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Dydrogesterone

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Chemistry

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Also known as: 152-62-5, Isopregnenone, Hydrogesterone, Duphaston, Hydrogestrone, Gynorest

Molecular Formula

C₂₁H₂₈O₂

Molecular Weight

312.4 g/mol

InChI Key

JGMOKGBVKVMRFX-HQZYFCCVSA-N

FDA UNII

90I02KLE8K

A synthetic progestational hormone with no androgenic or estrogenic properties. Unlike many other progestational compounds, dydrogesterone produces no increase in temperature and does not inhibit OVULATION.

1 2D Structure

Dydrogesterone

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(8S,9R,10S,13S,14S,17S)-17-acetyl-10,13-dimethyl-1,2,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-3-one

2.1.2 InChI

InChI=1S/C21H28O2/c1-13(22)17-6-7-18-16-5-4-14-12-15(23)8-10-20(14,2)19(16)9-11-21(17,18)3/h4-5,12,16-19H,6-11H2,1-3H3/t16-,17+,18-,19+,20+,21+/m0/s1

2.1.3 InChI Key

JGMOKGBVKVMRFX-HQZYFCCVSA-N

2.1.4 Canonical SMILES

CC(=O)C1CCC2C1(CCC3C2C=CC4=CC(=O)CCC34C)C

2.1.5 Isomeric SMILES

CC(=O)[C@H]1CC[C@@H]2[C@@]1(CC[C@@H]3[C@H]2C=CC4=CC(=O)CC[C@@]34C)C

2.2 Other Identifiers

2.2.1 UNII

90I02KLE8K

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 6 Dehydro 9 Beta 10 Alpha Progesterone

2. 6-dehydro-9 Beta-10 Alpha-progesterone

3. Dehydrogesterone

4. Duphaston

5. Isopregnenone

2.3.2 Depositor-Supplied Synonyms

1. 152-62-5

2. Isopregnenone

3. Hydrogesterone

4. Duphaston

5. Hydrogestrone

6. Gynorest

7. Gestatron

8. Diphaston

9. Dufaston

10. 10alpha-isopregnenone

11. Duvaron

12. Prodel

13. Retrone

14. Terolut

15. Retro-6-dehydroprogesterone

16. Didrogesterone [dcit]

17. Didrogesterone

18. Dydrogesteronum

19. Delta(6)-retroprogesterone

20. 6-dehydro-retro-progesterone

21. Dydrogesteronum [inn-latin]

22. Dydrogesterona [inn-spanish]

23. Delta(sup 6)-retroprogesterone

24. 9beta,10alpha-pregna-4,6-diene-3,20-dione

25. Retroprogesterone, 6-dehydro-

26. (8s,9r,10s,13s,14s,17s)-17-acetyl-10,13-dimethyl-1,2,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-3-one

