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Chemistry

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Also known as: 67392-87-4, Dihydrospirorenone, Dehydrospirorenone, Drospirenona, 1,2-dihydrospirorenone, Drsp
Molecular Formula
C24H30O3
Molecular Weight
366.5  g/mol
InChI Key
METQSPRSQINEEU-HXCATZOESA-N
FDA UNII
N295J34A25

Drospirenone
Drospirenone is a synthetic spironolactone analogue and progestin with progestational and anti-mineralocorticoid activity. Drospirenone binds to the progesterone receptor, the resulting complex becomes activated and binds to specific sites on DNA. This results in a suppression of LH activity and an inhibition of ovulation as well as an alteration in the cervical mucus and endometrium. This leads to an increased difficulty of sperm entry into the uterus and implantation. This drug is used in oral contraceptives.
Drospirenone is a Progestin.
1 2D Structure

Drospirenone

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
(1R,2R,4R,10R,11S,14S,15S,16S,18S,19S)-10,14-dimethylspiro[hexacyclo[9.8.0.02,4.05,10.014,19.016,18]nonadec-5-ene-15,5'-oxolane]-2',7-dione
2.1.2 InChI
InChI=1S/C24H30O3/c1-22-6-3-12(25)9-17(22)13-10-14(13)20-16(22)4-7-23(2)21(20)15-11-18(15)24(23)8-5-19(26)27-24/h9,13-16,18,20-21H,3-8,10-11H2,1-2H3/t13-,14+,15-,16+,18+,20-,21+,22-,23+,24+/m1/s1
2.1.3 InChI Key
METQSPRSQINEEU-HXCATZOESA-N
2.1.4 Canonical SMILES
CC12CCC(=O)C=C1C3CC3C4C2CCC5(C4C6CC6C57CCC(=O)O7)C
2.1.5 Isomeric SMILES
C[C@]12CCC(=O)C=C1[C@@H]3C[C@@H]3[C@@H]4[C@@H]2CC[C@]5([C@H]4[C@@H]6C[C@@H]6[C@@]57CCC(=O)O7)C
2.2 Other Identifiers
2.2.1 UNII
N295J34A25
2.3 Synonyms
2.3.1 MeSH Synonyms

1. 1,2-dihydro-spirorenone

2. 1,2-dihydrospirorenone

3. 6beta,7beta,15beta,16beta-dimethylen-3-oxo-17alpha-pregn-4-en-21,17-carbolacton

4. Dihydrospirorenone

5. Zk 30595

6. Zk30595

2.3.2 Depositor-Supplied Synonyms

1. 67392-87-4

2. Dihydrospirorenone

3. Dehydrospirorenone

4. Drospirenona

5. 1,2-dihydrospirorenone

6. Drsp

7. Drospirenonum

8. Drospirenonum [inn-latin]

9. Drospirenona [inn-spanish]

10. Zk 30595

11. Slynd

12. Zk-30595

13. Chebi:50838

14. N295j34a25

15. Nsc-760103

16. (6r,7r,8r,9s,10r,13s,14s,15s,16s,17s)-1,3',4',6,6a,7,8,9,10,11,12,13,14,15,15a,16-hexadecahydro-10,13-dimethylspiro-(17h-dicyclopropa(6,7:15,16)cyclopenta(a)phenanthrene-17,2'(5'h)-furan)-3,5'(2h)-dione

17. Drospirenone [inn]

18. Dsstox_cid_26465

19. Dsstox_rid_81639

20. Dsstox_gsid_46465

21. 6beta,7beta;15beta,16beta-dimethylene-3-oxo-17alpha-pregn-4-ene-21,17-carbolactone

22. (1r,2r,4r,10r,11s,14s,15s,16s,18s,19s)-10,14-dimethylspiro[hexacyclo[9.8.0.0^{2,4}.0^{5,10}.0^{14,19}.0^{16,18}]nonadecane-15,2'-oxolan]-5-ene-5',7-dione

