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MedKoo Cat#: 317761 | Name: Dydrogesterone
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Description:

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

Dydrogesterone is a synthetic progestin. Dydrogesterone alone or in combination with estrogen to endothelial cells results in neutral effects on NO synthesis and on the activity and expression of eNOS. Unlike many other progestational compounds, dydrogesterone produces no increase in temperature and does not inhibit ovulation.

Chemical Structure

Dydrogesterone
Dydrogesterone
CAS#152-62-5

Theoretical Analysis

MedKoo Cat#: 317761

Name: Dydrogesterone

CAS#: 152-62-5

Chemical Formula: C21H28O2

Exact Mass: 312.2089

Molecular Weight: 312.45

Elemental Analysis: C, 80.73; H, 9.03; O, 10.24

Price and Availability

Size Price Availability Quantity
10mg USD 350.00 2 Weeks
25mg USD 550.00 2 Weeks
50mg USD 950.00 2 Weeks
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Related CAS #
No Data
Synonym
Dydrogesterone; Isopregnenone; Hydrogesterone; Duphaston; Hydrogestrone; Dufaston; NSC 92336; NSC92336; NSC-92336;
IUPAC/Chemical 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
InChi Key
JGMOKGBVKVMRFX-HQZYFCCVSA-N
InChi Code
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
SMILES Code
CC(=O)[C@H]1CC[C@@H]2[C@@]1(CC[C@@H]3[C@H]2C=CC4=CC(=O)CC[C@@]34C)C
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:
Dydrogesterone is a potent, orally active progestogen indicated in a wide variety of gynaecological conditions related to progesterone deficiency.
In vitro activity:
This study found that dydrogesterone resembled progesterone mainly in its progestogenic effects and less in its androgenic, anti-androgenic, glucocorticoid and antiglucocorticoid effects; whereas, 20α-dihydrodydrogesterone showed reduced progestogenic potency with no androgenic, glucocorticoid and mineralocorticoid effects. Reference: Steroids. 2011 May;76(6):607-15. https://pubmed.ncbi.nlm.nih.gov/21376746/
In vivo activity:
On gestation Day 13, a highly elevated abortion rate was detected in stressed mice compared to control mice. Stressed animals presented lower levels of progesterone and PIBF in plasma and a reduced staining intensity of progesterone receptor at the feto-maternal interface. Injection of dydrogesterone abrogated the effect of stress on the abortion rate. Further, dydrogesterone increased levels of plasma PIBF in stressed mice, but did not affect progesterone levels. Interestingly, dydrogesterone dramatically increased the percentage of IL-4 positive decidual immune cells in stressed mice. These data suggest that dydrogesterone abrogates stress-triggered abortion by inducing a Th2 biased local immune response. Reference: Steroids. 2003 Nov;68(10-13):931-40. https://pubmed.ncbi.nlm.nih.gov/14667986/
Solvent mg/mL mM
Solubility
DMSO 47.7 152.55
Ethanol 62.0 198.43
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 312.45 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. Fu XD, Garibaldi S, Gopal S, Polak K, Palla G, Spina S, Mannella P, Genazzani AR, Genazzani AD, Simoncini T. Dydrogesterone exerts endothelial anti-inflammatory actions decreasing expression of leukocyte adhesion molecules. Mol Hum Reprod. 2012 Jan;18(1):44-51. doi: 10.1093/molehr/gar062. Epub 2011 Oct 4. PMID: 21971309. 2. Rižner TL, Brožič P, Doucette C, Turek-Etienne T, Müller-Vieira U, Sonneveld E, van der Burg B, Böcker C, Husen B. Selectivity and potency of the retroprogesterone dydrogesterone in vitro. Steroids. 2011 May;76(6):607-15. doi: 10.1016/j.steroids.2011.02.043. Epub 2011 Mar 3. PMID: 21376746. 3. Jiang YX, Shi WJ, Hu LX, Ma DD, Zhang H, Ong CN, Ying GG. Dydrogesterone disrupts lipid metabolism in zebrafish brain: A study based on metabolomics and Fourier transform infrared spectroscopy. Environ Pollut. 2023 Jan 15;317:120811. doi: 10.1016/j.envpol.2022.120811. Epub 2022 Dec 2. PMID: 36470458. 4. Joachim R, Zenclussen AC, Polgar B, Douglas AJ, Fest S, Knackstedt M, Klapp BF, Arck PC. The progesterone derivative dydrogesterone abrogates murine stress-triggered abortion by inducing a Th2 biased local immune response. Steroids. 2003 Nov;68(10-13):931-40. doi: 10.1016/j.steroids.2003.08.010. PMID: 14667986.
