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MedKoo Cat#: 540126 | Name: Ethisterone
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Description:

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

Ethisterone is a synthetic contraceptive and progesterone receptor agonist previously used in contraceptics. Derivatives inhibit prostate cancer cell growth.

Chemical Structure

Ethisterone
Ethisterone
CAS#434-03-7

Theoretical Analysis

MedKoo Cat#: 540126

Name: Ethisterone

CAS#: 434-03-7

Chemical Formula: C21H28O2

Exact Mass: 312.2089

Molecular Weight: 312.45

Elemental Analysis: C, 80.73; H, 9.03; O, 10.24

Price and Availability

Size Price Availability Quantity
1g USD 250.00 2 Weeks
5g USD 450.00 2 Weeks
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Related CAS #
No Data
Synonym
Aethisteron; 17α-Ethynyltestosterone; Pregneninolone; Etisterona; Progestoral; Ethisterone; NSC 9565; NSC-9565; NSC9565;
IUPAC/Chemical Name
(8R,9S,10R,13S,14S,17R)-17-ethynyl-17-hydroxy-10,13-dimethyl-1,2,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-3H-cyclopenta[a]phenanthren-3-one
InChi Key
CHNXZKVNWQUJIB-CEGNMAFCSA-N
InChi Code
InChI=1S/C21H28O2/c1-4-21(23)12-9-18-16-6-5-14-13-15(22)7-10-19(14,2)17(16)8-11-20(18,21)3/h1,13,16-18,23H,5-12H2,2-3H3/t16-,17+,18+,19+,20+,21+/m1/s1
SMILES Code
O=C1CC[C@]2(C)[C@@]3([H])CC[C@]4(C)[C@@](C#C)(O)CC[C@@]4([H])[C@]3([H])CCC2=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
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

