Risedronic acid

{{Short description|Chemical compound}} {{cs1 config|name-list-style=vanc|display-authors=6}} {{Drugbox | Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 417807800 | IUPAC_name = (1-hydroxy-1-phosphono-2-pyridin-3-yl-ethyl)phosphonic acid | image = Risedronate.svg | image_class = skin-invert-image | width = 161 | alt =

| tradename = Actonel, Atelvia, Benet, others | Drugs.com = {{drugs.com|monograph|risedronate-sodium}} | DailyMedID = Risedronic | pregnancy_AU = B3 | routes_of_administration = By mouth | ATC_prefix = M05 | ATC_suffix = BA07

| legal_AU = S4 | legal_UK = POM | legal_US = Rx-only | legal_US_comment = <ref name="Actonel FDA label">{{cite web | title = Actonel- risedronate sodium tablet, film coated | date = 1 November 2019 | website = DailyMed | url = https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=24ed00e0-25e2-49a8-97fc-66c1b417dc0b | access-date = 28 June 2022 }}</ref> | legal_status = Rx-only

| CAS_number_Ref = {{cascite|correct|??}} | CAS_number = 105462-24-6 | PubChem = 5245 | IUPHAR_ligand = 3176 | DrugBank_Ref = {{drugbankcite|changed|drugbank}} | DrugBank = DB00884 | ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} | ChemSpiderID = 5055 | UNII_Ref = {{fdacite|changed|FDA}} | UNII = KM2Z91756Z | KEGG_Ref = | KEGG = D00942 | KEGG2 = D03234 | ChEBI_Ref = | ChEBI = | ChEMBL_Ref = {{ebicite|changed|EBI}} | ChEMBL = 923 | NIAID_ChemDB = | PDB_ligand = RIS | synonyms =

| C=7 | H=11 | N=1 | O=7 | P=2 | SMILES = OC(Cc1cccnc1)(P(=O)(O)O)P(=O)(O)O | StdInChI_Ref = {{stdinchicite|changed|chemspider}} | StdInChI = 1S/C7H11NO7P2/c9-7(16(10,11)12,17(13,14)15)4-6-2-1-3-8-5-6/h1-3,5,9H,4H2,(H2,10,11,12)(H2,13,14,15) | StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} | StdInChIKey = IIDJRNMFWXDHID-UHFFFAOYSA-N }}

'''Risedronic acid''', often used as its sodium salt '''risedronate sodium''', is a bisphosphonate.<ref name="Actonel FDA label" /> It slows down the cells which break down bone.<ref name="Actonel FDA label" /> It's used to treat or prevent osteoporosis, and treat Paget's disease of bone.<ref name="Actonel FDA label" /> It is taken by mouth.<ref name="Actonel FDA label" />

It was patented in 1984 and approved for medical use in 1998.<ref name="Fischer_2006">{{cite book | vauthors = Fischer J, Ganellin CR | title = Analogue-based Drug Discovery | date = 2006 | publisher = John Wiley & Sons | isbn = 978-3-527-60749-5 | page = 523 | url = https://books.google.com/books?id=FjKfqkaKkAAC&pg=PA523 }}</ref>

==Pharmacology== {| class="wikitable" |+Relative potency<ref>{{cite book | vauthors = Tripathi KD | title = Essentials of medical pharmacology | location = New Delhi | date = 30 September 2013 | isbn = 978-93-5025-937-5 | edition = Seventh | publisher = Jaypee Brothers Medical Publishers Ltd. | oclc = 868299888 }}</ref> !Bisphosphonate !Relative potency |- |Etidronate |1 |- |Tiludronate |10 |- |Pamidronate |100 |- |Alendronate |100-500 |- |Ibandronate |500-1000 |- |Risedronate |1000 |- |Zoledronate |5000 |} == History == Risedronate, known as NE-58095 while under development, was discovered by scientists at the Cincinnati Miami Valley Laboratories and the Norwich Eaton Laboratories of Procter and Gamble. <ref> {{cite journal | vauthors = McClung MR, Ebetino FH | title = History of risedronate | journal = Bone | volume = 137 | issue = 115407 | date = August 2020 | article-number = 115407 | pmid = 32387834 | doi = 10.1016/j.bone.2020.115407 | url = https://www.sciencedirect.com/science/article/abs/pii/S8756328220301873#:~:text=Risedronate%20was%20shown%20to%20significantly,of%20osteoporosis%20was%20not%20performed. | issn = 8756-3282 | access-date = April 25, 2025 | url-access = subscription }} </ref>

