Ulipristal acetate

Ulipristal acetate
Clinical data
Trade namesElla, EllaOne, Esmya, others
Other namesCDB-2914; 11β-[4-(Dimethylamino)phenyl]-17α-acetoxy-19-norpregna-4,9-diene-3,20-dione
AHFS/Drugs.comMonograph
License data
Routes of
administration		By mouth
Drug classSelective progesterone receptor modulator[1]
ATC code
Legal status
Legal status
Pharmacokinetic data
BioavailabilityNearly 100%
Protein binding96.7–99.5%
MetabolismLikely CYP3A4
Elimination half-life32 hours[1]
Excretionca. 90% with feces
Identifiers
  • [(8S,11R,13S,14S,17R)-17-acetyl-11-[4-(dimethylamino)phenyl]-13-methyl-3-oxo-1,2,6,7,8,11,12,14,15,16-decahydrocyclopenta[a]phenanthren-17-yl] acetate
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.207.349 Edit this at Wikidata
Chemical and physical data
FormulaC30H37NO4
Molar mass475.629 g·mol−1
3D model (JSmol)
  • CC(=O)OC4(C(C)=O)CCC3C1CCC2=CC(=O)CCC2=C1C(CC34C)c5ccc(N(C)C)cc5
  • InChI=1S/C30H37NO4/c1-18(32)30(35-19(2)33)15-14-27-25-12-8-21-16-23(34)11-13-24(21)28(25)26(17-29(27,30)3)20-6-9-22(10-7-20)31(4)5/h6-7,9-10,16,25-27H,8,11-15,17H2,1-5H3/t25-,26+,27-,29-,30-/m0/s1 ☒N
  • Key:OOLLAFOLCSJHRE-ZHAKMVSLSA-N ☒N
 ☒NcheckY (what is this?)  (verify)

Ulipristal acetate, sold under the brand name Ella among others, is a medication used for emergency contraception (birth control) and uterine fibroids.[1][7][8] As emergency contraception it should be used within 120 hours of vaginally penetrating intercourse.[1] For fibroids it may be taken for up to six months.[9] It is taken by mouth.[1]

Common side effects include headache, nausea, feeling tired, and abdominal pain.[1] It should not be used in women who are already pregnant.[1] It is in the selective progesterone receptor modulator (SPRM) class of medications.[1] It works by preventing the effects of progesterone, therefore preventing ovulation but not affecting fertilization or implantation.[10][11]

Ulipristal acetate was approved for medical use in the United States in 2010.[1] It is on the World Health Organization's List of Essential Medicines.[12]

Medical uses

Emergency contraception

For emergency contraception[13] a 30 mg tablet is used within 120 hours (5 days) after unprotected intercourse or contraceptive failure.[6] It has been shown to prevent about 62–85% of expected pregnancies,[14] and prevents more pregnancies than emergency contraception with levonorgestrel.[15] Ulipristal acetate is available by prescription for emergency contraception in over 50 countries, with access through pharmacists without a prescription being tested in the United Kingdom.[16][17][18][19] In November 2014, the European Medicines Agency (EMA) recommended availability of ellaOne emergency contraceptive without prescription in the European Union.[20] In January 2015 the European Commission issued an implementing decision amending accordingly the marketing authorization of EllaOne in the EU.[21] Since July 2016, it is available without prescription in Israel.

Uterine fibroids

Ulipristal acetate is used for pre-operative treatment of moderate to severe symptoms of uterine fibroids in adult women of reproductive age.[22] The use of ulipristal acetate to treat fibroids was suspended in the European Union in March 2020.[22]

In November 2020, the Committee for Medicinal Products for Human Use (CHMP) of the European Medicines Agency (EMA) recommended that ulipristal acetate be used only to treat uterine fibroids in premenopausal women for whom surgical procedures (including uterine fibroid embolization) are not appropriate or have not worked.[23] In addition, the committee stated that ulipristal acetate must not be used for controlling symptoms of uterine fibroids while awaiting surgical treatment.[23]

Treatment of uterine fibroids with ulipristal acetate for 13 weeks effectively controlled excessive bleeding due to uterine fibroids and reduced the size of the fibroids.[24][25][26]

Two intermittent 3-months treatment courses of ulipristal acetate 10 mg resulted in amenorrhea at the end of the first treatment course in 79.5%, at the end of the second course in 88.5% of subjects. Mean myoma volume reduction observed during the first treatment course (−41.9%) was maintained during the second one (−43.7%).[22] After two to four 3-months courses of treatment, UPA-treated fibroids shown about -70% in volume reduction.[27]

