Abiraterone acetate

{{Short description|Chemical compound}} {{Use dmy dates|date=July 2022}} {{cs1 config|name-list-style=vanc|display-authors=6}} {{Infobox drug | Verifiedfields = verified | Watchedfields = verified | verifiedrevid = 477237325 | image = Abiraterone acetate.svg | image_class = skin-invert-image | width = 250 | alt = | image2 = Abiraterone-acetate-from-powder-xtal-Mercury-3D-balls-thin.png | image_class2 = bg-transparent | width2 = | alt2 = | caption = | USAN = abiraterone acetate | JAN = abiraterone acetate | BAN = abiraterone

| pronounce = a" bir a' ter one | tradename = Zytiga, Yonsa, others | Drugs.com = {{drugs.com|monograph|abiraterone-acetate}} | MedlinePlus = a611046 | DailyMedID = Abiraterone_acetate | pregnancy_AU = D | pregnancy_AU_comment = <ref name="Drugs.com pregnancy">{{cite web | title=Abiraterone Use During Pregnancy | website=Drugs.com | date=13 March 2020 | url=https://www.drugs.com/pregnancy/abiraterone.html | access-date=8 June 2020 | archive-date=25 November 2020 | archive-url=https://web.archive.org/web/20201125092244/https://www.drugs.com/pregnancy/abiraterone.html | url-status=live }}</ref> | pregnancy_category = | routes_of_administration = By mouth<ref name="Zytiga FDA label" /><ref name="Yonsa Label" /> | class = Antineoplastic | ATC_prefix = L02 | ATC_suffix = BX03 | ATC_supplemental =

| legal_AU = S4 | legal_AU_comment = <ref name=TGA /> | legal_BR =  | legal_BR_comment = | legal_CA = Rx-only | legal_CA_comment = | legal_DE =  | legal_DE_comment = | legal_NZ =  | legal_NZ_comment = | legal_UK = POM | legal_UK_comment = <ref name=EMC /> | legal_US = Rx-only | legal_US_comment = <ref name="Zytiga FDA label" /><ref name="Yonsa Label">{{cite web |title=Yonsa- abiraterone acetate tablet |url=https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=b8967e10-f768-47ce-ac9e-2324c8390132 |website=DailyMed |date=5 June 2018 |access-date=15 November 2019 |archive-date=13 August 2020 |archive-url=https://web.archive.org/web/20200813152826/https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=b8967e10-f768-47ce-ac9e-2324c8390132 |url-status=live }}</ref> | legal_EU = Rx-only | legal_EU_comment = <ref name="Zytiga EPAR" /> | legal_UN =  | legal_UN_comment = | legal_status = Rx-only

| bioavailability = Unknown, but may be 50% at most on empty stomach<ref name="pmid27106175">{{cite journal | vauthors = Benoist GE, Hendriks RJ, Mulders PF, Gerritsen WR, Somford DM, Schalken JA, van Oort IM, Burger DM, van Erp NP | title = Pharmacokinetic Aspects of the Two Novel Oral Drugs Used for Metastatic Castration-Resistant Prostate Cancer: Abiraterone Acetate and Enzalutamide | journal = Clin Pharmacokinet | volume = 55 | issue = 11 | pages = 1369–1380 | date = November 2016 | pmid = 27106175 | pmc = 5069300 | doi = 10.1007/s40262-016-0403-6 }}</ref> | protein_bound = Abiraterone: ~99.8% (to albumin and {{abbrlink|α1-AGp|alpha-1 acid glycoprotein}})<ref name="pmid27106175" /><ref name="Zytiga FDA label" /><ref name="Sternberg2014">{{cite journal | vauthors = Sternberg CN, Petrylak DP, Madan RA, Parker C | title = Progress in the treatment of advanced prostate cancer | journal = American Society of Clinical Oncology Educational Book. American Society of Clinical Oncology. Annual Meeting | issue = 34 | pages = 117–131 | date = May 2014 | pmid = 24857068 | doi = 10.14694/EdBook_AM.2014.34.117 | url = http://meetinglibrary.asco.org/content/114000117-144 | access-date = 9 September 2016 | url-status = live | archive-url = https://web.archive.org/web/20160920120942/http://meetinglibrary.asco.org/content/114000117-144 | archive-date = 20 September 2016 | url-access = subscription }}</ref> | metabolism = Esterases, CYP3A4, SULT2A1<ref name="Sternberg2014" /> | metabolites = Abiraterone, others<ref name="Zytiga FDA label" /><ref name="pmid27106175" /> | onset = | elimination_half-life = Abiraterone: 12–24 hours<ref name="Zytiga FDA label" /><ref name="pmid27106175" /><ref name="Yonsa Label" /> | duration_of_action = | excretion = Feces: 88%<ref name="Zytiga FDA label" /><ref name="Sternberg2014" /> Urine: 5%<ref name="Zytiga FDA label" /><ref name="Sternberg2014" /><ref name="Yonsa Label" />

| CAS_number_Ref = {{cascite|correct|CAS}} | CAS_number = 154229-18-2 | CAS_supplemental = 154229-19-3 (abiraterone) | PubChem = 9821849 | IUPHAR_ligand = 9288 | DrugBank_Ref = {{drugbankcite|correct|drugbank}} | DrugBank = DBSALT001173 | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID = 7997598 | UNII_Ref = {{fdacite|correct|FDA}} | UNII = EM5OCB9YJ6 | KEGG_Ref = | KEGG = D09701 | ChEBI_Ref = | ChEBI = 68639 | ChEMBL_Ref = {{ebicite|correct|EBI}} | ChEMBL = 271227 | NIAID_ChemDB = | PDB_ligand = | synonyms = CB-7630; JNJ-212082; 17-(3-Pyridinyl)androsta-5,16-dien-3β-ol acetate

| IUPAC_name = [(3''S'',8''R'',9''S'',10''R'',13''S'',14''S'')-10,13-dimethyl-17-pyridin-3-yl-2,3,4,7,8,9,11,12,14,15-decahydro-1''H''-cyclopenta[''a'']phenanthren-3-yl] acetate | C=26 | H=33 | N=1 | O=2 | SMILES = CC(=O)O[C@H]1CC[C@@]2([C@H]3CC[C@]4([C@H]([C@@H]3CC=C2C1)CC=C4C5=CN=CC=C5)C)C | StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI = 1S/C26H33NO2/c1-17(28)29-20-10-12-25(2)19(15-20)6-7-21-23-9-8-22(18-5-4-14-27-16-18)26(23,3)13-11-24(21)25/h4-6,8,14,16,20-21,23-24H,7,9-13,15H2,1-3H3/t20-,21-,23-,24-,25-,26+/m0/s1 | StdInChI_comment = | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey = UVIQSJCZCSLXRZ-UBUQANBQSA-N | density = | density_notes = | melting_point = 144 | melting_high = 145 | melting_notes = <ref>{{cite journal | vauthors = Potter GA, Barrie SE, Jarman M, Rowlands MG | title = Novel steroidal inhibitors of human cytochrome P45017 alpha (17 alpha-hydroxylase-C17,20-lyase): potential agents for the treatment of prostatic cancer | journal = Journal of Medicinal Chemistry | volume = 38 | issue = 13 | pages = 2463–2471 | date = June 1995 | pmid = 7608911 | doi = 10.1021/jm00013a022 }}</ref> | boiling_point = | boiling_notes = | solubility = | sol_units = | specific_rotation = }}

