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SML0550

Sigma-Aldrich

Nestorone

≥97% (HPLC)

Synonym(s):

17-(Acetyloxy)-16-methylene-19-norpregn-4-ene-3,20-dione, 17-Hydroxy-16-methylene-19-norpregn-4-ene-3,20-dione acetate, Elcometrine, Nestoron, ST-1435, ST1435

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About This Item

Empirical Formula (Hill Notation):
C23H30O4
CAS Number:
7759-35-5
Molecular Weight:
370.48
MDL number:
MFCD01711303
UNSPSC Code:
51111800
PubChem Substance ID:
329825546
NACRES:
NA.77

Quality Level

100

Assay

≥97% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 5 mg/mL, clear

storage temp.

2-8°C

SMILES string

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

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

InChI key

CKFBRGLGTWAVLG-GOMYTPFNSA-N

Gene Information

human ... PGR(5241)

Biochem/physiol Actions

Nestorone is a potent progesterone receptor agonist with no androgenic, estrogenic, or glucocorticoid-like activities. Nestorone has been used as a female contraceptive, and recent studies inidicate that it may be useful as a male contraceptive as well. It has also been shown to have neurogenic and neuroprotective activity.

Features and Benefits

This compound is featured on the Nuclear Receptors (Steroids) page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Vahid Mahabadi et al.
The Journal of clinical endocrinology and metabolism, 94(7), 2313-2320 (2009-04-16)
Testosterone (T) plus progestin combinations are the most promising hormonal male contraceptives. Nestorone (NES), a progestin without estrogenic or androgenic activity, when combined with T may be an excellent candidate for male contraception. Our objective was to determine the effect
Irving Sivin et al.
Contraception, 69(2), 137-144 (2004-02-05)
A 2-year trial of a single Nestorone (NES) rod implant was conducted at three Latin American centers, each enrolling 100 women. We studied the safety, effectiveness and acceptability of this progestin-releasing contraceptive implant. Three pregnancies occurred, the last at 18
Regine Sitruk-Ware
Human reproduction update, 12(2), 169-178 (2005-11-18)
The progestins have different pharmacologic properties depending upon the parent molecule, usually testosterone or progesterone (P), from which they are derived. Very small structural changes in the parent molecule may induce considerable differences in the activity of the derivative. In
Edith Weisberg et al.
Contraception, 72(1), 46-52 (2005-06-21)
We examined the clinical performance of contraceptive vaginal rings (rings) delivering Nestorone (NES) progestin and ethinyl estradiol (EE). Ring removal times were signaled by menstrual events. Bleeding patterns, adverse events, patterns of use and continuation rates were the principal parameters
E Lenzi et al.
The Journal of steroid biochemistry and molecular biology, 116(1-2), 15-20 (2009-04-23)
The aim of the present study was to evaluate the potential action of Nestorone (alone or in combination with estradiol valerate) on the level of allopregnanolone and of the opioid beta-endorphin in selected brain areas. Wistar ovariectomized rats were given
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