23. Cas-67392-87-4

24. Zk30595

25. Ccris 6523

26. Einecs 266-679-2

27. Brn 4765500

28. Unii-n295j34a25

29. Hsdb 7896

30. Ncgc00164590-01

31. Drospirenone [usan:usp:inn:ban]

32. Mfcd00867350

33. Sh-470

34. Drospirenone- Bio-x

35. Slynd (tn)

36. 1, 2-dihydrospirorenone

37. Drospirenone [mi]

38. Drospirenone [jan]

39. Drospirenone [usan]

40. 6-beta,7-beta;15-beta,16-beta-dimethylene-3-oxo-17-alpha-pregn-4-ene-21,17-carbolactone

41. Chembl1509

42. Drospirenone [vandf]

43. Drospirenone [mart.]

44. 17-hydroxy-6beta,7beta:15beta,16beta-dimethylene-3-oxo-17alpha-pregn-4-ene-21-carboxylic Acid, Gamma-lactone

45. Spiro(17h-dicyclopropa(6,7:15,16)cyclopenta(a)phenanthrene-17,2'(5'h)-furan)-3,5'(2h)-dione, 1,3',4',6,7,8,9,10,11,12,13,14,15,16,20,21-hexadecahydro-10,13-dimethyl-, (6r-(6alpha,7alpha,8beta,9alpha,10beta,13beta,14alpha,15alpha,16alpha,17beta))-

46. Drospirenone [usp-rs]

47. Drospirenone [who-dd]

48. Schembl153316

49. Drospirenone (jan/usp/inn)

50. Gtpl2874

51. Dtxsid7046465

52. Yaz Component Drospirenone

53. Drospirenone, >=98% (hplc)

54. Bcpp000250

55. Bdbm150275

56. Drospirenone [orange Book]

57. Beyaz Component Drospirenone

58. Drospirenone [ep Monograph]

59. Bcp27035

60. Drospirenone For Peak Identification

61. Ex-a3153

62. Hy-b0111

63. Yasmin Component Drospirenone

64. Zinc3927200

65. Drospirenone [usp Monograph]

66. Drospirenone Component Of Yaz

67. Tox21_112216

68. Angeliq Component Drospirenone

69. S1377

70. Safyral Component Drospirenone

71. Akos015895237

72. Drospirenone Component Of Beyaz

73. Tox21_112216_1

74. Bcp9000628

75. Ccg-268245

76. Cs-1863

77. Db01395

78. Drospirenone Component Of Yasmin

79. Nsc 760103

80. Zk 3059

81. 6beta,7beta,15beta,16beta-dimethylene-3-oxo-17alpha-pregn-4-ene-21,17 Carbolactone

82. Drospirenone Component Of Angeliq

83. Drospirenone Component Of Safyral

84. Ncgc00164590-02

85. Ncgc00164590-04

86. Nextstellis Component Drospirenone

87. As-13025

88. Bd166530

89. Us8987239, A

90. Drospirenone Component Of Nextstellis

91. D4209

92. D03917

93. Ab01274783-01

94. Ab01274783_02

95. 392d874

96. A846434

97. Ar-270/43507886

98. Q419646

99. Sr-01000942231

100. Q-101411

101. Sr-01000942231-1

102. Brd-k04394237-001-06-0

103. Drospirenone, European Pharmacopoeia (ep) Reference Standard

104. Drospirenone, United States Pharmacopeia (usp) Reference Standard

105. Drospirenone For Peak Identification, European Pharmacopoeia (ep) Reference Standard

106. (1r,2r,4r,10r,11s,14s,15s,16s,18s,19s)-10,14-dimethylspiro[hexacyclo[9.8.0.02,4.05,10.014,19.016,18]nonadec-5-ene-15,5'-oxolane]-2',7-dione

