Medroxyprogesterone | CAS#520-85-4 |

MedKoo Cat#: 592790 | Name: Medroxyprogesterone

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Description:

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

Medroxyprogesterone is used in the treatment of renal carcinoma. It is a synthetic progestational hormone used in veterinary practice as an estrus regulator.

Chemical Structure

Medroxyprogesterone

CAS#520-85-4

Theoretical Analysis

MedKoo Cat#: 592790

Name: Medroxyprogesterone

CAS#: 520-85-4

Chemical Formula: C22H32O3

Exact Mass: 344.2351

Molecular Weight: 344.50

Elemental Analysis: C, 76.70; H, 9.36; O, 13.93

Price and Availability

Size	Price	Availability	Quantity
100mg	USD 350.00	2 weeks
200mg	USD 550.00	2 Weeks

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Related CAS #

520-85-4 71-58-9 (acetate)

Synonym

Medroxyprogesterone; NSC 27408; NSC-27408; NSC27408

IUPAC/Chemical Name

Pregn-4-ene-3,20-dione, 17-hydroxy-6-alpha-methyl-

InChi Key

FRQMUZJSZHZSGN-HBNHAYAOSA-N

InChi Code

InChI=1S/C22H32O3/c1-13-11-16-17(20(3)8-5-15(24)12-19(13)20)6-9-21(4)18(16)7-10-22(21,25)14(2)23/h12-13,16-18,25H,5-11H2,1-4H3/t13-,16+,17-,18-,20+,21-,22-/m0/s1

SMILES Code

CC([C@@]1(O)CC[C@@]2([H])[C@]3([H])C[C@H](C)C4=CC(CC[C@]4(C)[C@@]3([H])CC[C@]12C)=O)=O

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

Shelf Life

>3 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

2934.99.03.00

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Medroxyprogesterone is a progestin, a synthetic variant of the human hormone progesterone and a potent progesterone receptor agonist.

In vitro activity:

MPA (medroxyprogesterone acetate) significantly impaired wound closure in both cell types and delayed the reestablishment of transepithelial resistance by epithelial cells. In contrast to MPA, NET selectively decreased wound closure by stromal fibroblasts but not epithelial cells. Reference: Sci Rep. 2021 Dec 1;11(1):23246. https://pubmed.ncbi.nlm.nih.gov/34853394/

In vivo activity:

DMPA (Depo-medroxyprogesterone) treatments of both athymic nude mice and heterozygous NU/J (Foxn1nu/+) but ovariectomized mice led to a significantly increased viral load at the anogenital tract, suggesting that endogenous sex hormones were involved in increased viral susceptibility by DMPA treatment. Consistent with previous reports, DMPA treatment suppressed host anti-viral activities at the lower genital tract. Reference: Viruses. 2022 May 6;14(5):980. https://pubmed.ncbi.nlm.nih.gov/35632722/

	Solvent	mg/mL	mM
Solubility
	DMSO	50.0	145.14
	Ethanol	1.0	2.90
	Methanol	1.0	2.90

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 344.50 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.