In vitro protocol:
1. Fu XD, Garibaldi S, Gopal S, Polak K, Palla G, Spina S, Mannella P, Genazzani AR, Genazzani AD, Simoncini T. Dydrogesterone exerts endothelial anti-inflammatory actions decreasing expression of leukocyte adhesion molecules. Mol Hum Reprod. 2012 Jan;18(1):44-51. doi: 10.1093/molehr/gar062. Epub 2011 Oct 4. PMID: 21971309. 2. Rižner TL, Brožič P, Doucette C, Turek-Etienne T, Müller-Vieira U, Sonneveld E, van der Burg B, Böcker C, Husen B. Selectivity and potency of the retroprogesterone dydrogesterone in vitro. Steroids. 2011 May;76(6):607-15. doi: 10.1016/j.steroids.2011.02.043. Epub 2011 Mar 3. PMID: 21376746.
In vivo protocol:
1. Jiang YX, Shi WJ, Hu LX, Ma DD, Zhang H, Ong CN, Ying GG. Dydrogesterone disrupts lipid metabolism in zebrafish brain: A study based on metabolomics and Fourier transform infrared spectroscopy. Environ Pollut. 2023 Jan 15;317:120811. doi: 10.1016/j.envpol.2022.120811. Epub 2022 Dec 2. PMID: 36470458. 2. Joachim R, Zenclussen AC, Polgar B, Douglas AJ, Fest S, Knackstedt M, Klapp BF, Arck PC. The progesterone derivative dydrogesterone abrogates murine stress-triggered abortion by inducing a Th2 biased local immune response. Steroids. 2003 Nov;68(10-13):931-40. doi: 10.1016/j.steroids.2003.08.010. PMID: 14667986.
1: Saharkhiz N, Zamaniyan M, Salehpour S, Zadehmodarres S, Hoseini S, Cheraghi L, Seif S, Baheiraei N. A comparative study of dydrogesterone and micronized progesterone for luteal phase support during in vitro fertilization (IVF) cycles. Gynecol Endocrinol. 2015 Nov 20:1-5. [Epub ahead of print] PubMed PMID: 26486011. 2: Raghupathy R, Al-Azemi M. Modulation of Cytokine Production by the Dydrogesterone Metabolite Dihydrodydrogesterone. Am J Reprod Immunol. 2015 Nov;74(5):419-26. doi: 10.1111/aji.12418. Epub 2015 Aug 7. PubMed PMID: 26250154. 3: Podzolkova N, Tatarchuk T, Doshchanova A, Eshimbetova G, Pexman-Fieth C. Dydrogesterone treatment for menstrual-cycle regularization in routine clinical practice: a multicenter observational study. Gynecol Endocrinol. 2015 Nov 27:1-4. [Epub ahead of print] PubMed PMID: 26613278. 4: Barbosa MW, Silva LR, Navarro PA, Ferriani RA, Nastri CO, Martins WP. Dydrogesterone versus progesterone for luteal-phase support: systematic review and meta-analysis of randomized controlled trials. Ultrasound Obstet Gynecol. 2015 Nov 18. doi: 10.1002/uog.15814. [Epub ahead of print] Review. PubMed PMID: 26577241. 5: Zaqout M, Aslem E, Abuqamar M, Abughazza O, Panzer J, De Wolf D. The Impact of Oral Intake of Dydrogesterone on Fetal Heart Development During Early Pregnancy. Pediatr Cardiol. 2015 Oct;36(7):1483-8. doi: 10.1007/s00246-015-1190-9. Epub 2015 May 15. PubMed PMID: 25972284. 6: Abboud R, Greige-Gerges H, Charcosset C. Effect of Progesterone, Its Hydroxylated and Methylated Derivatives, and Dydrogesterone on Lipid Bilayer Membranes. J Membr Biol. 2015 Aug;248(4):811-24. doi: 10.1007/s00232-015-9803-z. Epub 2015 Apr 25. PubMed PMID: 25911547. 7: Khosravi D, Taheripanah R, Taheripanah A, Tarighat Monfared V, Hosseini-Zijoud SM. Comparison of oral dydrogesterone with vaginal progesteronefor luteal support in IUI cycles: a randomized clinical trial. Iran J Reprod Med. 2015 Jul;13(7):433-8. PubMed PMID: 26494991; PubMed Central PMCID: PMC4609323. 8: Carp H. A systematic review of dydrogesterone for the treatment of recurrent miscarriage. Gynecol Endocrinol. 2015 Jun;31(6):422-30. doi: 10.3109/09513590.2015.1006618. Epub 2015 Mar 13. PubMed PMID: 25765519. 