MedKoo Biosciences

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

MedKoo CAT#: 540158

CAS#: 16320-04-0

Description: Gestrinone is a synthetic androgen receptor agonist and ER and progesterone receptor antagonist used to treat endometriosis. It also downregulates expression of the progesterone receptor, estrogen receptor, and p-Src, inhibiting growth of uterine leiomyoma cells.

Chemical Structure

Gestrinone

CAS# 16320-04-0

Product data Instruction

Theoretical Analysis

MedKoo Cat#: 540158
Name: Gestrinone
CAS#: 16320-04-0
Chemical Formula: C21H24O2
Exact Mass: 308.18
Molecular Weight: 308.420
Elemental Analysis: C, 81.78; H, 7.84; O, 10.37

Price and Availability

Size	Price	Availability	Quantity
50mg	USD 350
100mg	USD 550
200mg	USD 950
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. MedKoo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

Synonym: A 46 745; A46745; A-46-745; Dimetriose; Ethylnorgestrienone; R 2323; R2323; R-2323

IUPAC/Chemical Name: (8S,13S,14S,17S)-13-ethyl-17-ethynyl-17-hydroxy-1,2,6,7,8,13,14,15,16,17-decahydro-3H-cyclopenta[a]phenanthren-3-one

InChi Key: BJJXHLWLUDYTGC-IVAOSVALSA-N

InChi Code: InChI=1S/C21H24O2/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/h2,9,11,13,18-19,23H,3,5-8,10,12H2,1H3/t18-,19+,20+,21-/m1/s1

SMILES Code: C#C[C@@]1(O)CC[C@@]2([H])[C@]3([H])CCC4=CC(CCC4=C3C=C[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

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

Product Data:

Product Data

Instruction:

View handling instruction

Biological target:	Gestrinone (R2323) is a synthetic steroid hormone used to treat endometriosis. It inhibits leiomyoma cells with an IC50 of 43.67 μM.
In vitro activity:	The IC50 values of gestrinone in HeLa cells were 2.09 and 0.17 μM at 48 and 72 hours, respectively. The cell viability of other gynecological cancer cell lines was slightly reduced (Fig 2 E, F). Flow cytometry analysis revealed that almost 20% of HeLa cells arrested in the sub-G1 phase after treatment with 2.5 μM gestrinone for 48 hours (Fig 2 E–H). This indicates that gestrinone induces apoptosis and decreases the viability of HeLa cervical cancer cells. Reference: Transl Res. 2022 May;243:21-32. https://pubmed.ncbi.nlm.nih.gov/34921996/
In vivo activity:	TBD

Solubility Data

	Solvent	Max Conc. mg/mL	Max Conc. mM
Solubility
	DMF	20.0	64.85
	DMSO	35.0	113.48
	Ethanol	20.0	64.85
	Ethanol:PBS (pH 7.2) (1:5)	0.3	81.06
	Water	1.0	3.24

Preparing Stock Solutions

The following data is based on the product molecular weight 308.420000000000000000000000000000 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.

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. Ciou HH, Lee TH, Wang HC, Ding YR, Tseng CJ, Wang PH, Tsai MH, Tzeng SL. Repurposing gestrinone for tumor suppressor through P21 reduction regulated by JNK in gynecological cancer. Transl Res. 2022 May;243:21-32. doi: 10.1016/j.trsl.2021.12.002. Epub 2021 Dec 16. PMID: 34921996.
In vitro protocol:	1. Ciou HH, Lee TH, Wang HC, Ding YR, Tseng CJ, Wang PH, Tsai MH, Tzeng SL. Repurposing gestrinone for tumor suppressor through P21 reduction regulated by JNK in gynecological cancer. Transl Res. 2022 May;243:21-32. doi: 10.1016/j.trsl.2021.12.002. Epub 2021 Dec 16. PMID: 34921996.
In vivo protocol:	TBD