107. 17-hydroxy-6.beta.,7.beta.:15.beta.,16.beta.-dimethylene-3-oxo-17.alpha.-pregn-4-ene-21-carboxylic Acid, .gamma.-lactone

108. 3-oxo-6alpha,7alpha,15alpha,16alpha-tetrahydro-7'h,16'h-dicyclopropa[6,7;15,16]-17alpha-pregn-4-ene-21,17-carbolactone

109. 5a,7a-dimethyl-1,1a,3,3',4,4',5,5a,5b,6,7,7a,8a,9,9a,9b,9c,9d-octaadecahydrospiro(cyclopropa[4,5]cyclopenta[1,2-a]cyclopropa[l]phenanthren-8,5'-furan)-2',3-dione

110. 6beta,7beta:15beta,16beta -dimethylene-3-oxo-17alpha-pregn-4-ene-21,17-carbolactone, Dihydrospirorenone

111. Spiro[8h-cyclopropa[4,5]cyclopenta[1,2-a]cyclopropa[l]phenanthrene-8,2'(5'h)-furan]-3,5'(4h)-dione, 1,1a,3',4',5,5a,5b,6,7,7a,8a,9,9a,9b,9c,9d-hexadecahydro-5a,7a-dimethyl-, (1ar,5ar,5bs,7as,8s,8as,9a R,9bs,9cr,9dr)-

2.4 Create Date
2005-08-08
3 Chemical and Physical Properties
Molecular Weight 366.5 g/mol
Molecular Formula C24H30O3
XLogP33.5
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count3
Rotatable Bond Count0
Exact Mass366.21949481 g/mol
Monoisotopic Mass366.21949481 g/mol
Topological Polar Surface Area43.4 Ų
Heavy Atom Count27
Formal Charge0
Complexity828
Isotope Atom Count0
Defined Atom Stereocenter Count10
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Therapeutic Uses

Androstenes; Progesterone Congeners; Aldosterone Antagonists

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


Gianvi is indicated for the prevention of pregnancy in women who elect to use an oral contraceptive. /Included in US product label/

US Natl Inst Health; DailyMed. Current Medication Information GIANVI (drospirenone and ethinyl estradiol) kit (November 2010). Available from, as of February 22, 2011: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?id=31973


Gianvi is indicated for the treatment of symptoms of premenstrual dysphoric disorder (PMDD) in women who choose to use an oral contraceptive as their method of contraception. The effectiveness of Gianvi for PMDD when used for more than three menstrual cycles has not been evaluated. /Included in US product label/

US Natl Inst Health; DailyMed. Current Medication Information GIANVI (drospirenone and ethinyl estradiol) kit (November 2010). Available from, as of February 22, 2011: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?id=31973


Gianvi has not been evaluated for the treatment of premenstrual syndrome (PMS). /Included in US product label/

US Natl Inst Health; DailyMed. Current Medication Information GIANVI (drospirenone and ethinyl estradiol) kit (November 2010). Available from, as of February 22, 2011: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?id=31973


Gianvi is indicated for the treatment of moderate acne vulgaris in women at least 14 years of age, who have no known contraindications to oral contraceptive therapy and have achieved menarche. Gianvi should be used for the treatment of acne only if the patient desires an oral contraceptive for birth control. /included in US product label/

US Natl Inst Health; DailyMed. Current Medication Information GIANVI (drospirenone and ethinyl estradiol) kit (November 2010). Available from, as of February 22, 2011: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?id=31973


4.2 Drug Warning

/BOXED WARNING/ WARNING: CIGARETTE SMOKING AND SERIOUS CARDIOVASCULAR EVENTS. Cigarette smoking increases the risk of serious cardiovascular events from combination oral contraceptives (COC) use. This risk increases with age, particularly in women over 35 years of age, and with the number of cigarettes smoked. For this reason, COCs should not be used by women who are over 35 years of age and smoke

US Natl Inst Health; DailyMed. Current Medication Information GIANVI (drospirenone and ethinyl estradiol) kit (Updated: April 2012). Available from, as of April 23, 2015: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=723d0427-cf3f-4ad7-8b93-cb1250f345f6


Cigarette smoking increases the risk of serious cardiovascular side effects from oral contraceptive use. This risk increases with age and with heavy smoking (15 or more cigarettes per day) and is quite marked in women over 35 years of age. Women who use oral contraceptives should be strongly advised not to smoke.

