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Dienogest

Names

[ CAS No. ]:
65928-58-7

[ Name ]:
Dienogest

[Synonym ]:
[14C]-Dienogest
Acetonitrile, 2-[(17β)-17-hydroxy-3-oxoestra-4,9-dien-17-yl]-
[3H]-Dienogest
STS557
Dinagest
17a-CyanoMethyl-17b-hydroxyestra-4,9-dien-3-one
(17α)-17-Hydroxy-3-oxo-19-norpregna-4,9-diene-21-nitrile
17a-17-Hydroxy-3-oxo-19-norpregna-4,9-diene-21-nitrile
Dienogestril
STS 557
17a-Cyanomethyl-17b-hydroxy-estra-4,9(10)-dien-3-one
Endometrion
UNII-46M3EV8HHE
17a-Cyanomethyl-17-hydroxyestra-4,9-dien-3-one
Dienogestrel
Dienogest

Biological Activity

[Description]:

Dienogest(STS-557) is a specific progesterone receptor agonist with potent oral endometrial activity and is used in the treatment of endometriosis. Target: progesterone receptor agonistDienogest 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 [1]. Complete sperm suppression was observed in rats sacrificed either 60 or 90 days after dienogest (DNG)+ testosterone undecanoate (TU) administration, for two injections at 45-day interval. The neutral α-glucosidase activity in these treated rats remained in the normal range. Germ cell loss due to apoptosis was frequently observed both after 60 or 90 days of combination treatment. Significant decline in serum gonadotropin and testosterone, both serum and intratesticular levels, were observed in the treated rats. Following stoppage of treatment (given at 45-day interval) after two (0 and 45 days) or three injections (0, 45 and 90 days), complete restoration of spermatogenesis was observed by 120 and 165 days, respectively [2].Clinical indications: Adenomyosis; EndometriosisFDA Approved Date: 1995 Toxicity: weight gain; increased blood pressure; breast tenderness and nausea

[Related Catalog]:

Signaling Pathways >> Autophagy >> Autophagy
Signaling Pathways >> Others >> Progesterone Receptor
Research Areas >> Endocrinology

[References]

[1]. Oettel M, et al. Effect of ethinyl estradiol-dienogest combination on serum androgen concentrations. Zentralbl Gynakol. 1997;119(12):597-606.

[2]. Meena R, et al. Extended intervention time and evaluation of sperm suppression by dienogest plus testosterone undecanoate in male rat. Contraception. 2012 Jan;85(1):113-21.


[Related Small Molecules]

Mifepristone | Progesterone | Tanaproget | Megestrol acetate | Dydrogesterone | Drospirenone | Ethynodiol diacetate | 19-Norethindrone acetate | Altrenogest | Chlormadinone Acetate | Gestodene | Nestoron | Gestonorone Capronate

Chemical & Physical Properties

[ Density]:
1.2±0.1 g/cm3

[ Boiling Point ]:
549.0±50.0 °C at 760 mmHg

[ Melting Point ]:
210-214ºC

[ Molecular Formula ]:
C20H25NO2

[ Molecular Weight ]:
311.418

[ Flash Point ]:
285.8±30.1 °C

[ Exact Mass ]:
311.188538

[ PSA ]:
61.09000

[ LogP ]:
1.96

[ Vapour Pressure ]:
0.0±3.3 mmHg at 25°C

[ Index of Refraction ]:
1.589

[ Storage condition ]:
-20°C Freezer

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
RC8899500
CHEMICAL NAME :
19-Norpregna-4,9-diene-21-nitrile, 17-hydroxy-3-oxo-, (17-alpha)-
CAS REGISTRY NUMBER :
65928-58-7
LAST UPDATED :
199503
DATA ITEMS CITED :
28
MOLECULAR FORMULA :
C20-H25-N-O2
MOLECULAR WEIGHT :
311.46
WISWESSER LINE NOTATION :
L E5 B666 OV BU MUTJ E1 FQ F1CN

