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Details

Stereochemistry ABSOLUTE
Molecular Formula C20H25NO2
Molecular Weight 311.418
Optical Activity UNSPECIFIED
Defined Stereocenters 4 / 4
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DIENOGEST

SMILES

[H][C@@]12CC[C@@](O)(CC#N)[C@@]1(C)CCC3=C4CCC(=O)C=C4CC[C@@]23[H]

InChI

InChIKey=AZFLJNIPTRTECV-FUMNGEBKSA-N
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

HIDE SMILES / InChI

Molecular Formula C20H25NO2
Molecular Weight 311.418
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 4 / 4
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

Dienogest (Natazia) is a hybrid progestogen that combines properties of both the 19-nortestosterone derivatives and the progesterone derivatives. It is indicated for use by women to prevent pregnancy and for the treatment of heavy menstrual bleeding in women without organic pathology. Dienogest is also approved in Europe, Australia, Malaysia, Singapore and Japan for the treatment of endometriosis. It is lowers the risk of becoming pregnant primarily by suppressing ovulation. Other possible mechanisms may include cervical mucus changes that inhibit sperm penetration and endometrial changes that reduce the likelihood of implantation. Dienogest exhibits highly selective binding to the progesterone receptor. It has high progestational and significant antiandrogenic activity, but only moderate antigonadotrophic activity. The most common adverse reactions in clinical trials for Natazia are headache (including migraines), breast pain, menstrual disorders, nausea or vomiting, acne, mood changes and increased weight.

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
3.4 nM [EC50]
950.0 nM [IC50]
7.97 µM [IC50]
420.0 nM [EC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
NATAZIA
Preventing
NATAZIA
Primary
NATAZIA

Cmax

ValueDoseCo-administeredAnalytePopulation
85.2 ng/mL
3 mg 1 times / day steady-state, oral
DIENOGEST plasma
Homo sapiens
110.41 ng/mL
2 mg single, oral
DIENOGEST plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
828 ng × h/mL
3 mg 1 times / day steady-state, oral
DIENOGEST plasma
Homo sapiens
1827.014 ng × h/mL
2 mg single, oral
DIENOGEST plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
12.3 h
3 mg 1 times / day steady-state, oral
DIENOGEST plasma
Homo sapiens
14.82 h
2 mg single, oral
DIENOGEST plasma
Homo sapiens

Funbound

ValueDoseCo-administeredAnalytePopulation
10%
3 mg 1 times / day steady-state, oral
DIENOGEST plasma
Homo sapiens

Doses

Drug as perpetrator​

Drug as victim

Tox targets

PubMed

Sample Use Guides

In Vivo Use Guide
One tablet daily by mouth at the same time every day. Tablets must be taken in the order directed on the blister pack. Do not skip or delay intake by more than 12 hours.
Route of Administration: Oral
In Vitro Use Guide
After 12 days in the presence of oestradiol (10(-8) mol/l) plus dienogest (10(-6) mol/l), cultured human endometrial stromal cells underwent morphological differentiation and produced prolactin, a typical marker for decidualization.
Substance Class Chemical
Record UNII
46M3EV8HHE
Record Status Validated (UNII)
Record Version