Wikipedia

User:Mr. Ibrahem/Medroxyprogesterone

< User:Mr. Ibrahem
Not to be confused with progesterone, a natural and bioidentical progestogen.
Mr. Ibrahem/Medroxyprogesterone
Clinical data
Pronunciation/mɛˌdrɒksiproʊˈdʒɛstəroʊn ˈæsɪteɪt/ me-DROKS-ee-proh-JES-tər-ohn ASS-i-tayt[1]
Trade namesProvera, Depo-Provera, Depo-SubQ Provera 104, Curretab, Cycrin, Farlutal, Gestapuran, Perlutex, Veramix, others[2]
Other namesMPA; DMPA; methylhydroxyprogesterone acetate
AHFS/Drugs.comMonograph
MedlinePlusa604039
Routes of
administration		By mouth, sublingual, intramuscular injection, subcutaneous injection
Drug classProgestogen; progestin; antigonadotropin; steroidal antiandrogen
Legal status
Legal status
  • AU: S4 (Prescription only)
  • US: ℞-only
  • In general: ℞ (Prescription only)
Pharmacokinetic data
BioavailabilityBy mouth: ~100%[3][4]
Protein binding88% (to albumin)[4]
MetabolismLiver (hydroxylation (CYP3A4), reduction, conjugation)[5][3][9]
Elimination half-lifeBy mouth: 12–33 hours[5][3]
IM (aq. susp.Tooltip aqueous suspension): ~50 days[6]
SC (aq. susp.): ~40 days[7]
Duration of action3 months (depo injection)[8]
ExcretionUrine (as conjugates)[5]
Identifiers
  • [(6S,8R,9S,10R,13S,14S,17R)-17-acetyl-6,10,13-trimethyl-3-oxo-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthren-17-yl] acetate
Chemical and physical data
FormulaC24H34O4
Molar mass386.532 g·mol−1
3D model (JSmol)
Melting point207 to 209 °C (405 to 408 °F)
  • C[C@H]1C[C@@H]2[C@H](CC[C@]3([C@H]2CC[C@@]3(C(=O)C)OC(=O)C)C)[C@@]4(C1=CC(=O)CC4)C
  • InChI=InChI=1S/C24H34O4/c1-14-12-18-19(22(4)9-6-17(27)13-21(14)22)7-10-23(5)20(18)8-11-24(23,15(2)25)28-16(3)26/h13-14,18-20H,6-12H2,1-5H3/t14-,18+,19-,20-,22+,23-,24-/m0/s1
  • Key:PSGAAPLEWMOORI-PEINSRQWSA-N
  (verify)

Medroxyprogesterone acetate (MPA), also known as depot medroxyprogesterone acetate (DMPA) in injectable form and sold under the brand name Depo-Provera among others, is a hormonal medication of the progestin type.[10][3] It is used as a method of birth control and as a part of menopausal hormone therapy.[10][3] It is also used to treat endometriosis, abnormal uterine bleeding, abnormal sexuality in males, and certain types of cancer.[10] The medication is available both alone and in combination with an estrogen.[12][13] It is taken by mouth, used under the tongue, or by injection into a muscle or fat.[10]

Common side effects include menstrual disturbances such as absence of periods, abdominal pain, and headaches.[10] More serious side effects include bone loss, blood clots, allergic reactions, and liver problems.[10] Use is not recommended during pregnancy as it may harm the baby.[10] MPA is an artificial progestogen, and as such activates the progesterone receptor, the biological target of progesterone.[3] It also has weak glucocorticoid activity and very weak androgenic activity but no other important hormonal activity.[3][14] Due to its progestogenic activity, MPA decreases the body's release of gonadotropins and can suppress sex hormone levels.[15] It works as a form of birth control by preventing ovulation.[10]

MPA was discovered in 1956 and was introduced for medical use in the United States in 1959.[16][17][10] It is on the World Health Organization's List of Essential Medicines.[18] The wholesale cost in the developing world is about US$0.60–1.60 per vial.[19] In the United Kingdom this dose costs the NHS about £6.[20] In the United States it costs less than $25 a dose as of 2015.[21] MPA is the most widely used progestin in menopausal hormone therapy and in progestogen-only birth control.[22][23] DMPA is approved for use as a form of long-acting birth control in more than 100 countries.[24][25] In 2017, it was the 222nd most commonly prescribed medication in the United States, with more than two million prescriptions.[26][27]