US Natl Inst Health; DailyMed. Current Medication Information GIANVI (drospirenone and ethinyl estradiol) kit (November 2010). Available from, as of February 22, 2011: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?id=31973


Gianvi contains ... the progestin drospirenone that has antimineralocorticoid activity, including the potential for hyperkalemia in high-risk patients, comparable to a ... dose of spironolactone. Gianvi should not be used in patients with conditions that predispose to hyperkalemia (ie renal insufficiency, hepatic dysfunction and adrenal insufficiency). Women receiving daily, long-term treatment for chronic conditions or diseases with medications that may increase serum potassium should have their serum potassium level checked during the first treatment cycle. Medications that may increase serum potassium include ACE inhibitors, angiotensin - II receptor antagonists, potassium-sparing diuretics, potassium supplementation, heparin, aldosterone antagonists, and NSAIDS.

US Natl Inst Health; DailyMed. Current Medication Information GIANVI (drospirenone and ethinyl estradiol) kit (November 2010). Available from, as of February 22, 2011: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?id=31973


Use of oral contraceptives is associated with an increased risk of several serious conditions including thromboembolism, stroke, myocardial infarction, liver tumor, gallbladder disease, visual disturbances, fetal abnormalities, and hypertension. Cigarette smoking increases the risk of serious adverse cardiovascular effects during oral contraceptive use. This risk increases with age and with heavy smoking (15 or more cigarettes daily) and is markedly greater in women older than 35 years of age. Women who are receiving estrogen-progestin contraceptives should be strongly advised not to smoke. Women older than 35 years of age who smoke, and women with ischemic heart disease or a history of this disease, should not use estrogen-progestin contraceptives. Estrogen-progestin contraceptives should be used with caution in women with cardiovascular disease risk factors. /Estrogen-Progestin Combination/

American Society of Health System Pharmacists; AHFS Drug Information 2010. Bethesda, MD. (2010), p. 3112


For more Drug Warnings (Complete) data for Drospirenone (39 total), please visit the HSDB record page.


4.3 Drug Indication

Drospirenone, in combination with ethinyl estradiol or estetrol, is indicated as an oral contraceptive for the prevention of pregnancy. In addition to its use for contraceptive effects, this combination is used to treat moderate acne vulgaris and the symptoms of premenstrual dysphoric disorder. The drug has approved indications for combination with estrogens for the treatment of menopause-associated symptoms, such as vasomotor symptoms and vulvovaginal atrophy. Drospirenone combined with estrogen may also may aid in the prevention of osteoporosis in women who have been post-menopausal for at least a year and are not candidates for other therapies. It can sometimes be found in preparations containing estrogen and folic acid for folic acid replenishment during oral contraception. When used for the treatment of acne vulgaris, drospirenone-containing contraceptives should only be used in women 14 years of age who have experienced menarche, desire oral contraception, and do not have any contraindications to oral contraceptives. Off-label uses for this drug include the treatment of menstrual irregularities, dysmenorrhea, hirsutism, and endometriosis.


