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Bismuth subsalicylate

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Revision as of 03:26, 13 February 2012 by 128.239.178.8 (talk) (changed formula of bismuth salicylate slightly to have correct number of hydrogens directly bonded to phenyl ring)(diff) ← Previous revision | Latest revision (diff) | Newer revision → (diff) Pharmaceutical compound
Bismuth Subsalicylate
Clinical data
Trade namesPepto-bismol
MedlinePlusa607040
Routes of
administration		Oral
ATC code
  • none
Identifiers
IUPAC name
  • 2-hydroxy-2H,4H-benzo1,3-dioxa-2-bismacyclohexan-4-one
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.035.397 Edit this at Wikidata
Chemical and physical data
FormulaC7H5BiO4
Molar mass362.093 g/mol g·mol
3D model (JSmol)
SMILES
  • O1OC(=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, with a nominal chemical formula of C7H5BiO4, It is a colloidal substance obtained by hydrolysis of bismuth salicylate (Bi{C6H4(OH)CO2}3). The actual structure is unknown and the formulation is only approximate. Recent evidence indicates that it is composed of a bismuth oxide core structure with salicylate ions attached to the surface. A model structure has recently been published having the composition Bi38O44{C6H3(OH)CO2}26. It is a drug used to treat temporary discomforts of the stomach and gastrointestinal tract, such as diarrhea, heartburn and nausea. Commonly known as pink bismuth, it is the active ingredient in popular medications such as Pepto-Bismol and, since 2003, in Kaopectate.

Pharmacology

As a derivative of salicylic acid, bismuth salicylate displays anti-inflammatory action and also acts as an antacid.

Mechanism of action

Bismuth subsalicylate is used as an antidiarrheal and to treat some other gastro-intestinal diseases (oligodynamic effect).
The means by which this appears to work is still not well documented. It is thought to be some combination of:

  • Retarding the expulsion of fluids into the digestive system by irritated tissues, by "coating" them.
  • Reducing inflammation/irritation of stomach and intestinal lining
  • Killing some bacteria that cause diarrhea

Adverse effects and contraindications

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 gastrointestinal tract to form bismuth sulfide. This discoloration is temporary and harmless.

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 (such as Pepto-Bismol) because small amounts of the medication are excreted in breast milk and pose a theoretical risk of Reye's syndrome to nursing children.

Decomposition

Bismuth slag from decomposition of Pepto-Bismol

Bismuth subsalicylate is the only active ingredient in an over the counter medication that will leave a shiny metal oxide slag behind after being completely burnt with a blow torch.

References

  1. Merck Index, 11th Edition, 1299
  2. "I noticed that Pepto-Bismol sometimes darkens the tongue/stool..." Pepto-Bismol FAQ. Pepto-Bismol.
  3. "Bismuth Subsalicylate". MedlinePlus. National Institutes of Health.
  4. Sainsbury, S. J. (1991). "Fatal salicylate toxicity from bismuth subsalicylate". The Western Journal of Medicine. 155 (6): 637–639. PMC 1003120. PMID 1812638. {{cite journal}}: Unknown parameter |month= ignored (help)
  5. Vernace, M. A.; Bellucci, A. G; Wilkes B. M. (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. {{cite journal}}: Unknown parameter |month= ignored (help)CS1 maint: multiple names: authors list (link)
  6. Aspirin or Salicylate-Containing Medications, reyessyndrome.org
  7. CDC warning about breastfeeding while taking bismuth subsalicylate compounds
  8. Wesołowski, M. (1982). "Thermal decomposition of pharmaceutical preparations containing inorganic components". Microchimica Acta. 77 (5–6). Vienna: 451–464. doi:10.1007/BF01197125.
Salicylates
Bismuth compounds
Bismuth(III)
Organobismuth(III)
Bismuth(V)
Organobismuth(V)
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