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{{Short description|Chemical compound}}
{{Use dmy dates|date=July 2024}}
{{Drugbox {{Drugbox
| Verifiedfields = changed
| Watchedfields = changed | Watchedfields = changed
| verifiedrevid = 401687818 | verifiedrevid = 405300137
| image = Ulipristal acetate skeletal.svg
| IUPAC_name = (8''S'',11''S'',13''S'',14''R'',17''R'')-17-Acetoxy-11--19-norpregna-4,9-diene-3,20-dione
| image_class = skin-invert-image
| image = Ulipristal acetate skeletal.svg
| width = 250
| CAS_number = 126784-99-4
| alt =
| CAS_supplemental =

| ATC_prefix = G03
<!--Clinical data-->
| ATC_suffix = AD02
| Drugs.com = {{Drugs.com|monograph|ulipristal-acetate}}
| ATC_supplemental =
| tradename = Ella, EllaOne, Esmya, others
| PubChem = 130904
| DailyMedID = Ulipristal acetate
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
| ChemSpiderID =
| DrugBank = | pregnancy_category =
| routes_of_administration = ]
| chemical_formula =
| class = ]<ref name=AHFS2017/>
| ATC_prefix = G03
| ATC_suffix = AD02
| ATC_supplemental = {{ATC|G03|XB02}}

| legal_AU = S4
| legal_AU_comment = <ref>{{cite web | title=Prescription medicines: registration of new chemical entities in Australia, 2015 | website=Therapeutic Goods Administration (TGA) | date=21 June 2022 | url=https://www.tga.gov.au/prescription-medicines-registration-new-chemical-entities-australia-2015 | access-date=10 April 2023}}</ref>
| legal_CA = <!-- Schedule I, II, III, IV, V, VI, VII, VIII -->
| legal_UK = POM
| legal_UK_comment = /&nbsp;P<ref>{{cite web | title=ellaOne 30 mg - Summary of Product Characteristics (SmPC) | website=(emc) | date=1 July 2021 | url=https://www.medicines.org.uk/emc/product/6657/smpc | access-date=28 February 2022}}</ref><ref>{{cite web | title=Esmya 5 mg Tablets (ulipristal acetate) - Summary of Product Characteristics (SmPC) | website=(emc) | date=17 February 2021 | url=https://www.medicines.org.uk/emc/product/3951/smpc | access-date=28 February 2022}}</ref>
| legal_US = Rx-only
| legal_US_comment = <ref>{{cite web | title=Ella- ulipristal acetate tablet | website=DailyMed | date=1 November 2023 | url=https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=2bf93d23-cddd-4613-9066-5b5fa090404b | access-date=26 September 2024}}</ref>
| legal_EU = Rx-only
| legal_EU_comment = <ref name="ellaOne EPAR" />
| legal_status =

<!--Pharmacokinetic data-->
| bioavailability = Nearly 100%
| protein_bound = 96.7–99.5%
| metabolism = Likely ]
| elimination_half-life = 32 hours<ref name=AHFS2017/>
| excretion = ca. 90% with feces

<!--Identifiers-->
| IUPHAR_ligand = 7460
| CAS_number_Ref = {{cascite|correct|??}}
| CAS_number = 126784-99-4
| PubChem = 130904
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = DB08867
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
| ChemSpiderID = 115762
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = YF7V70N02B
| KEGG = D09687
| ChEBI_Ref = {{ebicite|changed|EBI}}
| ChEBI = 71025
| ChEMBL_Ref = {{ebicite|changed|EBI}}
| ChEMBL = 260538
| synonyms = CDB-2914; 11β--17α-acetoxy-19-norpregna-4,9-diene-3,20-dione