FDA Label


Prevention of pregnancy


5 Pharmacology and Biochemistry
5.1 Pharmacology

Drospirenone inhibits the maturation of follicles and inhibits ovulation, preventing pregnancy. It has antiandrogen effects, improving acne and hirsutism. When combined with ethinyl estradiol, it has been shown to have favorable effects on the plasma lipid profile. Due to its similarity to naturally occurring progesterone, drospirenone is thought to be associated with a lower incidence of progesterone contraceptive related adverse effects, such as breast tenderness and mood swings. **A note on venous thromboembolism risk and antimineralcorticoid effects** As with other oral contraceptives, the risk of venous thromboembolism and cardiovascular events may be increased when drospirenone is taken. The risk is especially higher in smokers and women aged 35 and older. Women taking this drug should be advised not to smoke. In addition, drospirenone, due to its antimineralcorticoid effects, may increase the risk of hyperkalemia. Patients at high risk for hyperkalemia should not be administered this drug. Consult the official prescribing information for detailed and updated information on the cardiovascular and other risks associated with drospirenone use.


5.2 MeSH Pharmacological Classification

Mineralocorticoid Receptor Antagonists

Drugs that bind to and block the activation of MINERALOCORTICOID RECEPTORS by MINERALOCORTICOIDS such as ALDOSTERONE. (See all compounds classified as Mineralocorticoid Receptor Antagonists.)


5.3 FDA Pharmacological Classification
5.3.1 Active Moiety
DROSPIRENONE
5.3.2 FDA UNII
N295J34A25
5.3.3 Pharmacological Classes
Established Pharmacologic Class [EPC] - Progestin
5.4 ATC Code

G03FA17

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

G03A - Hormonal contraceptives for systemic use

G03AC - Progestogens

G03AC10 - Drospirenone


5.5 Absorption, Distribution and Excretion

Absorption

The absolute bioavailability of drospirenone is approximately 76% due to first-pass effects. The maximum plasma concentration of drospirenone occurs within 1 to 2 hours after oral administration and is estimated to range between 60 and 87 ng/mL. A European prescribing monograph for the combination product of estradiol and drospirenone indicates that drospirenone is both completely and rapidly absorbed. It reports a Cmax of 21.9 ng/ml, achieved approximately 1-hour post-administration. The absolute bioavailability is reported to range between 76 to 85%.


Route of Elimination

Various metabolites of drospirenone are measured in the urine and feces. Drospirenone elimination from the body is almost after 10 days post-administration when negligible amounts of drospirenone are found unchanged in both the urine and feces. Between 38% to 47% of the metabolites are identified as glucuronide and sulfate conjugates in the urine. In the feces, approximately 17% to 20% of identifiable metabolites are found to be excreted as glucuronides and sulfates.


Volume of Distribution

The volume of distribution of drospirenone is estimated to be 4 L/kg, according to the FDA label for Yaz. Prescribing information from a combination of estradiol and drospirenone estimates the volume of distribution to range from 3.7- 4.2 L/kg.


Clearance

Drospirenone is rapidly cleared, typically within 2-3 days of administration of the last active tablet. The rate of clearance of drospirenone calculated in the serum ranges from 1.2-1.5 ml/min/kg, however, this value can vary by up to 25% according to the patient.


The absolute bioavailability of drospirenone (DRSP) from a single entity tablet is about 76%. Serum concentrations of DRSP and EE reached peak levels within 1-2 hours after administration of Gianvi.

US Natl Inst Health; DailyMed. Current Medication Information GIANVI (drospirenone and ethinyl estradiol) kit (November 2010). Available from, as of February 22, 2011: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?id=31973


The pharmacokinetics of DRSP are dose proportional following single doses ranging from 1-10 mg. Following daily dosing of Gianvi, steady state DRSP concentrations were observed after 8 days. There was about 2 to 3 fold accumulation in serum Cmax and AUC (0-24hr) values of DRSP following multiple dose administration of Gianvi.

US Natl Inst Health; DailyMed. Current Medication Information GIANVI (drospirenone and ethinyl estradiol) kit (November 2010). Available from, as of February 22, 2011: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?id=31973


The rate of absorption of DRSP and EE following single administration of a formulation similar to Gianvi was slower under fed (high fat meal) conditions with the serum Cmax being reduced about 40% for both components. The extent of absorption of DRSP, however, remained unchanged.