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1: Wu X, Xu Y. Gestrinone combined with ultrasound-guided aspiration and ethanol injection for treatment of chocolate cyst of ovary. J Obstet Gynaecol Res. 2015 May;41(5):712-6. doi: 10.1111/jog.12612. Epub 2014 Nov 25. PubMed PMID: 25420776. 2: Zhu Y, Zhang T, Xie S, Tu R, Cao Y, Guo X, Zhou J, Zhou X, Cao L. Gestrinone inhibits growth of human uterine leiomyoma may relate to activity regulation of ERα, Src and P38 MAPK. Biomed Pharmacother. 2012 Dec;66(8):569-77. doi: 10.1016/j.biopha.2012.02.003. Epub 2012 Mar 27. PubMed PMID: 23102719. 3: Duan H, Wang S, Hao M, Chen L, Tang J, Wang X, Peng YZ, Zhang SC, Cao LR, Yu JJ. [Research of gestrinone-related abnormal uterine bleeding and the intervention in the treatment: a multi-center, randomized, controlled clinical trial]. Zhonghua Fu Chan Ke Za Zhi. 2016 Feb;51(2):98-102. doi: 10.3760/cma.j.issn.0529-567X.2016.02.004. Chinese. PubMed PMID: 26917477. 4: Wu S, Dong J, Cong J, Wang C, VonHertzen H, Godfrey EM. Gestrinone compared with mifepristone for emergency contraception: a randomized controlled trial. Obstet Gynecol. 2010 Apr;115(4):740-4. doi: 10.1097/AOG.0b013e3181d43ae4. PubMed PMID: 20308833. 5: Brun EM, Hernández-Albors A, Ventura R, Puchades R, Maquieira A. Enzyme-linked immunosorbent assays for the synthetic steroid gestrinone. Talanta. 2010 Sep 15;82(4):1581-7. doi: 10.1016/j.talanta.2010.07.067. Epub 2010 Aug 3. PubMed PMID: 20801376. 6: Xue HL, Yu N, Wang J, Hao WJ, Li Y, Liu MY. Therapeutic effects of mifepristone combined with Gestrinone on patients with endometriosis. Pak J Med Sci. 2016 Sep-Oct;32(5):1268-1272. PubMed PMID: 27882034; PubMed Central PMCID: PMC5103146. 7: Coutinho EM. Gestrinone in the treatment of myomas. Acta Obstet Gynecol Scand Suppl. 1989;150:39-46. PubMed PMID: 2694740. 8: Utsunomiya T, Sumioki H, Korenaga S, Matsuoka K, Korenga M, Kadota T. [Laparoscopic diagnosis and evaluation of danazol or gestrinone therapy for endometriosis in sterility]. Nihon Sanka Fujinka Gakkai Zasshi. 1988 Apr;40(4):459-66. Japanese. PubMed PMID: 2967341. 9: Fedele L, Bianchi S, Viezzoli T, Arcaini L, Candiani GB. Gestrinone versus danazol in the treatment of endometriosis. Fertil Steril. 1989 May;51(5):781-5. PubMed PMID: 2523321. 10: Ohno Y, Kitagawa I, Tamura H, Hosoda S, Yamashita S, Honjo H, Okada H. Antiestrogenic effect of gestrinone as an inhibitor of [3H]-estradiol binding to nuclear type II sites. Gynecol Obstet Invest. 1991;31(2):97-101. PubMed PMID: 2037266. 11: Peters F. Multicentre study of gestrinone in cyclical breast pain. Lancet. 1992 Jan 25;339(8787):205-8. PubMed PMID: 1346172. 12: Thomas EJ, Cooke ID. Impact of gestrinone on the course of asymptomatic endometriosis. Br Med J (Clin Res Ed). 1987 Jan 31;294(6567):272-4. PubMed PMID: 3101839; PubMed Central PMCID: PMC1245293. 13: Forbes KL, Thomas FJ. Tissue and endocrine responses to gestrinone and danazol in the treatment of endometriosis. Reprod Fertil Dev. 1993;5(1):103-9. PubMed PMID: 8234886. 14: Tamaya T, Fujimoto J, Watanabe Y, Arahori K, Okada H. Gestrinone (R2323) binding to steroid receptors in human uterine endometrial cytosol. Acta Obstet Gynecol Scand. 1986;65(5):439-41. PubMed PMID: 3490730. 15: Zheng P, Zhang YF, Wang JD. [Effect of gestrinone on the lipid metabolic parameters and bone mineral density in patients with endometriosis]. Zhonghua Fu Chan Ke Za Zhi. 2005 Mar;40(3):175-7. Chinese. PubMed PMID: 15840312. 16: Triolo O, De Vivo A, Benedetto V, Falcone S, Antico F. Gestrinone versus danazol as preoperative treatment for hysteroscopic surgery: a prospective, randomized evaluation. Fertil Steril. 2006 Apr;85(4):1027-31. PubMed PMID: 16580390. 17: Gestrinone versus a gonadotropin-releasing hormone agonist for the treatment of pelvic pain associated with endometriosis: a multicenter, randomized, double-blind study. Gestrinone Italian Study Group. Fertil Steril. 1996 Dec;66(6):911-9. PubMed PMID: 8941054. 18: Ortega FJ, Bañuls MJ, Sanza FJ, Casquel R, Laguna MF, Holgado M, López-Romero D, Barrios CA, Maquieira Á, Puchades R. Biomolecular Interaction Analysis of Gestrinone-anti-Gestrinone Using Arrays of High Aspect Ratio SU-8 Nanopillars. Biosensors (Basel). 2012 Aug 14;2(3):291-304. doi: 10.3390/bios2030291. PubMed PMID: 25585931; PubMed Central PMCID: PMC4263551. 19: Gao X, Wu E, Chen G. Mechanism of emergency contraception with gestrinone: a preliminary investigation. Contraception. 2007 Sep;76(3):221-7. Epub 2007 Jul 26. PubMed PMID: 17707720. 20: Quereda F, Barroso J, Acién P. Individual and combined effects of triptoreline and gestrinone on experimental endometriosis in rats. Eur J Obstet Gynecol Reprod Biol. 1996 Jul;67(1):35-40. PubMed PMID: 8789747.

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