References edit

  1. ^ "Archive copy". Archived from the original on 2018-08-03. Retrieved 2018-07-20.{{cite web}}: CS1 maint: archived copy as title (link)
  2. ^ Index Nominum 2000: International Drug Directory. Taylor & Francis. January 2000. pp. 638–. ISBN 978-3-88763-075-1. Archived from the original on 2013-06-19.
  3. ^ a b c d e f g Kuhl H (2005). "Pharmacology of estrogens and progestogens: influence of different routes of administration" (PDF). Climacteric. 8 Suppl 1: 3–63. doi:10.1080/13697130500148875. PMID 16112947. Archived (PDF) from the original on 2016-08-22. Retrieved 2018-04-01.
  4. ^ a b Schindler AE, Campagnoli C, Druckmann R, Huber J, Pasqualini JR, Schweppe KW, Thijssen JH (2008). "Classification and pharmacology of progestins". Maturitas. 61 (1–2): 171–80. doi:10.1016/j.maturitas.2008.11.013. PMID 19434889.
  5. ^ a b c "Provera" (PDF). FDA. 2015. Archived from the original (PDF) on 11 February 2017. Retrieved 31 March 2018.
  6. ^ "Depo_Provera" (PDF). FDA. 2016. Archived (PDF) from the original on 29 July 2020. Retrieved 31 March 2018.
  7. ^ "depo-subQ Provera" (PDF). FDA. 2017. Archived (PDF) from the original on 14 June 2019. Retrieved 31 March 2018.
  8. ^ a b "MEDROXYPROGESTERONE injectable - Essential drugs". medicalguidelines.msf.org. Archived from the original on 5 December 2019. Retrieved 2 September 2020.
  9. ^ Stanczyk FZ, Bhavnani BR (September 2015). "Reprint of "Use of medroxyprogesterone acetate for hormone therapy in postmenopausal women: Is it safe?"". J. Steroid Biochem. Mol. Biol. 153: 151–9. doi:10.1016/j.jsbmb.2015.08.013. PMID 26291834.
  10. ^ a b c d e f g h i j "Medroxyprogesterone Acetate". The American Society of Health-System Pharmacists. Archived from the original on 24 December 2016. Retrieved 8 December 2016.
  11. ^ "WHOCC - ATC/DDD Index". www.whocc.no. Archived from the original on 26 September 2020. Retrieved 2 September 2020.
  12. ^ "Archive copy". Archived from the original on 2018-08-03. Retrieved 2017-11-24.{{cite web}}: CS1 maint: archived copy as title (link)
  13. ^ Sweetman, Sean C., ed. (2009). "Sex hormones and their modulators". Martindale: The Complete Drug Reference (36th ed.). London: Pharmaceutical Press. pp. 2113–2114. ISBN 978-0-85369-840-1. Archived from the original on 2021-08-28. Retrieved 2018-04-01.
  14. ^ Kemppainen JA, Langley E, Wong CI, Bobseine K, Kelce WR, Wilson EM (March 1999). "Distinguishing androgen receptor agonists and antagonists: distinct mechanisms of activation by medroxyprogesterone acetate and dihydrotestosterone". Molecular Endocrinology. 13 (3): 440–54. doi:10.1210/mend.13.3.0255. PMID 10077001.{{cite journal}}: CS1 maint: url-status (link)
  15. ^ Genazzani AR (15 January 1993). Frontiers in Gynecologic and Obstetric Investigation. Taylor & Francis. p. 320. ISBN 978-1-85070-486-7. Archived from the original on 20 May 2016.
  16. ^ Stanley M. Roberts (7 May 2013). Introduction to Biological and Small Molecule Drug Research and Development: Chapter 12. Hormone replacement therapy. Elsevier Science. pp. 9–. ISBN 978-0-12-806202-9. Archived from the original on 1 August 2020. Retrieved 3 April 2018. [...] medroxyprogesterone acetate, also known as Provera® (discovered simultaneously by Searle and Upjohn in 1956) [..]
  17. ^ Sneader, Walter (2005). "Chapter 18: Hormone analogs". Drug discovery: a history. New York: Wiley. p. 204. ISBN 0-471-89980-1.
  18. ^ World Health Organization (2019). World Health Organization model list of essential medicines: 21st list 2019. Geneva: World Health Organization. hdl:10665/325771. WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO.
  19. ^ "Medroxyprogesterone Acetate". International Drug Price Indicator Guide. Archived from the original on 22 January 2018. Retrieved 8 December 2016.
  20. ^ British National Formulary : BNF 69 (69th ed.). British Medical Association. 2015. p. 555. ISBN 978-0-85711-156-2.
  21. ^ Hamilton, Richart (2015). Tarascon Pocket Pharmacopoeia 2015 Deluxe Lab-Coat Edition. Jones & Bartlett Learning. p. 363. ISBN 9781284057560.
  22. ^ A. Wayne Meikle (1 June 1999). Hormone Replacement Therapy. Springer Science & Business Media. pp. 383–. ISBN 978-1-59259-700-0. Archived from the original on 1 August 2020. Retrieved 20 July 2018.
  23. ^ Special Programme of Research, Development, and Research Training in Human Reproduction (World Health Organization); World Health Organization (2002). Research on Reproductive Health at WHO: Biennial Report 2000-2001. World Health Organization. pp. 17–. ISBN 978-92-4-156208-9. Archived from the original on 2020-08-01. Retrieved 2018-07-20.{{cite book}}: CS1 maint: multiple names: authors list (link)
  24. ^ Bagade O, Pawar V, Patel R, Patel B, Awasarkar V, Diwate S (2014). "Increasing use of long-acting reversible contraception: safe, reliable, and cost-effective birth control" (PDF). World J Pharm Pharm Sci. 3 (10): 364–392. ISSN 2278-4357. Archived from the original (PDF) on 2017-08-10. Retrieved 2018-08-02.
  25. ^ Sulochana Gunasheela (14 March 2011). Practical Management of Gynecological Problems. JP Medical Ltd. pp. 39–. ISBN 978-93-5025-240-6. Archived from the original on 1 August 2020. Retrieved 2 August 2018.
  26. ^ "The Top 300 of 2020". ClinCalc. Archived from the original on 12 February 2021. Retrieved 11 April 2020.
  27. ^ "Medroxyprogesterone Acetate - Drug Usage Statistics". ClinCalc. Archived from the original on 2 July 2020. Retrieved 11 April 2020.
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