Risedronic acid: Difference between revisions
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{{Short description|Chemical compound}} |
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{{drugbox |
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{{Drugbox |
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| verifiedrevid = 372945218 |
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| Verifiedfields = changed |
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| Watchedfields = changed |
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| verifiedrevid = 417807800 |
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| IUPAC_name = (1-hydroxy-1-phosphono-2-pyridin-3-yl-ethyl)phosphonic acid |
| IUPAC_name = (1-hydroxy-1-phosphono-2-pyridin-3-yl-ethyl)phosphonic acid |
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| image = Risedronate.svg |
| image = Risedronate.svg |
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| |
| width = 161 |
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| |
| alt = |
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| CASNo_Ref = {{cascite}} |
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<!--Clinical data--> |
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| CAS_number = 105462-24-6 |
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| tradename = Actonel, Atelvia, Benet, others |
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| Drugs.com = {{drugs.com|monograph|risedronate-sodium}} |
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| DailyMedID = Risedronic |
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| pregnancy_AU = B3 |
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| routes_of_administration = [[Oral administration|By mouth]] |
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| ATC_prefix = M05 |
| ATC_prefix = M05 |
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| ATC_suffix = BA07 |
| ATC_suffix = BA07 |
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| PubChem = 5245 |
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| |
| legal_AU = S4 |
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| legal_UK = POM |
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| C = 7 |H = 11 |N = 1 |O = 7 |P = 2 |
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| legal_US = Rx-only |
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| molecular_weight = 283.112 [[Gram|g]]/[[Mole (unit)|mol]] |
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| legal_US_comment = <ref name="Actonel FDA label">{{cite web | title=Actonel- risedronate sodium tablet, film coated | website=DailyMed | date=1 November 2019 | url=https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=24ed00e0-25e2-49a8-97fc-66c1b417dc0b | access-date=28 June 2022}}</ref> |
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| smiles = OC(Cc1cccnc1)(P(=O)(O)O)P(=O)(O)O |
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| legal_status = Rx-only |
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<!--Pharmacokinetic data--> |
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| bioavailability = 0.63% |
| bioavailability = 0.63% |
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| protein_bound = ~24% |
| protein_bound = ~24% |
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| metabolism = None |
| metabolism = None |
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| elimination_half-life = 1.5 h |
| elimination_half-life = 1.5 h |
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| excretion = [[Kidney |
| excretion = [[Kidney]] and fecal |
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| pregnancy_AU = B3 |
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<!--Identifiers--> |
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| pregnancy_US = C |
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| CAS_number_Ref = {{cascite|correct|??}} |
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| legal_UK = POM |
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| |
| CAS_number = 105462-24-6 |
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| PubChem = 5245 |
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| routes_of_administration = Oral |
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| IUPHAR_ligand = 3176 |
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| DrugBank_Ref = {{drugbankcite|changed|drugbank}} |
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| DrugBank = DB00884 |
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| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} |
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| ChemSpiderID = 5055 |
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| UNII_Ref = {{fdacite|changed|FDA}} |
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| UNII = KM2Z91756Z |
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| KEGG_Ref = |
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| KEGG = D00942 |
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| KEGG2 = D03234 |
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| ChEBI_Ref = |
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| ChEBI = |
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| ChEMBL_Ref = {{ebicite|changed|EBI}} |
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| ChEMBL = 923 |
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| NIAID_ChemDB = |
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| PDB_ligand = RIS |
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| synonyms = |
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<!--Chemical data--> |
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| C=7 | H=11 | N=1 | O=7 | P=2 |
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| SMILES = OC(Cc1cccnc1)(P(=O)(O)O)P(=O)(O)O |
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| StdInChI_Ref = {{stdinchicite|changed|chemspider}} |
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| 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) |
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| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} |
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| StdInChIKey = IIDJRNMFWXDHID-UHFFFAOYSA-N |
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}} |
}} |
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'''Risedronic acid''' ([[International Nonproprietary Name|INN]]) or '''risedronate sodium''' ([[United States Adopted Name|USAN]], trade name '''Actonel''') is a [[bisphosphonate]] used to strengthen [[bone]], treat or prevent [[osteoporosis]], and treat [[Paget's disease]] of bone. It is produced and marketed by [[Warner Chilcott]] and [[Sanofi-Aventis]]. |
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'''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 [[Oral administration|by mouth]].<ref name="Actonel FDA label" /> |
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==Administration== |
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Risedronate is taken orally, usually 5 mg daily, 35 mg weekly or 150 mg monthly. Notably, if risedronate lodges in the [[esophagus]], it can lead to esophageal [[Peptic ulcer|ulcers]]. Therefore, it is recommended that risedronate be taken with the body upright, and followed by a glass of water. Moreover, risedronate is poorly absorbed when taken with food, so it is recommended that no food or drink other than water be taken for 2 hours before and 30 minutes after taking risedronate. Risedronate has a faster esophageal transit time and different chemical chain which results in less gastrointestinal side-effects than other drugs in this class. The dosage instructions also show that risedronate can be taken with less water than other drugs in the class. |