Volume reduction of uterine fibroid induced by ulipristal acetate was tentatively explained by the combination of multifactorial events involving control of proliferation of the tumor cells, induction of apoptosis and remodeling of the extracellular matrix[28] under the action of matrix metalloproteinases.[29]

In May 2018, the European Medicines Agency (EMA) recommended measures to minimize the risk of rare but serious liver injury with ulipristal, including contraindication in women with known liver problems; liver tests before, during and after stopping treatment; a card for women to inform them about the need for liver monitoring and to contact their doctor should they develop symptoms of liver injury. In addition, use of the medicine for more than one treatment course has been restricted to women who are not eligible for surgery.[30]

Contraindications

Ulipristal acetate should not be taken by women with severe liver diseases[31] because of its CYP mediated metabolism. It has not been studied in women under the age of 18.[32]: 33, 43 

It is also not recommended for women with severe asthma receiving glucocorticoid treatment because it has shown antiglucocorticoid effects in animal studies.[32]: 10, 44 

Pregnancy

Unlike levonorgestrel, and like mifepristone, ulipristal acetate is embryotoxic in animal studies.[32]: 16  Before taking the drug, a pregnancy must be excluded.[6] The EMA proposed to avoid any allusion to a possible use as an abortifacient in the package insert to avert off-label use.[32]: 41  It is unlikely that ulipristal acetate could effectively be used as an abortifacient, since it is used in much lower doses (30 mg) than the roughly equipotent mifepristone (600 mg), and since mifepristone has to be combined with a prostaglandin for the induction of abortion.[33] However, data on embryotoxicity in humans are very limited, and it is not clear what the risk for an abortion or for teratogenicity (birth defects) is. Of the 29 women studied who became pregnant despite taking ulipristal acetate, 16 had induced abortions, six had spontaneous abortions, six continued the pregnancies, and one was lost to follow-up.[32]: 37 

Lactation

It is not recommended to breast feed within seven days of taking the drug since ulipristal acetate is excreted into the breast milk, and possible effects on the infant have not been studied.[31][32]: 43 

Side effects

The most common side effects include headache, nausea (feeling sick), abdominal pain (stomach ache), and dysmenorrhea (period pains).[6]

Interactions

Ulipristal acetate is metabolized by CYP3A4 in vitro. Ulipristal acetate is likely to interact with substrates of CYP3A4, like rifampicin, phenytoin, St John's wort, carbamazepine or ritonavir, therefore concomitant use with these agents is not recommended.[22][32]: 12, 14  It might also interact with hormonal contraceptives and progestogens such as levonorgestrel and other substrates of the progesterone receptor, as well as with glucocorticoids.[22]

Pharmacology

Pharmacodynamics

As an SPRM, ulipristal acetate has partial agonistic as well as antagonistic effects on the progesterone receptor. Ulipristal acetate exhibits similar potency to antagonize progesterone receptor as mifepristone in vitro.[34] It also binds to the androgen receptor and the glucocorticoid receptor, but is only a weak antiandrogen and antiglucocorticoid relative to flutamide and mifepristone, respectively.[35][36] Ulipristal acetate has no relevant affinity to the estrogen and mineralocorticoid receptors.[37] Phase II clinical trials suggest that the mechanism might consist of blocking or delaying ovulation and of delaying the maturation of the endometrium.[32]: 22–23 

Pharmacokinetics

In animal studies, the drug was quickly and nearly completely absorbed from the gut. Intake of food delays absorption, but it is not known whether this is clinically relevant.[32]: 12, 20 

Ulipristal acetate is metabolized in the liver, most likely by CYP3A4, and to a small extent by CYP1A2 and CYP2D6. The two main metabolites have been shown to be pharmacologically active, but less than the original drug. The main excretion route is via the feces.[32]: 13–14, 21 

History

Ulipristal acetate was granted marketing authorization by the European Medicines Agency (EMA) in May 2009.[6] In 2014, the EMA recommended ulipristal be made available without a prescription in the European Union.[38][6]

The U.S. Food and Drug Administration (FDA) approved the drug for use in the United States on 13 August 2010,[39] following the FDA advisory committee's recommendation.[40][41] Watson Pharmaceuticals announced the availability of ulipristal acetate in the United States on 1 December 2010, in retail pharmacies, clinics, and one on-line pharmacy, KwikMed.[42]