'''Abiraterone acetate''', sold under the brand name '''Zytiga''' among others, is a medication used to treat prostate cancer.<ref name=AHFS2019/> Specifically it is used together with a corticosteroid for metastatic castration-resistant prostate cancer (mCRPC) and metastatic high-risk castration-sensitive prostate cancer (mCSPC).<ref name="Zytiga FDA label">{{cite web |title=Zytiga- abiraterone acetate tablet, film coated |url=https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=4e338e89-3cf2-48eb-b6e2-a06c608c6513 |website=DailyMed |date=13 June 2019 |access-date=15 November 2019 |archive-date=13 November 2014 |archive-url=https://web.archive.org/web/20141113055410/https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=4e338e89-3cf2-48eb-b6e2-a06c608c6513 |url-status=live }}</ref><ref name="Yonsa Label" /> It should either be used following removal of the testicles or along with a gonadotropin-releasing hormone (GnRH) analog.<ref name="Zytiga FDA label"/> It is taken by mouth.<ref name=AHFS2019/>

Common side effects include tiredness, vomiting, headache, joint pain, high blood pressure, swelling, low blood potassium, high blood sugar, hot flashes, diarrhea, and cough.<ref name=AHFS2019>{{cite web |title=Abiraterone Acetate Monograph for Professionals |url=https://www.drugs.com/monograph/abiraterone-acetate.html |website=Drugs.com |access-date=15 November 2019 |language=en |archive-date=6 May 2012 |archive-url=https://web.archive.org/web/20120506190123/https://www.drugs.com/monograph/abiraterone-acetate.html |url-status=live }}</ref><ref name="Zytiga FDA label"/> Other severe side effects may include liver failure and adrenocortical insufficiency.<ref name="Zytiga FDA label"/> In males whose partners can become pregnant, birth control is recommended.<ref name="Zytiga FDA label"/> Supplied as abiraterone acetate it is converted in the body to abiraterone.<ref name="Zytiga FDA label"/> Abiraterone acetate works by suppressing the production of androgens – specifically it inhibits CYP17A1 – and thereby decreases the production of testosterone.<ref name=AHFS2019/> In doing so, it prevents the effects of these hormones in prostate cancer.<ref name=AHFS2019/>

Abiraterone acetate was described in 1995, and approved for medical use in the United States and the European Union in 2011.<ref name=Scowcroft2011>{{cite journal |url=http://scienceblog.cancerresearchuk.org/2011/09/21/where-did-abiraterone-come-from/ |title=Where did abiraterone come from? |vauthors=Scowcroft H |journal=Journal of Medicinal Chemistry |date=21 September 2011 |volume=38 |issue=13 |pages=2463–2471 |publisher=Cancer Research UK |access-date=28 September 2011 |archive-date=25 September 2011 |archive-url=https://web.archive.org/web/20110925093704/http://scienceblog.cancerresearchuk.org/2011/09/21/where-did-abiraterone-come-from/ |url-status=live }}</ref><ref name="Zytiga FDA label"/> It is on the World Health Organization's List of Essential Medicines.<ref name="WHO23rd">{{cite book | 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 | publisher = World Health Organization | location = Geneva | id = WHO/MHP/HPS/EML/2023.02 | hdl-access=free }}</ref> It is available as a generic medication.<ref>{{cite web | title=First Generic Drug Approvals | website=U.S. Food and Drug Administration | date=17 October 2022 | url=https://www.fda.gov/drugs/drug-and-biologic-approval-and-ind-activity-reports/first-generic-drug-approvals | access-date=28 November 2022}}</ref>

==Medical uses== Abiraterone acetate is used in combination with prednisone, a corticosteroid, as a treatment for mCRPC (previously called hormone-resistant or hormone-refractory prostate cancer).<ref name="Zytiga FDA label" /><ref name="Zytiga EPAR">{{cite web|title=Zytiga EPAR|work=European Medicines Agency (EMA)|date=13 March 2019|access-date=15 November 2019|url=https://www.ema.europa.eu/en/medicines/human/EPAR/zytiga|archive-date=27 December 2020|archive-url=https://web.archive.org/web/20201227061227/https://www.ema.europa.eu/en/medicines/human/EPAR/zytiga|url-status=live}}</ref><ref name=EMC>{{cite web | title=Zytiga 500 mg film-coated tablets - Summary of Product Characteristics (SmPC) | work=electronic medicines compendium (emc) | publisher=Datapharm | date=4 March 2019 | url=https://www.medicines.org.uk/emc/product/2381/smpc | archive-url=https://web.archive.org/web/20191115191031/https://www.medicines.org.uk/emc/product/2381/smpc | archive-date=15 November 2019 | url-status=live | access-date=15 November 2019}}</ref><ref name=TGA>{{cite web|title=Zytiga abiraterone acetate product information|work=TGA eBusiness Services|publisher=Janssen-Cilag Pty Ltd|date=1 March 2012|access-date=24 January 2014|url=https://www.ebs.tga.gov.au/ebs/picmi/picmirepository.nsf/pdf?OpenAgent&id=CP-2012-PI-01395-3|format=PDF|archive-date=24 November 2020|archive-url=https://web.archive.org/web/20201124100354/https://www.ebs.tga.gov.au/ebs/picmi/picmirepository.nsf/pdf?OpenAgent&id=CP-2012-PI-01395-3|url-status=live}}</ref> This is a form of prostate cancer that is not responding to first-line androgen deprivation therapy or treatment with androgen receptor antagonists. Abiraterone acetate has received Food and Drug Administration (FDA) (28 April 2011), European Medicines Agency (EMA) (23 September 2011), Medicines and Healthcare products Regulatory Agency (MHRA) (5 September 2011) and Therapeutic Goods Administration (TGA) (1 March 2012) approval for this indication.<ref name="Zytiga FDA label"/><ref name="Zytiga EPAR"/><ref name=EMC/><ref name=TGA/>

