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

MedKoo Cat#: 326796 | Name: Segesterone acetate

Featured

Description:

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

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)

Theoretical Analysis

MedKoo Cat#: 326796

Name: Segesterone acetate

CAS#: 7759-35-5 (acetate)

Chemical Formula: C23H30O4

Exact Mass: 370.2144

Molecular Weight: 370.49

Elemental Analysis: C, 74.56; H, 8.16; O, 17.27

Price and Availability

Size	Price	Availability
5mg	USD 350.00	2 weeks
10mg	USD 500.00	2 weeks
50mg	USD 900.00	2 weeks

Bulk Inquiry

Buy Now

Add to Cart

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/

	Solvent	mg/mL	mM	comments
Solubility
	DMSO	33.3	89.96

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

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:

1: Drugs and Lactation Database (LactMed®) [Internet]. Bethesda (MD): National Institute of Child Health and Human Development; 2006–. Segesterone Acetate. 2024 Aug 15. PMID: 30371999. 2: Lee AL. Segesterone Acetate and Ethinyl Estradiol Vaginal Ring (Annovera) for Contraception. Am Fam Physician. 2020 May 15;101(10):618-620. PMID: 32412221. 3: Sitruk-Ware R, Sussman H, Brinton R, Schumacher M, Singer P, Kumar N, De Nicola AF, El-Etr M, Guennoun R, V Borlongan C. Nestorone (segesterone acetate) effects on neuroregeneration. Front Neuroendocrinol. 2024 Apr;73:101136. doi: 10.1016/j.yfrne.2024.101136. Epub 2024 Apr 25. PMID: 38670433. 4: Thirumalai A, Amory JK. Emerging approaches to male contraception. Fertil Steril. 2021 Jun;115(6):1369-1376. doi: 10.1016/j.fertnstert.2021.03.047. Epub 2021 Apr 27. PMID: 33931201; PMCID: PMC8169637. 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. PMID: 30831102; PMCID: PMC7357828. 6: Micks EA, Jensen JT. A technology evaluation of Annovera: a segesterone acetate and ethinyl estradiol vaginal ring used to prevent pregnancy for up to one year. Expert Opin Drug Deliv. 2020 Jun;17(6):743-752. doi: 10.1080/17425247.2020.1764529. Epub 2020 May 15. PMID: 32410464. 7: 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. PMID: 31526281. 8: Jensen JT, Archer DF, Westhoff CL, Nelson AL, Graham S, Bernick B. Satisfaction with a Segesterone Acetate and Ethinyl Estradiol Contraceptive Vaginal System Among Recent Oral Contraceptive or Hormonal Contraceptive Vaginal Ring Users. J Womens Health (Larchmt). 2023 Jul;32(7):808-815. doi: 10.1089/jwh.2022.0264. Epub 2023 May 29. PMID: 37253139. 9: Amory JK, Blithe DL, Sitruk-Ware R, Swerdloff RS, Bremner WJ, Dart C, Liu PY, Thirumalai A, Nguyen BT, Anawalt BD, Lee MS, Page ST, Wang C. Design of an international male contraceptive efficacy trial using a self-administered daily transdermal gel containing testosterone and segesterone acetate (Nestorone). Contraception. 2023 Aug;124:110064. doi: 10.1016/j.contraception.2023.110064. Epub 2023 May 18. PMID: 37210024. 10: Thompson RL, Hu J, Custodio P, Dart C, Jensen JT. The use of serum segesterone acetate levels to assess adherence of trial participants with a contraceptive vaginal ring. Contraception. 2022 Apr;108:61-64. doi: 10.1016/j.contraception.2021.12.004. Epub 2021 Dec 28. PMID: 34971614. 11: Erikson DW, Blue SW, Fecteau KM, Edelman AB, Jensen JT, Blithe DL. Simultaneous assay of segesterone acetate (Nestorone®), estradiol, progesterone, and estrone in human serum by LC-MS/MS. Contraception. 2020 Nov;102(5):361-367. doi: 10.1016/j.contraception.2020.08.006. Epub 2020 Aug 21. PMID: 32828731; PMCID: PMC7606573. 12: Aragon FFH, Haeck CM, Morais PC, Variano B. Polymorphism characterization of segesterone acetate: A comprehensive study using XRPD, FT-IR and Raman spectroscopy. Int J Pharm. 2021 Mar 1;596:120234. doi: 10.1016/j.ijpharm.2021.120234. Epub 2021 Jan 21. PMID: 33484926. 13: Liu JH, Plagianos M, Archer DF, Simon JA, Kaunitz AM, Graham S, Bernick B, Mirkin S. Segesterone acetate serum levels with a regression model of continuous use of the segesterone acetate/ethinyl estradiol contraceptive vaginal system. Contraception. 2021 Sep;104(3):229-234. doi: 10.1016/j.contraception.2021.03.024. Epub 2021 Mar 27. PMID: 33785318. 14: Kaufman MB. Pharmaceutical Approval Update. P T. 2018 Nov;43(11):659-661. PMID: 30410280; PMCID: PMC6205122. 15: 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. PMID: 29846284; PMCID: PMC7731586. 16: Chen MJ, Creinin MD, Turok DK, Archer DF, Barnhart KT, Westhoff CL, Thomas MA, Jensen JT, Variano B, Sitruk-Ware R, Shanker A, Long J, Blithe DL. Dose- finding study of a 90-day contraceptive vaginal ring releasing estradiol and segesterone acetate. Contraception. 2020 Sep;102(3):168-173. doi: 10.1016/j.contraception.2020.05.004. Epub 2020 May 19. Erratum in: Contraception. 2020 Dec;102(6):433. doi: 10.1016/j.contraception.2020.09.004. PMID: 32416145; PMCID: PMC7483386. 17: 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. PMID: 31231065; PMCID: PMC6624423. 18: 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. PMID: 31347613. 19: Al-Haddad S, Branham KKR, Clare CA. Advances in contraception: vaginal contraceptive rings. Ther Adv Reprod Health. 2023 Jul 14;17:26334941231186733. doi: 10.1177/26334941231186733. PMID: 37465002; PMCID: PMC10350750. 20: Louwagie EJ, Quinn GFL, Pond KL, Hansen KA. Male contraception: narrative review of ongoing research. Basic Clin Androl. 2023 Nov 9;33(1):30. doi: 10.1186/s12610-023-00204-z. PMID: 37940863; PMCID: PMC10634021.