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MedKoo Cat#: 317757 | Name: Drospirenone
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Drospirenone is a synthetic progestogen exhibiting antiandrogenic and antimineralocorticoid activity. This drug is used in oral contraceptives. 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.

Chemical Structure

Drospirenone
Drospirenone
CAS#67392-87-4

Theoretical Analysis

MedKoo Cat#: 317757

Name: Drospirenone

CAS#: 67392-87-4

Chemical Formula: C24H30O3

Exact Mass: 366.2195

Molecular Weight: 366.50

Elemental Analysis: C, 78.65; H, 8.25; O, 13.10

Price and Availability

Size Price Availability Quantity
25mg USD 350.00 2 Weeks
100mg USD 650.00 2 Weeks
250mg USD 950.00 2 Weeks
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Related CAS #
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Synonym
Drospirenone; dihydrospirorenone; drospirenone; ZK 30595; ZK30595; ZK-30595; Drospirenona; Drospirenonum; Dehydrospirorenone;
IUPAC/Chemical Name
(2'S,4aR,4bS,6aS,7aS,8aS,8bS,8cR,8dR,9aR)-4a,6a-dimethyl-4,4a,4b,5,6,6a,7a,8,8a,8b,8c,8d,9,9a-tetradecahydro-3'H-spiro[cyclopropa[4,5]cyclopenta[1,2-a]cyclopropa[l]phenanthrene-7,2'-furan]-2,5'(3H,4'H)-dione
InChi Key
METQSPRSQINEEU-DZJIEHTNSA-N
InChi Code
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
SMILES Code
O=C1CC[C@]2(C)[C@@]3([H])CC[C@@]([C@](OC4=O)(CC4)[C@]5([H])[C@@]6([H])C5)(C)[C@]6([H])[C@]3([H])C7C(C7)C2=C1
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO, not in water
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Drospirenone (Dihydrospirorenone) is a synthetic progestin that is an analog to spironolactone.
In vitro activity:
In the present study the affinity of drospirenone to the progesterone receptor (PR), the androgen receptor (AR), the glucocorticoid receptor (GR), the mineralocorticoid receptor (MR), and the estrogen receptor (ER) was re-evaluated by steroid binding assays and compared to those obtained for the natural hormone progesterone. Drospirenone displayed high affinity to PR and MR and low binding to AR, similar to progesterone. Reference: Contraception. 1996 Oct;54(4):243-51. https://pubmed.ncbi.nlm.nih.gov/8922878/
In vivo activity:
The high binding affinity of dihydrospirorenone to the binding sites of the mineralocorticoid receptor of rat kidney with an RBA value of 230% compared to aldosterone is remarkable. This reflects the strong antimineralocorticoid activity of this compound which was evaluated in adrenalectomized rats. Reference: Contraception. 1992 Dec;46(6):561-74. https://pubmed.ncbi.nlm.nih.gov/1493716/
Solvent mg/mL mM
Solubility
DMSO 61.5 167.80
Ethanol 12.0 32.74
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 366.50 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
1. Sabouni R, Archer DF, Jacot T. Drospirenone Effects on the Plasminogen Activator System in Immortalized Human Endometrial Endothelial Cells. Reprod Sci. 2021 Jul;28(7):1974-1980. doi: 10.1007/s43032-020-00433-x. Epub 2021 Feb 8. PMID: 33559058. 2. Fuhrmann U, Krattenmacher R, Slater EP, Fritzemeier KH. The novel progestin drospirenone and its natural counterpart progesterone: biochemical profile and antiandrogenic potential. Contraception. 1996 Oct;54(4):243-51. doi: 10.1016/s0010-7824(96)00195-3. PMID: 8922878. 3. Muhn P, Krattenmacher R, Beier S, Elger W, Schillinger E. Drospirenone: a novel progestogen with antimineralocorticoid and antiandrogenic activity. Pharmacological characterization in animal models. Contraception. 1995 Feb;51(2):99-110. doi: 10.1016/0010-7824(94)00015-o. PMID: 7750297. 4. Pollow K, Juchem M, Elger W, Jacobi N, Hoffmann G, Möbus V. Dihydrospirorenone (ZK30595): a novel synthetic progestagen--characterization of binding to different receptor proteins. Contraception. 1992 Dec;46(6):561-74. doi: 10.1016/0010-7824(92)90121-9. PMID: 1493716.