In Australia it is covered by the Pharmaceutical Benefits Scheme when being used to treat castration-resistant prostate cancer and given in combination with prednisone/prednisolone (subject to the conditions that the patient is not currently receiving chemotherapy, is either resistant or intolerant of docetaxel, has a WHO performance status of <2, and his disease has not since become progressive since treatment with PBS-subsidised abiraterone acetate has commenced).<ref>{{cite web|title=Pharmaceutical Benefits Scheme - Abiraterone|work=Pharmaceutical Benefits Scheme|access-date=24 January 2014|url=http://www.pbs.gov.au/medicine/item/2698B|archive-date=2 December 2020|archive-url=https://web.archive.org/web/20201202160545/https://www.pbs.gov.au/medicine/item/2698B|url-status=live}}</ref>

Abiraterone acetate/methylprednisolone, sold under the brand name Yonsa Mpred, is a composite package that contains both abiraterone acetate (Yonsa) and methylprednisolone.<ref name="Yonsa Mpred PI" /> It was approved for medical use in Australia in March 2022.<ref name="Yonsa Mpred PI">{{cite web | url=http://www.ebs.tga.gov.au/ebs/picmi/picmirepository.nsf/pdf?OpenAgent=&id=CP-2022-PI-01402-1 | title=TGA eBS - Product and Consumer Medicine Information Licence }}</ref><ref name="Yonsa Mpred Summary">[https://www.ebs.tga.gov.au/servlet/xmlmillr6?dbid=ebs/PublicHTML/pdfStore.nsf&docid=346890&agid=%28PrintDetailsPublic%29&actionid=1 YONSA MPRED abiraterone acetate 125 mg tablet bottle and methylprednisolone 4 mg tablet bottle composite pack]</ref><ref>[https://www.tga.gov.au/resources/artg/346890 YONSA MPRED (Sun Pharma ANZ Pty Ltd)]</ref>

==Contraindications== Contraindications include hypersensitivity to abiraterone acetate. Although documents state that it should not be taken by women who are or who may become pregnant,<ref name="Zytiga EPAR"/><ref name=PI>{{cite web|url=http://www.zytigahcp.com/pdf/full_prescribing_info.pdf|title=Zytiga prescribing information|date=May 2012|publisher=Janssen Biotech|access-date=4 March 2016|archive-url=https://web.archive.org/web/20141113044418/http://www.zytigahcp.com/pdf/full_prescribing_info.pdf|archive-date=13 November 2014}}</ref> there is no medical reason why any woman should take it. Women who are pregnant should not even touch the pills unless they are wearing gloves.<ref name=PI/> Other cautions include severe baseline hepatic impairment, mineralocorticoid excess, cardiovascular disease including heart failure and hypertension, uncorrected hypokalemia, and adrenocorticoid insufficiency.<ref name=MSR/>

==Side effects== '''<big>Side effects by frequency:</big>'''<ref name="Zytiga FDA label"/><ref name="Zytiga EPAR"/><ref name=EMC/><ref name=TGA/><ref name=MSR>{{cite web|title=Zytiga (abiraterone) dosing, indications, interactions, adverse effects, and more|work=Medscape Reference|publisher=WebMD|access-date=24 January 2014|url=http://reference.medscape.com/drug/zytiga-abiraterone-999651|archive-date=2 February 2014|archive-url=https://web.archive.org/web/20140202175321/http://reference.medscape.com/drug/zytiga-abiraterone-999651|url-status=live}}</ref>

'''Very common (>10% frequency):''' {{div col|colwidth=18em}} * Urinary tract infection * Hypokalemia * Hypertension * Diarrhea * Peripheral edema {{div col end}} '''Common (1-10% frequency):''' {{div col|colwidth=18em}} * Hypertriglyceridaemia * Sepsis * Cardiac failure * Angina pectoris * Arrhythmia * Atrial fibrillation * Tachycardia * Dyspepsia (indigestion) * Rash * Alanine aminotransferase increased * Aspartate aminotransferase increased * Fractures * Hematuria {{div col end}} '''Uncommon (0.1-1% frequency):''' * Adrenal insufficiency * Myopathy * Rhabdomyolysis '''Rare (<0.1% frequency):''' * Allergic alveolitis

==Overdose== Experience with overdose of abiraterone acetate is limited.<ref name="Zytiga FDA label" /> There is no specific antidote for abiraterone acetate overdose, and treatment should consist of general supportive measures, including monitoring of cardiac and liver function.<ref name="Zytiga FDA label" />

==Interactions== Abiraterone acetate is a CYP3A4 substrate and hence should not be administered concurrently with strong CYP3A4 inhibitors such as ketoconazole, itraconazole, clarithromycin, atazanavir, nefazodone, saquinavir, telithromycin, ritonavir, indinavir, nelfinavir, voriconazole) or inducers such as phenytoin, carbamazepine, rifampin, rifabutin, rifapentine, phenobarbital.<ref name=MSR/><ref name=PI/> It also inhibits CYP1A2, CYP2C9, and CYP3A4 and likewise should not be taken concurrently with substrates of any of these enzymes that have a narrow therapeutic index.<ref name=MSR/><ref name=PI/>

Spironolactone generally exerts anti-androgenic effects, but experimental evidence exists that it acts as an androgen receptor agonist in an androgen-depleted environment, capable of inducing prostate cancer proliferation.<ref>{{cite journal | vauthors = Luthy IA, Begin DJ, Labrie F | title = Androgenic activity of synthetic progestins and spironolactone in androgen-sensitive mouse mammary carcinoma (Shionogi) cells in culture | journal = Journal of Steroid Biochemistry | volume = 31 | issue = 5 | pages = 845–52 | date = November 1988 | pmid = 2462135 | doi = 10.1016/0022-4731(88)90295-6 }}</ref> This is supported by the observations described in several case reports.<ref>{{cite journal | vauthors = Dhondt B, Buelens S, Van Besien J, Beysens M, De Bleser E, Ost P, Lumen N | title = Abiraterone and spironolactone in prostate cancer: a combination to avoid | journal = Acta Clinica Belgica | volume = 74 | issue = 6 | pages = 439–444 | pmid = 30477405 | doi = 10.1080/17843286.2018.1543827 | year = 2019 | s2cid = 53738534 | url = https://biblio.ugent.be/publication/8582726/file/8582727 | url-access = subscription }}</ref>

