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Merck
CN

SML0550

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
NACRES:
NA.77
PubChem Substance ID:
329825546
UNSPSC Code:
51111800
MDL number:
MFCD01711303

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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 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 key

CKFBRGLGTWAVLG-GOMYTPFNSA-N

assay

≥97% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 5 mg/mL, clear

storage temp.

2-8°C

Quality Level

100

Gene Information

human ... PGR(5241)

Biochem/physiol Actions

Nestorone is a potent progesterone receptor agonist with no androgenic, estrogenic, or glucocorticoid-like activities.
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

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
0000362346
0000362346
0000126605
0000126605
0000175163

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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
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
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
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
Mandana Rad et al.
American journal of obstetrics and gynecology, 195(1), 72-77 (2006-03-21)
This study aimed to compare the effects on hemostasis variables of a contraceptive vaginal ring with those of an oral contraceptive. Twenty-three and 22 healthy premenopausal women were randomized to the contraceptive vaginal ring (150 microg Nestorone and 15 microg
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