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Revision as of 15:29, 10 November 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Script assisted update of identifiers for the Chem/Drugbox validation project (updated: 'UNII', 'CAS_number').← Previous edit Latest revision as of 18:29, 12 May 2024 edit undoInternetArchiveBot (talk | contribs)Bots, Pending changes reviewers5,384,787 edits Rescuing 2 sources and tagging 0 as dead.) #IABot (v2.0.9.5) (Whoop whoop pull up - 19463 
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{{Short description|Chemical compound}}
{{Drugbox {{Drugbox
| Verifiedfields = changed | Verifiedfields = changed
⚫ | verifiedrevid = 459979955
| Watchedfields = changed
⚫ | verifiedrevid = 250516617
| IUPAC_name = 2,7-dihydroxy-1,3,2-benzodioxabismole-5-carboxylic acid | IUPAC_name = 2,7-dihydroxy-1,3,2-benzodioxabismole-5-carboxylic acid
| image = Bismuth subgallate.svg | image = Bismuth subgallate.svg
| alt = Skeletal formula of bismuth subgallate

| image2 = Bismuth-subgallate-3D-balls.png
| alt2 = Ball-and-stick model of the bismuth subgallate molecule
<!--Clinical data--> <!--Clinical data-->
| tradename = | tradename =
Line 16: Line 18:
| legal_UK = <!-- GSL, P, POM, CD, or Class A, B, C --> | legal_UK = <!-- GSL, P, POM, CD, or Class A, B, C -->
| legal_US = OTC | legal_US = OTC
| routes_of_administration = | routes_of_administration = Oral

<!--Pharmacokinetic data--> <!--Pharmacokinetic data-->
| bioavailability = | bioavailability =
Line 24: Line 25:
| elimination_half-life = | elimination_half-life =
| excretion = | excretion =

<!--Identifiers--> <!--Identifiers-->
| CASNo_Ref = changed
| CAS_number_Ref = {{cascite|changed|??}} | CAS_number_Ref = {{cascite|changed|??}}
| CAS_number = <!-- blanked - oldvalue: 99-26-3 --> | CAS_number = 99-26-3
| ATC_prefix = A07 | ATC_prefix = A07
| ATC_suffix = BB | ATC_suffix = BB
| PubChem = 16682999 | PubChem = 16682999
| DrugBank_Ref = {{drugbankcite|correct|drugbank}} | DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = | DrugBank = DB13909
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 10607905 | ChemSpiderID = 10607905
| UNII_Ref = {{fdacite|changed|FDA}} | UNII_Ref = {{fdacite|changed|FDA}}
| UNII = <!-- blanked - oldvalue: YIW503MI7V --> | UNII = YIW503MI7V
| ChEBI_Ref = {{ebicite|changed|EBI}} | ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 31292 | ChEBI = 31292

<!--Chemical data--> <!--Chemical data-->
| chemical_formula = | chemical_formula =
| C=7 | H=5 | Bi=1 | O=6 | C=7 | H=5 | Bi=1 | O=6
| molecular_weight = 394.091 g·mol<sup>−1</sup>
| smiles = OC(=O)c2cc1O(O)Oc1c(O)c2 | smiles = OC(=O)c2cc1O(O)Oc1c(O)c2
⚫ | StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| InChI = 1/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/rC7H5BiO6/c9-4-1-3(7(10)11)2-5-6(4)14-8(12)13-5/h1-2,9,12H,(H,10,11)
| InChIKey = JAONZGLTYYUPCT-VWHLZXKRAW
⚫ | StdInChI_Ref = {{stdinchicite|changed|chemspider}}
| StdInChI = 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 | StdInChI = 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
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = JAONZGLTYYUPCT-UHFFFAOYSA-K | StdInChIKey = JAONZGLTYYUPCT-UHFFFAOYSA-K
| density = 1.1 | density = 1.1
}} }}


'''Bismuth subgallate''', with a chemical formula C<sub>7</sub>H<sub>5</sub>BiO<sub>6</sub>, is the active ingredient in '''Devrom''' (internal deodorant), an over-the-counter FDA-approved medicine commonly used to treat malodor by deodorizing ] and ]. Also, it has been used to treat '']'' infection and is used in wound therapy. As an internal deodorant, it is commonly used by individuals who have had ostomy surgery, bariatric surgery, fecal incontinence, and irritable bowel syndrome.<ref>{{cite journal '''Bismuth subgallate''', with a chemical formula C<sub>7</sub>H<sub>5</sub>BiO<sub>6</sub>, is commonly used to treat malodor by deodorizing ] and ]. 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 '']'' infection and is used in wound therapy. As an internal deodorant, it is commonly used by individuals who have had ] surgery, bariatric surgery, fecal incontinence, and irritable bowel syndrome.<ref>{{cite journal | vauthors = Gorbach SL | title = Bismuth therapy in gastrointestinal diseases | journal = Gastroenterology | volume = 99 | issue = 3 | pages = 863–75 | date = September 1990 | pmid = 2199292 | doi = 10.1016/0016-5085(90)90983-8 | author-link = Sherwood Gorbach }}</ref>
| title = Bismuth therapy in gastrointestinal diseases
| author = Gorbach S. L.
| journal = Gastroenterology
| year = 1990
| volume = 99
| issue = 3
| pages = 863–75
| pmid = 2199292
}}</ref>


