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{{Short description|Laxative}} |
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{{drugbox | verifiedrevid = 414040120 |
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{{Infobox drug |
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| Verifiedfields = changed |
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| Watchedfields = changed |
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| verifiedrevid = 414908012 |
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| IUPAC_name = (pyridin-2-ylmethanediyl)dibenzene-4,1-diyl diacetate<!--generated by ACD/Name--> <br /> OR <br /> 4,4'-(pyridin-2-ylmethylene)bis(4,1-phenylene) diacetate |
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| IUPAC_name = (pyridin-2-ylmethanediyl)dibenzene-4,1-diyl diacetate<!--generated by ACD/Name--> <br /> OR <br /> 4,4'-(pyridin-2-ylmethylene)bis(4,1-phenylene) diacetate |
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| image = Bisacodyl skeletal.svg |
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| image = Bisacodyl skeletal.svg |
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| image2 = Bisacodyl-from-xtal-3D-bs-17.png |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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<!--Clinical data--> |
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| tradename = Fleet, Dulcolax, Brooklax, others |
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| Drugs.com = {{drugs.com|monograph|bisacodyl}} |
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| MedlinePlus = a601027 |
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| pregnancy_category = B |
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| legal_status = OTC |
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| routes_of_administration = ] or rectal |
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<!--Pharmacokinetic data--> |
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| bioavailability = 15% |
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| metabolism = Liver (]-mediated) |
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| elimination_half-life = 16 Hours |
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| excretion = primarily in the feces, systemically absorbed drug is excreted in the urine |
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<!--Identifiers--> |
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| CAS_number_Ref = {{cascite|correct|??}} |
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| CAS_number = 603-50-9 |
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| ATC_prefix = A06 |
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| ATC_suffix = AB02 |
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| ATC_supplemental = {{ATC|A06|AG02}} |
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| PubChem = 2391 |
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| DrugBank_Ref = {{drugbankcite|changed|drugbank}} |
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| DrugBank = DB09020 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 2299 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = 10X0709Y6I |
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| UNII = 10X0709Y6I |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| KEGG = D00245 |
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| KEGG = D00245 |
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| InChI = 1/C22H19NO4/c1-15(24)26-19-10-6-17(7-11-19)22(21-5-3-4-14-23-21)18-8-12-20(13-9-18)27-16(2)25/h3-14,22H,1-2H3 |
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| smiles = O=C(Oc1ccc(cc1)C(c2ccc(OC(=O)C)cc2)c3ncccc3)C |
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| InChIKey = KHOITXIGCFIULA-UHFFFAOYAS |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| ChEMBL = 942 |
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| ChEMBL = 942 |
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<!--Chemical data--> |
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| C=22 | H=19 | N=1 | O=4 |
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| smiles = O=C(Oc1ccc(cc1)C(c2ccc(OC(=O)C)cc2)c3ncccc3)C |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI = 1S/C22H19NO4/c1-15(24)26-19-10-6-17(7-11-19)22(21-5-3-4-14-23-21)18-8-12-20(13-9-18)27-16(2)25/h3-14,22H,1-2H3 |
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| StdInChI = 1S/C22H19NO4/c1-15(24)26-19-10-6-17(7-11-19)22(21-5-3-4-14-23-21)18-8-12-20(13-9-18)27-16(2)25/h3-14,22H,1-2H3 |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = KHOITXIGCFIULA-UHFFFAOYSA-N |
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| StdInChIKey = KHOITXIGCFIULA-UHFFFAOYSA-N |
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| CAS_number = 603-50-9 |
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| ATC_prefix = A06 |
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| ATC_suffix = AB02 |
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| PubChem = 2391 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 2299 |
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| DrugBank = |
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| C=22|H=19|N=1|O=4 |
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| molecular_weight = 361.391 g/mol |
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| bioavailability = 15% |
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| protein_bound = |
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| metabolism = Hepatic (]-mediated) |