In vitro protocol:
1. Sabouni R, Archer DF, Jacot T. Drospirenone Effects on the Plasminogen Activator System in Immortalized Human Endometrial Endothelial Cells. Reprod Sci. 2021 Jul;28(7):1974-1980. doi: 10.1007/s43032-020-00433-x. Epub 2021 Feb 8. PMID: 33559058. 2. Fuhrmann U, Krattenmacher R, Slater EP, Fritzemeier KH. The novel progestin drospirenone and its natural counterpart progesterone: biochemical profile and antiandrogenic potential. Contraception. 1996 Oct;54(4):243-51. doi: 10.1016/s0010-7824(96)00195-3. PMID: 8922878.
In vivo protocol:
1. Muhn P, Krattenmacher R, Beier S, Elger W, Schillinger E. Drospirenone: a novel progestogen with antimineralocorticoid and antiandrogenic activity. Pharmacological characterization in animal models. Contraception. 1995 Feb;51(2):99-110. doi: 10.1016/0010-7824(94)00015-o. PMID: 7750297. 2. Pollow K, Juchem M, Elger W, Jacobi N, Hoffmann G, Möbus V. Dihydrospirorenone (ZK30595): a novel synthetic progestagen--characterization of binding to different receptor proteins. Contraception. 1992 Dec;46(6):561-74. doi: 10.1016/0010-7824(92)90121-9. PMID: 1493716.
1: Borgo MV, Claudio ER, Silva FB, Romero WG, Gouvea SA, Moysés MR, Santos RL, Almeida SA, Podratz PL, Graceli JB, Abreu GR. Hormonal therapy with estradiol and drospirenone improves endothelium-dependent vasodilation in the coronary bed of ovariectomized spontaneously hypertensive rats. Braz J Med Biol Res. 2016;49(1). pii: S0100-879X2016000100601. doi: 10.1590/1414-431X20154655. Epub 2016 Nov 17. PubMed PMID: 26577845; PubMed Central PMCID: PMC4678653. 2: Wang Q, Ma X, He J, Sun Q, Li Y, Li H. Binding properties of drospirenone with human serum albumin and lysozyme in vitro. Spectrochim Acta A Mol Biomol Spectrosc. 2016 Jan 15;153:612-8. doi: 10.1016/j.saa.2015.09.017. Epub 2015 Sep 30. PubMed PMID: 26448295. 3: Duijkers IJ, Heger-Mahn D, Drouin D, Colli E, Skouby S. Maintenance of ovulation inhibition with a new progestogen-only pill containing drospirenone after scheduled 24-h delays in pill intake. Contraception. 2015 Dec 16. pii: S0010-7824(15)30022-6. doi: 10.1016/j.contraception.2015.12.007. [Epub ahead of print] PubMed PMID: 26708301. 4: Wiesinger H, Berse M, Klein S, Gschwend S, Höchel J, Zollmann FS, Schütt B. Pharmacokinetic interaction between the CYP3A4 inhibitor ketoconazole and the hormone drospirenone in combination with ethinylestradiol or estradiol. Br J Clin Pharmacol. 2015 Dec;80(6):1399-410. doi: 10.1111/bcp.12745. Epub 2015 Oct 28. PubMed PMID: 26271371. 5: de Nadai MN, Nobre F, Ferriani RA, Vieira CS. Effects of two contraceptives containing drospirenone on blood pressure in normotensive women: a randomized-controlled trial. Blood Press Monit. 2015 Dec;20(6):310-5. doi: 10.1097/MBP.0000000000000139. PubMed PMID: 26154851. 6: Bhattacharya SM, Jha A, DasMukhopadhyay L. Comparison of two contraceptive pills containing drospirenone and 20μg or 30μg ethinyl estradiol for polycystic ovary syndrome. Int J Gynaecol Obstet. 2015 Nov 6. pii: S0020-7292(15)00651-7. doi: 10.1016/j.ijgo.2015.06.065. [Epub ahead of print] PubMed PMID: 26613823. 7: Giribela CR, Consolim-Colombo FM, Nisenbaum MG, Moraes TL, Giribela AH, Baracat EC, Melo NR. Effects of a combined oral contraceptive containing 20 mcg of ethinylestradiol and 3 mg of drospirenone on the blood pressure, renin-angiotensin-aldosterone system, insulin resistance, and androgenic profile of healthy young women. Gynecol Endocrinol. 2015 Nov;31(11):912-5. doi: 10.3109/09513590.2015.1062860. Epub 2015 Jul 14. PubMed PMID: 26172927. 8: Jourabchi N, Rhee SM, Lazarus GS. Pre-menstrual flares of pyoderma gangrenosum controlled with use of a combined oral contraceptive and antiandrogen (Ethinyl Estradiol/Drospirenone). Br J Dermatol. 