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Chemistry

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Also known as: 65928-58-7, Dienogestrel, Dienogestril, Sts 557, Endometrion, Dienogestum

Molecular Formula

C₂₀H₂₅NO₂

Molecular Weight

311.4 g/mol

InChI Key

AZFLJNIPTRTECV-FUMNGEBKSA-N

FDA UNII

46M3EV8HHE

Dienogest is an orally-active, semisynthetic, fourth generation, nonethinylated progestogen with antiproliferative, antiandrogenic, anti-inflammatory and antiangiogenic activities that is used in hormone therapy and as a female contraceptive. Upon oral administration, dienogest binds intracellular progesterone receptors which then translocate to the nucleus where the drug-receptor complex interacts with progesterone response elements, thus altering the expression of target genes. Dienogest reduces the production of estradiol, prevents ovulation and alters the cervical mucus and endometrium. In addition, dienogest appears to suppress the expression of cell cycle regulator cyclin D1. Altogether, this may prevent the growth of endometrial epithelial cells and may reduce symptoms associated with leiomyoma.

Dienogest is a Progestin.

1 2D Structure

Dienogest

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

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

2.1.2 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

2.1.3 InChI Key

AZFLJNIPTRTECV-FUMNGEBKSA-N

2.1.4 Canonical SMILES

CC12CCC3=C4CCC(=O)C=C4CCC3C1CCC2(CC#N)O

2.1.5 Isomeric SMILES

C[C@]12CCC3=C4CCC(=O)C=C4CC[C@H]3[C@@H]1CC[C@]2(CC#N)O

2.2 Other Identifiers

2.2.1 UNII

46M3EV8HHE

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 17 Alpha-cyanomethyl-17 Beta-hydroxy-13 Beta-methylgona-4,9-dien-3-one

2. 17 Alpha-cyanomethyl-17 Beta-hydroxyestra-4,9(10)-diene-3-one

3. 19-norpregna-4,9-diene-21-nitrile, 17-hydroxy-3-oxo-, (17alpha)-

4. Sts 557

5. Sts-557

2.3.2 Depositor-Supplied Synonyms

1. 65928-58-7

2. Dienogestrel

3. Dienogestril

4. Sts 557

5. Endometrion

6. Dienogestum

7. Dinagest

8. Natazia

9. Sts-557

10. Visanne

11. Mjr-35

12. 17alpha-17-hydroxy-3-oxo-19-norpregna-4,9-diene-21-nitrile

13. Bay86-5258

14. Bay 86-5258

15. 46m3ev8hhe

16. Zk 37659

17. 2-[(8s,13s,14s,17r)-17-hydroxy-13-methyl-3-oxo-1,2,6,7,8,11,12,14,15,16-decahydrocyclopenta[a]phenanthren-17-yl]acetonitrile

18. Chebi:70708

19. 17-alpha-cyanomethyl-17-beta-hydroxy-estra-4,9(10)-dien-3-one

20. M 18575

21. M-18575

22. 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

23. Zk-37659

24. Dienogest [inn]

25. Dienogestum [latin]

26. (17-hydroxy-3-oxoestra-4,9-dien-17beta-yl)acetonitrile

27. 17alpha-cyanomethyl-17beta-hydroxyestra-4,9(10)-dien-3-one

28. [(17beta)-17-hydroxy-3-oxoestra-4,9-dien-17-yl]acetonitrile

29. Unii-46m3ev8hhe

30. Dienogest [usan:inn:ban]

31. Endometrion (tn)

32. (17&alpha

33. Dienogest [jan]

34. 17-cyanomethyl-17-hydroxy-estra-4,9-dien-3-one

35. Dienogest [mi]

36. Dienogest [usan]

37. 17-alpha-cyanomethyl-17-beta-hydroxyestra-4,9(10)-diene-3-one

38. Dienogest [vandf]

39. 19-norpregna-4,9-diene-21-nitrile, 17-hydroxy-3-oxo-, (17alpha)-

40. Dienogest [mart.]

41. 17-hydroxy-3-oxo-19-norpregna-4,9-diene-21-nitrile

42. Dienogest [who-dd]

43. Schembl37293

44. Dienogest (jan/usan/inn)

45. Gtpl7654

46. Sts557

47. Dienogest [orange Book]

48. Dienogest For System Suitability

49. Chembl1201864

50. Dienogest [ep Monograph]

51. Dienogest, >=98% (hplc)

52. Sh-t00660aa

53. Dtxsid80891478

54. 17-hydroxy-3-oxo-19-nor-17alpha-pregna-4,9-diene-21-nitrile

55. Bcp22681

56. Hy-b0084

57. Zinc4215629

58. Mfcd00868356

59. S1251

60. 19-norpregna-4,9-diene-21-nitrile, 17-hydroxy-3-oxo-, (17-alpha)-

61. Akos015840152

62. Akos015896680

63. Ac-2166

64. Ccg-267594

65. Cs-1782

66. Db09123

67. Ncgc00346502-04

68. D5230

69. D03799

70. Ab01566807_01

71. 928d587

72. Q139160

73. Sr-01000942230

74. Sr-01000942230-1

75. Brd-k50853363-001-02-3

76. Dienogest, Europepharmacopoeia (ep) Reference Standard

77. [(17?)-17-hydroxy-3-oxoestra-4,9-dien-17-yl]acetonitrile

78. 17-hydroxy-3-oxo-19-nor-17.alpha.-pregna-4,9-diene-21-nitrile

79. 19-norpregna-4,9-diene-21-nitrile, 17-hydroxy-3-oxo-, (17.alpha.)-

80. Dienogest For System Suitability, Europepharmacopoeia (ep) Reference Standard

81. 17-hydroxy-3-oxo-19-norpregna-4,9-diene-21-nitrile, 17-cyanomethyl-17-hydroxy-estra-4,9-dien-3-one

