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Medroxyprogesterone

In today's world, Medroxyprogesterone has become a topic of great relevance and interest to a wide spectrum of people. Whether due to its impact on society, its influence in the cultural sphere, its relevance in history or its importance in personal development, Medroxyprogesterone has managed to capture the attention of millions of individuals around the world. As we explore this topic further, we enter a universe of diverse possibilities and perspectives, which invite us to reflect, question and discuss Medroxyprogesterone. Through this article, we will seek to delve into the various aspects that make Medroxyprogesterone such a relevant topic today, and we will explore its impact in different areas of daily life.

This article is about a non-clinically used progestin compound. For the pharmaceutical drug, see medroxyprogesterone acetate.
Medroxyprogesterone
Clinical data
Other namesMP; Methylhydroxyprogesterone; 6α-Methyl-17α-hydroxyprogesterone; 6α-Methyl-17α-hydroxypregn-4-en-3,20-dione
Drug classProgestin; Progestogen
ATC code
  • None
Legal status
Legal status
Identifiers
  • (6S,8R,9S,10R,13S,14S,17R)-17-acetyl-17-hydroxy-6,10,13-trimethyl-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopentaphenanthren-3-one
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
ECHA InfoCard100.007.545 Edit this at Wikidata
Chemical and physical data
FormulaC22H32O3
Molar mass344.495 g·mol−1
3D model (JSmol)
  • O=C4\C=C2/(1CC3((O)(C(=O)C)CC31C2C)C)(C)CC4
  • 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
  • Key:FRQMUZJSZHZSGN-HBNHAYAOSA-N

Medroxyprogesterone (MP), is a progestin which is not used medically. A derivative, medroxyprogesterone acetate (MPA), is used as a medication in humans, and is far more widely known in comparison. Medroxyprogesterone is sometimes used as a synonym for medroxyprogesterone acetate, and what is almost always being referred to when the term is used is MPA and not medroxyprogesterone.

Pharmacology

Pharmacodynamics

Compared to MPA, medroxyprogesterone is over two orders of magnitude less potent as a progestogen. Medroxyprogesterone is also notable in that it is a minor metabolite of MPA. In addition to its progestagenic activity, medroxyprogesterone is a weak antiandrogen in vitro on human androgen receptor.

MP and related steroids at the PR (nM)
Compound Ki EC50Tooltip Half-maximal effective concentrationa EC50b
Progesterone 4.3 0.9 25
Medroxyprogesterone 241 47 32
Medroxyprogesterone acetate 1.2 0.6 0.15
Values are nM. a = Coactivator recruitment. b = Reporter cell line.

Chemistry

See also: List of progestogens

Medroxyprogesterone, also known as 6α-methyl-17α-hydroxyprogesterone or as 6α-methyl-17α-hydroxypregn-4-en-3,20-dione, is a synthetic pregnane steroid and a derivative of progesterone. It is specifically a derivative of 17α-hydroxyprogesterone with a methyl group at the C6α position. The generic name of medroxyprogesterone is a contraction of 6α-methyl-17α-hydroxyprogesterone. It is closely related to medrogestone as well as other unesterified 17α-hydroxyprogesterone derivatives such as chlormadinone, cyproterone, and megestrol.

Society and culture

Generic names

Medroxyprogesterone is the generic name of the drug and its INNTooltip International Nonproprietary Name and BANTooltip British Approved Name.

Brand Name

Meprate 10 Tablets (practo)

References

  1. ^ "FDA-sourced list of all drugs with black box warnings (Use Download Full Results and View Query links.)". nctr-crs.fda.gov. FDA. Retrieved 22 Oct 2023.
  2. ^ a b c d e Elks J (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 657–. ISBN 978-1-4757-2085-3.
  3. ^ a b c d e Index Nominum 2000: International Drug Directory. Taylor & Francis. 2000. pp. 638–. ISBN 978-3-88763-075-1.
  4. ^ Morton IK, Hall JM (31 October 1999). Concise Dictionary of Pharmacological Agents: Properties and Synonyms. Springer Science & Business Media. pp. 173–. ISBN 978-0-7514-0499-9.
  5. ^ a b "Medroxyprogesterone".
  6. ^ a b "MedroxyPROGESTERone: Drug Information Provided by Lexi-Comp". Merck Manual. 2009-12-01. Retrieved 2010-07-08.
  7. ^ Lenco W, Mcknight M, Macdonald AS (January 1975). "Effects of cortisone acetate, methylprednisolone and medroxyprogesterone on wound contracture and epithelization in rabbits". Annals of Surgery. 181 (1): 67–73. doi:10.1097/00000658-197501000-00015. PMC 1343717. PMID 1119869.
  8. ^ a b Pullen MA, Laping N, Edwards R, Bray J (September 2006). "Determination of conformational changes in the progesterone receptor using ELISA-like assays". Steroids. 71 (9): 792–8. doi:10.1016/j.steroids.2006.05.009. PMID 16784762. S2CID 24703323.
  9. ^ Ishihara M, Kirdani Y, Osawa Y, Sandberg AA (January 1976). "The metabolic fate of medroxyprogesterone acetate in the baboon". Journal of Steroid Biochemistry. 7 (1): 65–70. doi:10.1016/0022-4731(76)90167-9. PMID 1271819.
  10. ^ Šauer P, Bořík A, Golovko O, Grabic R, Staňová AV, Valentová O, et al. (November 2018). "Do progestins contribute to (anti-)androgenic activities in aquatic environments?". Environmental Pollution. 242 (Pt A): 417–425. doi:10.1016/j.envpol.2018.06.104. PMID 29990947. S2CID 51622914.
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