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SML2321

Sigma-Aldrich

Gestrinone

≥97% (HPLC)

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Synonym(s):
(17α)-13-Ethyl-17-hydroxy-18,19-dinorpregna-4,9,11-trien-20-yn-3-one, Ethylnorgestrienone, R-2323, R2323, RU-2323
Empirical Formula (Hill Notation):
C21H24O2
CAS Number:
16320-04-0
Molecular Weight:
308.41
MDL number:
MFCD00865561
UNSPSC Code:
12352200
NACRES:
NA.77

Assay

≥97% (HPLC)

form

powder

optical activity

[α]/D +81 to +88°, c = 0.4 in ethanol

color

white to beige

solubility

DMSO: 2 mg/mL, clear

storage temp.

2-8°C

SMILES string

O[C@@]1(C#C)CC[C@@]2([H])[C@]3([H])CCC4=CC(CCC4=C3C=C[C@@]21CC)=O

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

InChI key

BJJXHLWLUDYTGC-ANULTFPQSA-N

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Biochem/physiol Actions

Gestrinone is a synthetic steroid, an analog of norgestrienone, which exhibits androgenic, anti-estrogenic and anti-progestogenic activities. Gestrinone is used for treatment of endometriosis.

Pictograms

Health hazard
GHS08

Signal Word

Warning

Hazard Statements

H361fd

Hazard Classifications

Repr. 2

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Regulatory Information

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Yan Zhu et al.
Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie, 66(8), 569-577 (2012-10-30)
The study was to investigate the effect of gestrinone on the growth of human uterine leiomyoma cells and on the levels and activity of p38, Src and estrogen receptor alpha (ERα). Human uterine leiomyoma cells were cultured and treated with
T Tamaya et al.
Acta obstetricia et gynecologica Scandinavica, 65(5), 439-441 (1986-01-01)
To understand the mechanism of biological action of gestrinone (R2323), which has a therapeutic effect against endometriosis, the binding of gestrinone to numerous classes of intracellular steroid binding proteins was studied in the human uterine endometrium. Gestrinone bound to endometrial
Alison K Death et al.
The Journal of clinical endocrinology and metabolism, 89(5), 2498-2500 (2004-05-06)
Tetrahydrogestrinone (THG) was recently identified as a novel steroid used illicitly to improve athletic performance. Although its structure is closely related to gestrinone, a 19-nor progestin, and resembles that of trenbolone, THG was never marketed, so information on its hormonal

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