Preparing Stock Solutions

The following data is based on the product molecular weight 312.45 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
1: Kumar D, Mishra KB, Mishra BB, Mondal S, Tiwari VK. Click chemistry inspired highly facile synthesis of triazolyl ethisterone glycoconjugates. Steroids. 2014 Feb;80:71-9. doi: 10.1016/j.steroids.2013.11.022. Epub 2013 Dec 5. PubMed PMID: 24316164. 2: Mishra KB, Mishra BB, Tiwari VK. Efficient synthesis of ethisterone glycoconjugate via bis-triazole linkage. Carbohydr Res. 2014 Nov 18;399:2-7. doi: 10.1016/j.carres.2014.09.001. Epub 2014 Sep 16. PubMed PMID: 25369262. 3: Guo WJ, Wang YT, Kong DX, Wang JY, Wei QH, Chen GN. Luminescent Ag6Au6 heterometallic ethisterone cluster and probe for estrogen receptor α. Chemistry. 2015 Mar 9;21(11):4205-8. doi: 10.1002/chem.201405925. Epub 2015 Jan 7. PubMed PMID: 25580911. 4: Levine PM, Lee E, Greenfield A, Bonneau R, Logan SK, Garabedian MJ, Kirshenbaum K. Androgen receptor antagonism by divalent ethisterone conjugates in castrate-resistant prostate cancer cells. ACS Chem Biol. 2012 Oct 19;7(10):1693-701. doi: 10.1021/cb300332w. Epub 2012 Aug 7. PubMed PMID: 22871957; PubMed Central PMCID: PMC3874888. 5: Ruiz J, Rodríguez V, Cutillas N, Espinosa A, Hannon MJ. Novel C,N-chelate platinum(II) antitumor complexes bearing a lipophilic ethisterone pendant. J Inorg Biochem. 2011 Apr;105(4):525-31. doi: 10.1016/j.jinorgbio.2010.12.005. Epub 2010 Dec 29. PubMed PMID: 21334280. 6: Szegvári D, Horváth P, Gergely A, Németh S, Görög S. CD spectrometric methods for the simultaneous determination of ethisterone and its delta5-isomer. Anal Bioanal Chem. 2003 Mar;375(5):713-7. Epub 2003 Feb 13. PubMed PMID: 12638059. 7: Beral V, Colwell L. Randomised trial of high doses of stilboestrol and ethisterone therapy in pregnancy: long-term follow-up of the children. J Epidemiol Community Health. 1981 Sep;35(3):155-60. PubMed PMID: 7035598; PubMed Central PMCID: PMC1052149. 8: Vance MA, Millington WR. Long-term follow-up of mothers who received high doses of stilboestrol and ethisterone in pregnancy. Br Med J. 1980 Dec 13;281(6255):1638. PubMed PMID: 7448547; PubMed Central PMCID: PMC1715108. 9: Ma X, Wang Q, Wang L, Huang Y, Liao X, Li H. Investigation on the Interaction of Norgestrel with Human Serum Albumin Using Spectroscopy and Molecular-Docking Method. J Biochem Mol Toxicol. 2016 Jun;30(6):287-94. doi: 10.1002/jbt.21790. Epub 2016 Jan 18. PubMed PMID: 26778492. 10: Beral V, Colwell L. Randomised trial of high doses of stilboestrol and ethisterone in pregnancy: long-term follow-up of mothers. Br Med J. 1980 Oct 25;281(6248):1098-101. PubMed PMID: 7000292; PubMed Central PMCID: PMC1714571. 11: Uwa H. The synthesis of collagen during the development of anal-fin processes in ethisterone-treated females of Oryzias latipes. Dev Growth Differ. 1971 Aug;13(2):119-24. PubMed PMID: 5117078. 12: Wang Y, Dehigaspitiya DC, Levine PM, Profit AA, Haugbro M, Imberg-Kazdan K, Logan SK, Kirshenbaum K, Garabedian MJ. Multivalent Peptoid Conjugates Which Overcome Enzalutamide Resistance in Prostate Cancer Cells. Cancer Res. 2016 Sep 1;76(17):5124-32. doi: 10.1158/0008-5472.CAN-16-0385. Epub 2016 Aug 3. PubMed PMID: 27488525; PubMed Central PMCID: PMC5010535. 13: MACGREGOR TN. Progesterone and ethisterone. Practitioner. 1958 Jan;180(1075):83-7. PubMed PMID: 13494335. 14: Uwa H. Hormonal inhibitions of ethisterone-induced process formation in adult females of the medaka, Oryzias latipes. Embryologia (Nagoya). 1968 Mar;10(2):147-54. PubMed PMID: 5692635. 15: Rose GL, Dowsett M, Mudge JE, White JO, Jeffcoate SL. The inhibitory effects of danazol, danazol metabolites, gestrinone, and testosterone on the growth of human endometrial cells in vitro. Fertil Steril. 1988 Feb;49(2):224-8. PubMed PMID: 3338580. 16: Uwa H. Changes in RNA-, DNA- and proteinsynthetic activity during the formation of analfin processes in ethisterone-treated females of Oryzias latipes. Dev Growth Differ. 1969 Oct;11(2):77-87. PubMed PMID: 5370066. 17: Kim JY, Choi MH, Kim SJ, Kyong JB, Chung BC. GC-MS characterization of urinary metabolites and changes of ethisterone and testosterone profile after oral administration of danazol in equine. J Vet Pharmacol Ther. 2001 Apr;24(2):147-53. PubMed PMID: 11442791. 18: Rodríguez-Molina B, Pozos A, Cruz R, Romero M, Flores B, Farfán N, Santillan R, Garcia-Garibay MA. Synthesis and solid state characterization of molecular rotors with steroidal stators: ethisterone and norethisterone. Org Biomol Chem. 2010 Jun 28;8(13):2993-3000. doi: 10.1039/c003778h. Epub 2010 May 12. PubMed PMID: 20464000. 19: Lim CE, Ho KK, Cheng NC, Wong FW. Combined oestrogen and progesterone for preventing miscarriage. Cochrane Database Syst Rev. 2013 Sep 25;(9):CD009278. doi: 10.1002/14651858.CD009278.pub2. Review. PubMed PMID: 24068368. 20: SALA PONSATI JM. [The gestagen, nor-ethisterone, in the treatment of sterility]. Acta Gynaecol Obstet Hisp Lusit. 1961;10:118-24. Spanish. PubMed PMID: 13745536.