== Society and culture == ===Brand names=== {{Unreferenced section|date=September 2023}} It is produced and marketed by Warner Chilcott, Sanofi-Aventis, and in Japan by Takeda under the trade names Actonel, Atelvia, and Benet. It is also available in a preparation that includes a calcium carbonate supplement, as Actonel with Calcium.

===Controversies=== In January 2006 P&G and its marketing partner Sanofi-Aventis filed a Lanham Act false claims lawsuit against rival drugmakers Roche and GlaxoSmithKline claiming false advertising about Boniva.<ref>{{cite web | title = P&G Press statement | url = http://www.uk.pg.com/news/newsReleases2006/jan0406_P%26G_Pharmaceuticals_Sanofi-AventisUSLLC_File_Lawsuit.html | publisher = Uk.pg.com | access-date = 2013-03-01 | archive-date = 2011-09-29 | archive-url = https://web.archive.org/web/20110929135317/http://www.uk.pg.com/news/newsReleases2006/jan0406_P%26G_Pharmaceuticals_Sanofi-AventisUSLLC_File_Lawsuit.html | url-status = dead }}</ref> The manufacturers of Boniva, a rival bisphosphonate, were accused in the suit of causing a "serious public health risk" through misrepresentation of scientific findings. In a ruling on September 7, 2006, U.S. District Judge Paul A. Crotty rejected P&G's attempted injunction. P&G was criticized for attempting to "preserve its market share by denigrating Boniva". Judge Crotty wrote that "Roche was clearly entitled to respond with its own data, provided that the data was truthfully and accurately presented".<ref>{{cite web | title = Boniva advertising 'not misleading' says US judge | date = 8 September 2006 | url = http://www.pharmatimes.com/news/boniva_advertising_not_misleading_says_us_judge_995913 | work = Pharma Times }}</ref>

In 2006, P&G faced controversy over its handling of clinical research involving risedronate (News Reports<ref>{{cite web | title = Actonel Case Media Reports | url = http://www.thejabberwock.org/wiki/index.php?title=Actonel_Case_Media_Reports | archive-url = https://web.archive.org/web/20090202055309/http://www.thejabberwock.org/wiki/index.php?title=Actonel_Case_Media_Reports | archive-date = 2 February 2009 | work = Scientific Misconduct Wiki }}</ref> and discussion).<ref>{{cite web | title = Scientific Misconduct Blog | url = http://www.scientific-misconduct.blogspot.com | publisher = Scientific-misconduct.blogspot.com | access-date = 2013-03-01 }}</ref>

In common with other bisphosphonate drugs, risedronate appears to be associated with the rare side effect osteonecrosis of the jaw, often preceded by dental procedures inducing trauma to the bone.

== References == {{reflist}}

== External links == * {{cite web | title = Risedronic acid | url = https://druginfo.nlm.nih.gov/drugportal/name/risedronic%20acid | archive-url = https://web.archive.org/web/20200610225844/https://druginfo.nlm.nih.gov/drugportal/name/risedronic%20acid | url-status = dead | archive-date = June 10, 2020 | publisher = U.S. National Library of Medicine | work = Drug Information Portal }} * {{cite web | title = Risedronate sodium | url = https://druginfo.nlm.nih.gov/drugportal/name/risedronate%20sodium | archive-url = https://web.archive.org/web/20200610225846/https://druginfo.nlm.nih.gov/drugportal/name/risedronate%20sodium | url-status = dead | archive-date = June 10, 2020 | publisher = U.S. National Library of Medicine | work = Drug Information Portal }}

{{DEFAULTSORT:Risedronic Acid}} Category:Bisphosphonates Category:Farnesyl pyrophosphate synthase inhibitors Category:Procter & Gamble Category:3-Pyridyl compounds Category:Drugs developed by AbbVie Category:Sanofi Category:Drugs developed by Takeda Pharmaceutical Company