General
Preferred name
DIENOGEST
Synonyms
Dienogestril ()
Dinagest ()
Oestradiol valerate and dienogest ()
STS 557 ()
Dienogest ()
ZK-37659 ()
M-18575 ()
M 18575 ()
ZK 37659 ()
Dienogest component of natazia ()
STS-557 ()
MJR-35 ()
Endometrion ()
Dienogest-d8 ()
P&D ID
PD009046
CAS
65928-58-7
2376035-92-4
Tags
available
drug
Approved by
PMDA
FDA
First approval
2010
Drug indication
Endometriosis
Contraception
Drug Status
approved
Max Phase
4.0
Probe control
Probe control not defined
Orthogonal probes
0
No orthogonal probes found
Similar probes
0
No structurally similar probes found
Structure
P&D probe-likeness score
Structure formats
[[ format ]]
[[ compound[format === 'MOL' ? 'molblock' : format.toLowerCase()] ]]
Description
(extracted from source data)
MOA
Dienogest acts as an agonist at the progesterone receptor (PR) with weak affinity that is comparable to that of progesterone but has a very potent progestagenic effect in the endometrium, causing endometrial atrophy after prolonged use [A20331]. It promotes antiproliferative, immunologic and antiangiogenic effects on endometrial tissue. Dienogest reduces the level of endogenous production of oestradiol and thereby suppressing the trophic effects of oestradiol on both the eutopic and ectopic endometrium [L932]. Continous administration of dienogest results in hyperprogestogenic and moderately hypoestrogenic endocrine environment, which causes initial decidualization of endometrial tissue [L931]. ; It is an antagonist at androgen receptors, improve androgenic symptoms such as acne and hirsutism [A16570].
DESCRIPTION
Note that the 2010 FDA approval is for the fixed-mixture combination oral contraceptive detailed in the Clinical data tab.
(GtoPdb)
PHARMACODYNAMICS
Dienogest exhibits a very potent progestagenic effect in the endometrium, and causes endometrial atrophy after prolonged use [A20331] . It also mediates an antiandrogenic effect that is equivalent to approximately one third that of cyproterone acetate [L931]. A dose of 2 mg inhibits the growth of ovarian follicles at 10 mm and maintains the concentration of progesterone at a low level, but has a weak inhibitory effect on FSH and LH. 1mg/kg of dienogest also directly inhibits ovulation [A20331]. In clinical trials composing of patients with endometriosis, dienogest therapy effectively reduced painful symptoms and endometriotic lesions associated with the disorder [A20330].; Dienogest displays no antiestrogenic activity as it activate neither estrogen receptor (ER) α nor ERβ [A16570], and causes hypoestrogenic effects instead as it is shown to decrease the relative expressions of ERβ and ERα [A20332]. It has no glucocorticoid or mineralocorticoid effects. In combined oral contraceptive pills (COCP) with ethinyloestradiol, dienogest conjuction therapy effectively reduces the symptoms of acne and hirsutism, as well as improving excessively heavy or prolonged menstrual bleeding [A20331].
DESCRIPTION
Dienogest (STS-557) is an orally active and selective progesterone receptor agonist that effectively reduces the gene expression of COX-2, mPGES-1 and aromatase. Dienogest also inhibits the mRNA and protein expression of PGE2 synthase and the activation of NF-¦ÊB. Dienogest can be used in studies of endometriosis, menopause and menorrhagia[1][2].
DESCRIPTION
Dienogest is a synthetic progestin and progesterone receptor agonist. It is indicated for use as the treatment of endometriosis alone and as a contraceptive in combination with ethinylestradiol.
(Enamine Bioactive Compounds)
[[ p.pathway_name ]]
[[ compound.targets[tid].gene_name ]]
Compound Sets
21
AdooQ Bioactive Compound Library
Axon Medchem Screening Library
ChEMBL Approved Drugs
ChEMBL Drugs
Drug Repurposing Hub
DrugBank
DrugBank Approved Drugs
DrugCentral
DrugCentral Approved Drugs
DrugMAP
DrugMAP Approved Drugs
Enamine Bioactive Compounds
Enamine BioReference Compounds
Guide to Pharmacology
MedChem Express Bioactive Compound Library
Natural product-based probes and drugs
NCATS Inxight Approved Drugs
Prestwick Chemical Library
ReFrame library
Selleckchem Bioactive Compound Library
[[ a.name ]]
[[ ligand_id ]]
free of charge
External IDs
39
Molecular Weight
311.19
Hydrogen Bond Acceptors
3
Hydrogen Bond Donors
1
Rotatable Bonds
1
Ring Count
4
Aromatic Ring Count
0
cLogP
3.84
TPSA
61.09
Fraction CSP3
0.7
Chiral centers
4.0
Largest ring
6.0
QED
0.8
Structural alerts
0
No structural alerts detected
Related compounds
Custom attributes
(extracted from source data)
Disease Area
endocrinology, obstetrics/gynecology
Indication
contraceptive, endometriosis
Target
PGR
PR agonist
Progesterone Receptor
Estrogen/progestogen Receptor
MOA
Progesterone receptor agonist
Biosynthetic Origin
Terpenoid (Steroid)
Therapeutic Indication
Endometriosis
Therapeutic Class
Hormone Therapy
Pathway
Vitamin D Related/Nuclear Receptor
Source data