9: Zhao Y, Castiglioni S, Fent K. Synthetic progestins medroxyprogesterone acetate and dydrogesterone and their binary mixtures adversely affect reproduction and lead to histological and transcriptional alterations in zebrafish (Danio rerio). Environ Sci Technol. 2015 Apr 7;49(7):4636-45. doi: 10.1021/es505575v. Epub 2015 Mar 17. PubMed PMID: 25742325. 10: Liu J, Lin H, Huang Y, Liu Y, Wang B, Su F. Cognitive effects of long-term dydrogesterone treatment used alone or with estrogen on rat menopausal models of different ages. Neuroscience. 2015 Apr 2;290:103-14. doi: 10.1016/j.neuroscience.2015.01.042. Epub 2015 Jan 28. PubMed PMID: 25637796. 11: Tomic V, Tomic J, Klaic DZ, Kasum M, Kuna K. Oral dydrogesterone versus vaginal progesterone gel in the luteal phase support: randomized controlled trial. Eur J Obstet Gynecol Reprod Biol. 2015 Mar;186:49-53. doi: 10.1016/j.ejogrb.2014.11.002. Epub 2014 Nov 20. PubMed PMID: 25622239. 12: El Behery MM, Saleh HS, Ibrahiem MA, Kamal EM, Kassem GA, Mohamed Mel S. Levonorgestrel-releasing intrauterine device versus dydrogesterone for management of endometrial hyperplasia without atypia. Reprod Sci. 2015 Mar;22(3):329-34. doi: 10.1177/1933719114542014. Epub 2014 Jul 6. PubMed PMID: 25001020. 13: Azizuddin, Saima Rasheed SR, Naz S, Naheed S, Choudhary MI. Comparative anti-glycation and α-glucosidase inhibition studies of microbial transformed compounds of dydrogesterone. Pak J Pharm Sci. 2015 Mar;28(2):521-3. PubMed PMID: 25730784. 14: Kumar A, Begum N, Prasad S, Aggarwal S, Sharma S. Oral dydrogesterone treatment during early pregnancy to prevent recurrent pregnancy loss and its role in modulation of cytokine production: a double-blind, randomized, parallel, placebo-controlled trial. Fertil Steril. 2014 Nov;102(5):1357-1363.e3. doi: 10.1016/j.fertnstert.2014.07.1251. Epub 2014 Sep 17. PubMed PMID: 25241364. 15: Ghosh S, Chattopadhyay R, Goswami S, Chaudhury K, Chakravarty B, Ganesh A. Assessment of sub-endometrial blood flow parameters following dydrogesterone and micronized vaginal progesterone administration in women with idiopathic recurrent miscarriage: a pilot study. J Obstet Gynaecol Res. 2014 Jul;40(7):1871-6. doi: 10.1111/jog.12456. PubMed PMID: 25056464. 16: Matsui S, Yasui T, Tani A, Kato T, Uemura H, Kuwahara A, Matsuzaki T, Arisawa K, Irahara M. Effect of ultra-low-dose estradiol and dydrogesterone on arterial stiffness in postmenopausal women. Climacteric. 2014 Apr;17(2):191-6. doi: 10.3109/13697137.2013.856399. Epub 2013 Dec 16. PubMed PMID: 24164272. 17: Zainul Rashid MR, Lim JF, Nawawi NH, Luqman M, Zolkeplai MF, Rangkuty HS, Mohamad Nor NA, Tamil A, Shah SA, Tham SW, Schindler AE. A pilot study to determine whether progestogen supplementation using dydrogesterone during the first trimester will reduce the incidence of gestational hypertension in primigravidae. Gynecol Endocrinol. 2014 Mar;30(3):217-20. doi: 10.3109/09513590.2013.860960. PubMed PMID: 24552449. 18: Rizzo MR, Leo S, De Franciscis P, Colacurci N, Paolisso G. Short-term effects of low-dose estrogen/drospirenone vs low-dose estrogen/dydrogesterone on glycemic fluctuations in postmenopausal women with metabolic syndrome. Age (Dordr). 2014 Feb;36(1):265-74. doi: 10.1007/s11357-013-9554-7. Epub 2013 Jul 7. PubMed PMID: 23832170; PubMed Central PMCID: PMC3889904. 19: Salehpour S, Tamimi M, Saharkhiz N. Comparison of oral dydrogesterone with suppository vaginal progesterone for luteal-phase support in in vitro fertilization (IVF): A randomized clinical trial. Iran J Reprod Med. 2013 Nov;11(11):913-8. PubMed PMID: 24639716; PubMed Central PMCID: PMC3941387. 20: Akashi D, Todo Y, Shimada C, Okamoto K, Minobe S, Kato H. Successful use of dydrogesterone as maintenance therapy in recurrent endometrial stromal sarcoma: a case report. Jpn J Clin Oncol. 2013 Nov;43(11):1145-9. doi: 10.1093/jjco/hyt142. Epub 2013 Sep 19. PubMed PMID: 24058200.

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