<!--Chemical data-->
| IUPAC_name = -13-methyl-3-oxo-1,2,6,7,8,11,12,14,15,16-decahydrocyclopentaphenanthren-17-yl] acetate
| C=30 | H=37 | N=1 | O=4 | C=30 | H=37 | N=1 | O=4
| SMILES = CC(=O)OC4(C(C)=O)CCC3C1CCC2=CC(=O)CCC2=C1C(CC34C)c5ccc(N(C)C)cc5
| molecular_weight = 475.62 g/mol
| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
| smiles = CC(=O)OC4(C(C)=O)CCC3C1CCC2=CC(=O)CCC2=C1C(CC34C)c5ccc(N(C)C)cc5
| StdInChI = 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
| bioavailability = Nearly 100%
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
| protein_bound = 96.7–99.5%
| StdInChIKey = OOLLAFOLCSJHRE-ZHAKMVSLSA-N
| metabolism = Likely ]
| elimination_half-life = 32 hours
| excretion = ca. 90% with faeces
| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
| pregnancy_US = <!-- A / B / C / D / X -->
| pregnancy_category= Contraindicated
| legal_AU = <!-- S2, S3, S4, S5, S6, S7, S8, S9 or Unscheduled-->
| legal_CA = <!-- Schedule I, II, III, IV, V, VI, VII, VIII -->
| legal_UK = POM
| legal_US = Rx-only
| legal_status =
| routes_of_administration = Oral
| licence_EU = Ellaone
| licence_US = Ulipristal
}} }}
'''Ulipristal acetate''' (trade name '''ellaOne''' in the ], '''ella''' in the ],<ref>{{cite press release |title=FDA grants approval of ella® for emergency contraception |url=http://www.hra-pharma.com/downloads/HRA%20FDA%20Approval%20FINAL.pdf |publisher=HRA Pharma |date=August 13, 2010 |accessdate=2010-08-15}}</ref> ]) is a ] (SPRM) for ]<ref>{{cite journal|pmid=17077229|year=2006|last1=Creinin|first1=MD|last2=Schlaff|first2=W|last3=Archer|first3=DF|last4=Wan|first4=L|last5=Frezieres|first5=R|last6=Thomas|first6=M|last7=Rosenberg|first7=M|last8=Higgins|first8=J|title=Progesterone receptor modulator for emergency contraception: a randomized controlled trial|volume=108|issue=5|pages=1089–97|journal=Obstetrics and gynecology|doi=10.1097/01.AOG.0000239440.02284.45|pmc=2853373}}</ref> within 120 hours (5 days) after an unprotected ] or contraceptive failure. It has shown to prevent about 60% of expected pregnancies,<ref>{{cite web|url=http://www.ema.europa.eu/docs/en_GB/document_library/EPAR_-_Summary_for_the_public/human/001027/WC500023671.pdf|title=European Public Assessment Report for Ellaone. Summary for the public|publisher=EMA|page=2|year=2009|accessdate=22 November 2009}}</ref> which is comparable to the emergency contraception scheme with ]. Ulipristal acetate is available by prescription only.


<!-- Definition and medical uses -->
==History==
'''Ulipristal acetate''', sold under the brand name '''Ella''' among others, is a ] used for ] (birth control) and ].<ref name=AHFS2017/><ref>{{cite journal | vauthors = Garnock-Jones KP, Duggan ST | title = Ulipristal Acetate: A Review in Symptomatic Uterine Fibroids | journal = Drugs | volume = 77 | issue = 15 | pages = 1665–1675 | date = October 2017 | pmid = 28900897 | doi = 10.1007/s40265-017-0812-3 | s2cid = 207489367 }}</ref><ref name="Drugs.com">{{cite web|title=Ulipristal - Drugs.com|url=https://www.drugs.com/international/ulipristal.html|website=Drugs.com|access-date=14 December 2017|url-status=live|archive-url=https://web.archive.org/web/20171214015214/https://www.drugs.com/international/ulipristal.html|archive-date=14 December 2017}}</ref> As emergency contraception it should be used within 120 hours of vaginally penetrating intercourse.<ref name=AHFS2017/> For fibroids it may be taken for up to six months.<ref name=BNF69>{{cite book|title=British national formulary : BNF 69|date=2015|publisher=British Medical Association|isbn=9780857111562|pages=510, 560|edition=69}}</ref> It is taken ].<ref name=AHFS2017/>
Ulipristal acetate was granted marketing authorization by the ] (EMA) in March 2009.<ref>{{cite web|url=http://www.ema.europa.eu/docs/en_GB/document_library/EPAR_-_Public_assessment_report/human/001027/WC500023673.pdf|title=Assessment Report for Ellaone|author=CHMP|authorlink=CHMP|publisher=EMA|year=2009|accessdate=22 November 2009|ref=harv}}</ref>