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. Patel MV, Rodriguez-Garcia M, Shen Z, Wira CR. Medroxyprogesterone acetate inhibits wound closure of human endometrial epithelial cells and stromal fibroblasts in vitro. Sci Rep. 2021 Dec 1;11(1):23246. doi: 10.1038/s41598-021-02681-6. PMID: 34853394; PMCID: PMC8636475. 2. Vanpouille C, Günaydın G, Jangard M, Clerici M, Margolis L, Broliden K, Introini A. The Progestin Medroxyprogesterone Acetate Affects HIV-1 Production in Human Lymphoid Tissue Explants in a Dose-Dependent and Glucocorticoid-like Fashion. Viruses. 2021 Nov 18;13(11):2303. doi: 10.3390/v13112303. PMID: 34835109; PMCID: PMC8621851. 3. Hu J, Brendle SA, Li JJ, Walter V, Cladel NM, Cooper T, Shearer DA, Balogh KK, Christensen ND. Depo Medroxyprogesterone (DMPA) Promotes Papillomavirus Infections but Does Not Accelerate Disease Progression in the Anogenital Tract of a Mouse Model. Viruses. 2022 May 6;14(5):980. doi: 10.3390/v14050980. PMID: 35632722; PMCID: PMC9147738. 4. Das R, Ragagnin G, Sjöstedt J, Johansson M, Haage D, Druzin M, Johansson S, Bäckström T. Medroxyprogesterone acetate positively modulates specific GABAA-receptor subtypes - affecting memory and cognition. Psychoneuroendocrinology. 2022 Jul;141:105754. doi: 10.1016/j.psyneuen.2022.105754. Epub 2022 Mar 31. PMID: 35395561.

In vitro protocol:

In vivo protocol:

1. Hu J, Brendle SA, Li JJ, Walter V, Cladel NM, Cooper T, Shearer DA, Balogh KK, Christensen ND. Depo Medroxyprogesterone (DMPA) Promotes Papillomavirus Infections but Does Not Accelerate Disease Progression in the Anogenital Tract of a Mouse Model. Viruses. 2022 May 6;14(5):980. doi: 10.3390/v14050980. PMID: 35632722; PMCID: PMC9147738. 2. Das R, Ragagnin G, Sjöstedt J, Johansson M, Haage D, Druzin M, Johansson S, Bäckström T. Medroxyprogesterone acetate positively modulates specific GABAA-receptor subtypes - affecting memory and cognition. Psychoneuroendocrinology. 2022 Jul;141:105754. doi: 10.1016/j.psyneuen.2022.105754. Epub 2022 Mar 31. PMID: 35395561.

