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Identification
Name Bismuth Subsalicylate
Accession Number DB01294 (DB01402)
Type small molecule
Groups approved
Description

Bismuth subsalicylate is the active ingredient in the popular medication Pepto-Bismol that is used to treat nausea, heartburn, indigestion, upset stomach, diarrhea, and other temporary discomforts of the stomach and gastrointestinal tract. It is also the main ingredient of Kaopectate. It displays anti-inflammatory action (due to salicylic acid) and also acts as an antacid and mild antibiotic.
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
Bismuth
Bismuth oxide salicylate
Bismuth oxysalicylate
Bismuth(III) subsalicylate
Bismuthi subsalicylas
Bismutum subsalicylicum
Salts Not Available
Brand names
Name Company
Bismatrol
Bismed
Bismuth caplets
Bismuth chewables
Extra strength bismuth
Extra-strength bismuth
Maalox multi action
Pepto-bismol
PMS-bismuth subsalicylate
Spiromak forte
Stabisol
Vismut
Wismutsubsalicylat
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Brand mixtures
Brand Name Ingredients
Bismuth + Antacid [Chewable Tablets] Bismuth Subsalicylate + Calcium Carbonate
Pepto-Bismol Chewables Bismuth Subsalicylate + Calcium Carbonate
Watkins Settelz Bismuth Subsalicylate + Pectin + Phenyl Salicylate
Categories
  • Antidiarrheals
CAS number 14882-18-9
Weight Average: 362.0926
Monoisotopic: 361.999166889
Chemical Formula C7H5BiO4
InChI Key InChIKey=ZREIPSZUJIFJNP-UHFFFAOYSA-K
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
Plain Text
IUPAC Name
2-hydroxy-2H,4H-benzo[d]1,3-dioxa-2-bismacyclohexan-4-one
SMILES
O[Bi]1OC(=O)C2=CC=CC=C2O1
Plain Text
Mass Spec Not Available
Taxonomy
Kingdom Organic
Classes
  • Benzoates
  • Salicylates and Derivatives
Substructures
  • Benzyl Alcohols and Derivatives
  • Acetates
  • Benzoates
  • Salicylates and Derivatives
  • Phenols and Derivatives
  • Benzene and Derivatives
  • Heterocyclic compounds
  • Aromatic compounds
  • Benzoyl Derivatives
  • Phenyl Esters
Pharmacology
Indication Used to treat nausea, heartburn, indigestion, upset stomach, diarrhea, and other temporary discomforts of the stomach and gastrointestinal tract.
Pharmacodynamics Bismuth subsalicylate displays anti-inflammatory action (due to salicylic acid) and also acts as an antacid and mild antibiotic. It can also cause a black tongue and black stools in some users of the drug, when it combines with trace amounts of sulfur in their saliva and gastrointestinal tract. This discoloration is temporary and harmless.
Mechanism of action As an antidiarrheal, the exact mechanism has not been determined. Bismuth subsalicylate may exert its antidiarrheal action not only by stimulating absorption of fluid and electrolytes across the intestinal wall (antisecretory action) but also, when hydrolyzed to salicylic acid, by inhibiting synthesis of a prostaglandin responsible for intestinal inflammation and hypermotility. In addition, bismuth subsalicylate binds toxins produced by Escherichia coli. Both bismuth subsalicylate and the intestinal reaction products, bismuth oxychloride and bismuth hydroxide, are believed to have bactericidal action. As an antacid, bismuth has weak antacid properties.
Absorption Following oral administration, absorption of the salicylate component from the small intestine is generally rapid and complete (>90%).
Volume of distribution Not Available
Protein binding Not Available
Metabolism
Based on in vitro dissociation data and in vivo animal data, bismuth subsalicylate is believed to be largely hydrolyzed in the stomach to bismuth oxychloride and salicylic acid. In the small intestine, nondissociated bismuth subsalicylate reacts with other anions (bicarbonate and phosphate) to form insoluble bismuth salts. In the colon, nondissociated bismuth subsalicylate and other bismuth salts react with hydrogen sulfide to produce bismuth sulfide, a highly insoluble black salt responsible for the darkening of the stools.
Route of elimination Not Available
Half life Not Available
Clearance Not Available
Toxicity Not Available
Affected organisms Not Available
Pathways Not Available
Pharmacoeconomics
Manufacturers Not Available
Packagers
Dosage forms
Form Route Strength
Dressing Topical