<!-- Side effects and mechanism -->
The ] approved the drug for use in the United States on August 13, 2010,<ref>{{cite press release |title=FDA grants approval of ella® for emergency contraception |url=http://www.hra-pharma.com/downloads/HRA%20FDA%20Approval%20FINAL.pdf |publisher=HRA Pharma |date=August 13, 2010 |accessdate=2010-08-15}}</ref> following the FDA advisory committee's recommendation.<ref>{{cite web|url=http://www.medscape.com/viewarticle/723822 | title=FDA Panel Gives Ulipristal Acetate Unanimous Positive Vote for Emergency Contraception Indication| author= Emma Hitt | date=18 June 2010|accessdate=06-22-2010}}</ref><ref>{{cite news | last = Harris | first = Gardiner | title = F.D.A. Approves 5-Day Emergency Contraceptive | url = http://www.nytimes.com/2010/08/14/health/policy/14pill.html | work = ] | date = August 14, 2010 | accessdate = August 14, 2010}}</ref> ] announced the availability of ulipristal acetate in the United States on December 1, 2010, in retail pharmacies, clinics, and one on-line pharmacy, ].<ref>{{cite web|url=http://ir.watson.com/phoenix.zhtml?c=65778&p=irol-newsArticle&ID=1501974 | title=Watson Launches ella(R)(ulipristal acetate)| author= Watson PR | date=1 December 2010|accessdate=12-1-2010}}</ref>
Common side effects include headache, nausea, feeling tired, and abdominal pain.<ref name=AHFS2017/> It should not be used in women who are already ].<ref name=AHFS2017/> It is in the ] (SPRM) class of medications.<ref name=AHFS2017>{{cite web|title=Ulipristal Acetate|url=https://www.drugs.com/monograph/ulipristal-acetate.html|publisher=The American Society of Health-System Pharmacists|access-date=8 December 2017|url-status=live|archive-url=https://web.archive.org/web/20171210072239/https://www.drugs.com/monograph/ulipristal-acetate.html|archive-date=10 December 2017}}</ref> It works by preventing the effects of ], therefore preventing ] but not affecting ] or ].<ref name=Li2016>{{cite book| vauthors = Likis FE |title=Women's Gynecologic Health|date=2016|publisher=Jones & Bartlett Publishers|isbn=9781284076028|page=243|url=https://books.google.com/books?id=VRm3DAAAQBAJ&pg=PA243|language=en|url-status=live|archive-url=https://web.archive.org/web/20171210071647/https://books.google.ca/books?id=VRm3DAAAQBAJ&pg=PA243|archive-date=10 December 2017}}</ref><ref>{{cite journal | vauthors = Li HW, Resche-Rigon M, Bagchi IC, Gemzell-Danielsson K, Glasier A | title = Does ulipristal acetate emergency contraception (ella®) interfere with implantation? | journal = Contraception | volume = 100 | issue = 5 | pages = 386–390 | date = November 2019 | pmid = 31351035 | doi = 10.1016/j.contraception.2019.07.140 | s2cid = 198952998 }}</ref>


<!-- History, society, and culture -->
==Pharmacokinetics==
Ulipristal acetate was approved for medical use in the United States in 2010.<ref name=AHFS2017/> It is on the ].<ref name="WHO23rd">{{cite book | vauthors = ((World Health Organization)) | title = The selection and use of essential medicines 2023: web annex A: World Health Organization model list of essential medicines: 23rd list (2023) | year = 2023 | hdl = 10665/371090 | author-link = World Health Organization | publisher = World Health Organization | location = Geneva | id = WHO/MHP/HPS/EML/2023.02 | hdl-access=free }}</ref>
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.<ref>{{harvcoltxt|CHMP|2009|pp=12, 20}}</ref>


==Medical uses==
Ulipristal acetate is metabolized in the liver, most likely by ], and to a small extent by ] and ]. The two main metabolites have been shown to be pharmacologically active, but less than the original drug. The main excretion route is via the faeces.<ref>{{harvcoltxt|CHMP|2009|pp=13–14, 21}}</ref>