1: Okojie AK, Oyekunle OA. Depo-provera effects on Wistar rat performance in the Y-maze. Metab Brain Dis. 2014 Jun;29(2):529-31. doi: 10.1007/s11011-013-9460-9. Epub 2013 Dec 13. PubMed PMID: 24338027. 2: Spark MJ. Is progesterone a synonym for medroxyprogesterone acetate? Climacteric. 2014 Feb;17(1):97. doi: 10.3109/13697137.2013.850481. Epub 2013 Oct 28. PubMed PMID: 24161031. 3: Frank LA, Watson JB. Treatment of alopecia X with medroxyprogesterone acetate. Vet Dermatol. 2013 Dec;24(6):624-7, e153-4. doi: 10.1111/vde.12073. Epub 2013 Sep 2. PubMed PMID: 23992376. 4: Cameron S. Subcutaneous depo-medroxyprogesterone acetate. J Fam Plann Reprod Health Care. 2013 Apr;39(2):75-7. doi: 10.1136/jfprhc-2012-100517. PubMed PMID: 23493590. 5: Zeman S, Havlík P, Zemanová J, Němec D. [Status of bone mineral density after the long-standing application of contraception Depo-Provera]. Ceska Gynekol. 2013 Jan;78(1):116-24. Review. Czech. PubMed PMID: 23607391. 6: Porphyre V, Rakotoharinome M, Randriamparany T, Pognon D, Prévost S, Le Bizec B. Residues of medroxyprogesterone acetate detected in sows at a slaughterhouse, Madagascar. Food Addit Contam Part A Chem Anal Control Expo Risk Assess. 2013;30(12):2108-13. doi: 10.1080/19440049.2013.848293. Epub 2013 Nov 20. PubMed PMID: 24251849. 7: Cappelletti M, Ethun K, Meeker T, Von Scherr G, Wallen K. Early adolescent Depo-Provera exposure increases stillbirths in adult sooty mangabeys. Reproduction. 2015 Dec;150(6):497-505. doi: 10.1530/REP-15-0314. Epub 2015 Sep 30. PubMed PMID: 26424807. 8: Nakayiza O, Wamala R, Kwagala B. Determinants of preference of source of injectable contraceptives among rural women in Uganda: a case study of Depo-Provera. Afr J Reprod Health. 2014 Sep;18(3):48-56. PubMed PMID: 25438509. 9: Green W. The FDA, contraceptive marketing approval and products liability litigation: Depo-Provera and the risk of osteoporosis. Food Drug Law J. 2013;68(2):115-35, i. PubMed PMID: 24640465. 10: Cao J, Zhang J, Li C, Feng J. Sleep-induced hypoxaemia: remember medroxyprogesterone and acetazolamide. Br J Hosp Med (Lond). 2013 Nov;74(11):655. PubMed PMID: 24344371. 11: Medford AR. Sleep-induced hypoxaemia:remember medroxyprogesterone and acetazolamide. Br J Hosp Med (Lond). 2013 Nov;74(11):654-5. PubMed PMID: 24344370. 12: Harper KN. Two recent studies find Depo-Provera use increases HIV risk. AIDS. 2015 Jun 1;29(9):N1. doi: 10.1097/QAD.0000000000000660. PubMed PMID: 25870992. 13: Nasir SA, Sharma A, Khanam R, Vohora D. Effect of medroxyprogesterone on development of pentylenetetrazole-induced kindling in mice. Neuroscience. 2012 Apr 5;207:283-7. doi: 10.1016/j.neuroscience.2012.01.031. Epub 2012 Jan 25. PubMed PMID: 22314318. 14: Skinner JR, Vandenberg JI. Is medroxyprogesterone safe in women with long QT syndrome? Heart Rhythm. 2012 Jul;9(7):1148-9. doi: 10.1016/j.hrthm.2012.02.029. Epub 2012 Mar 6. PubMed PMID: 22401936. 15: Meng Q, Sun X, Wang J, Wang Y. [Mechanism of thioridazine plus medroxyprogesterone in the treatment of endometrial cancer]. Zhonghua Yi Xue Za Zhi. 2015 May 19;95(19):1540-3. Chinese. PubMed PMID: 26178512. 16: Nooh AM, Abdeldayem HM, Girbash EF, Arafa EM, Atwa K, Abdel-Raouf SM. Depo-Provera Versus Norethisterone Acetate in Management of Endometrial Hyperplasia Without Atypia. Reprod Sci. 2016 Apr;23(4):448-54. doi: 10.1177/1933719115623643. Epub 2015 Dec 29. PubMed PMID: 26718306. 17: Kline W. Bodies of evidence: activists, patients, and the FDA regulation of Depo-Provera. J Womens Hist. 2010;22(3):64-87. PubMed PMID: 20857592. 18: Sanders-Beer B, Babas T, Mansfield K, Golightly D, Kramer J, Bowlsbey A, Sites D, Nieves-Duran L, Lin S, Rippeon S, Donnelly G, Rhodes L, Spano YE. Depo-Provera does not alter disease progression in SIVmac-infected female Chinese rhesus macaques. AIDS Res Hum Retroviruses. 2010 Apr;26(4):433-43. doi: 10.1089/aid.2009.0185. PubMed PMID: 20377424; PubMed Central PMCID: PMC2864058. 19: Lam C, Murthy AS. Depo-Provera (depot medroxyprogesterone acetate) use after bariatric surgery. Open Access J Contracept. 2016 Sep 29;7:143-150. doi: 10.2147/OAJC.S84097. eCollection 2016. Review. PubMed PMID: 29386945; PubMed Central PMCID: PMC5683152. 20: Dempsey A, Roca C, Westhoff C. Vaginal estrogen supplementation during Depo-Provera initiation: a randomized controlled trial. Contraception. 2010 Sep;82(3):250-5. doi: 10.1016/j.contraception.2010.04.003. Epub 2010 May 11. PubMed PMID: 20705153.