Also, a double blind study in 1974 reported its effectiveness as a flatulence/stool deodorant in ileostomy patients.<ref>{{cite journal | vauthors = Sparberg M | title = Correspondence: Bismuth subgallate as an effective means for the control of ileostomy odor: a double blind study | journal = Gastroenterology | volume = 66 | issue = 3 | pages = 476 | date = March 1974 | pmid = 4813513 | doi = 10.1016/S0016-5085(74)80150-2 | doi-access = free }}</ref>
It can cause darkening of the tongue and stools, which is temporary and harmless.
A reversible ] was noted and examined in a few subjects taking bismuth subgallate.<ref>{{cite journal
| title = Reversible encephalopathy possibly associated with bismuth subgallate ingestion
| author = Burns R., Thomas D. W., Barron V. J.
| journal = British Medical Journal
| year = 1974
| volume = 9
| issue = 1
| pages = 220–3
| pmid = 4818163
| pmc = 1633100
}}</ref>


==Safety== ==Adverse effects==
It can cause darkening of the tongue and stools, which is temporary.<ref name=medscape>{{cite web|title=Bismuth subgallate (OTC) Devrom|url=http://reference.medscape.com/drug/bismuth-subgallate-999413|website=]|access-date=2015-12-02}}</ref>
It is quite nontoxic, but it may cause minor irritation.


In 1974, a reversible ] was noted and examined in four colon cancer patients taking bismuth subgallate after ].<ref>{{cite journal | vauthors = Burns R, Thomas DW, Barron VJ | title = Reversible encephalopathy possibly associated with bismuth subgallate ingestion | journal = British Medical Journal | volume = 1 | issue = 5901 | pages = 220–3 | date = February 1974 | pmid = 4818163 | pmc = 1633100 | doi = 10.1136/bmj.1.5901.220 }}</ref>
⚫ ==See also==

Bismuth subgallate is contraindicated in case of ] to the substance, and should be used with caution in people with ] or ].<ref name=medscape/> It is grouped in ]<ref name=medscape/> (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 ], very little bismuth subgallate passes over to the child.<ref name=medscape/>

== Structure ==
]

Crystal structure determination of bismuth subgallate revealed it is a ] with the formula <sub>n</sub>2nH<sub>2</sub>O.<ref name="BSGstructure">{{cite journal | vauthors = Wang Y, Takki S, Cheung O, Xu H, Wan W, Öhrström L, Inge AK | title = Elucidation of the elusive structure and formula of the active pharmaceutical ingredient bismuth subgallate by continuous rotation electron diffraction | journal = Chemical Communications | volume = 53 | issue = 52 | pages = 7018–7021 | date = July 2017 | pmid = 28613325 | doi = 10.1039/C7CC03180G | doi-access = free }}</ref> 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.<ref name = "BSGstructure" />
{{-}}

⚫ == See also ==
* ] * ]
* ] * ]


==External links== == External links ==
* American Cancer Society: Ileostomy Guide * American Cancer Society: Ileostomy Guide {{Webarchive|url=https://web.archive.org/web/20070929091245/http://www.cancer.org/docroot/CRI/content/CRI_2_6x_Ileostomy.asp |date=2007-09-29 }}
* Cleveland Clinic-Having an Ileostomy– A Primer for New Ostomates * Cleveland Clinic-Having an Ileostomy– A Primer for New Ostomates {{Webarchive|url=https://web.archive.org/web/20120616223912/http://my.clevelandclinic.org/Documents/Digestive_Disease/HavingIleostomy.pdf |date=2012-06-16 }}
⚫ * The Ostomy Files:The Issue of Oral Medications and a Fecal Ostomy {{Webarchive|url=https://web.archive.org/web/20120206053300/http://www.o-wm.com/article/3825 |date=2012-02-06 }}
* United Ostomy Association of America-Ileostomy Guide
⚫ * The Ostomy Files:The Issue of Oral Medications and a Fecal Ostomy
* Devrom website * Devrom website


==References== == References ==
{{reflist}} {{reflist}}


{{Bismuth compounds}}
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