27. Nsc-92336

28. (9beta,10alpha)-pregna-4,6-diene-3,20-dione

29. Mls002153947

30. 90i02kle8k

31. Chebi:31527

32. Dydrogesterona

33. Dsstox_cid_2974

34. Dsstox_rid_76812

35. Dsstox_gsid_22974

36. Didrogesterona

37. Duphaston (tn)

38. Gynorest (tn)

39. 6-dehydro-9beta,10alpha-progesterone

40. Cas-152-62-5

41. Ccris 9069

42. Hsdb 3321

43. Mls002695106

44. 6-dehydroretroprogesterone

45. Einecs 205-806-8

46. 9-beta,10alpha-pregna-4,6-diene-3,20-dione

47. Nsc 92336

48. (9-beta,10-alpha)-pregna-4,6-diene-3,20-dione

49. Pregna-4,6-diene-3,20-dione, (9beta,10alpha)-

50. Unii-90i02kle8k

51. Nsc92336

52. 9-beta,10-alpha-pregna-4,6-diene-3,20-dione

53. Ncgc00016413-01

54. Dydrogesterone [usan:usp:inn:ban:jan]

55. 6-dehydro-9.beta.,10.alpha.-progesterone

56. Prestwick0_000671

57. Prestwick1_000671

58. Prestwick2_000671

59. Prestwick3_000671

60. Dydrogesterone [mi]

61. Pregna-4,6-diene-3,20-dione, (9b,10a)-

62. .delta.6-retroprogesterone

63. Dydrogesterone [inn]

64. Dydrogesterone [jan]

65. Schembl37703

66. Bspbio_000761

67. Dydrogesterone [hsdb]

68. Dydrogesterone [usan]

69. 9.beta.,10.alpha.-pregna-4,6-diene-3,20-dione

70. Spbio_002682

71. Dydrogesterone [mart.]

72. Bpbio1_000839

73. Gtpl2878

74. Pregna-4,6-diene-3,20-dione, (9-beta,10-alpha)-

75. Dydrogesterone [usp-rs]

76. Dydrogesterone [who-dd]

77. Chembl1200853

78. Dtxsid1022974

79. Hy-b0257a

80. 9.beta.,6-diene-3,20-dione

81. Dydrogesterone (jp17/usp/inn)

82. Hms1570g03

83. Hms2097g03

84. Hms2230c10

85. Hms3714g03

86. 9-.beta.,6-diene-3,20-dione

87. Amy23414

88. Bcp12878

89. Zinc3875998

90. Dydrogesterone [orange Book]

91. Tox21_110429

92. Dydrogesterone [ep Monograph]

93. S4097

94. Dydrogesterone [usp Monograph]

95. Akos015895532

96. Tox21_110429_1

97. Ccg-220671

98. Db00378

99. Gs-6735

100. Ncgc00179445-01

101. Ncgc00179445-03

102. Ncgc00179445-04

103. Smr001233286

104. Ab00513884

105. (9?,10?)-pregna-4,6-diene-3,20-dione

106. D01217

107. H10151

108. Pregna-4,20-dione, (9.beta.,10.alpha.)-

109. Ab00513884_04

110. 152d625

111. Sr-01000841256

112. Q4161380

113. Sr-01000841256-2

114. W-108050

115. Brd-k68620903-001-03-1

116. Brd-k68620903-001-11-4

117. Pregna-4,6-diene-3,20-dione, (9.beta.,10.alpha.)

118. (1r,2s,10s,11s,14s,15s)-14-acetyl-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-6,8-dien-5-one

119. (8s,9r,10s,13s,14s,17s)-17-acetyl-10,13-dimethyl-8,9,10,11,12,13,14,15,16,17-decahydro-1h-cyclopenta[a]phenanthren-3(2h)-one

2.4 Create Date

2005-03-26

3 Chemical and Physical Properties

Molecular Formula	C₂₁H₂₈O₂
Molecular Weight	312.4 g/mol
XLogP3	3.8
Hydrogen Bond Donor Count	0
Hydrogen Bond Acceptor Count	2
Rotatable Bond Count	1
Exact Mass	312.208930132 g/mol
Monoisotopic Mass	312.208930132 g/mol
Topological Polar Surface Area	34.1 Å²
Heavy Atom Count	23
Formal Charge	0
Complexity	628
Isotope Atom Count	0
Defined Atom Stereocenter Count	6
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 Therapeutic Uses

Progestational Hormones, Synthetic

National Library of Medicine's Medical Subject Headings online file (MeSH, 2009)

/Dydrogesterone is indicated as/ Hormone replacement therapy (HRT) for estrogen deficiency symptoms in peri and postmenopausal women. Prevention of osteoporosis in postmenopausal women at high risk of future fractures who are intolerant of, or contraindicated for, other medicinal products approved for the prevention of osteoporosis.