===Emergency contraception===
==Pharmacodynamics==
For ]<ref>{{cite journal | vauthors = Creinin MD, Schlaff W, Archer DF, Wan L, Frezieres R, Thomas M, Rosenberg M, Higgins J | display-authors = 6 | title = Progesterone receptor modulator for emergency contraception: a randomized controlled trial | journal = Obstetrics and Gynecology | volume = 108 | issue = 5 | pages = 1089–1097 | date = November 2006 | pmid = 17077229 | pmc = 2853373 | doi = 10.1097/01.AOG.0000239440.02284.45 }}</ref> a 30&nbsp;mg tablet is used within 120 hours (5 days) after unprotected ] or contraceptive failure.<ref name="ellaOne EPAR" /> It has been shown to prevent about 62–85% of expected pregnancies,<ref>{{cite journal | vauthors = Trussell J, Raymond EG, Cleland K |year=2014 |title=Emergency Contraception: A Last Chance to Prevent Unintended Pregnancy |journal=Contemporary Readings in Law and Social Justice |volume=6 |issue=2 |pages=7–38 |url=http://ec.princeton.edu/questions/ec-review.pdf |url-status=live |archive-url=https://web.archive.org/web/20100923040101/http://ec.princeton.edu/questions/ec-review.pdf |archive-date=23 September 2010 }}</ref> and prevents more pregnancies than emergency contraception with ].<ref>{{cite journal | vauthors = Glasier AF, Cameron ST, Fine PM, Logan SJ, Casale W, Van Horn J, Sogor L, Blithe DL, Scherrer B, Mathe H, Jaspart A, Ulmann A, Gainer E | display-authors = 6 | title = Ulipristal acetate versus levonorgestrel for emergency contraception: a randomised non-inferiority trial and meta-analysis | journal = Lancet | volume = 375 | issue = 9714 | pages = 555–562 | date = February 2010 | pmid = 20116841 | doi = 10.1016/S0140-6736(10)60101-8 | s2cid = 26771153 }}</ref> 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.<ref>{{cite web | vauthors = Trussell J, Wynn L |date=13 February 2013 |title=Dedicated emergency contraceptive pills worldwide |location=Princeton |publisher=Office of Population Research at Princeton University, Association of Reproductive Health Professionals |url=http://ec.princeton.edu/pills/Dedicated_ECPs.pdf |access-date=25 March 2014 |url-status=live |archive-url=https://web.archive.org/web/20160304190311/http://ec.princeton.edu/pills/Dedicated_ECPs.pdf |archive-date=4 March 2016 }}</ref><ref>{{cite web |author=ICEC |year=2014 |title=EC pill types and countries of availability, by brand |location=New York |publisher=International Consortium for Emergency Contraception (ICEC) |url=http://www.cecinfo.org/country-by-country-information/status-availability-database/ec-pill-types-and-countries-of-availability-by-brand/ |access-date=25 March 2014 |url-status=usurped |archive-url=https://web.archive.org/web/20160405095026/http://www.cecinfo.org/country-by-country-information/status-availability-database/ec-pill-types-and-countries-of-availability-by-brand/ |archive-date=5 April 2016 }}</ref><ref>{{cite web |author=HRA Pharma |date=March 2013 |title=Countries where ellaOne was launched |location=Paris |publisher=] |url=http://www.ellaone.com |access-date=25 March 2014 |url-status=dead |archive-url=https://web.archive.org/web/20130728203014/http://www.ellaone.com/ |archive-date=28 July 2013 }}</ref><ref>{{cite web |author=ECEC |year=2014 |title=Emergency contraception availability in Europe |location=New York |publisher=European Consortium for Emergency Contraception (ECEC) |url=http://www.ec-ec.org/emergency-contraception-in-europe/emergency-contraception-availability-in-europe/ |access-date=25 March 2014 |quote=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|date=July 2020}} UPA ECPs are sold with a prescription in all countries, although provision without a prescription is currently{{when|date=July 2020}} being tested in the United Kingdom. |url-status=live |archive-url=https://web.archive.org/web/20140325221722/http://www.ec-ec.org/emergency-contraception-in-europe/emergency-contraception-availability-in-europe/ |archive-date=25 March 2014 }}</ref> In November 2014, the ] (EMA) recommended availability of ellaOne emergency contraceptive without prescription in the European Union.<ref>{{cite web|url=http://www.ema.europa.eu/ema/index.jsp?curl=pages/news_and_events/news/2014/11/news_detail_002223.jsp&mid=WC0b01ac058004d5c1|title=EMA recommends availability of ellaOne emergency contraceptive without prescription|website=ema.europa.eu|access-date=7 May 2018|url-status=live|archive-url=https://web.archive.org/web/20171108095021/http://www.ema.europa.eu/ema/index.jsp?curl=pages%2Fnews_and_events%2Fnews%2F2014%2F11%2Fnews_detail_002223.jsp&mid=WC0b01ac058004d5c1|archive-date=8 November 2017}}</ref> In January 2015 the ] issued an implementing decision amending accordingly the marketing authorization of EllaOne in the EU.<ref>{{cite web |url=http://ec.europa.eu/health/documents/community-register/2015/20150107130448/dec_130448_en.pdf |title=Amending the marketing authorisation granted by Decision C(2009)4049 for "ellaOne - ulipristal acetate", a medicinal product for human use |access-date=4 February 2016 |url-status=live |archive-url=https://web.archive.org/web/20171108095133/http://ec.europa.eu/health/documents/community-register/2015/20150107130448/dec_130448_en.pdf |archive-date=8 November 2017 }}</ref> Since July 2016, it is available without prescription in Israel.
As a SPRM, ulipristal acetate has ]ic as well as ] effects on the ]. It also binds to the ], but has no relevant affinity to the ], ] and ]s.<ref>{{pmid|15120421}}</ref> Phase II ]s suggest that the mechanism might consist of blocking or delaying ] and of delaying the maturation of the ].<ref>{{harvcoltxt|CHMP|2009|pp=22–23}}</ref>

