Gestodene

Gestodene

Systematic (IUPAC) name
(8R,9S,10R,13S,14S,17R)-13-Ethyl-17-ethynyl-17-hydroxy-1,2,6,7,8,9,10,11,12,14-decahydrocyclopenta[a]phenanthren-3-one
Clinical data
AHFS/Drugs.com	International Drug Names
Pregnancy category	X
Routes of administration	oral administration
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
ATC code	G03AA10 (WHO) G03AB06 (only combinations with estrogens)
PubChem	CID 3033968
DrugBank	DB06730
ChemSpider	2298532
UNII	1664P6E6MI
KEGG	D04316
ChEMBL	CHEMBL1213583
Chemical data
Formula	C21H26O2
Molar mass	310.430 g/mol
SMILES O=C4\C=C3/[C@@H]([C@H]2CC[C@]1([C@@H](/C=C\[C@]1(C#C)O)[C@@H]2CC3)CC)CC4
InChI InChI=1S/C21H26O2/c1-3-20-11-9-17-16-8-6-15(22)13-14(16)5-7-18(17)19(20)10-12-21(20,23)4-2/h2,10,12-13,16-19,23H,3,5-9,11H2,1H3/t16-,17+,18+,19-,20-,21-/m0/s1 Key:SIGSPDASOTUPFS-XUDSTZEESA-N
(verify)

Gestodene is a progestogen 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

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

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]

See also

• Etonogestrel
• Ethynerone
• Gestrinone

Footnotes

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 3202015. PMID 22027398.