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Key Documents

SML1468

Sigma-Aldrich

Dienogest

≥98% (HPLC)

Synonym(s):

(17a)-17-Hydroxy-3-oxo-19-norpregna-4,9-diene-21-nitrile, 17-Hydroxy-3-oxo-19-norpregna-4,9-diene-21-nitrile, 17-cyanomethyl-17-hydroxy-estra-4,9-dien-3-one

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About This Item

Empirical Formula (Hill Notation):
C20H25NO2
CAS Number:
Molecular Weight:
311.42
MDL number:
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.77

Quality Level

Assay

≥98% (HPLC)

form

powder

optical activity

[α]/D -305 to -325°, c = 1 in dichloromethane

color

white to beige

solubility

DMSO: 5 mg/mL, clear (warmed)

storage temp.

2-8°C

SMILES string

O[C@@]1(CC#N)CC[C@@]2([H])[C@]3([H])CCC4=CC(CCC4=C3CC[C@@]21C)=O

InChI

1S/C20H25NO2/c1-19-8-6-16-15-5-3-14(22)12-13(15)2-4-17(16)18(19)7-9-20(19,23)10-11-21/h12,17-18,23H,2-10H2,1H3/t17-,18+,19+,20-/m1/s1

InChI key

AZFLJNIPTRTECV-FUMNGEBKSA-N

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Biochem/physiol Actions

Dienogest is a fourth-generation progestin, an orally active synthetic progestogen with approximately 10% of the relative affinity of progesterone, but has a very potent progestagenic effect in the endometrium with some antiandrogenic activity and without any androgenic, glucocorticoid or mineralocorticoid effects. It has been used alone or in combination as a contraceptive and to treat uterine fibroids. Dienogest inhibits ovulation primarily through peripheral action rather than by central action on gonadotrophin secretion.
Dienogest is used to treat endometriosis. It might also help to decrease the levels of plasma estradiol by stimulating cell death of granulosa cells in the ovary.

Pictograms

Health hazard

Signal Word

Warning

Hazard Statements

Hazard Classifications

Repr. 2

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable


Certificates of Analysis (COA)

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Adolf E Schindler
International journal of women's health, 3, 175-184 (2011-07-28)
Endometriosis is a chronic disease primarily affecting women of childbearing age, in which endometriotic lesions form outside the uterus, typically leading to painful symptoms, fatigue, and infertility. The symptoms of endometriosis may cause significant impairment in quality of life and

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