2.4 Create Date

2005-08-08

3 Chemical and Physical Properties

Molecular Formula	C₂₀H₂₅NO₂
Molecular Weight	311.4 g/mol
XLogP3	1.8
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	3
Rotatable Bond Count	1
Exact Mass	311.188529040 g/mol
Monoisotopic Mass	311.188529040 g/mol
Topological Polar Surface Area	61.1 Å²
Heavy Atom Count	23
Formal Charge	0
Complexity	679
Isotope Atom Count	0
Defined Atom Stereocenter Count	4
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Drug Indication

Indicated for use as the treatment of endometriosis alone and as a contraceptive in combination with ethinylestradiol.

Treatment of endometriosis

5 Pharmacology and Biochemistry

5.1 Pharmacology

Dienogest exhibits a very potent progestagenic effect in the endometrium, and causes endometrial atrophy after prolonged use . It also mediates an antiandrogenic effect that is equivalent to approximately one third that of cyproterone acetate. 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. In clinical trials composing of patients with endometriosis, dienogest therapy effectively reduced painful symptoms and endometriotic lesions associated with the disorder. Dienogest displays no antiestrogenic activity as it activate neither estrogen receptor (ER) nor ER, and causes hypoestrogenic effects instead as it is shown to decrease the relative expressions of ER and ER. 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.

5.2 MeSH Pharmacological Classification

Antineoplastic Agents, Hormonal

Antineoplastic agents that are used to treat hormone-sensitive tumors. Hormone-sensitive tumors may be hormone-dependent, hormone-responsive, or both. A hormone-dependent tumor regresses on removal of the hormonal stimulus, by surgery or pharmacological block. Hormone-responsive tumors may regress when pharmacologic amounts of hormones are administered regardless of whether previous signs of hormone sensitivity were observed. The major hormone-responsive cancers include carcinomas of the breast, prostate, and endometrium; lymphomas; and certain leukemias. (From AMA Drug Evaluations Annual 1994, p2079) (See all compounds classified as Antineoplastic Agents, Hormonal.)

Contraceptives, Oral, Hormonal

Oral contraceptives which owe their effectiveness to hormonal preparations. (See all compounds classified as Contraceptives, Oral, Hormonal.)

Contraceptive Agents, Male

Chemical substances or agents with contraceptive activity in males. Use for male contraceptive agents in general or for which there is no specific heading. (See all compounds classified as Contraceptive Agents, Male.)

Hormone Antagonists

Chemical substances which inhibit the function of the endocrine glands, the biosynthesis of their secreted hormones, or the action of hormones upon their specific sites. (See all compounds classified as Hormone Antagonists.)

5.3 FDA Pharmacological Classification

5.3.1 Active Moiety

DIENOGEST

5.3.2 FDA UNII

46M3EV8HHE

5.3.3 Pharmacological Classes

Chemical Structure [CS] - Progesterone Congeners

5.4 ATC Code

G03DB08

S76 | LUXPHARMA | Pharmaceuticals Marketed in Luxembourg | Pharmaceuticals marketed in Luxembourg, as published by d'Gesondheetskeess (CNS, la caisse nationale de sante, www.cns.lu), mapped by name to structures using CompTox by R. Singh et al. (in prep.). List downloaded from https://cns.public.lu/en/legislations/textes-coordonnes/liste-med-comm.html. Dataset DOI:10.5281/zenodo.4587355

G - Genito urinary system and sex hormones

G03 - Sex hormones and modulators of the genital system

G03D - Progestogens

G03DB - Pregnadien derivatives

G03DB08 - Dienogest

5.5 Absorption, Distribution and Excretion

Absorption

Dienogest is rapidly absorbed following oral administration, with 91% bioavailability. The peak plasma concentration of 47 ng/mL is reached at about 1.5 hours after single ingestion of 2 mg. The stable concentrations of the drug are reached after two days of initial treatment.

Route of Elimination

The ratio of renal elimination to fecal elimination of dienogest is 3:1, where dienogest is predominantly excreted in the form of inactive metabolites. Most of orally administered drug is excreted in the urine within the first 24 hours of ingestion.

Volume of Distribution

The apparent volume of distribution (Vd/F) of dienogest is 40 L.

Clearance

The metabolic clearance rate from serum (Cl/F) is 64 mL/min.

5.6 Metabolism/Metabolites

Dienogest undergoes complete metabolism that is mainly mediated by CYP3A4. The metabolites are pharmacologically inactive and rapidly eliminated from the plasma.

5.7 Biological Half-Life

Elimination half-life of dienogest is around 9-10 hours. The half-life of urinary metabolites excretion is 14 hours.

5.8 Mechanism of Action

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. 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. Continous administration of dienogest results in hyperprogestogenic and moderately hypoestrogenic endocrine environment, which causes initial decidualization of endometrial tissue. It is an antagonist at androgen receptors, improve androgenic symptoms such as acne and hirsutism.

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