Society and culture

Brand names

Ulipristal acetate is marketed in the United States under the brand name Ella and in Canada under the brand name Fibristal.[8] It is also marketed under the brand names EllaOne and Esmya in many countries including the United Kingdom and Ireland.[8] A few less-widely used brand names also exist.[8]

References

  1. ^ a b c d e f g h i "Ulipristal Acetate". The American Society of Health-System Pharmacists. Archived from the original on 10 December 2017. Retrieved 8 December 2017.
  2. ^ "Prescription medicines: registration of new chemical entities in Australia, 2015". Therapeutic Goods Administration (TGA). 21 June 2022. Retrieved 10 April 2023.
  3. ^ "ellaOne 30 mg - Summary of Product Characteristics (SmPC)". (emc). 1 July 2021. Retrieved 28 February 2022.
  4. ^ "Esmya 5 mg Tablets (ulipristal acetate) - Summary of Product Characteristics (SmPC)". (emc). 17 February 2021. Retrieved 28 February 2022.
  5. ^ "Ella- ulipristal acetate tablet". DailyMed. 1 November 2023. Retrieved 26 September 2024.
  6. ^ a b c d e f "ellaOne EPAR". European Medicines Agency (EMA). 3 June 2009. Retrieved 8 July 2020.
  7. ^ Garnock-Jones KP, Duggan ST (October 2017). "Ulipristal Acetate: A Review in Symptomatic Uterine Fibroids". Drugs. 77 (15): 1665–1675. doi:10.1007/s40265-017-0812-3. PMID 28900897. S2CID 207489367.
  8. ^ a b c d "Ulipristal - Drugs.com". Drugs.com. Archived from the original on 14 December 2017. Retrieved 14 December 2017.
  9. ^ British national formulary : BNF 69 (69 ed.). British Medical Association. 2015. pp. 510, 560. ISBN 9780857111562.
  10. ^ Likis FE (2016). Women's Gynecologic Health. Jones & Bartlett Publishers. p. 243. ISBN 9781284076028. Archived from the original on 10 December 2017.
  11. ^ Li HW, Resche-Rigon M, Bagchi IC, Gemzell-Danielsson K, Glasier A (November 2019). "Does ulipristal acetate emergency contraception (ella®) interfere with implantation?". Contraception. 100 (5): 386–390. doi:10.1016/j.contraception.2019.07.140. PMID 31351035. S2CID 198952998.
  12. ^ World Health Organization (2023). The selection and use of essential medicines 2023: web annex A: World Health Organization model list of essential medicines: 23rd list (2023). Geneva: World Health Organization. hdl:10665/371090. WHO/MHP/HPS/EML/2023.02.
  13. ^ Creinin MD, Schlaff W, Archer DF, Wan L, Frezieres R, Thomas M, et al. (November 2006). "Progesterone receptor modulator for emergency contraception: a randomized controlled trial". Obstetrics and Gynecology. 108 (5): 1089–1097. doi:10.1097/01.AOG.0000239440.02284.45. PMC 2853373. PMID 17077229.
  14. ^ Trussell J, Raymond EG, Cleland K (2014). "Emergency Contraception: A Last Chance to Prevent Unintended Pregnancy" (PDF). Contemporary Readings in Law and Social Justice. 6 (2): 7–38. Archived (PDF) from the original on 23 September 2010.
  15. ^ Glasier AF, Cameron ST, Fine PM, Logan SJ, Casale W, Van Horn J, et al. (February 2010). "Ulipristal acetate versus levonorgestrel for emergency contraception: a randomised non-inferiority trial and meta-analysis". Lancet. 375 (9714): 555–562. doi:10.1016/S0140-6736(10)60101-8. PMID 20116841. S2CID 26771153.
  16. ^ Trussell J, Wynn L (13 February 2013). "Dedicated emergency contraceptive pills worldwide" (PDF). Princeton: Office of Population Research at Princeton University, Association of Reproductive Health Professionals. Archived (PDF) from the original on 4 March 2016. Retrieved 25 March 2014.
  17. ^ ICEC (2014). "EC pill types and countries of availability, by brand". New York: International Consortium for Emergency Contraception (ICEC). Archived from the original on 5 April 2016. Retrieved 25 March 2014.
  18. ^ HRA Pharma (March 2013). "Countries where ellaOne was launched". Paris: HRA Pharma. Archived from the original on 28 July 2013. Retrieved 25 March 2014.
  19. ^ ECEC (2014). "Emergency contraception availability in Europe". New York: European Consortium for Emergency Contraception (ECEC). Archived from the original on 25 March 2014. Retrieved 25 March 2014. Ulipristal acetate Emergency Contraception Pills (UPA ECPs), while available in most European countries since 2010, are not yet available in Albania, Estonia, Macedonia, Malta, Switzerland and Turkey. For now[when?] UPA ECPs are sold with a prescription in all countries, although provision without a prescription is currently[when?] being tested in the United Kingdom.
  20. ^ "EMA recommends availability of ellaOne emergency contraceptive without prescription". ema.europa.eu. Archived from the original on 8 November 2017. Retrieved 7 May 2018.
  21. ^ "Amending the marketing authorisation granted by Decision C(2009)4049 for "ellaOne - ulipristal acetate", a medicinal product for human use" (PDF). Archived (PDF) from the original on 8 November 2017. Retrieved 4 February 2016.