====Antiandrogenic activity==== Abiraterone, the active metabolite of abiraterone acetate, inhibits CYP17A1, which manifests as two enzymes, 17α-hydroxylase ({{abbrlink|IC50|half-maximal inhibitory concentration}} = 2.5 nM) and 17,20-lyase ({{abbr|IC50|half-maximal inhibitory concentration}} = 15 nM) (approximately 6-fold more selective for inhibition of 17α-hydroxylase over 17,20-lyase)<ref name="Neidle2013">{{cite book| vauthors = Neidle S | title=Cancer Drug Design and Discovery|url=https://books.google.com/books?id=HS6IAAAAQBAJ&pg=PA342|date=30 September 2013|publisher=Academic Press|isbn=978-0-12-397228-6|pages=341–342}}</ref><ref>{{cite journal | vauthors = Fernández-Cancio M, Camats N, Flück CE, Zalewski A, Dick B, Frey BM, Monné R, Torán N, Audí L, Pandey AV | title = Mechanism of the Dual Activities of Human CYP17A1 and Binding to Anti-Prostate Cancer Drug Abiraterone Revealed by a Novel V366M Mutation Causing 17,20 Lyase Deficiency | journal = Pharmaceuticals | volume = 11 | issue = 2 | page = 37 | date = April 2018 | pmid = 29710837 | doi = 10.3390/ph11020037 | pmc=6027421| doi-access = free }}</ref> that are expressed in testicular, adrenal, and prostatic tumor tissues. CYP17A1 catalyzes two sequential reactions: (a) the conversion of pregnenolone and progesterone to their 17α-hydroxy derivatives by its 17α-hydroxylase activity, and (b) the subsequent formation of dehydroepiandrosterone (DHEA) and androstenedione, respectively, by its 17,20-lyase activity.<ref name="pmid16287438">{{cite journal | vauthors = Attard G, Belldegrun AS, de Bono JS | title = Selective blockade of androgenic steroid synthesis by novel lyase inhibitors as a therapeutic strategy for treating metastatic prostate cancer | journal = BJU International | volume = 96 | issue = 9 | pages = 1241–6 | date = December 2005 | pmid = 16287438 | doi = 10.1111/j.1464-410X.2005.05821.x | s2cid = 36575315 | doi-access = }}</ref> DHEA and androstenedione are androgens and precursors of testosterone. Inhibition of CYP17A1 activity by abiraterone acetate thus decreases circulating levels of androgens such as DHEA, testosterone, and dihydrotestosterone (DHT). Abiraterone acetate, via abiraterone, has the capacity to lower circulating testosterone levels to less than 1 ng/dL (i.e., undetectable) when added to castration.<ref name="Neidle2013"/><ref name="Small2014">{{cite journal | vauthors = Small EJ | title = Can targeting the androgen receptor in localized prostate cancer provide insights into why men with metastatic castration-resistant prostate cancer die? | journal = Journal of Clinical Oncology | volume = 32 | issue = 33 | pages = 3689–91 | date = November 2014 | pmid = 25311216 | doi = 10.1200/JCO.2014.57.8534 | quote = Abiraterone acetate is a prodrug for abiraterone, a CYP17 inhibitor, which has the capacity to lower serum testosterone levels to less than 1 ng/dL (compared with levels closer to 20 ng/dL that are achieved with conventional ADT).19 [...] Relative to LHRHa alone, the addition of abiraterone resulted in an 85% decline in dihydrotestosterone (DHT) levels, a 97% to 98% decline in dehydroepiandrosterone (DHEA) levels, and a 77% to 78% decline in androstenedione levels. | doi-access = free }}</ref> These concentrations are considerably lower than those achieved by castration alone (~20 ng/dL).<ref name="Small2014" /> The addition of abiraterone acetate to castration was found to reduce levels of DHT by 85%, DHEA by 97 to 98%, and androstenedione by 77 to 78% relative to castration alone.<ref name="Small2014" /> In accordance with its antiandrogenic action, abiraterone acetate decreases the weights of the prostate gland, seminal vesicles, and testes.<ref name="TindallJames2009">{{cite book | vauthors = Tindall DJ, Mohler J | title = Androgen Action in Prostate Cancer|url=https://books.google.com/books?id=L6NMZizNLMoC&pg=PA748|date=20 April 2009|publisher=Springer Science & Business Media|isbn=978-0-387-69179-4|pages=748–}}</ref>

Abiraterone also acts as a partial antagonist of the androgen receptor (AR), and as an inhibitor of the enzymes 3β-hydroxysteroid dehydrogenase (3β-HSD), CYP11B1 (steroid 11β-hydroxylase), CYP21A2 (Steroid 21-hydroxylase), and other CYP450s (e.g., CYP1A2, CYP2C9, and CYP3A4).<ref name="MSR"/><ref name="pmid24276076">{{cite journal | vauthors = Yin L, Hu Q | title = CYP17 inhibitors--abiraterone, C17,20-lyase inhibitors and multi-targeting agents | journal = Nature Reviews. Urology | volume = 11 | issue = 1 | pages = 32–42 | date = January 2014 | pmid = 24276076 | doi = 10.1038/nrurol.2013.274 | s2cid = 7131777 }}</ref><ref>{{cite journal | vauthors = Malikova J, Brixius-Anderko S, Udhane SS, Parween S, Dick B, Bernhardt R, Pandey AV | title = CYP17A1 inhibitor abiraterone, an anti-prostate cancer drug, also inhibits the 21-hydroxylase activity of CYP21A2 | journal = The Journal of Steroid Biochemistry and Molecular Biology | volume = 174 | pages = 192–200 | date = November 2017 | pmid = 28893623 | doi = 10.1016/j.jsbmb.2017.09.007 | s2cid = 6270824 | url = https://boris.unibe.ch/110055/7/SBMB-D-17-00297R1.pdf | access-date = 10 September 2020 | archive-date = 4 December 2020 | archive-url = https://web.archive.org/web/20201204091955/https://boris.unibe.ch/110055/7/SBMB-D-17-00297R1.pdf | url-status = live }}</ref><ref>{{cite journal | vauthors = Udhane SS, Dick B, Hu Q, Hartmann RW, Pandey AV | title = Specificity of anti-prostate cancer CYP17A1 inhibitors on androgen biosynthesis | journal = Biochemical and Biophysical Research Communications | volume = 477 | issue = 4 | pages = 1005–1010 | date = September 2016 | pmid = 27395338 | doi = 10.1016/j.bbrc.2016.07.019 | bibcode = 2016BBRC..477.1005U | doi-access = free }}</ref> In addition to abiraterone itself, part of the activity of the drug has been found to be due to a more potent active metabolite, δ4-abiraterone (D4A), which is formed from abiraterone by 3β-HSD.<ref name="LiBishop2015">{{cite journal | vauthors = Li Z, Bishop AC, Alyamani M, Garcia JA, Dreicer R, Bunch D, Liu J, Upadhyay SK, Auchus RJ, Sharifi N | title = Conversion of abiraterone to D4A drives anti-tumour activity in prostate cancer | journal = Nature | volume = 523 | issue = 7560 | pages = 347–51 | date = July 2015 | pmid = 26030522 | pmc = 4506215 | doi = 10.1038/nature14406 | bibcode = 2015Natur.523..347L }}</ref> D4A is an inhibitor of CYP17A1, 3β-hydroxysteroid dehydrogenase/Δ5-4 isomerase, and 5α-reductase, and has also been found to act as a competitive antagonist of the AR reportedly comparable to the potent antagonist enzalutamide.<ref name="LiBishop2015" /> However, the initial 5α-reduced metabolite of D4A, 3-keto-5α-abiraterone, is an agonist of the AR, and promotes prostate cancer progression.<ref name="LiAlyamani2016">{{cite journal | vauthors = Li Z, Alyamani M, Li J, Rogacki K, Abazeed M, Upadhyay SK, Balk SP, Taplin ME, Auchus RJ, Sharifi N | title = Redirecting abiraterone metabolism to fine-tune prostate cancer anti-androgen therapy | journal = Nature | volume = 533 | issue = 7604 | pages = 547–51 | date = May 2016 | pmid = 27225130 | doi = 10.1038/nature17954 | url = https://dash.harvard.edu/bitstream/handle/1/29626087/5111629.pdf?sequence=1 | pmc = 5111629 | bibcode = 2016Natur.533..547L | access-date = 4 November 2018 | archive-date = 4 November 2018 | archive-url = https://web.archive.org/web/20181104211052/https://dash.harvard.edu/bitstream/handle/1/29626087/5111629.pdf?sequence=1 | url-status = live }}</ref> Its formation can be blocked by the coadministration of dutasteride, a potent and selective 5α-reductase inhibitor.<ref name="LiAlyamani2016" />

