Dienogest

Dienogest is an orally active synthetic progesterone (or progestin). It is available for use as an oral contraceptive in combination with ethinylestradiol. It has antiandrogenic activity and as a result can improve androgenic symptoms. It is a non-ethinylated progestin which is structurally related to testosterone. Dienogest given in isolation is available for the treatment of endometriosis under the trade name Visanne.

Product information

CAS Number: 65928-58-7

Molecular Weight: 311.42

Formula: C20H25NO2

Synonym:

BAY86-5258

BAY 86-5258

BAY-86-5258

Dinagest

Endometrion

M 18575

MJR-35

STS 557

Visanne

ZK 37659

Chemical Name: 2-((8S, 13S, 14S, 17R)-17-hydroxy-13-methyl-3-oxo-2, 3, 6, 7, 8, 11, 12, 13, 14, 15, 16, 17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl)acetonitrile

Smiles: C[C@]12CCC3[C@@H](CCC4=CC(=O)CCC4=3)[C@@H]1CC[C@@]2(O)CC#N

InChiKey: AZFLJNIPTRTECV-FUMNGEBKSA-N

InChi: 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

Technical Data

Appearance: Solid Power

Purity: ≥98% (or refer to the Certificate of Analysis)

Solubility: DMSO: 62 mg/mL(199.08 mM). Water: Insoluble.

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical or refer to Certificate of Analysis

Storage Condition: Dry, dark and -20 ^oC for 1 year or refer to the Certificate of Analysis.

Shelf Life: ≥12 months if stored properly.

Stock Solution Storage: 0 - 4 ^oC for 1 month or refer to the Certificate of Analysis.

Drug Formulation: To be determined

HS Tariff Code: 382200

How to use

In Vitro:

Dienogest activates progesterone receptor (EC50=3.4 or 10.5 nM) with antagonistic activity on androgen receptor (EC50=420.6 or 775.0 nM) but not agonistic nor antagonistic action on GR, MR (3000 nM). Dienogest combined with Oestradiol leads to an increase in the levels of prolactin mRNA and prolactin production in a dose-dependent manner in human endometrial stromal cells (ESC). Dienogest directly acts on endometrial tissue in progestogenic response, such as decidualization, increases prolactin production and growth retardation. Dienogest at concentration of 0.1 μM and 1 μM significantly inhibits BrdU incorporation into DNA at 24 and 48 hours in the cultured endometriotic stromal cells. Dienogest significantly increases the cells in G0/G1 phase and reduces the cells in S phase and G2/M phase in 24 and 48 hours in the cultured endometriotic stromal cells.

In Vivo:

Dienogest (0.1-1 mg/kg per day, p.o.) reduces the endometrial implant volume to the same extent as Danazol (100 mg/kg per day, p.o.) in rats. Dienogest ameliorates the endometrial implant-induced alterations of the immune system: i.e. it increases the natural killer activity of peritoneal fluid cells and splenic cells, decreases the number of peritoneal fluid cells, and decreases interleukin-1beta production by peritoneal macrophages. Dienogest (0.1 mg/kg per day) combined with Buserelin (0.3 mg/kg per day) suppresses the bone mineral loss induced by buserelin alone, with no reduction of the effect on endometrial implants.

References:

1. Fu L, et al. Fertil Steril, 2008, 89(5 Suppl), 1344-1347.
2. Okada H, et al. Mol Hum Reprod, 2001, 7(4), 341-347.
3. Sasagawa S, et al. Steroids, 2008, 73(2), 222-231.

Products are for research use only. Not for human use.