2015 Nov 30. doi: 10.1111/bjd.14332. [Epub ahead of print] PubMed PMID: 26616160. 9: Archer DF, Ahrendt HJ, Drouin D. Drospirenone-only oral contraceptive: results from a multicenter noncomparative trial of efficacy, safety and tolerability. Contraception. 2015 Nov;92(5):439-44. doi: 10.1016/j.contraception.2015.07.014. Epub 2015 Jul 29. PubMed PMID: 26232513. 10: Fan X, Chen X, Wang C, Dai J, Lu Y, Wang K, Liu J, Zhang J, Wu X. Drospirenone enhances GPIb-IX-V-mediated platelet activation. J Thromb Haemost. 2015 Oct;13(10):1918-24. doi: 10.1111/jth.13109. Epub 2015 Sep 14. PubMed PMID: 26264726. 11: Takeda T, Kondo A, Koga S, Hayakawa J, Hayakawa K, Hiramatsu K, Yaegashi N. Effectiveness of ethinylestradiol/drospirenone for premenstrual symptoms in Japanese patients with dysmenorrhea: Open-label pilot study. J Obstet Gynaecol Res. 2015 Oct;41(10):1584-90. doi: 10.1111/jog.12774. Epub 2015 Aug 26. PubMed PMID: 26310836. 12: Santhamma B, Acosta K, Chavez-Riveros A, Nickisch K. A new approach towards the synthesis of drospirenone and steroidal spirolactones. Steroids. 2015 Oct;102:60-4. doi: 10.1016/j.steroids.2015.07.008. Epub 2015 Jul 26. PubMed PMID: 26216206. 13: Kim N, Yoo HN, Hyun HS, Lee DY, Yoon BK, Choi DS. Efficacy and safety of a 24-day regimen of drospirenone-containing combined oral contraceptive in Korean women. Obstet Gynecol Sci. 2015 Sep;58(5):397-400. doi: 10.5468/ogs.2015.58.5.397. Epub 2015 Sep 22. PubMed PMID: 26430665; PubMed Central PMCID: PMC4588845. 14: Al-Jefout M, Nawaiseh N. Continuous Norethisterone Acetate versus Cyclical Drospirenone 3 mg/Ethinyl Estradiol 20 μg for the Management of Primary Dysmenorrhea in Young Adult Women. J Pediatr Adolesc Gynecol. 2015 Sep 3. pii: S1083-3188(15)00310-1. doi: 10.1016/j.jpag.2015.08.009. [Epub ahead of print] PubMed PMID: 26342733. 15: Sun X, Wu X, Zhou Y, Yu X, Zhang W. Evaluation of Apelin and Insulin Resistance in Patients with PCOS and Therapeutic Effect of Drospirenone-Ethinylestradiol Plus Metformin. Med Sci Monit. 2015 Aug 28;21:2547-52. doi: 10.12659/MSM.894926. PubMed PMID: 26314870; PubMed Central PMCID: PMC4556163. 16: Taniguchi F, Enatsu A, Ota I, Toda T, Arata K, Harada T. Effects of low dose oral contraceptive pill containing drospirenone/ethinylestradiol in patients with endometrioma. Eur J Obstet Gynecol Reprod Biol. 2015 Aug;191:116-20. doi: 10.1016/j.ejogrb.2015.06.006. Epub 2015 Jun 16. PubMed PMID: 26115056. 17: Zhao Y, Castiglioni S, Fent K. Environmental Progestins Progesterone and Drospirenone Alter the Circadian Rhythm Network in Zebrafish (Danio rerio). Environ Sci Technol. 2015 Aug 18;49(16):10155-64. doi: 10.1021/acs.est.5b02226. Epub 2015 Jul 28. PubMed PMID: 26161812. 18: Miyashita M, Koga K, Izumi G, Makabe T, Hasegawa A, Hirota Y, Hirata T, Harada M, Fujii T, Osuga Y. Drospirenone induces decidualization in human eutopic endometrial stromal cells and reduces DNA synthesis of human endometriotic stromal cells. Fertil Steril. 2015 Jul;104(1):217-24.e2. doi: 10.1016/j.fertnstert.2015.03.023. Epub 2015 Apr 29. PubMed PMID: 25935489. 19: Cheng J, Zhang Z. [Clinical and metabolic effects of drospirenone-estradiol versus tibolone in postmenopausal women:a comparative study]. Zhonghua Yi Xue Za Zhi. 2015 Jun 16;95(23):1815-8. Chinese. PubMed PMID: 26712397. 20: Paoletti AM, Cagnacci A, Di Carlo C, Orrù MM, Neri M, D'Alterio MN, Melis GB. Clinical effect of hormonal replacement therapy with estradiol associated with noretisterone or drospirenone. A prospective randomized placebo controlled study. Gynecol Endocrinol. 2015 May;31(5):384-7. doi: 10.3109/09513590.2014.1003294. Epub 2015 Feb 23. PubMed PMID: 25703254.

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