Bismuth subgallate

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]

Bismuth subgallate

Clinical data
AHFS/Drugs.com	International Drug Names
Routes of administration	Oral
ATC code	A07BB (WHO)
Legal status
Legal status	US: OTC
Identifiers
IUPAC name 2,7-dihydroxy-1,3,2-benzodioxabismole-5-carboxylic acid
CAS Number	99-26-3 N
PubChem CID	16682999
DrugBank	DB13909 Y
ChemSpider	10607905 Y
UNII	YIW503MI7V
ChEBI	CHEBI:31292 Y
CompTox Dashboard (EPA)	DTXSID3046588
ECHA InfoCard	100.002.493
Chemical and physical data
Formula	C7H5BiO6
Molar mass	394.091 g·mol−1
3D model (JSmol)	Interactive image
Density	1.1 g/cm3
SMILES 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 Y Key:JAONZGLTYYUPCT-UHFFFAOYSA-K Y
NY (what is this?)  (verify)

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

• Bismuth
• Gallic acid

External links

• American Cancer Society: Ileostomy Guide Archived 2007-09-29 at the Wayback Machine
• Cleveland Clinic-Having an Ileostomy– A Primer for New Ostomates Archived 2012-06-16 at the Wayback Machine
• The Ostomy Files:The Issue of Oral Medications and a Fecal Ostomy Archived 2012-02-06 at the Wayback Machine
• Devrom website