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| elimination_half-life = 16 Hours |
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| excretion = primarily in the feces, systemically absorbed drug is excreted in the urine |
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| pregnancy_category = C |
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| legal_status = OTC |
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| routes_of_administration = Oral, rectal |
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}} |
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}} |
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'''Bisacodyl''' (]) is a stimulant ] drug. It is typically prescribed for relief of ] and for the management of ] as well as part of bowel preparation before medical examinations, such as for a ].<ref>{{cite journal |
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'''Bisacodyl''' (]) is an ] that is used as a stimulant ] drug. It works directly on the ] to produce a bowel movement. It is typically prescribed for relief of episodic and chronic ] and for the management of ], as well as part of bowel preparation before medical examinations, such as for a ].<ref>{{cite journal | vauthors = Wexner SD, Beck DE, Baron TH, Fanelli RD, Hyman N, Shen B, Wasco KE | title = A consensus document on bowel preparation before colonoscopy: prepared by a task force from the American Society of Colon and Rectal Surgeons (ASCRS), the American Society for Gastrointestinal Endoscopy (ASGE), and the Society of American Gastrointestinal and Endoscopic Surgeons (SAGES) | journal = Gastrointestinal Endoscopy | volume = 63 | issue = 7 | pages = 894–909 | date = June 2006 | pmid = 16733101 | doi = 10.1016/j.gie.2006.03.918 | author8-link = American Society of Colon and Rectal Surgeons }}</ref><ref name="Wald2016">{{cite journal | vauthors = Wald A | title = Constipation: Advances in Diagnosis and Treatment | journal = JAMA | volume = 315 | issue = 2 | pages = 185–91 | date = January 2016 | pmid = 26757467 | doi = 10.1001/jama.2015.16994 | type = Review }}</ref> |
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| last = Wexner |
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| first = SD |
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| coauthors = Beck, DE; Baron, TH; Fanelli, RD; Hyman, N; Shen, B; Wasco, KE; American Society of Colon and Rectal Surgeons; American Society for Gastrointestinal Endoscopy; Society of American Gastrointestinal and Endoscopic Surgeons |
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| year = 2006 |
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| month = June |
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| title = A consensus document on bowel preparation before colonoscopy: prepared by a task force from the American Society of Colon and Rectal Surgeons (ASCRS), the American Society for Gastrointestinal Endoscopy (ASGE), and the ] (SAGES) |
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| journal = Gastrointest Endosc. |
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| volume = 63 |
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| issue = 7 |
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| pages = 894–909 |
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| issn = 0016-5107 |
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| pmid = 16733101 |
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| accessdate = 2007-10-22 |
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| doi = 10.1016/j.gie.2006.03.918 |
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}} |
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Bisacodyl is a derivative of ]. It was first used as a laxative in 1953 because of its structural similarity to ].<ref>{{cite journal | vauthors = Stiens SA, Luttrel W, Binard JE | title = Polyethylene glycol versus vegetable oil based bisacodyl suppositories to initiate side-lying bowel care: a clinical trial in persons with spinal cord injury | journal = Spinal Cord | volume = 36 | issue = 11 | pages = 777–81 | date = November 1998 | pmid = 9848486 | doi = 10.1038/sj.sc.3100702 | doi-access = free }}</ref><ref>{{cite journal | vauthors = Evans IL | url= | title = Methods and techniques: The use of Bisacodyl suppositories in preparation for sigmoidoscopy | journal = Gut | series = British Medical Journal | date = 1964 | volume = 5 | pages = 271–3 | doi = 10.1136/gut.5.3.271 | pmid = 14178715 | pmc = 1552120 }}</ref> |
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</ref> Bisacodyl is a ] (in fact, a modified ]) derivative and was first used as a laxative in 1953 due to its similarity to ].<ref></ref> |
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It is on the ].<ref name="WHO22nd">{{cite book | vauthors = ((World Health Organization)) | title = World Health Organization model list of essential medicines: 22nd list (2021) | year = 2021 | hdl = 10665/345533 | author-link = World Health Organization | publisher = World Health Organization | location = Geneva | id = WHO/MHP/HPS/EML/2021.02 | hdl-access=free }}</ref> |
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==Mechanism of action== |
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Bisacodyl works by stimulating ] to cause ], i.e., colonic contractions. It is also a ]; it increases fluid and salt secretion. The action of bisacodyl on the ] is negligible; stimulant laxatives mainly promote evacuation of the colon.<ref name=Ullmann/> |
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==Available forms== |
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==Available forms== |
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Bisacodyl is sold under the trade names '''Dulcolax/Durolax''', '''Fleet''', '''Alophen''', '''Correctol''', and '''Carter's Little Pills''' (formerly '''Carter's Little Liver Pills'''<ref>{{cite news| url=http://www.time.com/time/magazine/article/0,9171,814704,00.html | work=Time | title=Medicine: Cut Out the Liver | date=1951-04-16 | accessdate=2010-04-26}}</ref>) as well as ]. It is usually sold as 5 mg tablets, 10 mg suppositories, or 5 mg pediatric suppositories. It is also available as a 1.25 fluid ounce prepackaged enema containing a 10 mg delivered dose of liquid bisacodyl. |
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Bisacodyl is marketed under the trade names '''Dulcolax/Durolax''', '''Muxol''', '''Fleet''', '''Nourilax''', '''Alophen''', '''Correctol''', and '''Carter's Little Pills''' (formerly ]),<ref>{{ cite news | url = http://www.time.com/time/magazine/article/0,9171,814704,00.html | archive-url = https://web.archive.org/web/20071108214845/https://time.com/time/magazine/article/0,9171,814704,00.html | archive-date = 8 November 2007 | work = Time | title = Medicine: Cut Out the Liver | date = 1951-04-16 | url-status = dead | access-date = 2010-04-26 }}</ref> as well as being available ]. It is usually sold as 5 mg tablets, 10 mg ], or 5 mg pediatric suppositories. It is also available as a {{Convert|1.25|USoz||abbr=}} pre-packaged ] containing a 10 mg delivered dose of liquid bisacodyl.<ref name=Ullmann>{{cite encyclopedia | vauthors = Engelhorn R, Seeger E, Zwaving JH | chapter = Laxatives | title = Ullmann's Encyclopedia of Industrial Chemistry | publisher = Wiley-VCH | location = Weinheim | date = 2000 | doi = 10.1002/14356007.a15_183 | isbn = 3527306730 }}</ref> |
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==Administration== |
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==Administration== |
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When bisacodyl is administered orally, it is usually taken at bedtime. This is due to the relatively long onset of the drug when taken orally (around 6–10 hours). When administered rectally in suppository form, it is usually effective in 15 to 60 minutes. As an enema, a bowel movement usually occurs in 5 to 20 minutes. |
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When bisacodyl is administered orally, it is usually taken at breakfast. Oral administration is known to produce no action for more than eight hours and then to work suddenly and relatively quickly. This is especially true if more than 10 mg is taken at one time. Normally, the dosage is 5 or 10 mg, but up to 30 mg can be taken for complete cleansing of the bowel before a procedure. |
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When administered rectally in suppository form, it is usually effective in 15 to 60 minutes. For optimal use, if used as a suppository, it is recommended that bisacodyl be given after breakfast to synchronize with the ].<ref name="Wald2016"/> Two suppositories can be inserted at once if a very strong, purgative, enema-like result is needed. A few hours after the initial evacuation, there can be a secondary action which will continue as long as there is unexpelled bisacodyl present in the rectum. |
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==Mechanism of action== |
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Bisacodyl works by stimulating enteric nerves to cause colonic mass movements. It is also a contact laxative; it increases fluid and NaCl secretion. Action of bisacodyl on small intestine is negligible; stimulant laxatives mainly promote evacuation of the colon. |
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As a commercially prepared ], it is usually effective in 5 to 20 minutes.<ref name=Ullmann/> |
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==In popular culture== |
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'''Carter's Little Liver Pills''' predated the other available forms of bisacodyl and was a very popular and heavily advertised ] up into the 1960s, spawning a common saying (with variants) in the first half of the 20th Century: "He/She has more _________ than Carter has Little Liver Pills". |
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== See also == |
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The senator ], after winning re-election in 2000, is quoted as saying, "West Virginia has always had four friends, God Almighty, Sears Roebuck, Carter's Liver Pills and Robert C. Byrd." <ref>{{cite news| url=http://online.wsj.com/article/BT-CO-20100628-703075.html | work=Wall Street Journal | title=Robert Byrd, Longest-Serving US Senator, Dies at 92 | accessdate=2010-06-28 | date=2010-06-28}} {{Dead link|date=October 2010|bot=H3llBot}}</ref> |
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==References== |
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== References == |
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{{reflist}} |
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{{reflist}} |
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==External links== |
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== External links == |
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*{{dead link|date=July 2021|bot=medic}}{{cbignore|bot=medic}} |
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{{Laxatives}} |
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{{Laxatives}} |
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