Datapharm Communications Ltd; Electronic Medicines Compendium (eMC), Summary of Product Characteristics (SPC) for Femoston (Last updated February 2011). Available from, as of March 2, 2011: https://www.medicines.org.uk/EMC/medicine/2493/SPC/Femoston+1+10mg/

/EXPTL THER:/ The aim of the present study was to evaluate dydrogesterone for luteal-phase support in assisted reproductive technologies (ART) and to compare it with micronized vaginal progesterone. All patients underwent long-term downregulation with gonadotropin-releasing hormone agonists. In phase I, 498 patients were divided into three groups: long protocol and not at risk of ovarian hyperstimulation syndrome (OHSS) (group A); long protocol and at risk of OHSS (group B); and those in a donor oocyte program (group C). All patients received micronized progesterone 600 mg/day, vaginally. They were also randomized to dydrogesterone 20 mg/day (n = 218) or placebo (n = 280). The pregnancy rate was higher with dydrogesterone than with placebo in group A (33.0% vs. 23.6%), group B (36.8% vs. 28.1%) and group C (42.9% vs. 15.6%; p < 0.001). In phase II, 675 patients were divided into the same three groups (groups D, E and F) and were randomized to dydrogesterone 30 mg/day (n = 366) or micronized progesterone 600 mg/day (n = 309). The pregnancy rate was significantly higher with dydrogesterone than with progesterone in group D (39.1% vs. 26.7%; p < 0.01), group E (41.2% vs. 35.6%; p < 0.01) and group F (48.2% vs. 33.9%; p < 0.001). In conclusion, dydrogesterone is effective in luteal-phase support in ART.

PMID:17943542 Patki A, Pawar VC; Gynecol Endocrinol 23 Suppl 1: 68-72 (2007)

Dydrogesterone has no inherent estrogenic activity and no androgenic effects. Priming with estrogen is necessary prior to use. Drug is claimed to be nonthermogenic and does not consistently inhibit ovulation.

American Medical Association, AMA Department of Drugs, AMA Drug Evaluations. 3rd ed. Littleton, Massachusetts: PSG Publishing Co., Inc., 1977., p. 568

Spectrum of progestin therapy has changed & expanded during last few yr. Drug-therapy of choice in endometriosis is medication of progestins for at least 6 months. If patient wants additional children the "more gentle" dydrogesterone should be considered.

VOLKER W; FORTSCHR MED 95(2) 68 (1977)

4.2 Drug Warning

There is no conclusive evidence for improvement of cognitive function. There is some evidence from the WHI trial of increased risk of probable dementia in women who start using continuous combined CEE and MPA after the age of 65. It is unknown whether the findings apply to younger post-menopausal women or other HRT products.

For the treatment of postmenopausal symptoms, HRT should only be initiated for symptoms that adversely affect quality of life. In all cases, a careful appraisal of the risks and benefits should be undertaken at least annually and HRT should only be continued as long as the benefit outweighs the risk.

Known, past or suspected breast cancer; Known or suspected estrogen-dependent malignant tumours (eg endometrial cancer); Undiagnosed genital bleeding; Untreated endometrial hyperplasia; Previous idiopathic or current venous thromboembolism (deep vein thrombosis, pulmonary embolism); Active or recent arterial thromboembolic disease (eg angina, myocardial infarction); Acute liver disease or a history of liver disease as long as liver function tests have failed to return to normal; Known hypersensitivity to the active substances or to any of the excipients; Porphyria.

Femoston is not indicated during pregnancy. If pregnancy occurs during medication with Femoston, treatment should be withdrawn immediately.

For more Drug Warnings (Complete) data for DYDROGESTERONE (26 total), please visit the HSDB record page.

4.3 Drug Indication

Used to treat irregular duration of cycles and irregular occurrence and duration of periods caused by progesterone deficiency. Also used to prevent natural abortion in patients who have a history of habitual abortions.