====Estrogenic activity==== There has been interest in the use of abiraterone acetate for the treatment of breast cancer due to its ability to lower estrogen levels.<ref name="pmid27083183">{{cite journal | vauthors = Capper CP, Larios JM, Sikora MJ, Johnson MD, Rae JM | title = The CYP17A1 inhibitor abiraterone exhibits estrogen receptor agonist activity in breast cancer | journal = Breast Cancer Research and Treatment | volume = 157 | issue = 1 | pages = 23–30 | date = May 2016 | pmid = 27083183 | doi = 10.1007/s10549-016-3774-3 | s2cid = 9912289 }}</ref> However, abiraterone has been found to act as a direct agonist of the estrogen receptor, and induces proliferation of human breast cancer cells ''in vitro''.<ref name="pmid27083183" /> If abiraterone acetate is used in the treatment of breast cancer, it should be combined with an estrogen receptor antagonist like fulvestrant.<ref name="pmid27083183" /> In spite of its antiandrogenic and estrogenic properties, abiraterone acetate does not appear to produce gynecomastia as a side effect.<ref name="AlesiniIacovelli2013">{{cite journal | vauthors = Alesini D, Iacovelli R, Palazzo A, Altavilla A, Risi E, Urbano F, Manai C, Passaro A, Magri V, Cortesi E | title = Multimodality treatment of gynecomastia in patients receiving antiandrogen therapy for prostate cancer in the era of abiraterone acetate and new antiandrogen molecules | journal = Oncology | volume = 84 | issue = 2 | pages = 92–9 | year = 2013 | pmid = 23128186 | doi = 10.1159/000343821 | s2cid = 207547652 }}</ref>

====Other activities==== Due to inhibition of glucocorticoid biosynthesis, abiraterone acetate can cause glucocorticoid deficiency, mineralocorticoid excess, and associated adverse effects.<ref name="FiggChau2010">{{cite book| vauthors = Figg WD, Chau CH, Small EJ |title=Drug Management of Prostate Cancer|url=https://books.google.com/books?id=4KDrjeWA5-UC&pg=PA97|date=14 September 2010|publisher=Springer Science & Business Media|isbn=978-1-60327-829-4|page=97|access-date=14 April 2018|archive-date=22 February 2021|archive-url=https://web.archive.org/web/20210222133552/https://books.google.com/books?id=4KDrjeWA5-UC&pg=PA97|url-status=live}}</ref> This is why the medication is combined with prednisone, a corticosteroid, which serves as a means of glucocorticoid replacement and prevents mineralocorticoid excess.<ref name="RosenthalBurchum2017">{{cite book| vauthors = Rosenthal L, Burchum J |title=Lehne's Pharmacotherapeutics for Advanced Practice Providers - E-Book|url=https://books.google.com/books?id=gfYoDgAAQBAJ&pg=PA936|date=17 February 2017|publisher=Elsevier Health Sciences|isbn=978-0-323-44779-9|page=936|access-date=14 April 2018|archive-date=22 February 2021|archive-url=https://web.archive.org/web/20210222132459/https://books.google.com/books?id=gfYoDgAAQBAJ&pg=PA936|url-status=live}}</ref>

Abiraterone acetate, along with galeterone, has been identified as an inhibitor of sulfotransferases (SULT2A1, SULT2B1b, SULT1E1), which are involved in the sulfation of DHEA and other endogenous steroids and compounds, with Ki values in the sub-micromolar range.<ref name="pmid29436390">{{cite journal | vauthors = Yip CK, Bansal S, Wong SY, Lau AJ | title = Identification of Galeterone and Abiraterone as Inhibitors of Dehydroepiandrosterone Sulfonation Catalyzed by Human Hepatic Cytosol, SULT2A1, SULT2B1b, and SULT1E1 | journal = Drug Metabolism and Disposition | volume = 46 | issue = 4 | pages = 470–482 | date = April 2018 | pmid = 29436390 | doi = 10.1124/dmd.117.078980 | doi-access = free }}</ref>

===Pharmacokinetics=== After oral administration, abiraterone acetate, the prodrug form in the commercial preparation, is converted into the active form, abiraterone. This conversion is likely to be esterase-mediated and not CYP-mediated. Administration with food increases absorption of the drug and thus has the potential to result in increased and highly variable exposures; the drug should be consumed on an empty stomach at least one hour before or two hours after food. The drug is highly protein bound (>99%), and is metabolized in the liver by CYP3A4 and SULT2A1 to inactive metabolites. The drug is excreted in feces (~88%) and urine (~5%), and has a terminal half-life of 12 ± 5 hours.<ref name=PI/>

