Gestodene-d6
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MedKoo CAT#: 464412

CAS#: 1542211-40-4

Description: Gestodene-d6 is intended for use as an internal standard for the quantification of gestodene by GC- or LC-MS. Gestodene is a progestin. It selectively binds to the progesterone receptor over the estrogen receptor. Gestodene induces transcriptional activity mediated by the progesterone receptor, and, weakly, the androgen receptor in reporter assays. It increases the growth of MCF-7 cells when used at concentrations ranging from 0.1 to 1 µM.4 In contrast, gestodene (0.1 mg/kg) reduces tumor growth in an estrogen-dependent model of rat mammary tumors induced by DMBA. Formulations containing gestodene, in combination with ethynyl estradiol have been used as oral contraceptives.

Chemical Structure

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Gestodene-d6
CAS# 1542211-40-4
Product data Instruction

Theoretical Analysis

MedKoo Cat#: 464412
Name: Gestodene-d6
CAS#: 1542211-40-4
Chemical Formula: C21H20D6O2
Exact Mass: 316.23
Molecular Weight: 316.474
Elemental Analysis: C, 79.70; H, 10.19; O, 10.11

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1mg USD 420 2 Weeks
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Synonym: Gestodene-d6; Gestodene d6;

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-2,2,4,6,6,10-d6

InChi Key: SIGSPDASOTUPFS-PWFLSJGKSA-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/i5D2,6D2,13D,16D

SMILES Code: CC[C@]12[C@]([H])([C@]3([C@]([H])(CC2)[C@@]4(C(C([2H])(C3)[2H])=C(C(C([2H])(C4)[2H])=O)[2H])[2H])[H])C=C[C@]1(C#C)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: To be determined

Shelf Life: >2 years if stored properly

Drug Formulation: To be determined

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-d6 (SHB 331-d6) is the deuterium labeled Gestodene. Gestodene(SHB 331) 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

Preparing Stock Solutions

The following data is based on the product molecular weight 316.47 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: Chen S, Lin C, Tan J, Wang Y, Wang X, Wang X, Liu L, Li J, Hou L, Liu J, Leung JYS. Reproductive potential of mosquitofish is reduced by the masculinizing effect of a synthetic progesterone, gestodene: Evidence from morphology, courtship behaviour, ovary histology, sex hormones and gene expressions. Sci Total Environ. 2021 May 15;769:144570. doi: 10.1016/j.scitotenv.2020.144570. Epub 2021 Jan 18. PMID: 33486178.

2: Svigruha R, Fodor I, Padisak J, Pirger Z. Progestogen-induced alterations and their ecological relevance in different embryonic and adult behaviours of an invertebrate model species, the great pond snail (Lymnaea stagnalis). Environ Sci Pollut Res Int. 2020 Dec 21. doi: 10.1007/s11356-020-12094-z. Epub ahead of print. PMID: 33349911.

3: Treger S, Ackerman S, Kaplan V, Ghanem S, Nadir Y. Progestin type affects the increase of heparanase level and procoagulant activity mediated by the estrogen receptor. Hum Reprod. 2021 Jan 1;36(1):61-69. doi: 10.1093/humrep/deaa263. PMID: 33306105.

4: Silva-Bermudez LS, Toloza FJK, Perez-Matos MC, de Souza RJ, Banfield L, Vargas-Villanueva A, Mendivil CO. Effects of oral contraceptives on metabolic parameters in adult premenopausal women: a meta-analysis. Endocr Connect. 2020 Oct;9(10):978-998. doi: 10.1530/EC-20-0423. PMID: 33048062; PMCID: PMC7576645.

5: Jirakittidul P, Angsuwathana S, Rattanachaiyanont M, Thiampong T, Neungton C, Chotrungrote B. The effectiveness of quick starting oral contraception containing nomegestrol acetate and 17-β estradiol on ovulation inhibition: A randomized controlled trial. Sci Rep. 2020 May 29;10(1):8782. doi: 10.1038/s41598-020-65642-5. PMID: 32472012; PMCID: PMC7260215.

6: Céolin R, Allouchi H, Rietveld IB. On the dimorphism and the pressure- temperature state diagram of gestodene, a steroidal progestogen contraceptive. Ann Pharm Fr. 2020 Jul;78(4):303-309. doi: 10.1016/j.pharma.2020.03.002. Epub 2020 Mar 29. PMID: 32444029.

7: Khialani D, le Cessie S, Lijfering WM, Cannegieter SC, Rosendaal FR, van Hylckama Vlieg A. The joint effect of genetic risk factors and different types of combined oral contraceptives on venous thrombosis risk. Br J Haematol. 2020 Oct;191(1):90-97. doi: 10.1111/bjh.16666. Epub 2020 Apr 27. PMID: 32342502; PMCID: PMC7586802.

8: Yang X, Lin H, Zhang Y, He Z, Dai X, Zhang Z, Li Y. Sorption and desorption of seven steroidal synthetic progestins in five agricultural soil-water systems. Ecotoxicol Environ Saf. 2020 Jun 15;196:110586. doi: 10.1016/j.ecoenv.2020.110586. Epub 2020 Apr 6. PMID: 32272348.

