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

MedKoo CAT#: 317970

CAS#: 60282-87-3

Description: 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

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Gestodene
CAS# 60282-87-3
Product data Instruction

Theoretical Analysis

MedKoo Cat#: 317970
Name: Gestodene
CAS#: 60282-87-3
Chemical Formula: C21H26O2
Exact Mass: 310.19
Molecular Weight: 310.437
Elemental Analysis: C, 81.25; H, 8.44; O, 10.31

Price and Availability

Size Price Availability Quantity
100mg USD 285 2 Weeks
1g USD 850 2 Weeks
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Synonym: Gestodene; Gestoden; Gestodenum; Gestodeno; Gestodenum [INN-Latin]; 17-alpha-ethinyl-13-ethyl-17 beta-hydroxy-4,15-gonadien-3-one; Gestoden; Gestodene; Gestodene, ((17alpha)-(+-))-isomer; SH B 3331;

IUPAC/Chemical Name: (17α)-13-Ethyl-17-hydroxy-18,19-dinorpregna-5,15-dien-20-yn-3-one

InChi Key: PCGOZSMTJRCWQF-ZUHHCLADSA-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/h2,5,10,12,16-19,23H,3,6-9,11,13H2,1H3/t16-,17+,18+,19-,20-,21+/m0/s1

SMILES Code: C#C[C@@]1(O)C=C[C@@]2([H])[C@]3([H])CC=C4CC(CC[C@]4([H])[C@@]3([H])CC[C@]12CC)=O

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:
Product Data
Instruction:
View handling instruction
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

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
Acetonitrile 1.0 3.22
DMSO 81.0 260.92
Ethanol 9.5 30.60
Methanol 1.0 3.22

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

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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.