Liquid Oral
Liquid Sublingual
Solution / drops Oral
Suppository Rectal
Suspension Oral
Suspension Oral
Tablet Oral
Prices
Unit description Cost Unit
Kaopectate 262 mg caplet 0.37 USD caplet
Gas-x with maalox chew tablet 0.25 USD tablet
Bismuth subsalicylate powdr 0.17 USD g
Jr maalox plus antigas tablet chew 0.17 USD tablet
Calcium carb 500 mg tablet chew 0.14 USD tablet
Pepto-bismol caplet 0.14 USD caplet
Soothe caplets 0.12 USD caplet
Bismatrol 262 mg tablet 0.09 USD tablet
Maalox advanced tablet chew 0.09 USD tablet
Maalox quick dissolve tablet 0.09 USD tablet
Maalox max quick dissolve tablet 0.06 USD tablet
Stomach relief tablet 0.06 USD tablet
Magnesium-aluminum suspension 0.03 USD ml
Bismuth 262 mg/15ml susp 0.02 USD ml
Maalox max strength multi symp 0.02 USD ml
Maalox maximum strength susp 0.02 USD ml
Pepto-bismol max str susp 0.02 USD ml
Pub calcium carb 1000 mg tablet 0.02 USD tablet
Maalox plus x-strength susp 0.01 USD ml
Maalox total relief (bismuth) 0.01 USD ml
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DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents Not Available
Properties
State solid
Experimental Properties Not Available
Predicted Properties
Property Value Source
water solubility 5.97e+01 g/l ALOGPS
logP 0.37 ALOGPS
logP 1.11 ChemAxon
logS -0.78 ALOGPS
pKa (strongest acidic) 14.3 ChemAxon
pKa (strongest basic) -3.1 ChemAxon
physiological charge 0 ChemAxon
hydrogen acceptor count 3 ChemAxon
hydrogen donor count 1 ChemAxon
polar surface area 55.76 ChemAxon
rotatable bond count 0 ChemAxon
refractivity 35.72 ChemAxon
polarizability 15.67 ChemAxon
References
Synthesis Reference Not Available
General Reference
  1. Goldenberg MM, Honkomp LJ, Burrous SE, Castellion AW: Protective effect of Pepto-Bismol liquid on the gastric mucosa of rats. Gastroenterology. 1975 Sep;69(3):636-40. Pubmed
External Links
Resource Link
KEGG Drug D00728 Link_out
KEGG Compound C07870 Link_out
PubChem Compound 16682734 Link_out
PubChem Substance 46507128 Link_out
ChemSpider 17615374 Link_out
ChEBI 261649 Link_out
ChEMBL 261649 Link_out
PharmGKB PA164774805 Link_out
Drug Product Database 2262363 Link_out
RxList http://www.rxlist.com/cgi/generic/pylera.htm Link_out
Drugs.com http://www.drugs.com/cdi/bismuth-subsalicylate.html Link_out
Wikipedia http://en.wikipedia.org/wiki/Bismuth_subsalicylate Link_out
ATC Codes
  • A02BX05
  • A02BA07
  • A02BX12
AHFS Codes
  • 84:92.00
  • 56:04.00
  • 52:92.00
  • 56:08.00
  • 92:02.00*
PDB Entries Not Available
FDA label Not Available
MSDS show (73.6 KB)
Interactions
Drug Interactions
Drug Interaction
Acetazolamide The salicylate, bismuth subsalicylate, at high dose increases the effect of the carbonic anhydrase inhibitor, acetazolamide.
Amprenavir The antiacid decreases the absorption of amprenavir
Atazanavir This gastric pH modifier decreases the levels/effects of atazanavir
Betamethasone The corticosteroid, betamethasone, may decrease the effect of the salicylate, bismuth subsalicylate.
Fludrocortisone The corticosteroid, fludrocortisone, may decrease the effect of the salicylate, bismuth subsalicylate.
Gliclazide The salicylate, bismuth subsalicylate, increases the effect of the sulfonylurea, gliclazide.
Glyburide The salicylate, bismuth subsalicylate, increases the effect of the sulfonylurea, glibenclamide.
Hydrocortisone The corticosteroid, hydrocortisone, may decrease the effect of the salicylate, bismuth subsalicylate.
Methazolamide The salicylate, bismuth subsalicylate, at high dose increases the effect of the carbonic anhydrase inhibitor, methazolamide.
Methotrexate The salicylate, bismuth subsalicylate, increases the effect and toxicity of methotrexate.
Minocycline Formation of non-absorbable complexes
Prednisolone The corticosteroid, prednisolone, may decrease the effect of the salicylate, bismuth subsalicylate.
Prednisone The corticosteroid, prednisone, may decrease the effect of the salicylate, bismuth subsalicylate.
Probenecid The salicylate, bismuth subsalicylate, decreases the uricosuric effect of probenecid.
Tetracycline Formation of non-absorbable complexes
Triamcinolone The corticosteroid, triamcinolone, may decrease the effect of the salicylate, bismuth subsalicylate.
Food Interactions Not Available
Carriers

