Segesterone acetate | ST-1435 | nestorone | CAS#7759-35-5 | progesterone receptor agonist

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

MedKoo CAT#: 326796

CAS#: 7759-35-5 (acetate)

Description: Segesterone acetate, also known as ST-1435 or nestorone, is a progesterone receptor agonist, which is a potential female-contraceptive agent. Nestorone holds back proinflammatory mediators and neuropathology in the wobbler mouse model of motoneuron degeneration. Nestorone protected against hippocampus abnormalities and improved functional outcomes of EAE mice, suggesting its potential value for MS.

Chemical Structure

Segesterone acetate

CAS# 7759-35-5 (acetate)

Product data Instruction

Theoretical Analysis

MedKoo Cat#: 326796
Name: Segesterone acetate
CAS#: 7759-35-5 (acetate)
Chemical Formula: C23H30O4
Exact Mass: 370.21
Molecular Weight: 370.490
Elemental Analysis: C, 74.56; H, 8.16; O, 17.27

Price and Availability

Size	Price	Availability
5mg	USD 350	2 weeks
10mg	USD 500	2 weeks
50mg	USD 900	2 weeks
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.

Related CAS #: 7690-08-6 (free base) 7759-35-5 (acetate)

Synonym: ST-1435; ST1435; ST1435; Elcometrine; Nestorone; segesterone acetate; Annovera.

IUPAC/Chemical Name: (8R,9S,10R,13S,14S,17R)-17-acetyl-13-methyl-16-methylene-3-oxo-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl acetate

InChi Key: CKFBRGLGTWAVLG-GOMYTPFNSA-N

InChi Code: InChI=1S/C23H30O4/c1-13-11-21-20-7-5-16-12-17(26)6-8-18(16)19(20)9-10-22(21,4)23(13,14(2)24)27-15(3)25/h12,18-21H,1,5-11H2,2-4H3/t18-,19+,20+,21-,22-,23-/m0/s1

SMILES Code: CC([C@@]1(OC(C)=O)C(C[C@@]2([H])[C@]3([H])CCC4=CC(CC[C@]4([H])[C@@]3([H])CC[C@]12C)=O)=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: 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:

Product Data:

Product Data

Instruction:

View handling instruction

Biological target:	Segesterone acetate is a synthetic progestin that binds to the progesterone receptor (EC50 = 50.3 nM). It also binds to the glucocorticoid receptor (EC50 = 56 nM) but does not have in vivo glucocorticoid activity.
In vitro activity:	To be determined
In vivo activity:	This study demonstrated that stand-alone treatments of Nestorone or human amniotic fluid-derived stem cells (hAFSc) led to significant improvements in behavioral function and reductions in infarction and peri-infarct cell loss in adult rats with ischemic stroke. There were significantly lower levels of pro-inflammatory signals and enhanced levels of stem cell proliferation and differentiation in the brains and spleens of stroke rats treated with stand-alone or combined Nestorone and hAFSc. Reference: Free Radic Biol Med. 2022 Apr;183:138-145. https://pubmed.ncbi.nlm.nih.gov/35341914/

Solubility Data

	Solvent	Max Conc. mg/mL	Max Conc. mM
Solubility
	DMSO	33.3	89.96

Preparing Stock Solutions

The following data is based on the product molecular weight 370.49 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. Lee JY, Castelli V, Kumar N, Sitruk-Ware R, Borlongan CV. Contraceptive drug, Nestorone, enhances stem cell-mediated remodeling of the stroke brain by dampening inflammation and rescuing mitochondria. Free Radic Biol Med. 2022 Apr;183:138-145. doi: 10.1016/j.freeradbiomed.2022.03.020. Epub 2022 Mar 25. PMID: 35341914. 2. Fréchou M, Zhu X, Kumar N, Sitruk-Ware R, Schumacher M, Mattern C, Guennoun R. Sex differences in the cerebroprotection by Nestorone intranasal delivery following stroke in mice. Neuropharmacology. 2021 Oct 15;198:108760. doi: 10.1016/j.neuropharm.2021.108760. Epub 2021 Aug 23. PMID: 34437904.
In vitro protocol:	To be de1. Lee JY, Castelli V, Kumar N, Sitruk-Ware R, Borlongan CV. Contraceptive drug, Nestorone, enhances stem cell-mediated remodeling of the stroke brain by dampening inflammation and rescuing mitochondria. Free Radic Biol Med. 2022 Apr;183:138-145. doi: 10.1016/j.freeradbiomed.2022.03.020. Epub 2022 Mar 25. PMID: 35341914. 2. Fréchou M, Zhu X, Kumar N, Sitruk-Ware R, Schumacher M, Mattern C, Guennoun R. Sex differences in the cerebroprotection by Nestorone intranasal delivery following stroke in mice. Neuropharmacology. 2021 Oct 15;198:108760. doi: 10.1016/j.neuropharm.2021.108760. Epub 2021 Aug 23. PMID: 34437904.termined
In vivo protocol:

