CAS 65928-58-7|Dienogest

Introduction：Basic information about CAS 65928-58-7|Dienogest, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.

Table of Contents

1. Names
2. Dienogest BiologicalActivity
3. Chemical & Physical Properties
4. Toxicological Information
CHEMICAL IDENTIFICATION
HEALTH HAZARD DATA
ACUTE TOXICITY DATA
MUTATION DATA
5. Safety Information
6. Synonyms

Common Name	Dienogest
CAS Number	65928-58-7	Molecular Weight	311.418
Density	1.2±0.1 g/cm3	Boiling Point	549.0±50.0 °C at 760 mmHg
Molecular Formula	C₂₀H₂₅NO₂	Melting Point	210-214ºC
MSDS	ChineseUSA	Flash Point	285.8±30.1 °C
Symbol	GHS08	Signal Word	Warning

Names

Name	dienogest
Synonym	More Synonyms

Dienogest BiologicalActivity

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 >>AutophagySignaling Pathways >>Others >>Progesterone ReceptorResearch 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.

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 >>AutophagySignaling Pathways >>Others >>Progesterone ReceptorResearch 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.

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
InChIKey	AZFLJNIPTRTECV-FUMNGEBKSA-N
SMILES	CC12CCC3=C4CCC(=O)C=C4CCC3C1CCC2(O)CC#N
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

Synonyms

[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

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