===Uterine fibroids===
Ulipristal acetate is used for pre-operative treatment of moderate to severe symptoms of ] in adult women of reproductive age.<ref name="Esmya EPAR">{{cite web | title=Esmya EPAR | website=] (EMA) | date=15 March 2012 | url=https://www.ema.europa.eu/en/medicines/human/EPAR/esmya | access-date=8 July 2020}}</ref> The use of ulipristal acetate to treat fibroids was suspended in the European Union in March 2020.<ref name="Esmya EPAR" />

In November 2020, the ] (CHMP) of the ] (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.<ref name="EMA PR 20201113">{{cite web | title=Ulipristal acetate for uterine fibroids: EMA recommends restricting use | website=] (EMA) | date=13 November 2020 | url=https://www.ema.europa.eu/en/news/ulipristal-acetate-uterine-fibroids-ema-recommends-restricting-use | access-date=13 November 2020}} Text was copied from this source which is copyright European Medicines Agency. Reproduction is authorized provided the source is acknowledged.</ref> In addition, the committee stated that ulipristal acetate must not be used for controlling symptoms of uterine fibroids while awaiting surgical treatment.<ref name="EMA PR 20201113" />

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.<ref>{{cite journal | vauthors = Nieman LK, Blocker W, Nansel T, Mahoney S, Reynolds J, Blithe D, Wesley R, Armstrong A | display-authors = 6 | title = Efficacy and tolerability of CDB-2914 treatment for symptomatic uterine fibroids: a randomized, double-blind, placebo-controlled, phase IIb study | journal = Fertility and Sterility | volume = 95 | issue = 2 | pages = 767–72.e1–2 | date = February 2011 | pmid = 21055739 | pmc = 4180231 | doi = 10.1016/j.fertnstert.2010.09.059 }}</ref><ref>{{cite journal | vauthors = Levens ED, Potlog-Nahari C, Armstrong AY, Wesley R, Premkumar A, Blithe DL, Blocker W, Nieman LK | display-authors = 6 | title = CDB-2914 for uterine leiomyomata treatment: a randomized controlled trial | journal = Obstetrics and Gynecology | volume = 111 | issue = 5 | pages = 1129–1136 | date = May 2008 | pmid = 18448745 | pmc = 2742990 | doi = 10.1097/AOG.0b013e3181705d0e }}</ref><ref>{{cite journal | vauthors = Donnez J, Tatarchuk TF, Bouchard P, Puscasiu L, Zakharenko NF, Ivanova T, Ugocsai G, Mara M, Jilla MP, Bestel E, Terrill P, Osterloh I, Loumaye E | display-authors = 6 | title = Ulipristal acetate versus placebo for fibroid treatment before surgery | journal = The New England Journal of Medicine | volume = 366 | issue = 5 | pages = 409–420 | date = February 2012 | pmid = 22296075 | doi = 10.1056/NEJMoa1103182 | doi-access = free }}</ref>

Two intermittent 3-months treatment courses of ulipristal acetate 10&nbsp;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%).<ref name="Esmya EPAR"/> After two to four 3-months courses of treatment, UPA-treated fibroids shown about -70% in volume reduction.<ref>{{cite journal | vauthors = Donnez J, Vázquez F, Tomaszewski J, Nouri K, Bouchard P, Fauser BC, Barlow DH, Palacios S, Donnez O, Bestel E, Osterloh I, Loumaye E | display-authors = 6 | title = Long-term treatment of uterine fibroids with ulipristal acetate ☆ | journal = Fertility and Sterility | volume = 101 | issue = 6 | pages = 1565–73.e1–18 | date = June 2014 | pmid = 24630081 | doi = 10.1016/j.fertnstert.2014.02.008 | doi-access = free }}</ref>