US Natl Inst Health; DailyMed. Current Medication Information GIANVI (drospirenone and ethinyl estradiol) kit (November 2010). Available from, as of February 22, 2011: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?id=31973


DRSP and EE serum levels decline in two phases. The apparent volume of distribution of DRSP is approximately 4 L/kg and that of EE is reported to be approximately 4-5 L/kg.

US Natl Inst Health; DailyMed. Current Medication Information GIANVI (drospirenone and ethinyl estradiol) kit (November 2010). Available from, as of February 22, 2011: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?id=31973


For more Absorption, Distribution and Excretion (Complete) data for Drospirenone (10 total), please visit the HSDB record page.


5.6 Metabolism/Metabolites

Drospirenone is heavily metabolized. The two major inactive metabolites identified are the acid form of drospirenone produced by the opening of its lactone ring, known as M11, and the 4,5-dihydro-drospirenone-3-sulfate (M14). Drospirenone also undergoes oxidative metabolism via the hepatic cytochrome enzyme CYP3A4.


The two main metabolites of DRSP found in human plasma were identified to be the acid form of DRSP generated by opening of the lactone ring and the 4,5-dihydrodrospirenone-3-sulfate. These metabolites were shown not to be pharmacologically active. In in vitro studies with human liver microsomes, DRSP was metabolized only to a minor extent mainly by Cytochrome P450 3A4 (CYP3A4).

US Natl Inst Health; DailyMed. Current Medication Information GIANVI (drospirenone and ethinyl estradiol) kit (November 2010). Available from, as of February 22, 2011: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?id=31973


5.7 Biological Half-Life

The serum half-life of drospirenone is estimated to be 30 hours. The half-life of drospirenone metabolite excretion in the urine and feces is approximately 40 hours.


DRSP serum levels are characterized by a terminal disposition phase half-life of approximately 30 hours after both single and multiple dose regimens.

US Natl Inst Health; DailyMed. Current Medication Information GIANVI (drospirenone and ethinyl estradiol) kit (November 2010). Available from, as of February 22, 2011: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?id=31973


5.8 Mechanism of Action

Drospirenone and ethinyl estradiol in combination suppress the release of follicle stimulating hormone (FSH) and luteinizing hormone (LH), preventing ovulation. Other changes induced by this drug which may aid in the prevention of pregnancy include alterations in cervical mucus consistency, hindering sperm movement, and lowering the chance of embryo implantation. Drospirenone is an analog of the diuretic spironolactone, which exerts anti-mineralocorticoid activity, blocking aldosterone receptors, which increases sodium and water excretion. Studies in animals have demonstrated that drospirenone administration leads to antiandrogenic activity. This activity helps to oppose the effects of naturally occurring androgens, inhibiting the binding of dihydrotestosterone (DHT) to its receptor, and preventing androgen synthesis in the ovaries, helping to treat acne and hirsutism. Drospirenone may also decrease the level of edema in sebaceous follicle during the second half of the menstrual cycle, when acne often appears.


Combination oral contraceptives (COCs) act by suppression of gonadotropins. Although the primary mechanism of this action is inhibition of ovulation, other alterations include changes in the cervical mucus (which increases the difficulty of sperm entry into the uterus) and the endometrium (which reduces the likelihood of implantation).

US Natl Inst Health; DailyMed. Current Medication Information GIANVI (drospirenone and ethinyl estradiol) kit (November 2010). Available from, as of February 22, 2011: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?id=31973


Drospirenone is a spironolactone analogue with antimineralocorticoid activity. Preclinical studies in animals and in vitro have shown that drospirenone has no androgenic, estrogenic, glucocorticoid, or antiglucocorticoid activity. Preclinical studies in animals have also shown that drospirenone has antiandrogenic activity.

