Back أسيتات ميدروكسي بروجستيرون Arabic مێدرۆکسی پرۆجێسترۆن ئاستەیت CKB 17-acetato de medroxiprogesterona Spanish مدروکسی پروژسترون استات Persian Medroksiprogesteroniasetaatti Finnish Acétate de médroxyprogestérone French Acetato de medroxiproxesterona Galician Medroksiprogesteron asetat ID メドロキシプロゲステロン Japanese Medroksiprogesteron asetat MAD

Medroxyprogesterone acetate

Not to be confused with progesterone, a natural and bioidentical progestogen.

Medroxyprogesterone acetate
Clinical data
Pronunciation/mɛˌdrɒksiproʊˈdʒɛstəroʊn ˈæsɪteɪt/ me-DROKS-ee-proh-JES-tər-ohn ASS-i-tayt[1]
Trade namesDepo-Provera, others
Other namesMPA; DMPA; Methylhydroxyprogesterone acetate; Methylacetoxyprogesterone; MAP; Methypregnone; Metipregnone; 6α-Methyl-17α-hydroxyprogesterone acetate; 6α-Methyl-17α-acetoxyprogesterone; 6α-Methyl-17α-hydroxypregn-4-ene-3,20-dione acetate; NSC-26386
AHFS/Drugs.comMonograph
MedlinePlusa604039
Pregnancy
category
  • AU: D
Routes of
administration		By mouth, sublingual, intramuscular injection, subcutaneous injection
Drug classProgestogen; Progestin; Progestogen ester; Antigonadotropin; Steroidal antiandrogen
ATC code
Legal status
Legal status
Pharmacokinetic data
BioavailabilityBy mouth: ~100%[4][5]
Protein binding88% (to albumin)[5]
MetabolismLiver (hydroxylation (CYP3A4), reduction, conjugation)[6][4][9]
Elimination half-lifeBy mouth: 12–33 hours[6][4]
IM (aq. susp.Tooltip aqueous suspension): ~50 days[7]
SC (aq. susp.): ~40 days[8]
ExcretionUrine (as conjugates)[6]
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
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.000.689 Edit this at Wikidata
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][4] It is used as a method of birth control and as a part of menopausal hormone therapy.[10][4] It is also used to treat endometriosis, abnormal uterine bleeding, paraphilia, and certain types of cancer.[10] The medication is available both alone and in combination with an estrogen.[11][12] 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.[4] It also has androgenic activity and weak glucocorticoid activity. Due to its progestogenic activity, MPA decreases the body's release of gonadotropins and can suppress sex hormone levels.[13] 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.[14][15][10] It is on the World Health Organization's List of Essential Medicines.[16] MPA is the most widely used progestin in menopausal hormone therapy and in progestogen-only birth control.[17][18] DMPA is approved for use as a form of long-acting birth control in more than 100 countries.[19][20] In 2021, it was the 238th most commonly prescribed medication in the United States, with more than 1 million prescriptions.[21][22]

  1. ^ "Medroxyprogesterone Uses, Dosage & Side Effects".
  2. ^ "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 October 2023.
  3. ^ "Product monograph brand safety updates". Health Canada. February 2024. Retrieved 24 March 2024.
  4. ^ a b c d e f 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. S2CID 24616324.
  5. ^ 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.
  6. ^ a b c "Provera" (PDF). FDA. 2015. Archived from the original (PDF) on 11 February 2017. Retrieved 31 March 2018.
  7. ^ "Depo_Provera" (PDF). FDA. 2016. Retrieved 31 March 2018.
  8. ^ "depo-subQ Provera" (PDF). FDA. 2017. Retrieved 31 March 2018.
  9. ^ Cite error: The named reference pmid26291834 was invoked but never defined (see the help page).
  10. ^ a b c d e f g h i "Medroxyprogesterone Acetate". The American Society of Health-System Pharmacists. Archived from the original on 24 December 2016. Retrieved 8 December 2016.
  11. ^ Cite error: The named reference Drugs.com was invoked but never defined (see the help page).
  12. ^ Cite error: The named reference Martindale was invoked but never defined (see the help page).
  13. ^ Cite error: The named reference Genazzani1993 was invoked but never defined (see the help page).
  14. ^ Roberts SM (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. [...] medroxyprogesterone acetate, also known as Provera (discovered simultaneously by Searle and Upjohn in 1956) [..]
  15. ^ Sneader W (2005). "Chapter 18: Hormone analogs". Drug discovery: a history. New York: Wiley. p. 204. ISBN 0-471-89980-1.
  16. ^ 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.
  17. ^ Meikle AW (1 June 1999). Hormone Replacement Therapy. Springer Science & Business Media. pp. 383–. ISBN 978-1-59259-700-0.
  18. ^ 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.{{cite book}}: CS1 maint: multiple names: authors list (link)
  19. ^ Cite error: The named reference BagadePawar2014c was invoked but never defined (see the help page).
  20. ^ Cite error: The named reference Gunasheela2011 was invoked but never defined (see the help page).
  21. ^ "The Top 300 of 2021". ClinCalc. Archived from the original on 15 January 2024. Retrieved 14 January 2024.
  22. ^ "Medroxyprogesterone - Drug Usage Statistics". ClinCalc. Retrieved 14 January 2024.

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