1. Serum albumin

Actions: binder

Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloidal osmotic pressure of blood

UniProt ID: P02768 Link_out
Gene: ALB Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Sun H, Li H, Mason AB, Woodworth RC, Sadler PJ: Competitive binding of bismuth to transferrin and albumin in aqueous solution and in blood plasma. J Biol Chem. 2001 Mar 23;276(12):8829-35. Epub 2000 Dec 7. Pubmed
  2. Sun H, Szeto KY: Binding of bismuth to serum proteins: implication for targets of Bi(III) in blood plasma. J Inorg Biochem. 2003 Feb 1;94(1-2):114-20. Pubmed
  3. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed

2. Serotransferrin

Transferrins are iron binding transport proteins which can bind two Fe(3+) ions in association with the binding of an anion, usually bicarbonate. It is responsible for the transport of iron from sites of absorption and heme degradation to those of storage and utilization. Serum transferrin may also have a further role in stimulating cell proliferation

UniProt ID: P02787 Link_out
Gene: TF Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Sun H, Li H, Mason AB, Woodworth RC, Sadler PJ: Competitive binding of bismuth to transferrin and albumin in aqueous solution and in blood plasma. J Biol Chem. 2001 Mar 23;276(12):8829-35. Epub 2000 Dec 7. Pubmed
  2. Sun H, Szeto KY: Binding of bismuth to serum proteins: implication for targets of Bi(III) in blood plasma. J Inorg Biochem. 2003 Feb 1;94(1-2):114-20. Pubmed
  3. Zhang M, Gumerov DR, Kaltashov IA, Mason AB: Indirect detection of protein-metal binding: interaction of serum transferrin with In3+ and Bi3+. J Am Soc Mass Spectrom. 2004 Nov;15(11):1658-64. Pubmed
  4. Miquel G, Nekaa T, Kahn PH, Hemadi M, El Hage Chahine JM: Mechanism of formation of the complex between transferrin and bismuth, and interaction with transferrin receptor 1. Biochemistry. 2004 Nov 23;43(46):14722-31. Pubmed
  5. Ge R, Sun H: Bioinorganic chemistry of bismuth and antimony: target sites of metallodrugs. Acc Chem Res. 2007 Apr;40(4):267-74. Epub 2007 Mar 2. Pubmed
Comments
Drug created on June 30, 2007 08:17 / Updated on February 08, 2013 16:20