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.