MedKoo Cat#: 317970 | Name: Gestodene
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

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.

Chemical Structure

Gestodene
Gestodene
CAS#60282-87-3

Theoretical Analysis

MedKoo Cat#: 317970

Name: Gestodene

CAS#: 60282-87-3

Chemical Formula: C21H26O2

Exact Mass: 310.1933

Molecular Weight: 310.44

Elemental Analysis: C, 81.25; H, 8.44; O, 10.31

Price and Availability

Size Price Availability Quantity
50mg USD 250.00 2 Weeks
100mg USD 400.00 2 Weeks
250mg USD 750.00 2 Weeks
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Related CAS #
No Data
Synonym
Gestodene; Gestoden; Gestodenum; Gestodeno; Gestinol;
IUPAC/Chemical Name
(8R,9S,10R,13S,14S,17R)-13-ethyl-17-ethynyl-17-hydroxy-1,2,6,7,8,9,10,11,12,13,14,17-dodecahydro-3H-cyclopenta[a]phenanthren-3-one
InChi Key
SIGSPDASOTUPFS-XUDSTZEESA-N
InChi Code
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
SMILES Code
O=C1CC[C@@]2([H])C(CC[C@]3([H])[C@]2([H])CC[C@@]4(CC)[C@@]3([H])C=C[C@@]4(O)C#C)=C1
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO, not in water
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info
Product Data
Biological target:
Gestodene (SHB 331;WL 70) is a progestogen hormonal contraceptive.
In vitro activity:
These studies suggest that the 19-norprogestins norgestrel and gestodene stimulate MCF-7 breast cancer cell growth by activating the oestrogen receptor. Reference: Br J Cancer. 1993 May;67(5):945-52. https://pubmed.ncbi.nlm.nih.gov/8494728/
In vivo activity:
TBD
Solvent mg/mL mM
Solubility
Acetonitrile 1.0 3.22
DMSO 81.0 260.92
Ethanol 9.5 30.60
Methanol 1.0 3.22
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 310.44 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
1. Catherino WH, Jeng MH, Jordan VC. Norgestrel and gestodene stimulate breast cancer cell growth through an oestrogen receptor mediated mechanism. Br J Cancer. 1993 May;67(5):945-52. doi: 10.1038/bjc.1993.175. PMID: 8494728; PMCID: PMC1968434.
In vitro protocol:
1. Catherino WH, Jeng MH, Jordan VC. Norgestrel and gestodene stimulate breast cancer cell growth through an oestrogen receptor mediated mechanism. Br J Cancer. 1993 May;67(5):945-52. doi: 10.1038/bjc.1993.175. PMID: 8494728; PMCID: PMC1968434.
In vivo protocol:
TBD
1: 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 Jan;36(1):106-13. doi: 10.3109/01443615.2015.1041882. Epub 2015 Sep 30. PubMed PMID: 26421957. 2: Winkler J, Goldammer M, Ludwig M, Rohde B, Zurth C. Pharmacokinetic drug-drug interaction between ethinyl estradiol and gestodene, administered as a transdermal fertility control patch, and two CYP3A4 inhibitors and a CYP3A4 substrate. Eur J Drug Metab Pharmacokinet. 2015 Dec;40(4):389-99. doi: 10.1007/s13318-014-0215-8. Epub 2014 Jul 6. PubMed PMID: 24997757. 3: 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 J Clin Pharmacol Ther. 2014 Oct;52(10):856-66. doi: 10.5414/CP202085. PubMed PMID: 25138681. 4: Westhoff CL, Reinecke I, Bangerter K, Merz M. Impact of body mass index on suppression of follicular development and ovulation using a transdermal patch containing 0.55-mg ethinyl estradiol/2.1-mg gestodene: a multicenter, open-label, uncontrolled study over three treatment cycles. Contraception. 2014 Sep;90(3):272-9. doi: 10.1016/j.contraception.2014.04.018. Epub 2014 May 20. PubMed PMID: 24969733. 5: Stanczyk FZ, Archer DF. Gestodene: a review of its pharmacology, potency and tolerability in combined contraceptive preparations. Contraception. 2014 Apr;89(4):242-52. doi: 10.1016/j.contraception.2013.12.003. Epub 2013 Dec 19. Review. PubMed PMID: 24485094. 6: Li CX, Wang YK, Ning MY. [Preparation and release mechanism of gestodene reservoir-type intravaginal rings]. Yao Xue Xue Bao. 2014 Mar;49(3):399-405. Chinese. PubMed PMID: 24961114. 7: Merz M, Grunert J. Effects of an ethinyl estradiol/gestodene transdermal contraceptive patch on the endometrium: a single-center, uncontrolled study. Womens Health (Lond Engl). 