5 Pharmacology and Biochemistry

5.1 Pharmacology

Dydrogesterone is an orally active progestogen which acts directly on the uterus, producing a complete secretory endometrium in an estrogen-primed uterus. At therapeutic levels, dydrogesterone has no contraceptive effect as it does not inhibit or interfere with ovulation or the corpus luteum. Furthermore, dydrogesterone is non-androgenic, non-estrogenic, non-corticoid, non-anabolic and is not excreted as pregnanediol. Dydrogesterone helps to regulate the healthy growth and normal shedding of the uterus lining. Therefore, it may be useful in the treatment of menstrual disorders such as absent, irregular or painful menstrual periods, infertility, premenstrual syndrome and endometriosis.

5.2 MeSH Pharmacological Classification

Progestins

Compounds that interact with PROGESTERONE RECEPTORS in target tissues to bring about the effects similar to those of PROGESTERONE. Primary actions of progestins, including natural and synthetic steroids, are on the UTERUS and the MAMMARY GLAND in preparation for and in maintenance of PREGNANCY. (See all compounds classified as Progestins.)

5.3 ATC Code

G03DB01

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

G03DB01 - Dydrogesterone

5.4 Absorption, Distribution and Excretion

Absorption

Rapidly absorbed in the gastrointestinal tract with a bioavailability of 28%.

After oral administration of labelled dydrogesterone, on average 63% of the dose is excreted into the urine. Within 72 hours, excretion is complete.

After oral administration of dydrogesterone, plasma concentrations of DHD are substantially higher as compared to the parent drug. The AUC and Cmax ratios of DHD to dydrogesterone are in the order of 40 and 25, respectively. Dydrogesterone is rapidly absorbed. The Tmax values of dydrogesterone and DHD vary between 0.5 and 2.5 hours.

The dihydrodydrogesterone Caverage is 13 ng/mL, the Cmin is 4.1 ng/mL and the Cmax is 63 ng/mL. The dydrogesterone Caverage is 0.38 ng/mL the Cmin is <0.1 ng/mL and the Cmax is 2.5 ng/mL.

Progestins are reportedly distributed into milk. The possible effects of progestins in milk on nursing infants have not been determined. /Progestins General Statement/

American Society of Health System Pharmacists; AHFS Drug Information 2010. Bethesda, MD. (2010), p. 3270

5.5 Metabolism/Metabolites

Metabolism is complete to a 20-dihydrodydrogesterone (DHD) metabolite.

In man, dydrogesterone is completely metabolised. The main metabolite of dydrogesterone is 20alpha-dihydrodydrogesterone (DHD) and is present in the urine predominantly as the glucuronic acid conjugate. A common feature of all metabolites characterized is the retention of the 4,6 diene-3-one configuration of the parent compound and the absence of 17alpha-hydroxylation. This explains the absence of estrogenic and androgenic activity.

Datapharm Communications Ltd; Electronic Medicines Compendium (eMC), Summary of Product Characteristics (SPC) for Femoston (Last updated February 2011). Available from, as of March 2, 2011 : https://www.medicines.org.uk/EMC/medicine/2493/SPC/Femoston+1+10mg/

Dydrogesterone is not excreted in urine as pregnanediol, like progesterone. Analysis of endogenous progesterone production based on pregnanediol excretion therefore remains possible.

Datapharm Communications Ltd; Electronic Medicines Compendium (eMC), Summary of Product Characteristics (SPC) for Femoston (Last updated February 2011). Available from, as of March 2, 2011:: https://www.medicines.org.uk/EMC/medicine/2493/SPC/Femoston+1+10mg/

5.6 Biological Half-Life

Dydrogesterone: 5-7 hours, 20-dihydrodydrogesterone (DHD) metabolite: 14-17 hours

Mean terminal half lives of dydrogesterone and DHD vary between 5 to 7 and 14 to 17 hours, respectively.

5.7 Mechanism of Action

Dydrogesterone is a progestogen that works by regulating the healthy growth and normal shedding of the womb lining by acting on progesterone receptors in the uterus.

Dydrogesterone is an orally-active progestagen. The addition of a progestagen greatly reduces the estrogen-induced risk of endometrial hyperplasia and cancer in non-hysterectomised women, by reducing the growth of the endometrium.

