Medroxyprogesterone

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Medroxyprogesterone
Medroxyprogesterone.svg
Medroxiprogesterona3D.png
Clinical data
Trade names Controlestril
Synonyms MP; 6α-Methyl-17α-hydroxyprogesterone; 6α-Methyl-17α-hydroxypregn-4-en-3,20-dione
Pregnancy
category
  • X
ATC code
  • None
Identifiers
CAS Number
PubChem CID
ChemSpider
ECHA InfoCard 100.007.545
Chemical and physical data
Formula C22H32O3
Molar mass 344.488 g/mol
3D model (JSmol)

Medroxyprogesterone (abbreviated as MP), sold under the brand name Controlestril, is a progestin which is used in veterinary medicine in France to control estrus in animals.[1][2][3][4] A derivative, medroxyprogesterone acetate (MPA), is used as a medication in humans, and is far more widely known in comparison.[5] Compared to MPA, MP is over two orders of magnitude less potent as a progestogen.[6] MP is also notable in that it is a metabolite of MPA.[7] Medroxyprogesterone is sometimes used as a synonym for medroxyprogesterone acetate,[5] and what is almost always being referred to when the term is used is MPA and not MP.[8]

Chemistry[edit]

MP, 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.[1][2] It is specifically a derivative of 17α-hydroxyprogesterone with a methyl group at the C6α position.[1][2] The generic name of MP 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.[1][2]

Society and culture[edit]

Generic names[edit]

Medroxyprogesterone is the generic name of the drug and its INN and BAN.[1][2][4]

References[edit]

  1. ^ a b c d e J. Elks (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 657–. ISBN 978-1-4757-2085-3. 
  2. ^ a b c d e Index Nominum 2000: International Drug Directory. Taylor & Francis. 2000. pp. 638–. ISBN 978-3-88763-075-1. 
  3. ^ I.K. Morton; Judith M. Hall (31 October 1999). Concise Dictionary of Pharmacological Agents: Properties and Synonyms. Springer Science & Business Media. pp. 173–. ISBN 978-0-7514-0499-9. 
  4. ^ a b https://www.drugs.com/international/medroxyprogesterone.html
  5. ^ a b "MedroxyPROGESTERone: Drug Information Provided by Lexi-Comp". Merck Manual. 2009-12-01. Retrieved 2010-07-08. 
  6. ^ 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. 
  7. ^ Ishihara M, Kirdani Y, Osawa Y, Sandberg AA (January 1976). "The metabolic fate of medroxyprogesterone acetate in the baboon". J. Steroid Biochem. 7 (1): 65–70. doi:10.1016/0022-4731(76)90167-9. PMID 1271819. 
  8. ^ Lenco W, Mcknight M, Macdonald AS (January 1975). "Effects of cortisone acetate, methylprednisolone and medroxyprogesterone on wound contracture and epithelization in rabbits". Ann. Surg. 181 (1): 67–73. doi:10.1097/00000658-197501000-00015. PMC 1343717Freely accessible. PMID 1119869.