  22. ^ a b c d e "Esmya EPAR". European Medicines Agency (EMA). 15 March 2012. Retrieved 8 July 2020.
  23. ^ a b "Ulipristal acetate for uterine fibroids: EMA recommends restricting use". European Medicines Agency (EMA). 13 November 2020. Retrieved 13 November 2020. Text was copied from this source which is copyright European Medicines Agency. Reproduction is authorized provided the source is acknowledged.
  24. ^ Nieman LK, Blocker W, Nansel T, Mahoney S, Reynolds J, Blithe D, et al. (February 2011). "Efficacy and tolerability of CDB-2914 treatment for symptomatic uterine fibroids: a randomized, double-blind, placebo-controlled, phase IIb study". Fertility and Sterility. 95 (2): 767–72.e1–2. doi:10.1016/j.fertnstert.2010.09.059. PMC 4180231. PMID 21055739.
  25. ^ Levens ED, Potlog-Nahari C, Armstrong AY, Wesley R, Premkumar A, Blithe DL, et al. (May 2008). "CDB-2914 for uterine leiomyomata treatment: a randomized controlled trial". Obstetrics and Gynecology. 111 (5): 1129–1136. doi:10.1097/AOG.0b013e3181705d0e. PMC 2742990. PMID 18448745.
  26. ^ Donnez J, Tatarchuk TF, Bouchard P, Puscasiu L, Zakharenko NF, Ivanova T, et al. (February 2012). "Ulipristal acetate versus placebo for fibroid treatment before surgery". The New England Journal of Medicine. 366 (5): 409–420. doi:10.1056/NEJMoa1103182. PMID 22296075.
  27. ^ Donnez J, Vázquez F, Tomaszewski J, Nouri K, Bouchard P, Fauser BC, et al. (June 2014). "Long-term treatment of uterine fibroids with ulipristal acetate ☆". Fertility and Sterility. 101 (6): 1565–73.e1–18. doi:10.1016/j.fertnstert.2014.02.008. PMID 24630081.
  28. ^ Courtoy GE, Donnez J, Marbaix E, Dolmans MM (August 2015). "In vivo mechanisms of uterine myoma volume reduction with ulipristal acetate treatment". Fertility and Sterility. 104 (2): 426–34.e1. doi:10.1016/j.fertnstert.2015.04.025. PMID 26003270.
  29. ^ Courtoy GE, Henriet P, Marbaix E, de Codt M, Luyckx M, Donnez J, Dolmans MM (April 2018). "Matrix Metalloproteinase Activity Correlates With Uterine Myoma Volume Reduction After Ulipristal Acetate Treatment". The Journal of Clinical Endocrinology and Metabolism. 103 (4): 1566–1573. doi:10.1210/jc.2017-02295. PMID 29408988.
  30. ^ "Esmya: new measures to minimise risk of rare but serious liver injury". European Medicines Agency (EMA). 8 August 2018. Text was copied from this source which is copyright European Medicines Agency. Reproduction is authorized provided the source is acknowledged.
  31. ^ a b "ellaOne: EPAR - Product Information" (PDF). European Medicines Agency (EMA). 26 May 2020.
  32. ^ a b c d e f g h i j CHMP (2009). "Assessment Report for Ellaone" (PDF). EMA. Retrieved 22 November 2009.
  33. ^ RCOG (2004). The Care of Women Requesting Induced Abortion : Evidence-based clinical guideline number 7 (PDF). London: RCOG Press. ISBN 1-904752-06-3. Archived from the original (PDF) on 27 February 2008.
  34. ^ Šauer P, Stará A, Golovko O, Valentová O, Bořík A, Grabic R, Kroupová HK (June 2018). "Two synthetic progestins and natural progesterone are responsible for most of the progestagenic activities in municipal wastewater treatment plant effluents in the Czech and Slovak republics". Water Research. 137: 64–71. Bibcode:2018WatRe.137...64S. doi:10.1016/j.watres.2018.02.065. PMID 29544204. S2CID 4726126.
  35. ^ 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. Bibcode:2018EPoll.242..417S. doi:10.1016/j.envpol.2018.06.104. PMID 29990947. S2CID 51622914.
  36. ^ Hilal-Dandan R, Brunton L (2013). Goodman and Gilman's Manual of Pharmacology and Therapeutics. McGraw Hill Professional. ISBN 978-0-07-176917-4.[page needed]
  37. ^ Attardi BJ, Burgenson J, Hild SA, Reel JR (March 2004). "In vitro antiprogestational/antiglucocorticoid activity and progestin and glucocorticoid receptor binding of the putative metabolites and synthetic derivatives of CDB-2914, CDB-4124, and mifepristone". The Journal of Steroid Biochemistry and Molecular Biology. 88 (3): 277–288. doi:10.1016/j.jsbmb.2003.12.004. PMID 15120421. S2CID 23958876.
  38. ^ "EMA recommends availability of ellaOne emergency contraceptive without prescription". European Medicines Agency (EMA) (Press release). Retrieved 7 July 2020.
  39. ^ "FDA grants approval of ella for emergency contraception" (PDF) (Press release). HRA Pharma. 13 August 2010. Retrieved 15 August 2010.[permanent dead link‍]
  40. ^ Hitt E (18 June 2010). "FDA Panel Gives Ulipristal Acetate Unanimous Positive Vote for Emergency Contraception Indication". Archived from the original on 9 March 2011. Retrieved 22 June 2010.
  41. ^ Harris G (14 August 2010). "F.D.A. Approves 5-Day Emergency Contraceptive". The New York Times. Archived from the original on 3 April 2012. Retrieved 14 August 2010.
  42. ^ Watson PR (1 December 2010). "Watson Launches ella(R)(ulipristal acetate)". Retrieved 12 January 2010.[permanent dead link‍]

