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Identification
NameBismuth Subsalicylate
Accession NumberDB01294  (DB01402)
Typesmall molecule
Groupsapproved
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
Synonyms
SynonymLanguageCode
2-Hydroxy-benzo[1,3,2]dioxabismin-4-oneNot AvailableNot Available
Basic bismuth salicylateNot AvailableNot Available
Bismuth oxide salicylateNot AvailableNot Available
Bismuth oxysalicylateNot AvailableNot Available
Bismuth subsalicylateNot AvailableNot Available
pink bismuthNot AvailableNot Available
WismutsubsalicylatNot AvailableNot Available
SaltsNot Available
Brand names
NameCompany
BismatrolNot Available
Maalox Multi-ActionNot Available
Pepto-bismolNot Available
Brand mixtures
Brand NameIngredients
Pepto-Bismol ChewablesBismuth Subsalicylate + Calcium Carbonate
Watkins SettelzBismuth Subsalicylate + Pectin + Phenyl Salicylate
Categories
CAS number14882-18-9
WeightAverage: 362.0926
Monoisotopic: 361.999166889
Chemical FormulaC7H5BiO4
InChI KeyZREIPSZUJIFJNP-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
IUPAC Name
2-hydroxy-2H,4H-benzo[d]1,3-dioxa-2-bismacyclohexan-4-one
SMILES
O[Bi]1OC(=O)C2=CC=CC=C2O1
Mass SpecNot Available
Taxonomy
KingdomOrganic Compounds
SuperclassBenzenoids
ClassBenzene and Substituted Derivatives
SubclassNot Available
Direct parentBenzene and Substituted Derivatives
Alternative parentsPolyamines; Metalloheterocyclic Compounds; Carboxylic Acids and Derivatives
Substituentspolyamine; carboxylic acid derivative
Classification descriptionThis compound belongs to the benzene and substituted derivatives. These are aromatic compounds containing at least one benzene ring.
Pharmacology
IndicationUsed to treat nausea, heartburn, indigestion, upset stomach, diarrhea, and other temporary discomforts of the stomach and gastrointestinal tract.
PharmacodynamicsBismuth 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 actionAs 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.
AbsorptionFollowing oral administration, absorption of the salicylate component from the small intestine is generally rapid and complete (>90%).
Volume of distributionNot Available
Protein bindingNot 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 eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organismsNot Available
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
Property Value Probability
Human Intestinal Absorption + 0.9086
Blood Brain Barrier + 0.9387
Caco-2 permeable + 0.5187
P-glycoprotein substrate Non-substrate 0.7003
P-glycoprotein inhibitor I Non-inhibitor 0.8865
P-glycoprotein inhibitor II Non-inhibitor 0.9885
Renal organic cation transporter Non-inhibitor 0.9091
CYP450 2C9 substrate Non-substrate 0.7983
CYP450 2D6 substrate Non-substrate 0.8434
CYP450 3A4 substrate Non-substrate 0.6608
CYP450 1A2 substrate Non-inhibitor 0.5106
CYP450 2C9 substrate Non-inhibitor 0.6648
CYP450 2D6 substrate Non-inhibitor 0.8639
CYP450 2C19 substrate Non-inhibitor 0.7378
CYP450 3A4 substrate Non-inhibitor 0.7081
CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.887
Ames test Non AMES toxic 0.6317
Carcinogenicity Non-carcinogens 0.8734
Biodegradation Not ready biodegradable 0.8052
Rat acute toxicity 2.6494 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Weak inhibitor 0.7517
hERG inhibition (predictor II) Non-inhibitor 0.9359
Pharmacoeconomics
ManufacturersNot Available
Packagers
Dosage forms
FormRouteStrength
DressingTopical
LiquidOral
LiquidSublingual
Solution / dropsOral
SuppositoryRectal
SuspensionOral
SuspensionOral
TabletOral
Prices
Unit descriptionCostUnit
Kaopectate 262 mg caplet0.37USDcaplet
Gas-x with maalox chew tablet0.25USDtablet
Bismuth subsalicylate powdr0.17USDg
Jr maalox plus antigas tablet chew0.17USDtablet
Calcium carb 500 mg tablet chew0.14USDtablet
Pepto-bismol caplet0.14USDcaplet
Soothe caplets0.12USDcaplet
Bismatrol 262 mg tablet0.09USDtablet
Maalox advanced tablet chew0.09USDtablet
Maalox quick dissolve tablet0.09USDtablet
Maalox max quick dissolve tablet0.06USDtablet
Stomach relief tablet0.06USDtablet
Magnesium-aluminum suspension0.03USDml
Bismuth 262 mg/15ml susp0.02USDml
Maalox max strength multi symp0.02USDml
Maalox maximum strength susp0.02USDml
Pepto-bismol max str susp0.02USDml
Pub calcium carb 1000 mg tablet0.02USDtablet
Maalox plus x-strength susp0.01USDml
Maalox total relief (bismuth)0.01USDml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
PatentsNot Available
Properties
Statesolid
Experimental PropertiesNot Available
Predicted Properties
PropertyValueSource
water solubility5.97e+01 g/lALOGPS
logP0.37ALOGPS
logP1.11ChemAxon
logS-0.78ALOGPS
pKa (strongest acidic)14.3ChemAxon
pKa (strongest basic)-3.1ChemAxon
physiological charge0ChemAxon
hydrogen acceptor count3ChemAxon
hydrogen donor count1ChemAxon
polar surface area55.76ChemAxon
rotatable bond count0ChemAxon
refractivity35.72ChemAxon
polarizability15.67ChemAxon
number of rings2ChemAxon
bioavailability1ChemAxon
rule of fiveYesChemAxon
Ghose filterNoChemAxon
Veber's ruleNoChemAxon
MDDR-like ruleNoChemAxon
Spectra
SpectraNot Available
References
Synthesis Reference

