Bismuth subsalicylate - wikipedia Bismuth subsalicylate Bismuth subsalicylate Clinical data Trade names Pepto - Bismol AHFS / Drugs.com Multum Consumer Information MedlinePlus a607040 Routes of administration Oral ATC code none Legal status Legal status UK : P ( Pharmacy medicines ) US : OTC Identifiers IUPAC name 2 - Hydroxy - 2H, 4H - benzo ( d ) 1, 3 - dioxa - 2 - bismacyclohexan - 4 - one CAS Number 14882 - 18 - 9 PubChem CID 16682734 DrugBank DB01294 ChemSpider 17215772 UNII 62TEY51RR1 KEGG D00728 ChEBI CHEBI : 261649 ChEMBL CHEMBL1120 ECHA InfoCard 100.035. 397 Chemical and physical data Formula C H Bi O Molar mass 362.093 g / mol 3D model ( JSmol ) Interactive image SMILES O ( Bi ) 1OC ( = O ) c2ccccc2O1 InChI InChI = 1S / C7H6O3. Bi. H2O / c8 - 6 - 4 - 2 - 1 - 3 - 5 ( 6 ) 7 ( 9 ) 10 ; ; / h1 - 4, 8H, ( H, 9, 10 ) ; ; 1H2 / q ; + 3 ; / p - 3 Key : ZREIPSZUJIFJNP - UHFFFAOYSA - K ( what is this ? ) ( verify ) Bismuth subsalicylate, sold under the brand name Pepto - Bismol, is an antacid medication used to treat temporary discomforts of the stomach and gastrointestinal tract, such as diarrhea, indigestion, heartburn and nausea. It is also commonly known as pink bismuth. Bismuth subsalicylate has the empirical chemical formula of C H BiO, and it is a colloidal substance obtained by hydrolysis of bismuth salicylate ( Bi ( C H ( OH ) CO ) ). The actual structure is unknown and the formulation is only approximate. Contents 1 Medical uses 2 Adverse effects 3 Mechanism of action 4 Decomposition 5 History 6 References 7 External links Medical uses A generic version of Pepto - Bismol, back view As a derivative of salicylic acid, bismuth subsalicylate displays anti-inflammatory and bactericidal action. It also acts as an antacid. Adverse effects There are some adverse effects. It can cause a black tongue and black stools in some users of the drug, when it combines with trace amounts of sulfur in saliva and the colon to form bismuth sulfide. Bismuth sulfide is a highly insoluble black salt, and the discoloration seen is temporary and harmless. Long - term use ( greater than 6 weeks ) may lead to accumulation and toxicity. Some of the risks of salicylism can apply to the use of bismuth subsalicylate. Children should not take medication with bismuth subsalicylate while recovering from influenza or chicken pox, as epidemiologic evidence points to an association between the use of salicylate - containing medications during certain viral infections and the onset of Reye 's syndrome. For the same reason, it is typically recommended that nursing mothers not use medication containing bismuth subsalicylate because small amounts of the medication are excreted in human breast milk, and these pose a theoretical risk of Reye 's syndrome to nursing children. Salicylates are very toxic to cats, and thus bismuth subsalicylate should not be administered to cats. Mechanism of action Bismuth subsalicylate is used as an antacid and antidiarrheal, and to treat some other gastrointestinal symptoms, such as nausea. The means by which this occurs is still not well documented. It is thought to be some combination of the following : Retarding the expulsion of fluids into the digestive system by irritated tissues, by `` coating '' them. Stimulation of absorption of fluids and electrolytes by the intestinal wall ( antisecretory action ) As a salicylate, reducing inflammation / irritation of stomach and intestinal lining through inhibition of prostaglandin G / H synthase 1 / 2 Reduction in hypermotility of the stomach Binding of toxins produced by Escherichia coli Bactericidal action of a number of its subcomponents, including salicylic acid Bactericidal action via a so - called oligodynamic effect in which small amounts of heavy metals such as bismuth are toxic for a number of microbes Weak antacid properties In vitro and in vivo data have shown that bismuth subsalicylate hydrolyzes in the gut to bismuth oxychloride and salicylic acid and less commonly bismuth hydroxide. In the stomach, this is likely an acid - catalyzed hydrolysis. The salicylic acid is absorbed and therapeutical concentrations of salicylic acid can be found in blood after bismuth subsalicylate administration. Bismuth oxychloride and bismuth hydroxide are both believed to have bactericidal effects, as is salicylic acid for enterotoxigenic E. coli a common cause of `` traveler 's diarrhea. '' Organobismuth compounds have historically been used in growth media for selective isolation of microorganisms. Such salts have been shown to inhibit proliferation of Helicobacter pylori, other enteric bacteria, and some fungi. Decomposition Bismuth slag from decomposition of Pepto - Bismol Bismuth subsalicylate is the only active ingredient in an over-the - counter drug that can leave a shiny metal oxide slag behind after being completely burnt with a blow torch. History 1957 Life Magazine ad for the product While bismuth salts were in use in Europe by the late 1700s, the combination of bismuth subsalicylate and zinc salts for astringency with salol ( phenyl salicilate ) appears to have begun in the US in the early 1900s as a remedy for life - threatening diarrhea in infants with cholera. At first sold directly to physicians, it was first marketed as Bismosal in 1918. Pepto - Bismol began being sold in 1900 or 1901 by a doctor in New York. It was originally sold as a remedy for infant diarrhea by Norwich Pharmacal Company under the name `` Bismosal : Mixture Cholera Infantum ''. It was renamed Pepto - Bismol in 1919. Norwich Eaton Pharmaceuticals was acquired by Procter and Gamble in 1982. As of 1946, Canadian advertisements placed by Norwich show the product as Pepto - Besmol both in graphic and text. Pepto - Bismol is an over-the - counter drug currently produced by the Procter & Gamble company in the United States, Canada and the United Kingdom. Pepto - Bismol is made in chewable tablets and swallowable caplets, but it is best known for its original formula, which is a thick liquid. This original formula is a medium pink in color, with a strong wintergreen or cherry flavor. References Jump up ^ Merck Index, 11th Edition, 1299 Jump up ^ Madisch, A. ; Morgner, A. ; Stolte, M. ; Miehlke, S. ( Dec 2008 ). `` Investigational treatment options in microscopic colitis ''. Expert Opin Investig Drugs. 17 ( 12 ) : 1829 -- 37. doi : 10.1517 / 13543780802514500. PMID 19012499. Jump up ^ DuPont, HL. ( Apr 2005 ). `` Travelers ' diarrhea : antimicrobial therapy and chemoprevention ''. Nat Clin Pract Gastroenterol Hepatol. 2 ( 4 ) : 191 -- 8 ; quiz 1 p following 198. doi : 10.1038 / ncpgasthep0142. PMID 16265184. Jump up ^ `` Why does Pepto - Bismol sometimes darken the tongue / stool and how long does it last ? ''. Pepto - Bismol FAQ. Pepto - Bismol. Jump up ^ Gorbach, SL. ( Sep 1990 ). `` Bismuth therapy in gastrointestinal diseases ''. Gastroenterology. 99 ( 3 ) : 863 -- 75. PMID 2199292. Jump up ^ `` Bismuth Subsalicylate ''. MedlinePlus. National Institutes of Health. Jump up ^ Sainsbury, S.J. ( December 1991 ). `` Fatal salicylate toxicity from bismuth subsalicylate ''. The Western Journal of Medicine. 155 ( 6 ) : 637 -- 639. PMC 1003120. PMID 1812638. Jump up ^ Vernace, M.A. ; Bellucci, A. G ; Wilkes B.M. ( September 1994 ). `` Chronic salicylate toxicity due to consumption of over-the - counter bismuth subsalicylate ''. The American Journal of Medicine. 