9: Louw-du Toit R, Hapgood JP, Africander D. A direct comparison of the transcriptional activities of progestins used in contraception and menopausal hormone therapy via the mineralocorticoid receptor. Biochem Biophys Res Commun. 2020 May 28;526(2):466-471. doi: 10.1016/j.bbrc.2020.03.100. Epub 2020 Mar 28. PMID: 32234237; PMCID: PMC7287572.

10: Rauchenzauner M, Deichmann S, Pittschieler S, Bergmann M, Prieschl M, Unterberger I, Rösing B, Seger C, Moser C, Wildt L, Luef G. Bidirectional interaction between oral contraception and lamotrigine in women with epilepsy - Role of progestins. Seizure. 2020 Jan;74:89-92. doi: 10.1016/j.seizure.2019.11.011. Epub 2019 Nov 25. PMID: 31869755.

11: Šauer P, Tumová J, Steinbach C, Golovko O, Komen H, Maillot-Maréchal E, Máchová J, Grabic R, Aït-Aïssa S, Kocour Kroupová H. Chronic simultaneous exposure of common carp (Cyprinus carpio) from embryonic to juvenile stage to drospirenone and gestodene at low ng/L level caused intersex. Ecotoxicol Environ Saf. 2020 Jan 30;188:109912. doi: 10.1016/j.ecoenv.2019.109912. Epub 2019 Nov 6. PMID: 31706240.

12: Laszlo CF, Paz Montoya J, Shamseddin M, De Martino F, Beguin A, Nellen R, Bruce SJ, Moniatte M, Henry H, Brisken C. A high resolution LC-MS targeted method for the concomitant analysis of 11 contraceptive progestins and 4 steroids. J Pharm Biomed Anal. 2019 Oct 25;175:112756. doi: 10.1016/j.jpba.2019.07.004. Epub 2019 Jul 25. PMID: 31387028.

13: Guida M, Rega A, Vivone I, Saccone G, Sarno L, Di Carlo C, Aquino CI, Troisi J. Variations in sleep associated with different types of hormonal contraceptives. Gynecol Endocrinol. 2020 Feb;36(2):166-170. doi: 10.1080/09513590.2019.1640204. Epub 2019 Jul 17. PMID: 31311352.

14: Maged AM, Shoab AY, Dieb AS. Antepartum and postpartum uterine artery impedance in women with pre-eclampsia: a case control study. J Obstet Gynaecol. 2019 Jul;39(5):633-638. doi: 10.1080/01443615.2018.1563054. Epub 2019 Apr 19. PMID: 31001993.

15: Lampert A, Haefeli WE, Seidling HM. Informationslücken in Packungsbeilagen: fehlende Hinweise zum richtigen Umgang mit Transdermalen Therapeutischen Systemen [Information Gaps in Package Inserts Cause Insufficient Patient Information on Correct Handling of Transdermal Patches]. Dtsch Med Wochenschr. 2019 Mar;144(5):e36-e41. German. doi: 10.1055/a-0722-7419. Epub 2019 Mar 5. PMID: 30836398.

16: Rott H. Birth Control Pills and Thrombotic Risks: Differences of Contraception Methods with and without Estrogen. Hamostaseologie. 2019 Feb;39(1):42-48. doi: 10.1055/s-0039-1677806. Epub 2019 Jan 22. PMID: 30669160.

17: Grandi G, Barra F, Ferrero S, Sileo FG, Bertucci E, Napolitano A, Facchinetti F. Hormonal contraception in women with endometriosis: a systematic review. Eur J Contracept Reprod Health Care. 2019 Feb;24(1):61-70. doi: 10.1080/13625187.2018.1550576. Epub 2019 Jan 21. PMID: 30664383.

18: Mazzarino M, Rizzato N, Stacchini C, de la Torre X, Botrè F. A further insight into the metabolic profile of the nuclear receptor Rev-erb agonist, SR9009. Drug Test Anal. 2018 Nov;10(11-12):1670-1681. doi: 10.1002/dta.2538. Epub 2018 Nov 22. PMID: 30395700.

19: Ljubojević Hadžavdić S, Marinović Kulišić S, Ljubojević Grgec D, Poljanac A, Ilić B. Autoimmune Progesterone Dermatitis Diagnosed by Lymphocyte Transformation Test and Progesterone Provocation Test. Acta Dermatovenerol Croat. 2018 Oct;26(3):276-277. PMID: 30390735.

20: Plu-Bureau G, Sabbagh E, Hugon-Rodin J. Contraception hormonale et risque vasculaire. RPC Contraception CNGOF [Hormonal contraception and vascular risk: CNGOF Contraception Guidelines]. Gynecol Obstet Fertil Senol. 2018 Dec;46(12):823-833. French. doi: 10.1016/j.gofs.2018.10.007. Epub 2018 Oct 30. PMID: 30389542.