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1: Nelson AL. Comprehensive overview of the recently FDA-approved contraceptive vaginal ring releasing segesterone acetate and ethinylestradiol: A new year-long, patient controlled, reversible birth control method. Expert Rev Clin Pharmacol. 2019 Oct;12(10):953-963. doi: 10.1080/17512433.2019.1669448. Epub 2019 Oct 1. Review. PubMed PMID: 31526281.

2: Vieira CS, Fraser IS, Plagianos MG, Burke AE, Westhoff CL, Jensen J, Brache V, Bahamondes L, Merkatz R, Sitruk-Ware R, Blithe DL. Bleeding profile associated with 1-year use of the segesterone acetate/ethinyl estradiol contraceptive vaginal system: pooled analysis from Phase 3 trials. Contraception. 2019 Dec;100(6):438-444. doi: 10.1016/j.contraception.2019.07.145. Epub 2019 Aug 6. PubMed PMID: 31398307; PubMed Central PMCID: PMC6893119.

3: Paton DM. Contraceptive vaginal ring containing segesterone acetate and ethinyl estradiol: long-acting, patient-controlled, procedure-free, reversible prescription birth control. Drugs Today (Barc). 2019 Jul;55(7):449-457. doi: 10.1358/dot.2019.55.7.2965363. PubMed PMID: 31347613.

4: Archer DF, Merkatz RB, Bahamondes L, Westhoff CL, Darney P, Apter D, Jensen JT, Brache V, Nelson AL, Banks E, Bártfai G, Portman DJ, Plagianos M, Dart C, Kumar N, Creasy GW, Sitruk-Ware R, Blithe DL. Efficacy of the 1-year (13-cycle) segesterone acetate and ethinylestradiol contraceptive vaginal system: results of two multicentre, open-label, single-arm, phase 3 trials. Lancet Glob Health. 2019 Aug;7(8):e1054-e1064. doi: 10.1016/S2214-109X(19)30265-7. Epub 2019 Jun 20. PubMed PMID: 31231065; PubMed Central PMCID: PMC6624423.

5: Gemzell-Danielsson K, Sitruk-Ware R, Creinin MD, Thomas M, Barnhart KT, Creasy G, Sussman H, Alami M, Burke AE, Weisberg E, Fraser I, Miranda MJ, Gilliam M, Liu J, Carr BR, Plagianos M, Roberts K, Blithe D. Segesterone acetate/ethinyl estradiol 12-month contraceptive vaginal system safety evaluation. Contraception. 2019 Jun;99(6):323-328. doi: 10.1016/j.contraception.2019.02.001. Epub 2019 Mar 1. PubMed PMID: 30831102.

6: Chen S, Kumar N, Mao Z, Sitruk-Ware R, Brinton RD. Therapeutic progestin segesterone acetate promotes neurogenesis: implications for sustaining regeneration in female brain. Menopause. 2018 Oct;25(10):1138-1151. doi: 10.1097/GME.0000000000001135. PubMed PMID: 29846284.

7: Simmons KB, Kumar N, Plagianos M, Roberts K, Hoskin E, Han L, Alami M, Creasy G, Variano B, Merkatz R. Effects of concurrent vaginal miconazole treatment on the absorption and exposure of Nestorone® (segesterone acetate) and ethinyl estradiol delivered from a contraceptive vaginal ring: a randomized, crossover drug-drug interaction study. Contraception. 2018 Mar;97(3):270-276. doi: 10.1016/j.contraception.2017.10.010. Epub 2017 Oct 31. PubMed PMID: 29097225.

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