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 ] and remodeling of the ]<ref>{{cite journal | vauthors = Courtoy GE, Donnez J, Marbaix E, Dolmans MM | title = In vivo mechanisms of uterine myoma volume reduction with ulipristal acetate treatment | journal = Fertility and Sterility | volume = 104 | issue = 2 | pages = 426–34.e1 | date = August 2015 | pmid = 26003270 | doi = 10.1016/j.fertnstert.2015.04.025 | doi-access = free }}</ref> under the action of ]s.<ref>{{cite journal | vauthors = Courtoy GE, Henriet P, Marbaix E, de Codt M, Luyckx M, Donnez J, Dolmans MM | title = Matrix Metalloproteinase Activity Correlates With Uterine Myoma Volume Reduction After Ulipristal Acetate Treatment | journal = The Journal of Clinical Endocrinology and Metabolism | volume = 103 | issue = 4 | pages = 1566–1573 | date = April 2018 | pmid = 29408988 | doi = 10.1210/jc.2017-02295 | doi-access = free }}</ref>

In May 2018, the ] (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.<ref>{{Cite web|url=https://www.ema.europa.eu/en/medicines/human/referrals/esmya|title=Esmya: new measures to minimise risk of rare but serious liver injury|date=8 August 2018|website=] (EMA) }} Text was copied from this source which is copyright European Medicines Agency. Reproduction is authorized provided the source is acknowledged.</ref>


==Contraindications== ==Contraindications==
Ulipristal acetate should not be taken by women with severe liver diseases<ref name="Leaflet">{{cite web|url=http://www.ema.europa.eu/docs/en_GB/document_library/EPAR_-_Product_Information/human/001027/WC500023670.pdf|title=Summary of Product Characteristics: ellaOne 30&nbsp;mg tablet|accessdate=20 November 2010}}</ref> because of its CYP mediated metabolism. It has not been studied in women under the age of 18.<ref>{{harvcoltxt|CHMP|2009|pp=33, 43}}</ref> Ulipristal acetate should not be taken by women with severe liver diseases<ref name="ellaOne product information">{{cite web | url=https://www.ema.europa.eu/documents/product-information/ellaone-epar-product-information_en.pdf | title=ellaOne: EPAR - Product Information | date=26 May 2020 | website=] (EMA) }}</ref> because of its CYP mediated metabolism. It has not been studied in women under the age of 18.<ref name = "CHMP_2009" />{{rp|33,43}}

It is also not recommended for women with severe asthma receiving ] treatment because it has shown antiglucocorticoid effects in animal studies.<ref name = "CHMP_2009" />{{rp|10,44}}


===Pregnancy=== ===Pregnancy===
Unlike levonorgestrel, and like ], ulipristal acetate is embryotoxic in animal studies.<ref>{{harvcoltxt|CHMP|2009|p=16}}</ref> Before taking the drug, a pregnancy must be excluded.<ref name="Leaflet" /> The EMA proposed to avoid any allusion to a possible use as an ] in the package insert to avert ].<ref>{{harvcoltxt|CHMP|2009|p=41}}</ref> It is unlikely that Ellaone could effectively be used as an abortifacient, since it is used in much lower doses (30&nbsp;mg) than the roughly equipotent mifepristone (600&nbsp;mg), and since mifepristone has to be combined with a ] for the induction of abortion.<ref name="rcog guideline">{{cite book |author=] |year=2004 |title=The Care of Women Requesting Induced Abortion : Evidence-based clinical guideline number 7 |location=London |publisher=RCOG Press |url=http://web.archive.org/web/20080227213507/http://www.rcog.org.uk/resources/Public/pdf/induced_abortionfull.pdf |isbn=1-904752-06-3|format=PDF}}</ref> However, data on embryotoxicity in humans are very limited, and it is not clear what the risk for an abortion or for ]icity (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".<ref name="CHMP37">{{harvcoltxt|CHMP|2009|p=37}}</ref> Unlike levonorgestrel, and like ], ulipristal acetate is embryotoxic in animal studies.<ref name = "CHMP_2009" />{{rp|16}} Before taking the drug, a pregnancy must be excluded.<ref name="ellaOne EPAR" /> The EMA proposed to avoid any allusion to a possible use as an ] in the package insert to avert ].<ref name = "CHMP_2009" />{{rp|41}} It is unlikely that ulipristal acetate could effectively be used as an abortifacient, since it is used in much lower doses (30&nbsp;mg) than the roughly equipotent mifepristone (600&nbsp;mg), and since mifepristone has to be combined with a ] for the induction of abortion.<ref name="rcog guideline">{{cite book |author=RCOG |year=2004 |title=The Care of Women Requesting Induced Abortion : Evidence-based clinical guideline number 7 |location=London |publisher=RCOG Press |url=http://www.rcog.org.uk/resources/Public/pdf/induced_abortionfull.pdf |isbn=1-904752-06-3 |archive-url=https://web.archive.org/web/20080227213507/http://www.rcog.org.uk/resources/Public/pdf/induced_abortionfull.pdf |archive-date=27 February 2008|author-link=Royal College of Obstetricians and Gynaecologists }}</ref> However, data on embryotoxicity in humans are very limited, and it is not clear what the risk for an abortion or for ]icity (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 ].<ref name = "CHMP_2009" />{{rp|37}}