2014 Jan;10(1):37-43. doi: 10.2217/whe.13.71. PubMed PMID: 24328597. 8: Saxena A, Gupta A, Kasibhatta R, Bob M, Kumar VP, Purwar B. Rapid and sensitive method for quantification of gestodene in human plasma as the oxime derivative by liquid chromatography-tandem mass spectrometry (LC-MS/MS) and its application to bioequivalence study. J Chromatogr B Analyt Technol Biomed Life Sci. 2014 Jan 15;945-946:240-6. doi: 10.1016/j.jchromb.2013.12.003. Epub 2013 Dec 8. PubMed PMID: 24361980. 9: Junge W, Heger-Mahn D, Trummer D, Merz M. Investigation of the hemostatic effect of a transdermal patch containing 0.55 mg ethinyl estradiol and 2.1 mg gestodene compared with a monophasic oral contraceptive containing 0.03 mg ethinyl estradiol and 0.15 mg levonorgestrel: an open-label, randomized, crossover study. Drugs R D. 2013 Sep;13(3):223-33. doi: 10.1007/s40268-013-0028-2. PubMed PMID: 24043457; PubMed Central PMCID: PMC3784047. 10: Jaithitivit L, Jaisamrarn U, Taneepanichskul S. Cycle control, safety and acceptability of a new oral contraceptive containing ethinylestradiol 15 micrograms and gestodene 60 micrograms. J Med Assoc Thai. 2012 May;95(5):630-5. PubMed PMID: 22994020. 11: Heinemann LA, Dinger JC, Assmann A, Minh TD. Use of oral contraceptives containing gestodene and risk of venous thromboembolism: outlook 10 years after the third-generation "pill scare". Contraception. 2010 May;81(5):401-7. doi: 10.1016/j.contraception.2009.12.014. Epub 2010 Jan 27. PubMed PMID: 20399946. 12: Xiong Z, Sun X, Huo T, Li N, Zheng Y, Sun Y. Development and validation of UPLC-MS/MS method for simultaneous determination of gestodene and ethinyl estradiol in rat plasma. Biomed Chromatogr. 2010 Feb;24(2):160-8. doi: 10.1002/bmc.1265. PubMed PMID: 19591119. 13: Liu XF, Ding CG, Ge QH, Zhou Z, Zhi XJ. [Simultaneous determination of gestodene, etonogestrel and ethinylestradiol in plasma by LC-MS/MS following derivatization]. Yao Xue Xue Bao. 2010 Jan;45(1):87-92. Chinese. PubMed PMID: 21351455. 14: Yildizhan R, Yildizhan B, Adali E, Yoruk P, Birol F, Suer N. Effects of two combined oral contraceptives containing ethinyl estradiol 30 microg combined with either gestodene or drospirenone on hemostatic parameters, lipid profiles and blood pressure. Arch Gynecol Obstet. 2009 Aug;280(2):255-61. doi: 10.1007/s00404-008-0907-x. Epub 2009 Jan 6. PubMed PMID: 19125264. 15: Gao Y, Liang J, Liu J, Xiao Y. Double-layer weekly sustained release transdermal patch containing gestodene and ethinylestradiol. Int J Pharm. 2009 Jul 30;377(1-2):128-34. doi: 10.1016/j.ijpharm.2009.05.017. Epub 2009 May 20. PubMed PMID: 19463930. 16: Oranratanaphan S, Taneepanichskul S. A double blind randomized control trial, comparing effect of drospirenone and gestodene to sexual desire and libido. J Med Assoc Thai. 2006 Oct;89 Suppl 4:S17-22. PubMed PMID: 17726807. 17: Matejícek D, Kubán V. High performance liquid chromatography/ion-trap mass spectrometry for separation and simultaneous determination of ethynylestradiol, gestodene, levonorgestrel, cyproterone acetate and desogestrel. Anal Chim Acta. 2007 Apr 11;588(2):304-15. Epub 2007 Feb 20. PubMed PMID: 17386825. 18: Colombo D, Bombieri G, Lenna R, Marchini N, Modica E, Scala A. Structure elucidation of new compounds from acidic treatment of the progestins gestodene and drospirenone. Steroids. 2006 Aug;71(8):745-50. PubMed PMID: 16769098. 19: Heger-Mahn D, Warlimont C, Faustmann T, Gerlinger C, Klipping C. Combined ethinylestradiol/gestodene contraceptive patch: two-center, open-label study of ovulation inhibition, acceptability and safety over two cycles in female volunteers. Eur J Contracept Reprod Health Care. 2004 Sep;9(3):173-81. PubMed PMID: 15697107. 20: Uchikova E, Terzhumanov R, Milchev N, Iacheva T. [The effect of two low dose oral contraceptive with gestodene on the systems of natural inhibitors of coagulation]. Akush Ginekol (Sofiia). 2004;43(6):19-23. Bulgarian. PubMed PMID: 15669648.