Bismuth subgallate

Chemical compound
  • A07BB (WHO)
Legal statusLegal status
  • US: OTC
Identifiers
  • 2,7-dihydroxy-1,3,2-benzodioxabismole-5-carboxylic acid
CAS Number
  • 99-26-3 ☒N
PubChem CID
  • 16682999
DrugBank
  • DB13909 checkY
ChemSpider
  • 10607905 checkY
UNII
  • YIW503MI7V
ChEBI
  • CHEBI:31292 checkY
CompTox Dashboard (EPA)
  • DTXSID3046588 Edit this at Wikidata
ECHA InfoCard100.002.493 Edit this at WikidataChemical and physical dataFormulaC7H5BiO6Molar mass394.091 g·mol−13D model (JSmol)
  • Interactive image
Density1.1 g/cm3
  • OC(=O)c2cc1O[Bi](O)Oc1c(O)c2
InChI
  • InChI=1S/C7H6O5.Bi.H2O/c8-4-1-3(7(11)12)2-5(9)6(4)10;;/h1-2,8-10H,(H,11,12);;1H2/q;+3;/p-3 checkY
  • Key:JAONZGLTYYUPCT-UHFFFAOYSA-K checkY
 ☒NcheckY (what is this?)  (verify)

Bismuth subgallate, with a chemical formula C7H5BiO6, is commonly used to treat malodor by deodorizing flatulence and stools. In the United States, it (bismuth subgallate) is the active ingredient in Devrom (internal deodorant), an over-the-counter FDA-approved medicine. Also, it has been used to treat Helicobacter pylori infection and is used in wound therapy. As an internal deodorant, it is commonly used by individuals who have had gastrointestinal stoma surgery, bariatric surgery, fecal incontinence, and irritable bowel syndrome.[1]

Also, a double blind study in 1974 reported its effectiveness as a flatulence/stool deodorant in ileostomy patients.[2]

Adverse effects

It can cause darkening of the tongue and stools, which is temporary.[3]

In 1974, a reversible encephalopathy was noted and examined in four colon cancer patients taking bismuth subgallate after abdominoperineal resection.[4]

Bismuth subgallate is contraindicated in case of hypersensitivity to the substance, and should be used with caution in people with liver disease or kidney disease.[3] It is grouped in pregnancy category C[3] (risk not ruled out: Animal reproduction studies have shown an adverse effect on the fetus and there are no adequate and well-controlled studies in humans, but potential benefits may warrant use of the drug in pregnant women despite potential risks). During lactation, very little bismuth subgallate passes over to the child.[3]

Structure

The crystal structure of bismuth subgallate.[5]

Crystal structure determination of bismuth subgallate revealed it is a coordination polymer with the formula [Bi(C6H2(O)3COOH)(H2O)]n2nH2O.[5] The phenolate oxygen atoms of the gallate ligand chelate to bismuth cations and form chains. The material is nanoporous and the open-channels can be filled with small gas molecules such as carbon dioxide.[5]

See also

External links

  • American Cancer Society: Ileostomy Guide [1]
  • Cleveland Clinic-Having an Ileostomy– A Primer for New Ostomates [2] Archived 2012-06-16 at the Wayback Machine
  • The Ostomy Files:The Issue of Oral Medications and a Fecal Ostomy [3]
  • Devrom website [4]

References

  1. ^ Gorbach SL (September 1990). "Bismuth therapy in gastrointestinal diseases". Gastroenterology. 99 (3): 863–75. doi:10.1016/0016-5085(90)90983-8. PMID 2199292.
  2. ^ Sparberg M (March 1974). "Correspondence: Bismuth subgallate as an effective means for the control of ileostomy odor: a double blind study". Gastroenterology. 66 (3): 476. doi:10.1016/S0016-5085(74)80150-2. PMID 4813513.
  3. ^ a b c d "Bismuth subgallate (OTC) Devrom". Medscape. Retrieved 2015-12-02.
  4. ^ Burns R, Thomas DW, Barron VJ (February 1974). "Reversible encephalopathy possibly associated with bismuth subgallate ingestion". British Medical Journal. 1 (5901): 220–3. doi:10.1136/bmj.1.5901.220. PMC 1633100. PMID 4818163.
  5. ^ a b c Wang Y, Takki S, Cheung O, Xu H, Wan W, Öhrström L, Inge AK (July 2017). "Elucidation of the elusive structure and formula of the active pharmaceutical ingredient bismuth subgallate by continuous rotation electron diffraction". Chemical Communications. 53 (52): 7018–7021. doi:10.1039/C7CC03180G. PMID 28613325.
  • v
  • t
  • e
Bismuth(III)
Organobismuth(III)
  • C4H4BiH
Bismuth(V)
  • NaBiO3
  • Pb(BiO3)2
  • BiF5
  • Bi2O5
Organobismuth(V)
  • Bi(CH3)5
  • Bi(C6H5)5