Gestodene

  • CAT Number: A000576
  • CAS Number: 60282-87-3
  • Molecular Formula: C21H26O2
  • Molecular Weight: 310.4
  • Purity: ≥95%
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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.

Catalog Number A000576
CAS Number 60282-87-3
Molecular Formula

C21H26O2

Purity 95%
Target Estrogen/progestogen 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
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
Devel Ther. 2017 Mar 10;11:725-731. doi: 10.2147/DDDT.S131123. eCollection 2017.
PubMed PMID: 28331292; PubMed Central PMCID: PMC5354542.
<br>

2: Enríquez J, García G, Herrero B, Larrea F. The synthetic progestin, gestodene,
affects functional biomarkers in neonatal rat osteoblasts through an estrogen
receptor-related mechanism of action. Endocr Res. 2017 Nov;42(4):269-280. doi:
10.1080/07435800.2017.1294603. Epub 2017 Mar 22. PubMed PMID: 28328298.
<br>

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
Health. 2016 Dec;14(6):980-988. PubMed PMID: 27959876.
<br>

4: Li C, Ning M, Yao X, Wang Y, Liu Y. Preparation and in vitro/in vivo
evaluation of gestodene (GEST) intravaginal ring. Pak J Pharm Sci. 2016
Sep;29(5):1545-1553. PubMed PMID: 27731811.
<br>

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.
<br>

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.
<br>

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:
10.1021/acs.est.6b00799. Epub 2016 May 19. PubMed PMID: 27129041.
<br>

8: gestodene + ethinvlestradiol (APLEEK&#8304;). No place for a patch containing a
third-generation progestin. Prescrire Int. 2016 Jan;25(167):10. PubMed PMID:
26942251.

<br>
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.
<br>

10: H&#246;chel 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
J Clin Pharmacol Ther. 2014 Oct;52(10):856-66. doi: 10.5414/CP202085. PubMed
PMID: 25138681.

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