US Natl Inst Health; DailyMed. Current Medication Information GIANVI (drospirenone and ethinyl estradiol) kit (November 2010). Available from, as of February 22, 2011: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?id=31973


Acne vulgaris is a skin condition with a multifactorial etiology including androgen stimulation of sebum production. While the combination of ethinyl estradiol and drospirenone increases sex hormone binding globulin (SHBG) and decreases free testosterone, the relationship between these changes and a decrease in the severity of facial acne in otherwise healthy women with this skin condition has not been established. The impact of the antiandrogenic activity of drospirenone on acne is not known.

US Natl Inst Health; DailyMed. Current Medication Information GIANVI (drospirenone and ethinyl estradiol) kit (November 2010). Available from, as of February 22, 2011: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?id=31973


.... The pharmacological properties of drospirenone were investigated in vitro by receptor binding and transactivation experiments and in vivo in appropriate animal models. In qualitative agreement with progesterone, the compound binds strongly to the progesterone and the mineralocorticoid receptor and with lower affinity to androgen and glucocorticoid receptors. There is no detectable binding to the estrogen receptor. Steroid hormone agonistic and antagonistic activities of progesterone and drospirenone were compared in transactivation experiments. Individual steroid hormone receptors were artificially expressed together with a reporter gene in appropriate cell lines. Both hormones were unable to induce any androgen receptor-mediated agonistic activity. Rather, both progesterone and drospirenone distinctly antagonized androgen-stimulated transcriptional activation. Likewise, both compounds only very weakly activated the mineralocorticoid receptor but showed potent aldosterone antagonistic activity. Drospirenone did not induce glucocorticoid receptor-driven transactivation. Progesterone was a weak agonist in this respect. Drospirenone exerts potent progestogenic and antigonadotropic activity which was studied in various animal species. It efficiently promotes the maintenance of pregnancy in ovariectomized rats, inhibits ovulation in rats and mice and stimulates endometrial transformation in the rabbit. Furthermore, drospirenone shows potent antigonadotropic, i.e., testosterone-lowering activity in male cynomolgus monkeys. The progestogenic potency of drospirenone was found to be in the range of that of norethisterone acetate. The majority of clinically used progestogens are androgenic. Drospirenone, like progesterone, has no androgenic but rather an antiandrogenic effect. This property was demonstrated in castrated, testosterone propionate substituted male rats by a dose-dependent inhibition of accessory sex organ growth (seminal vesicles, prostate). In this model, the potency of drospirenone was about a third that of cyproterone acetate. Drospirenone, like progesterone, shows antimineralocorticoid activity, which causes moderately increased sodium and water excretion. This is an outstanding characteristic which has not been described for any other synthetic progestogen before. Drospirenone is eight to ten times more effective in this respect than spironolactone. The natriuretic effect was demonstrable for at least three weeks upon daily treatment of rats with a dose of 10 mg/animal. Drospirenone is devoid of any estrogenic, glucocorticoid or antiglucocorticoid activity. In summary, drospirenone, like progesterone, combines potent progestogenic with antimineralocorticoid and antiandrogenic activity in a similar dose range.

PMID:7625729 Muhn P et al; Ann N Y Acad Sci. 761: 311-35 (1995)


For more Mechanism of Action (Complete) data for Drospirenone (9 total), please visit the HSDB record page.


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06-Feb-2021
29-Aug-2024
KGS
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Average Price (USD/KGS)

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Quantity (KGS) & Unit rate (USD/KGS) over time

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DOSAGE - TABLET;ORAL - 0.25MG;0.5MG

USFDA APPLICATION NUMBER - 21355

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DOSAGE - TABLET;ORAL - 0.5MG;1MG

USFDA APPLICATION NUMBER - 21355

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DOSAGE - TABLET;ORAL - 3MG;0.02MG

USFDA APPLICATION NUMBER - 21676

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