Richard William Hess, “Pigmentary bright primrose yellow monoclinic bismuth vanadate and processes for the preparation thereof.” U.S. Patent US4115142, issued December, 1925.

US4115142
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
ResourceLink
KEGG DrugD00728
KEGG CompoundC07870
PubChem Compound16682734
PubChem Substance46507128
ChemSpider17615374
ChEBI261649
ChEMBLCHEMBL1120
PharmGKBPA164774805
Drug Product Database2262363
RxListhttp://www.rxlist.com/cgi/generic/pylera.htm
Drugs.comhttp://www.drugs.com/cdi/bismuth-subsalicylate.html
WikipediaBismuth_subsalicylate
ATC CodesA02BX05A02BX12
AHFS Codes
  • 84:92.00
  • 56:04.00
  • 52:92.00
  • 56:08.00
  • 92:02.00*
PDB EntriesNot Available
FDA labelNot Available
MSDSshow(73.6 KB)
Interactions
Drug Interactions
Drug
AcetazolamideThe salicylate, bismuth subsalicylate, at high dose increases the effect of the carbonic anhydrase inhibitor, acetazolamide.
AmprenavirThe antiacid decreases the absorption of amprenavir
AtazanavirThis gastric pH modifier decreases the levels/effects of atazanavir
BetamethasoneThe corticosteroid, betamethasone, may decrease the effect of the salicylate, bismuth subsalicylate.
FludrocortisoneThe corticosteroid, fludrocortisone, may decrease the effect of the salicylate, bismuth subsalicylate.
GliclazideThe salicylate, bismuth subsalicylate, increases the effect of the sulfonylurea, gliclazide.
GlyburideThe salicylate, bismuth subsalicylate, increases the effect of the sulfonylurea, glibenclamide.
HydrocortisoneThe corticosteroid, hydrocortisone, may decrease the effect of the salicylate, bismuth subsalicylate.
MethazolamideThe salicylate, bismuth subsalicylate, at high dose increases the effect of the carbonic anhydrase inhibitor, methazolamide.
MethotrexateThe salicylate, bismuth subsalicylate, increases the effect and toxicity of methotrexate.
MinocyclineFormation of non-absorbable complexes
PrednisoloneThe corticosteroid, prednisolone, may decrease the effect of the salicylate, bismuth subsalicylate.
PrednisoneThe corticosteroid, prednisone, may decrease the effect of the salicylate, bismuth subsalicylate.
ProbenecidThe salicylate, bismuth subsalicylate, decreases the uricosuric effect of probenecid.
TetracyclineFormation of non-absorbable complexes
TriamcinoloneThe corticosteroid, triamcinolone, may decrease the effect of the salicylate, bismuth subsalicylate.
Food InteractionsNot Available

Carriers

1. Serum albumin

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: binder

Components

Name UniProt ID Details
Serum albumin P02768 Details

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

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Serotransferrin P02787 Details

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

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Drug created on June 30, 2007 08:17 / Updated on September 16, 2013 17:14