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Japanese manga series Rurouni redirects here. For the related word for wandering samurai, see Rōnin. Rurouni Kenshin28th tankōbon volume cover, featuring Himura Kenshin (front) and Kamiya Kaoru (back)るろうに剣心 -明治剣客浪漫譚-(Rurōni Kenshin -Meiji Kenkaku Roman Tan-)GenreAdventure[1]Martial arts[2]Romance[2] MangaWritten byNobuhiro WatsukiPublished byShueishaEnglish publisherNA: Viz MediaImprintJump ComicsMagazineWeekly Shōnen JumpDemogra...

 

2022–2023 mpox outbreak in the United States

Ongoing viral outbreak 2022–2023 mpox outbreak in the United StatesSpread of mpox by US state as of September 24, 2022 DiseaseMpoxVirus strainMonkeypox virus (West African clade)LocationUnited StatesIndex caseBoston, Massachusetts[1]Arrival dateMay 17, 2022 (2 years, 2 months and 3 days ago)Dateas of April 13, 2023Confirmed cases30,344[2]Deaths42[2]Government websitewww.cdc.gov/poxvirus/mpox/response/2022/ The 2022–2023 mpox outbreak in the United St...

Radián

El radián (símbolo: r a d {\displaystyle rad} ) es una unidad de la amplitud de ángulos. El radián mide el ángulo presentado como central a una circunferencia y su medida es igual a la razón entre la longitud del arco que comprende de dicha circunferencia y la longitud del radio, es decir, mide la cantidad de veces que la longitud del radio traza ese determinado arco en la circunferencia. Hasta 1995 tuvo la categoría de unidad suplementaria en el Sistema Internacional de Unidades, junt...

 

Laurence Kettle

Irish engineer (1878–1960) Laurence J. Kettle Laurence Joseph Kettle D.Sc. (27 February 1878 – 27 August 1960) was a key figure in the industrial and scientific advancement of early twentieth-century Ireland, serving as Chief Engineer of the Dublin Corporation,[1] before being elected as President of The Institution of Civil Engineers and becoming the first chairman of the Industrial Research Committee. He was a founding member of the World Power Conference, a fellow of the Instit...