97 ( 3 ) : 308 -- 309. doi : 10.1016 / 0002 - 9343 ( 94 ) 90017 - 5. PMID 8092182. Jump up ^ Aspirin or Salicylate - Containing Medications, reyessyndrome.org Jump up ^ `` Food - borne and Waterborne Illness - Breastfeeding -- CDC ''. cdc.gov. Jump up ^ Cat Owner 's Home Veterinary Handbook, Carlson and Giffin, page 390 Jump up ^ Bismuth subsalicylate, DrugBank ^ Jump up to : Sox, TE ; Olson, CA ( December 1989 ). `` Binding and killing of bacteria by bismuth subsalicylate ''. Antimicrob. Agents Chemother. 33 ( 12 ) : 207582. doi : 10.1128 / AAC. 33.12. 2075. PMC 172824. PMID 2694949. Jump up ^ Dodge, A.G. ; Wackett, L.P. ( 2005 ). `` Metabolism of Bismuth Subsalicylate and Intracellular Accumulation of Bismuth by Fusarium sp. Strain BI ''. Applied and Environmental Microbiology. 71 ( 2 ) : 87682. doi : 10.1128 / AEM. 71.2. 876 - 882.2005. PMC 546758. PMID 15691943. Jump up ^ Wesołowski, M. ( 1982 ). `` Thermal decomposition of pharmaceutical preparations containing inorganic components ''. Microchimica Acta. Vienna. 77 ( 5 -- 6 ) : 451 -- 464. doi : 10.1007 / BF01197125. ^ Jump up to : Ws. Bierer, Dr. Douglas ( January -- February 1990 ). `` Bismuth Subsalicylate : History, Chemistry, and Safety ''. Reviews of Infectious Diseases. 12 ( Supplement 1 ) : S3. doi : 10.1093 / clinids / 12. supplement_1. s3. Retrieved 21 December 2016. Jump up ^ Menegas, M.D., Jeff. `` How was Pepto Bismol invented ? ''. Quora. Quora, Inc. Retrieved 21 December 2016. Jump up ^ Davis, Dyer ; et al. ( May 1, 2004 ). Rising Tide : Lessons from 165 Years of Brand Building at Procter and Gamble. Harvard Business Press. p. 424. Retrieved 2013 - 05 - 07. Jump up ^ `` '' Simple Diarrhoea '' ad ``. Toronto Daily Star. 16 August 1946. p. 33. Jump up ^ The trademark was extended to cover the tablets in 1973. Registration No. 0972198, November 6, 1973. http://tess2.uspto.gov/bin/showfield?f=doc&state=b8i462.2.2. Jump up ^ The capsules were introduced in 1983. Registration No. 1269605, March 13, 1984 ; cancelled July 16, 1990. http://tess2.uspto.gov/bin/showfield?f=doc&state=b8i462.2.1. External links Wikimedia Commons has media related to Salicylate salts. Andrews, Philip C. ; Deacon, Glen B. ; Forsyth, Craig M. ; Junk, Peter C. ; Kumar, Ish ; Maguire, Melissa ( 2006 ). `` Towards a Structural Understanding of the Anti-Ulcer and Anti-Gastritis Drug Bismuth Subsalicylate ''. Angewandte Chemie International Edition. 45 ( 34 ) : 5638 -- 5642. doi : 10.1002 / anie. 200600469. PMID 16865763. Salicylates Salicylic acid Aspirin Aloxiprin Methyl salicylate Magnesium salicylate Ethyl salicylate Bismuth subsalicylate Sodium salicylate Salicylamide Salicin Benorilate Salsalate Ethenzamide Diflunisal Trolamine salicylate Homosalate Salicylmethylecgonine Octyl salicylate Aluminon Benzyl salicylate Copper aspirinate Potassium salicylate Bismuth compounds Bismuth ( III ) BiBr BiCl Bi Ge O BiOCl Bi Se Bi O ( CO ) Bi Te BiF BiI Bi O Bi ( OH ) Bi S BiH BiOHOCOC H O Organobismuth ( III ) C H BiH Bismuth ( V ) NaBiO BiF Bi SiO Bi O Retrieved from `` https://en.wikipedia.org/w/index.php?title=Bismuth_subsalicylate&oldid=805042477 '' Categories : Drugs not assigned an ATC code Antidiarrhoeals Drugs acting on the gastrointestinal system and metabolism Salicylates Bismuth compounds Hidden categories : Template : drugs.com link with non-standard subpage Articles with changed KEGG identifier ECHA InfoCard ID from Wikidata Drugboxes which contain changes to verified fields Drugboxes which contain changes to watched fields Wikipedia articles needing clarification from May 2017 All articles with unsourced statements Articles with unsourced statements from September 2017 Commons category with local link different than on Wikidata Talk Contents About Wikipedia تۆرکجه Deutsch Español Français Italiano עברית Polski Русский Српски / srpski Srpskohrvatski / српскохрватски தமிழ் 中文 Edit links This page was last edited on 12 October 2017, at 18 : 03. 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Question: where does the name pepto bismol come from
Answer: Bismosal