==Chemistry== {{See also|Steroidal antiandrogen|List of steroidal antiandrogens}}

Abiraterone acetate, also known as 17-(3-pyridinyl)androsta-5,16-dien-3β-ol acetate, is a synthetic androstane steroid and a derivative of androstadienol (androsta-5,16-dien-3β-ol), an endogenous androstane pheromone.<ref name="WilliamAndrewPublishing2013">{{cite book|author=William Andrew Publishing|title=Pharmaceutical Manufacturing Encyclopedia, 3rd Edition|url=https://books.google.com/books?id=_J2ti4EkYpkC&pg=PA12|date=22 October 2013|publisher=Elsevier|isbn=978-0-8155-1856-3|pages=12–|access-date=8 June 2020|archive-date=8 June 2020|archive-url=https://web.archive.org/web/20200608020417/https://books.google.com/books?id=_J2ti4EkYpkC&pg=PA12|url-status=live}}</ref> It is specifically a derivative of androstadienol with a pyridine ring attached at the C17 position and an acetate ester attached to the C3β hydroxyl group.<ref name="WilliamAndrewPublishing2013" /> Abiraterone acetate is the C3β acetate ester of abiraterone.<ref name="WilliamAndrewPublishing2013" />

==History== In the early 1990s, Mike Jarman, Elaine Barrie, and Gerry Potter of the Cancer Research UK Centre for Cancer Therapeutics in the Institute of Cancer Research in London set out to develop drug treatments for prostate cancer. With the nonsteroidal androgen synthesis inhibitor ketoconazole as a model, they developed abiraterone acetate, filing a patent in 1993 and publishing the first paper describing it the following year.<ref name=Scowcroft2011/><ref>{{cite web|url=http://www.icr.ac.uk/press/recent_featured_articles/Story_Abiraterone/index.shtml|title=A new way to treat prostate cancer: The story of abiraterone|date=10 September 2012|publisher=The Institute of Cancer Research|access-date=12 November 2012|archive-date=9 July 2012|archive-url=https://web.archive.org/web/20120709060439/http://www.icr.ac.uk/press/recent_featured_articles/Story_Abiraterone/index.shtml|url-status=live}}</ref> Rights for commercialization of the drug were assigned to BTG, a UK-based specialist healthcare company. BTG then licensed the product to Cougar Biotechnology, which began development of the commercial product.<ref name="urlCougar Biotechnology, Inc.">{{cite web|url=http://www.cougarbiotechnology.com/cb7630.html|title=Abiraterone Acetate (CB7630)|publisher=Cougar Biotechnology|access-date=20 August 2008|archive-url=https://web.archive.org/web/20080907194739/http://www.cougarbiotechnology.com/cb7630.html|archive-date=7 September 2008}}</ref> In 2009, Cougar was acquired by Johnson & Johnson, which developed and sells the commercial product, and is conducting ongoing clinical trials to expand its clinical uses.<ref name="urlCougar">{{cite press release|url=http://www.cougarbiotechnology.com/pr052109.html|title=Johnson & Johnson Announces Definitive Agreement to Acquire Cougar Biotechnology, Inc.|date=11 May 2009|publisher=Cougar Biotechnology|access-date=3 June 2009|archive-url=https://web.archive.org/web/20090529115329/http://www.cougarbiotechnology.com/pr052109.html|archive-date=29 May 2009}}</ref>

Abiraterone acetate was approved by the United States Food and Drug Administration on 28 April 2011 for mCRPC.<ref name="Drugs@FDA">{{cite web|title=Drugs@FDA - FDA Approved Drug Products - Zytiga|url=https://www.accessdata.fda.gov/scripts/cder/daf/index.cfm?event=overview.process&ApplNo=202379|website=U.S. Food and Drug Administration (FDA)|access-date=4 March 2016|archive-date=1 May 2017|archive-url=https://web.archive.org/web/20170501045619/https://www.accessdata.fda.gov/scripts/cder/daf/index.cfm?event=overview.process&ApplNo=202379|url-status=live}}</ref><ref name="urlFDA approves Zytiga for late-stage prostate cancer">{{cite press release | url = https://www.fda.gov/NewsEvents/Newsroom/PressAnnouncements/ucm253055.htm | title = FDA approves Zytiga for late-stage prostate cancer | date = 28 April 2011 | publisher = Food and Drug Administration (FDA) | archive-url=https://wayback.archive-it.org/7993/20170112024032/https://www.fda.gov/NewsEvents/Newsroom/PressAnnouncements/ucm253055.htm | archive-date=12 January 2017 }}</ref> The FDA press release made reference to a phase III clinical trial in which abiraterone acetate use was associated with a median survival of 14.8 months versus 10.9 months with placebo; the study was stopped early because of the successful outcome.<ref>{{cite web | url = http://www.cancer.gov/cancertopics/druginfo/fda-abirateroneacetate | title = FDA Approval for Abiraterone Acetate | publisher = U.S. Department of Health and Human Services, National Institutes of Health, National Cancer Institute | access-date = 4 September 2011 | archive-date = 28 July 2011 | archive-url = https://web.archive.org/web/20110728040613/http://www.cancer.gov/cancertopics/druginfo/fda-abirateroneacetate }}</ref> Abiraterone acetate was also licensed by the European Medicines Agency.<ref>{{cite web| url = http://www.ema.europa.eu/ema/index.jsp?curl=pages/medicines/human/medicines/002321/human_med_001499.jsp&mid=WC0b01ac058001d124| title = EMA assessment of Zytiga (abiraterone)| work = European Medicines Agency| access-date = 6 July 2022| archive-date = 20 June 2018| archive-url = https://web.archive.org/web/20180620165426/http://www.ema.europa.eu/ema//index.jsp?curl=pages%2Fmedicines%2Fhuman%2Fmedicines%2F002321%2Fhuman_med_001499.jsp&mid=WC0b01ac058001d124| url-status = live}}</ref> Until May 2012 the National Institute for Health and Clinical Excellence (NICE) did not recommend use of the drug within the NHS on cost-effectiveness grounds. This position was reversed when the manufacturer submitted revised costs.<ref>{{cite web | url = http://www.nice.org.uk/nicemedia/live/13484/59217/59217.pdf | title = Prostate cancer (metastatic, castration resistant) - abiraterone (following cytoxic therapy): final appraisal determination guidance | archive-url = https://web.archive.org/web/20130219063336/http://www.nice.org.uk/nicemedia/live/13484/59217/59217.pdf | archive-date = 19 February 2013 | work = NICE guidance | date = 15 May 2012 }}</ref> The use is currently limited to men who have already received one docetaxel-containing chemotherapy regimen.<ref>{{cite web | url = http://www.nice.org.uk/guidance/ta259/chapter/1-guidance | title = NICE technology appraisal guidance [TA259] | work = NICE guidance | date = June 2012 | access-date = 6 March 2015 | archive-date = 19 February 2015 | archive-url = https://web.archive.org/web/20150219030030/http://www.nice.org.uk/guidance/TA259/chapter/1-guidance | url-status = live }}</ref><ref>{{cite web | url = http://www.nice.org.uk/nice-appraisal-of-earlier-treatment-with-abiraterone-for-prostate-cancer | title = NICE appraisal of earlier treatment with abiraterone for prostate cancer | work = NICE press release | date = 14 August 2014 | access-date = 6 March 2015 | archive-date = 2 April 2015 | archive-url = https://web.archive.org/web/20150402110522/http://www.nice.org.uk/nice-appraisal-of-earlier-treatment-with-abiraterone-for-prostate-cancer | url-status = live }}</ref> It was subsequently approved for the treatment of mCSPC in 2018.<ref name="Cancer.gov2018">{{cite web | author = NCI Staff | title = Abiraterone Approved for Earlier Use in Men with Metastatic Prostate Cancer | date = 15 February 2018 | url = https://www.cancer.gov/news-events/cancer-currents-blog/2018/abiraterone-fda-prostate-hormone-sensitive | publisher = National Cancer Institute (NCI) | access-date = 14 April 2018 | archive-date = 14 April 2018 | archive-url = https://web.archive.org/web/20180414234712/https://www.cancer.gov/news-events/cancer-currents-blog/2018/abiraterone-fda-prostate-hormone-sensitive | url-status = live }}</ref>