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Risedronate is also available as a 75mg tablet to be taken on two consecutive days each month (2CDM) in order to optimize patient adherence. This formulation has been studied in a randomized, double-blind, parallel-group, multinational trial in 1229 postmenopausal women with osteoporosis.<ref name="risedronate">Frampton JE.[http://adisonline.com/aging/abstract/2009/26040/Risedronate_on_Two_Consecutive_Days_per_Month.6.aspx].Drugs&Aging 2009; 26(4):355-362.doi: 10.2165/00002512-200926040-00006.</ref> |
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It was patented in 1984 and approved for medical use in 1998.<ref name=Fis2006>{{cite book | vauthors = Fischer J, Ganellin CR |title= Analogue-based Drug Discovery |date=2006 |publisher=John Wiley & Sons |isbn=9783527607495 |page=523 |url=https://books.google.com/books?id=FjKfqkaKkAAC&pg=PA523 }}</ref> |
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==Pharmacology== |
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{| class="wikitable" |
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|+Relative potency<ref>{{cite book |title=Essentials of medical pharmacology | vauthors = Tripathi KD |date = 30 September 2013|isbn=9789350259375|edition= Seventh|location=New Delhi|oclc=868299888}}</ref> |
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!Bisphosphonate |
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!Relative potency |
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|- |
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|[[Etidronic acid|Etidronate]] |
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|1 |
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|- |
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|[[Tiludronic acid|Tiludronate]] |
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|10 |
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|- |
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|[[Pamidronic acid|Pamidronate]] |
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|100 |
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|- |
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|[[Alendronic acid|Alendronate]] |
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|100-500 |
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|- |
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|[[Ibandronic acid|Ibandronate]] |
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|500-1000 |
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|- |
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|Risedronate |
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|1000 |
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|- |
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|[[Zoledronic acid|Zoledronate]] |
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|5000 |
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|} |
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== Society and culture == |
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==Controversies== |
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===Brand names=== |
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In January 2006 P&G and its marketing partner [[Sanofi-Aventis]] filed a [[Lanham Act]] false claims lawsuit against rival drugmakers [[Hoffmann-La Roche|Roche]] and [[GlaxoSmithKline]] claiming false advertising about [[Ibandronic_acid|Boniva]].<ref>[http://www.uk.pg.com/news/newsReleases2006/jan0406_P&G_Pharmaceuticals_Sanofi-AventisUSLLC_File_Lawsuit.html P&G Press statement]</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>[http://www.topix.net/content/ap/3458843697085346378233666743703364096132 NY fed judge finds promotions for bone drug Boniva are fair Associated Press, 7 Sept 2006]</ref> |
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{{Unreferenced section|date=September 2023}} |
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It is produced and marketed by [[Warner Chilcott]], [[Sanofi-Aventis]], and in Japan by [[Takeda Pharmaceutical Company|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. |
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===Controversies=== |
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In 2006 P&G faced controversy over its handling of clinical research involving risedronate ([http://www.thejabberwock.org/wiki/index.php?title=Actonel_Case_Media_Reports News Reports] and [http://www.scientific-misconduct.blogspot.com discussion]). |
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In January 2006 [[Procter & Gamble|P&G]] and its marketing partner [[Sanofi-Aventis]] filed a [[Lanham Act]] false claims lawsuit against rival drugmakers [[Hoffmann-La Roche|Roche]] and [[GlaxoSmithKline]] claiming false advertising about [[Ibandronic acid|Boniva]].<ref>{{cite web|url=http://www.uk.pg.com/news/newsReleases2006/jan0406_P&G_Pharmaceuticals_Sanofi-AventisUSLLC_File_Lawsuit.html |title=P&G Press statement |publisher=Uk.pg.com |access-date=2013-03-01}}</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 | url = http://www.pharmatimes.com/news/boniva_advertising_not_misleading_says_us_judge_995913 | date = 8 September 2006 | work = Pharma Times }}</ref> |
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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|url=http://www.scientific-misconduct.blogspot.com |title=Scientific Misconduct Blog |publisher=Scientific-misconduct.blogspot.com |access-date=2013-03-01}}</ref> |
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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. |
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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. |
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==See also== |
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[[Richard Eastell]] |
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==References== |
== References == |
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{{reflist}} |
{{reflist}} |
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== External links == |
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* {{cite web | url = https://druginfo.nlm.nih.gov/drugportal/name/risedronic%20acid | publisher = U.S. National Library of Medicine | work = Drug Information Portal | title = Risedronic acid }} |
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* {{cite web | url = https://druginfo.nlm.nih.gov/drugportal/name/risedronate%20sodium | publisher = U.S. National Library of Medicine | work = Drug Information Portal | title = Risedronate sodium }} |
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{{Bisphosphonates}} |
{{Bisphosphonates}} |
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{{Portal bar | Medicine}} |
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{{DEFAULTSORT:Risedronic Acid}} |
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[[Category:Bisphosphonates]] |
[[Category:Bisphosphonates]] |
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[[Category:Farnesyl pyrophosphate synthase inhibitors]] |
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[[Category:Procter & Gamble]] |
[[Category:Procter & Gamble]] |
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[[Category: |
[[Category:3-Pyridyl compounds]] |
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[[Category:Drugs developed by AbbVie]] |
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[[Category:Sanofi]] |
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[[de:Risedronsäure]] |
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[[Category:Drugs developed by Takeda Pharmaceutical Company]] |
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[[sr:Risedronska kiselina]] |