===Lactation=== ===Lactation===
It is not recommended to breast feed within 36 hours of taking the drug since it is not known whether ulipristal acetate or its metabolites are excreted into the breast milk.<ref name="Leaflet" /><ref>{{harvcoltxt|CHMP|2009|p=43}}</ref> 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.<ref name="ellaOne product information" /><ref name = "CHMP_2009" />{{rp|43}}


==Adverse effects== ==Side effects==
Common side effects include ] and ].<ref name="Leaflet" /> The most common side effects include headache, nausea (feeling sick), abdominal pain (stomach ache), and dysmenorrhea (period pains).<ref name="ellaOne EPAR" />


==Interactions== == Interactions ==
No interaction studies have been conducted. Ulipristal acetate is likely to interact with substrates of CYP3A4, like ] or ], but this might not be clinically relevant because only a single dose of the drug is taken.<ref>{{harvcoltxt|CHMP|2009|p=12, 14}}</ref> It might also interact with levonorgestrel and other substrates of the progesterone receptor, as well as with ].


Ulipristal acetate is metabolized by CYP3A4 in vitro. Ulipristal acetate is likely to interact with substrates of CYP3A4, like ], ], ], ] or ], therefore concomitant use with these agents is not recommended.<ref name="Esmya EPAR" /><ref name = "CHMP_2009" />{{rp|12,14}} It might also interact with hormonal contraceptives and ] such as ] and other substrates of the progesterone receptor, as well as with ].<ref name="Esmya EPAR" />
==References==

{{reflist|colwidth=30em}}
==Pharmacology==

===Pharmacodynamics===
As an SPRM, ulipristal acetate has ]ic as well as ] effects on the ]. Ulipristal acetate exhibits similar potency to antagonize ] as ] ''in vitro''.<ref>{{cite journal | vauthors = Šauer P, Stará A, Golovko O, Valentová O, Bořík A, Grabic R, Kroupová HK | title = 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 | journal = Water Research | volume = 137 | pages = 64–71 | date = June 2018 | pmid = 29544204 | doi = 10.1016/j.watres.2018.02.065 | s2cid = 4726126 | bibcode = 2018WatRe.137...64S }}</ref> It also binds to the ] and the ], but is only a weak ] and ] relative to ] and ], respectively.<ref>{{cite journal | vauthors = Šauer P, Bořík A, Golovko O, Grabic R, Staňová AV, Valentová O, Stará A, Šandová M, Kocour Kroupová H | display-authors = 6 | title = Do progestins contribute to (anti-)androgenic activities in aquatic environments? | journal = Environmental Pollution | volume = 242 | issue = Pt A | pages = 417–425 | date = November 2018 | pmid = 29990947 | doi = 10.1016/j.envpol.2018.06.104 | bibcode = 2018EPoll.242..417S | s2cid = 51622914 }}</ref><ref name="Hilal-DandanBrunton2013">{{cite book | vauthors = Hilal-Dandan R, Brunton L |title=Goodman and Gilman's Manual of Pharmacology and Therapeutics |url={{Google books|McsTAgAAQBAJ|plainurl=yes}} |year=2013 |publisher=McGraw Hill Professional |isbn=978-0-07-176917-4}}{{page needed|date=April 2016}}</ref> Ulipristal acetate has no relevant ] to the ] and ]s.<ref>{{cite journal | vauthors = Attardi BJ, Burgenson J, Hild SA, Reel JR | title = 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 | journal = The Journal of Steroid Biochemistry and Molecular Biology | volume = 88 | issue = 3 | pages = 277–288 | date = March 2004 | pmid = 15120421 | doi = 10.1016/j.jsbmb.2003.12.004 | s2cid = 23958876 }}</ref> Phase II ]s suggest that the mechanism might consist of blocking or delaying ] and of delaying the maturation of the ].<ref name = "CHMP_2009" />{{rp|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.<ref name = "CHMP_2009" />{{rp|12,20}}