==Society and culture==

===Names=== ''Abiraterone'' is the {{abbrlink|INN|International Nonproprietary Name}} and {{abbrlink|BAN|British Approved Name}} of abiraterone acetate's major active metabolite abiraterone.<ref name="Drugs.com">{{cite web | title = Abiraterone | url = https://www.drugs.com/international/abiraterone.html | work = Drugs.com | access-date = 14 April 2018 | archive-date = 30 November 2014 | archive-url = https://web.archive.org/web/20141130182833/https://www.drugs.com/international/abiraterone.html | url-status = live }}</ref><ref>{{cite web |title=abiraterone |url=https://mednet-communities.net/inn/db/ViewINN.aspx?i=7375 |website=mednet-communities.net |access-date=15 November 2019 |archive-date=29 August 2021 |archive-url=https://web.archive.org/web/20210829101935/https://extranet.who.int/soinn/?i=7375 |url-status=live }}</ref> ''Abiraterone acetate'' is the {{abbrlink|USAN|United States Adopted Name}}, {{abbrlink|BANM|British Approved Name Modified}}, and {{abbrlink|JAN|Japanese Accepted Name}} of abiraterone acetate.<ref name="Drugs.com" /> It is also known by its developmental code names ''CB-7630'' and ''JNJ-212082'', while ''CB-7598'' was the developmental code name of abiraterone.<ref name="Drugs.com" /><ref name="AdisInsight" />

Abiraterone acetate is marketed by Janssen Biotech (a subsidiary of Johnson & Johnson) under the brand name Zytiga,<ref name="Drugs.com"/> and by Sun Pharmaceutical under the brand name Yonsa.<ref name="Drugs.com"/>

Generic versions of abiraterone acetate have been approved in the United States.<ref>{{cite web | title = Generic Zytiga Availability | url = https://www.drugs.com/availability/generic-zytiga.html | work = Drugs.com | access-date = 14 April 2018 | archive-date = 14 April 2018 | archive-url = https://web.archive.org/web/20180414234617/https://www.drugs.com/availability/generic-zytiga.html | url-status = live }}</ref> Generic versions of Yonsa are not available {{as of|November 2019|lc=yes}}.<ref>{{cite web | title = Generic Yonsa Availability | url = https://www.drugs.com/availability/generic-yonsa.html | work = Drugs.com | access-date = 18 November 2019 | archive-date = 18 November 2019 | archive-url = https://web.archive.org/web/20191118004828/https://www.drugs.com/availability/generic-yonsa.html | url-status = live }}</ref> In May 2019, the United States Court of Appeals for the Federal Circuit upheld a Patent Trial and Appeal Board decision invalidating a patent by Johnson & Johnson on abiraterone acetate.<ref>{{cite web | url=http://www.cafc.uscourts.gov/node/24791 | title=BTG International Limited v. Amneal Pharmaceuticals LLC | date=14 May 2019 | id=19-1147 | publisher=United States Court of Appeals for the Federal Circuit | access-date=17 November 2019 | archive-date=29 August 2021 | archive-url=https://web.archive.org/web/20210829101933/http://www.cafc.uscourts.gov/node/24791 | url-status=live }}</ref>

Intas Pharmaceuticals markets the drug under the brand name Abiratas, Cadila Pharmaceuticals markets the drug as Abretone, and Glenmark Pharmaceuticals as Abirapro.{{Citation needed|date=April 2018}} It is marketed as Yonsa by Sun Pharmaceutical Industries (licensed from Churchill Pharmaceuticals).<ref>{{cite web|url=https://www.biospace.com/article/sun-pharma-gets-fda-go-ahead-for-yonsa-for-prostate-cancer/|title=Sun Pharma Gets FDA Go-Ahead for Yonsa for Prostate Cancer|website=BioSpace|date=24 May 2018 |access-date=16 May 2019|archive-date=11 April 2019|archive-url=https://web.archive.org/web/20190411214955/https://www.biospace.com/article/sun-pharma-gets-fda-go-ahead-for-yonsa-for-prostate-cancer/|url-status=live}}</ref><ref>{{cite press release | title=Sun Pharma Announces USFDA Approval of YONSA (abiraterone acetate) To Treat Metastatic Castration-Resistant Prostate Cancer In Combination With Methylprednisolone | publisher=Sun Pharmaceutical Industries Limited/Churchill Pharmaceuticals |via=Business Wire | date=23 May 2018 | url=https://www.businesswire.com/news/home/20180522006497/en/Sun-Pharma-Announces-USFDA-Approval-YONSA%C2%AE-abiraterone | archive-url=https://web.archive.org/web/20191115063852/https://www.businesswire.com/news/home/20180522006497/en/Sun-Pharma-Announces-USFDA-Approval-YONSA%C2%AE-abiraterone | archive-date=15 November 2019 | url-status=live | access-date=14 November 2019}}</ref>