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
4 gm/kg
TOXIC EFFECTS :
Behavioral - somnolence (general depressed activity)
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
1 gm/kg
TOXIC EFFECTS :
Behavioral - convulsions or effect on seizure threshold Behavioral - coma
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
5 gm/kg
TOXIC EFFECTS :
Behavioral - somnolence (general depressed activity)
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rabbit
DOSE/DURATION :
1 gm/kg
TOXIC EFFECTS :
Behavioral - convulsions or effect on seizure threshold Endocrine - other changes Nutritional and Gross Metabolic - weight loss or decreased weight gain
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - rabbit
DOSE/DURATION :
1500 mg/kg
TOXIC EFFECTS :
Behavioral - convulsions or effect on seizure threshold Endocrine - other changes Nutritional and Gross Metabolic - weight loss or decreased weight gain
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
1820 mg/kg/26W-I
TOXIC EFFECTS :
Blood - changes in serum composition (e.g. TP, bilirubin, cholesterol) Biochemical - Metabolism (Intermediary) - other proteins
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
300 mg/kg
SEX/DURATION :
male 60 day(s) pre-mating
TOXIC EFFECTS :
Reproductive - Paternal Effects - testes, epididymis, sperm duct Reproductive - Paternal Effects - prostate, seminal vesicle, Cowper's gland, accessory glands
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
1500 mg/kg
SEX/DURATION :
male 60 day(s) pre-mating
TOXIC EFFECTS :
Reproductive - Paternal Effects - spermatogenesis (incl. genetic material, sperm morphology, motility, and count) Reproductive - Fertility - mating performance (e.g. # sperm positive females per # females mated; # copulations per # estrus cycles)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
461 mg/kg
SEX/DURATION :
male 21 day(s) pre-mating
TOXIC EFFECTS :
Reproductive - Paternal Effects - testes, epididymis, sperm duct Reproductive - Paternal Effects - prostate, seminal vesicle, Cowper's gland, accessory glands Reproductive - Paternal Effects - other effects on male
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Subcutaneous
DOSE :
8 mg/kg
SEX/DURATION :
female 1 day(s) after conception
TOXIC EFFECTS :
Reproductive - Fertility - other measures of fertility
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Subcutaneous
DOSE :
25 mg/kg
SEX/DURATION :
female 1-4 day(s) after conception
TOXIC EFFECTS :
Reproductive - Fertility - female fertility index (e.g. # females pregnant per # sperm positive females; # females pregnant per # females mated) Reproductive - Fertility - pre-implantation mortality (e.g. reduction in number of implants per female; total number of implants per corpora lutea)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Subcutaneous
DOSE :
84 mg/kg
SEX/DURATION :
male 21 day(s) pre-mating
TOXIC EFFECTS :
Reproductive - Paternal Effects - testes, epididymis, sperm duct Reproductive - Fertility - male fertility index (e.g. # males impregnating females per # males exposed to fertile nonpregnant females)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Subcutaneous
DOSE :
42 mg/kg
SEX/DURATION :
male 21 day(s) pre-mating
TOXIC EFFECTS :
Reproductive - Paternal Effects - spermatogenesis (incl. genetic material, sperm morphology, motility, and count)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
10 mg/kg
SEX/DURATION :
female 1 day(s) after conception
TOXIC EFFECTS :
Reproductive - Fertility - other measures of fertility
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
500 mg/kg
SEX/DURATION :
female 13-17 day(s) after conception
TOXIC EFFECTS :
Reproductive - Fertility - litter size (e.g. # fetuses per litter; measured before birth) Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
500 ug/kg
SEX/DURATION :
female 3-7 day(s) after conception
TOXIC EFFECTS :
Reproductive - Specific Developmental Abnormalities - musculoskeletal system
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
500 mg/kg
SEX/DURATION :
female 8-12 day(s) after conception
TOXIC EFFECTS :
Reproductive - Fertility - abortion
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Subcutaneous
DOSE :
200 mg/kg
SEX/DURATION :
female 1-4 day(s) after conception
TOXIC EFFECTS :
Reproductive - Fertility - female fertility index (e.g. # females pregnant per # sperm positive females; # females pregnant per # females mated) Reproductive - Fertility - pre-implantation mortality (e.g. reduction in number of implants per female; total number of implants per corpora lutea)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Subcutaneous
DOSE :
700 mg/kg
SEX/DURATION :
male 35 day(s) pre-mating
TOXIC EFFECTS :
Reproductive - Fertility - pre-implantation mortality (e.g. reduction in number of implants per female; total number of implants per corpora lutea)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
80 ug/kg
SEX/DURATION :
female 1-4 day(s) after conception
TOXIC EFFECTS :
Reproductive - Fertility - female fertility index (e.g. # females pregnant per # sperm positive females; # females pregnant per # females mated)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
600 ug/kg
SEX/DURATION :
female 3 day(s) pre-mating
TOXIC EFFECTS :
Reproductive - Fertility - other measures of fertility
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intramuscular
DOSE :
84 mg/kg
SEX/DURATION :
male 7 week(s) pre-mating
TOXIC EFFECTS :
Reproductive - Paternal Effects - spermatogenesis (incl. genetic material, sperm morphology, motility, and count)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
80 mg/kg
SEX/DURATION :
male 56 day(s) pre-mating
TOXIC EFFECTS :
Reproductive - Paternal Effects - spermatogenesis (incl. genetic material, sperm morphology, motility, and count) Reproductive - Fertility - mating performance (e.g. # sperm positive females per # females mated; # copulations per # estrus cycles) Reproductive - Fertility - male fertility index (e.g. # males impregnating females per # males exposed to fertile nonpregnant females)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
100 ug/kg
SEX/DURATION :
female 1 day(s) after conception
TOXIC EFFECTS :
Reproductive - Fertility - pre-implantation mortality (e.g. reduction in number of implants per female; total number of implants per corpora lutea)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
13500 ug/kg
SEX/DURATION :
female 3 day(s) pre-mating
TOXIC EFFECTS :
Reproductive - Fertility - female fertility index (e.g. # females pregnant per # sperm positive females; # females pregnant per # females mated)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
4500 ug/kg
SEX/DURATION :
female 3 day(s) pre-mating
TOXIC EFFECTS :
Reproductive - Fertility - other measures of fertility

MUTATION DATA

TEST SYSTEM :
Rodent - mouse
DOSE/DURATION :
700 mg/kg/35D
REFERENCE :
ENDKAC Endokrinologie. (Leipzig, Ger. Dem. Rep.) V.1-80, 1928-82. For publisher information, see EXCEDS. Volume(issue)/page/year: 76,13,1980

Safety Information

[ Symbol ]:

GHS08

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H361

[ Precautionary Statements ]:
P280

[ Hazard Codes ]:
Xn

[ RIDADR ]:
NONH for all modes of transport

Synthetic Route

Precursor & DownStream


Related Compounds