Gestodene

• CAT Number: A000576
• CAS Number: 60282-87-3
• Molecular Formula: C21H26O2
• Molecular Weight: 310.4
• Purity: ≥95%
• Synonyms: 60282-87-3; Gestoden; Gestinol; Gestodeno; Gestodenum
• Target: Progesterone Receptor
• Solubility: >12.7mg/mL in DMSO
• Storage: -20°C
• 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
• InChIKey: SIGSPDASOTUPFS-XUDSTZEESA-N
• SMILES: CCC12CCC3C(C1C=CC2(C#C)O)CCC4=CC(=O)CCC34

Gestodene is a progestogen hormonal contraceptive. Gestodene has been shown to be androgenically neutral meaning that contraceptive pills containing gestodene do not exhibit the androgenic side effects associated with second-generation contraceptive pills.

Reference

1: Zhang C, Li H, Xiong X, Zhai S, Wei Y, Zhang S, Zhang Y, Xu L, Liu L. An
open-label, two-period comparative study on pharmacokinetics and safety of a
combined ethinylestradiol/gestodene transdermal contraceptive patch. Drug Des
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2: Enríquez J, García G, Herrero B, Larrea F. The synthetic progestin, gestodene,
affects functional biomarkers in neonatal rat osteoblasts through an estrogen
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3: Nájera-Aguilar HA, Gutiérrez-Hernández RF, González de Los Santos R,
García-Lara C, Méndez-Novelo R, Rojas-Valencia MN. Degradation of gestodene
(GES)-17α-ethinylestradiol (EE2) mixture by electrochemical oxidation. J Water
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4: Li C, Ning M, Yao X, Wang Y, Liu Y. Preparation and in vitro/in vivo
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5: Zurth C, Schuett B, Casjens M, Ludwig M, Waellnitz K. Pharmacokinetics and
adhesion of a transdermal patch containing ethinyl estradiol and gestodene under
conditions of heat, humidity, and exercise: A single-center, open-label,
randomized, crossover study. Clin Pharmacol Drug Dev. 2015 Jul;4(4):245-55. doi:
10.1002/cpdd.185. Epub 2015 May 8. PubMed PMID: 27136904.

6: Liu D, Zhang C, Zhang X, Zhen Z, Wang P, Li J, Yi D, Jin Y, Yang D. Permeation
measurement of gestodene for some biodegradable materials using Franz diffusion
cells. Saudi Pharm J. 2015 Sep;23(4):413-20. doi: 10.1016/j.jsps.2015.01.012.
Epub 2015 Jan 12. PubMed PMID: 27134544; PubMed Central PMCID: PMC4834674.

7: Frankel TE, Meyer MT, Kolpin DW, Gillis AB, Alvarez DA, Orlando EF. Exposure
to the Contraceptive Progestin, Gestodene, Alters Reproductive Behavior, Arrests
Egg Deposition, and Masculinizes Development in the Fathead Minnow (Pimephales
promelas). Environ Sci Technol. 2016 Jun 7;50(11):5991-9. doi:
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8: gestodene + ethinvlestradiol (APLEEK⁰). No place for a patch containing a
third-generation progestin. Prescrire Int. 2016 Jan;25(167):10. PubMed PMID:
26942251.

9: Waellnitz K, Duijkers I, Klipping C, Rautenberg T, Rohde B, Zurth C. A
two-centre, open-label, randomised study of ovulation inhibition with three
transdermal contraceptive patches, each containing different amounts of ethinyl
estradiol and gestodene in healthy, young women. J Obstet Gynaecol.
2016;36(1):106-13. doi: 10.3109/01443615.2015.1041882. Epub 2015 Sep 30. Erratum
in: J Obstet Gynaecol. 2016;36(1):i. PubMed PMID: 26421957.

10: Höchel J, Schuett B, Ludwig M, Zurth C. Implications of different application
sites on the bioavailability of a transdermal contraceptive patch containing
ethinyl estradiol and gestodene: an open-label, randomized, crossover study. Int
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PMID: 25138681.