===Brand names=== Abiraterone acetate is marketed widely throughout the world, including in the United States, Canada, the United Kingdom, Ireland, elsewhere in Europe, Australia, New Zealand, Latin America, Asia, and Israel.<ref name="Drugs.com" />

=== Economics === A generic version is available in India at a price of $238 a month {{as of|2019|lc=yes}}.<ref name=Pro2019WHO>{{cite web |title=Proposal For The Inclusion Of Enzalutamide And Abiraterone Acetate In The Who Model List Of Essential Medicines For The Treatment Of Metastatic Castration Resistant Prostate Cancer |url=https://www.who.int/selection_medicines/committees/expert/22/applications/8.3_enzalutamide-abiraterone.pdf |access-date=26 November 2019 |pages=22, 25 |archive-date=29 August 2021 |archive-url=https://web.archive.org/web/20210829101931/https://www.who.int/selection_medicines/committees/expert/22/applications/8.3_enzalutamide-abiraterone.pdf |url-status=live }}</ref> The National Centre for Pharmacoeconomics initially found abiraterone acetate to not be cost effective based on prices in 2012, however following an agreement to supply at a lower price it was accepted in 2014.<ref name=Pro2019WHO/><ref>{{cite web |title=Zytiga Generic (Abiraterone) - $250 Per Month Total Cost |url=https://www.medixocentre.com/abiraterone-cost |website=Medixocentre.com |access-date=1 August 2020 |archive-date=28 September 2020 |archive-url=https://web.archive.org/web/20200928043801/https://www.medixocentre.com/abiraterone-cost |url-status=live }}</ref> A generic Zytiga version is available in India at a price of under $230 a month as of 2020.<ref>{{cite web| url = https://www.medixocentre.com/abiraterone-cost| publisher = India Medixo Centre| title = Abiraterone cost| access-date = 1 August 2020| archive-date = 28 September 2020| archive-url = https://web.archive.org/web/20200928043801/https://www.medixocentre.com/abiraterone-cost| url-status = live}}</ref>

==Research== Abiraterone acetate is under development for the treatment of breast cancer and ovarian cancer and as of March 2018, is in phase II clinical trials for these indications.<ref name="AdisInsight">{{cite web | title = Abiraterone acetate - Johnson & Johnson | url = http://adisinsight.springer.com/drugs/800005133 | work = Adis Insight | access-date = 4 December 2016 | archive-date = 20 December 2016 | archive-url = https://web.archive.org/web/20161220060607/http://adisinsight.springer.com/drugs/800005133 | url-status = live }}</ref> It was also under investigation for the treatment of congenital adrenal hyperplasia, but no further development has been reported for this potential use.<ref name="AdisInsight" />

=== Prostate cancer === In people previously treated with docetaxel survival is increased by 3.9 months (14.8 months versus 10.9 months for placebo).<ref name="NEJM2">{{cite journal | vauthors = de Bono JS, Logothetis CJ, Molina A, Fizazi K, North S, Chu L, Chi KN, Jones RJ, Goodman OB, Saad F, Staffurth JN, Mainwaring P, Harland S, Flaig TW, Hutson TE, Cheng T, Patterson H, Hainsworth JD, Ryan CJ, Sternberg CN, Ellard SL, Fléchon A, Saleh M, Scholz M, Efstathiou E, Zivi A, Bianchini D, Loriot Y, Chieffo N, Kheoh T, Haqq CM, Scher HI | title = Abiraterone and increased survival in metastatic prostate cancer | journal = The New England Journal of Medicine | volume = 364 | issue = 21 | pages = 1995–2005 | date = May 2011 | pmid = 21612468 | pmc = 3471149 | doi = 10.1056/NEJMoa1014618 }}</ref>

In people with castration-refractory prostate cancer but who had not received chemotherapy those who received abiraterone acetate had a progression-free survival of 16.5 months rather than 8.3 months with placebo. After a median follow-up period of 22.2 months, overall survival was better with abiraterone acetate.<ref name="pmid23228172">{{cite journal | vauthors = Ryan CJ, Smith MR, de Bono JS, Molina A, Logothetis CJ, de Souza P, Fizazi K, Mainwaring P, Piulats JM, Ng S, Carles J, Mulders PF, Basch E, Small EJ, Saad F, Schrijvers D, Van Poppel H, Mukherjee SD, Suttmann H, Gerritsen WR, Flaig TW, George DJ, Yu EY, Efstathiou E, Pantuck A, Winquist E, Higano CS, Taplin ME, Park Y, Kheoh T, Griffin T, Scher HI, Rathkopf DE | title = Abiraterone in metastatic prostate cancer without previous chemotherapy | journal = The New England Journal of Medicine | volume = 368 | issue = 2 | pages = 138–48 | date = January 2013 | pmid = 23228172 | pmc = 3683570 | doi = 10.1056/NEJMoa1209096 }}</ref>

Abiraterone acetate may be useful for prevention of the testosterone flare at the initiation of GnRH agonist therapy in men with prostate cancer.<ref name="pmid26150586">{{cite journal | vauthors = Pokuri VK, Nourkeyhani H, Betsy B, Herbst L, Sikorski M, Spangenthal E, Fabiano A, George S | title = Strategies to Circumvent Testosterone Surge and Disease Flare in Advanced Prostate Cancer: Emerging Treatment Paradigms | journal = J Natl Compr Canc Netw | volume = 13 | issue = 7 | pages = e49–55 | date = July 2015 | pmid = 26150586 | doi = 10.6004/jnccn.2015.0109 | doi-access = free }}</ref>

==References== {{Reflist}}

{{Androgens and antiandrogens}} {{Androgen receptor modulators}} {{Estrogen receptor modulators}} {{Portal bar | Medicine}}

{{DEFAULTSORT:Abiraterone Acetate}} Category:11β-Hydroxylase inhibitors Category:3β-Hydroxysteroid dehydrogenase inhibitors Category:5α-Reductase inhibitors Category:Acetate esters Category:Androstanes Category:Antiestrogens Category:Antiglucocorticoids Category:Combination cancer drugs Category:Conjugated dienes Category:CYP2D6 inhibitors Category:CYP17A1 inhibitors Category:Hormonal antineoplastic drugs Category:Drugs developed by Johnson & Johnson Category:Prodrugs Category:Prostate cancer Category:3-Pyridyl compounds Category:Steroid sulfotransferase inhibitors Category:Steroidal antiandrogens Category:Synthetic estrogens Category:World Health Organization essential medicines Category:Wikipedia medicine articles ready to translate