Progestins cannot be equated as group with progesterone because some are inherently estrogenic, some slightly androgenic, and some purely progestational; correspondingly, their ovulation-inhibiting potentialities may be mediated in somewhat different ways. /Progestins/

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 1444

The 17-hydroxy or acetoxy compounds, on the other hand, elicit responses more nearly resembling those of progesterone. They have little or no estrogenic or androgenic activity and may produce catabolic and slight diuretic effects. The 19-nor derivatives are more effective in postponing the normal menstrual period. /Progestins/

American Society of Health System Pharmacists; AHFS Drug Information 2010. Bethesda, MD. (2010), p. 3271

Accumulating evidence indicates that the neuropeptide substance P (SP) is predominantly involved in neurogenic inflammation and pain perception via its high-affinity neurokinin 1 receptor (NK-1R). Intriguingly, decreased pain sensitivity is found to be associated with high plasma progesterone levels. We hypothesize that progesterone may attenuate nociception and associated inflammatory response via NK-1R-dependent pathways. To address our hypothesis, we incubated splenic lymphocytes from CBA/J female mice with different concentrations of the progesterone derivative dydrogesterone. Subsequently, the expressions of NK-1R and T helper (Th1)-type cytokines were analyzed by flow cytometry. Next, we subcutaneously injected CBA/J mice with 1.25 mg of dydrogesterone in 200-microl sesame oil; control mice were sham-injected. Tail flick test to detect the nociceptive threshold was performed in 30-min intervals upon injection. Lymphocytes were isolated from blood and uterus and analyzed for NK-1R surface expression. Immunohistochemical analyses were performed to investigate the uterine tissue distribution of NK-1R. Dydrogesterone induced a decrease in the percentage of NK-1R+ lymphocytes in vitro and in vivo. Additionally, an increase in Th2-type and a decrease in Th1-type cytokines could be detected in vitro after incubation with dydrogesterone. An increased tail flick latency following dydrogesterone injection supported the concept that decreased expression of the NK-1R on lymphocytes is associated with an increased pain threshold. Taken together, these results clearly reveal a pathway by which dydrogesterone or progesterone respectively modulates the cross talk of the nervous, endocrine and immune systems in inflammation and pain.

PMID:16389545 Orsal AS et al; J Mol Med 84 (2): 159-67 (2006)

For more Mechanism of Action (Complete) data for DYDROGESTERONE (6 total), please visit the HSDB record page.

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About the Company : Gonane Pharma, is a contract pharmaceutical company located in Gujarat, India, specializing in the manufacturing and marketing of Corticosteroids, Hormones, Antivirals, and Oncolog...

Gonane Pharma, is a contract pharmaceutical company located in Gujarat, India, specializing in the manufacturing and marketing of Corticosteroids, Hormones, Antivirals, and Oncology products. The company's core strength lies in its dedicated team, and its promoters bring over 25 years of experience in manufacturing, promoting products, and managing audits for regulated markets such as the EU, Mexico, China, Korea, and Russia. GONANE PHARMA is actively engaged in discussions with Japanese customers and anticipates further expansion into additional markets.

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Antibody Engineering

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Shanghai Minbiotech is the leading producer of biopharmaceuticals and a variety of high-end generic & innovative drugs.

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Dydrogesterone

About the Company : Headquartered in Fengxian District, Shanghai Minbiotech Co., Ltd. is a company specializing in the R&D and production of advanced pharmaceutical intermediates and biological API...

Headquartered in Fengxian District, Shanghai Minbiotech Co., Ltd. is a company specializing in the R&D and production of advanced pharmaceutical intermediates and biological APIs. There are more than 1000 square meters of R&D centers in Nantong, Jiangsu and Jinan, Shandong, with more than 13,000㎡ of production sites. While supplying products to customers, the company also provides services such as technology development, technology transfer and technology exchange, aiming to provide customers with comprehensive supply and solutions in the biomedical industry.

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Antibody Engineering

Not Confirmed

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