Misplaced Pages

Bismuth subgallate: Difference between revisions

Article snapshot taken from Wikipedia with creative commons attribution-sharealike license. Give it a read and then ask your questions in the chat. We can research this topic together.
Browse history interactively← Previous editContent deleted Content addedVisualWikitext
Revision as of 03:15, 24 October 2011 editCheMoBot (talk | contribs)Bots141,565 edits Updating {{drugbox}} (changes to verified and watched fields - updated 'ChEMBL_Ref', 'KEGG_Ref', 'CAS_number_Ref') per Chem/Drugbox validation (report errors or bugs)← Previous edit Latest revision as of 18:29, 12 May 2024 edit undoInternetArchiveBot (talk | contribs)Bots, Pending changes reviewers5,386,254 edits Rescuing 2 sources and tagging 0 as dead.) #IABot (v2.0.9.5) (Whoop whoop pull up - 19463 
(42 intermediate revisions by 29 users not shown)
Line 1: Line 1:
{{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 = 99-26-3 | CAS_number = 99-26-3
Line 33: Line 32:
| 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 = 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}}
⚫ ]
⚫ ]


⚫ ]
]
⚫ ]
]
]

Latest revision as of 18:29, 12 May 2024

Chemical compound Pharmaceutical compound
Bismuth subgallate
Skeletal formula of bismuth subgallate
Ball-and-stick model of the bismuth subgallate molecule
Clinical data
AHFS/Drugs.comInternational Drug Names
Routes of
administration		Oral
ATC code
Legal status
Legal status
Identifiers
IUPAC name
  • 2,7-dihydroxy-1,3,2-benzodioxabismole-5-carboxylic acid
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
ChEBI
CompTox Dashboard (EPA)
ECHA InfoCard100.002.493 Edit this at Wikidata
Chemical and physical data
FormulaC7H5BiO6
Molar mass394.091 g·mol
3D model (JSmol)
Density1.1 g/cm
SMILES
  • OC(=O)c2cc1O(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
  • Key:JAONZGLTYYUPCT-UHFFFAOYSA-K
  (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.

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

Adverse effects

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

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

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. It is grouped in pregnancy category C (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.

Structure

The crystal structure of bismuth subgallate.

Crystal structure determination of bismuth subgallate revealed it is a coordination polymer with the formula n2nH2O. 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.

See also

External links

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. ^ "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. ^ 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.
Bismuth compounds
Bismuth(III)
Organobismuth(III)
Bismuth(V)
Organobismuth(V)
Categories: