pills, such as those containing levonorgestrel.[2]

The synthetic estrogen dosage in third-generation contraceptive pills (including those containing gestodene) is lower than that in second-generation oral contraceptives, reducing the likelihood of weight gain, breast tenderness and migraine.[3]

Third-generation oral contraceptives are also suitable for use in patients with diabetes or lipid disorders because they have minimal impact on blood glucose levels and the lipid profile.[4]

Adverse effects[edit]

Women who take oral contraceptives containing gestodene are 5.6 times as likely to develop thromboembolism than women who do not take any contraceptive pill, and 1.6 times as likely to develop thromboembolism compared to women taking oral contraceptives containing levonorgestrel.[5]

Pharmacology[edit]

Gestodene is a potent progestogen, and also possesses weak androgenic, glucocorticoid, and antimineralocorticoid activity.[6][7] It binds to sex hormone-binding globulin.[7]

History[edit]

Gestodene was introduced in 1987.[8]

See also[edit]

Footnotes[edit]

  1. ^ http://www.bayerscheringpharma.es/ebbsc/cms/es/_galleries/download/s_mujer/prospectos/MelodeneS.pdf
  2. ^ http://dermnetnz.org/treatments/antiandrogens.html
  3. ^ Festin (2006). "Progestogens in combined oral contraceptives for contraception". The WHO Reproductive Health Library. 
  4. ^ Cerel-Suhl (1999). "Update on Oral Contraceptive Pills". American Family Physician. 60 (7): 2073–2084. 
  5. ^ Lidegaard; et al. (2011). "Risk of venous thromboembolism from use of oral contraceptives containing different progestogens and oestrogen doses". BMJ. 343: 1–15. doi:10.1136/bmj.d6423. PMC 3202015free to read. PMID 22027398. 
  6. ^ Fuhrmann, Ulrike; Slater, Emily P.; Fritzemeier, Karl-Heinrich (1995). "Characterization of the novel progestin gestodene by receptor binding studies and transactivation assays". Contraception. 51 (1): 45–52. doi:10.1016/0010-7824(94)00003-F. ISSN 0010-7824. 
  7. ^ a b Schindler, Adolf E; Campagnoli, Carlo; Druckmann, René; Huber, Johannes; Pasqualini, Jorge R; Schweppe, Karl W; Thijssen, Jos H.H (2003). "Classification and pharmacology of progestins". Maturitas. 46: 7–16. doi:10.1016/j.maturitas.2003.09.014. ISSN 0378-5122. 
  8. ^ Benno Clemens Runnebaum; Thomas Rabe; Ludwig Kiesel (6 December 2012). Female Contraception: Update and Trends. Springer Science & Business Media. pp. 13–. ISBN 978-3-642-73790-9.