Ulipristal acetate is ] in the ], most likely by ], and to a small extent by ] and ]. The two main ]s have been shown to be pharmacologically active, but less than the original drug. The main ] route is via the ].<ref name = "CHMP_2009" />{{rp|13–14,21}}

==History==
Ulipristal acetate was granted marketing authorization by the ] (EMA) in May 2009.<ref name="ellaOne EPAR">{{cite web | title=ellaOne EPAR | website=] (EMA) | date=3 June 2009 | url=https://www.ema.europa.eu/en/medicines/human/EPAR/ellaone | access-date=8 July 2020}}</ref> In 2014, the EMA recommended ulipristal be made available without a prescription in the European Union.<ref>{{Cite press release |title=EMA recommends availability of ellaOne emergency contraceptive without prescription|url=https://www.ema.europa.eu/en/news/ema-recommends-availability-ellaone-emergency-contraceptive-without-prescription|access-date=7 July 2020|website=] (EMA)}}</ref><ref name="ellaOne EPAR" />

The U.S. ] (FDA) approved the drug for use in the United States on 13 August 2010,<ref name="HRA Pharma">{{cite press release |title=FDA grants approval of ella for emergency contraception |url=http://www.hra-pharma.com/downloads/HRA%20FDA%20Approval%20FINAL.pdf |publisher=] |date=13 August 2010 |access-date=15 August 2010 }}{{Dead link|date=July 2020 |bot=InternetArchiveBot |fix-attempted=yes }}</ref> following the FDA advisory committee's recommendation.<ref>{{cite web| url=http://www.medscape.com/viewarticle/723822| title=FDA Panel Gives Ulipristal Acetate Unanimous Positive Vote for Emergency Contraception Indication| vauthors = Hitt E | date=18 June 2010| access-date=22 June 2010| url-status=live| archive-url=https://web.archive.org/web/20110309022401/http://www.medscape.com/viewarticle/723822| archive-date=9 March 2011}}</ref><ref>{{cite news | vauthors = Harris G | title = F.D.A. Approves 5-Day Emergency Contraceptive | url = https://www.nytimes.com/2010/08/14/health/policy/14pill.html | work = The New York Times | date = 14 August 2010 | access-date = 14 August 2010 | url-status = live | archive-url = https://web.archive.org/web/20120403202943/http://www.nytimes.com/2010/08/14/health/policy/14pill.html | archive-date = 3 April 2012 }}</ref> ] announced the availability of ulipristal acetate in the United States on 1 December 2010, in retail pharmacies, clinics, and one on-line pharmacy, ].<ref>{{cite web| url=http://ir.watson.com/phoenix.zhtml?c=65778&p=irol-newsArticle&ID=1501974| title=Watson Launches ella(R)(ulipristal acetate)| vauthors = Watson PR| date=1 December 2010| access-date=12 January 2010}}{{Dead link|date=July 2020 |bot=InternetArchiveBot |fix-attempted=yes }}</ref>

==Society and culture==

===Brand names===

Ulipristal acetate is marketed as an emergency contraceptive (30 mg) in over 75 countries, under different brands such as ella, ellaOne, Dvella, FemelleOne, Femke, Lencya, Prevent One, ulip, Ulipristal Stada, Ulipristal Mylan, Ulipristal acetate Sandoz and others. <ref name="https://www.ec-ec.org/emergency-contraception-in-the-world"/>

Ulipristal acetate is also marketed for treatment of uterine firboids, under different brands such as Esmya or Primette. />

== References ==
{{Reflist|refs =

<ref name = "CHMP_2009">{{cite web |url=http://www.ema.europa.eu/docs/en_GB/document_library/EPAR_-_Public_assessment_report/human/001027/WC500023673.pdf |title=Assessment Report for Ellaone |author=CHMP |authorlink=Committee for Medicinal Products for Human Use |publisher=EMA |year=2009 |accessdate=22 November 2009 }}
</ref>

}}


{{sex hormones}}
{{Birth control methods}} {{Birth control methods}}
{{Progestogens and antiprogestogens}}
{{Progesterone receptor modulators}}
{{Glucocorticoid receptor modulators}}
{{Other sex hormones and modulators of the genital system}}
{{Portal bar|Medicine}}


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