Bismuth Subsalicylate

Identification

Name
Bismuth Subsalicylate
Accession Number
DB01294  (DB01402)
Type
Small Molecule
Groups
Approved, Vet 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
Synonyms
  • 2-Hydroxy-benzo[1,3,2]dioxabismin-4-one
  • Basic bismuth salicylate
  • Bismuth oxide salicylate
  • Bismuth oxysalicylate
  • Bismuth subsalicylate
  • pink bismuth
  • Wismutsubsalicylat
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
7 Select Pink BismuthSuspension1050 mg/30mLOral7 Eleven2014-04-17Not applicableUs
7-Select Pepto BismolTablet, chewable262 mg/1OralLil' Drug Store Products, Inc.2011-08-01Not applicableUs
Being Well stomach relief original strengthSuspension525 mg/30mLOralSave A Lot Food Stores, Ltd.2006-02-25Not applicableUs
BismatrolLiquid262 mg/15mLOralProficient Rx LP2008-05-30Not applicableUs
BismatrolLiquid262 mg/15mLOralAidarex Pharmaceuticals LLC2008-05-30Not applicableUs
BismatrolLiquid262 mg/15mLOralMajor2008-05-30Not applicableUs
BismatrolLiquid525 mg/15mLOralMajor2009-01-05Not applicableUs
BismatrolLiquid262 mg/15mLOralAtlantic Biologicals Corps.2008-05-30Not applicableUs
BismatrolTablet, chewable262 mg/1OralProficient Rx LP2003-01-03Not applicableUs
BismatrolTablet, chewable262 mg/1OralAidarex Pharmaceuticals LLC2003-01-03Not applicableUs
Unapproved/Other Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Pepto ReliefTablet, chewable262 mg/1OralRichmond Pharmaceuticals, Inc2015-06-01Not applicableUs
International/Other Brands
Maalox Multi-Action
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Bismed Chewable TabletsBismuth Subsalicylate (300 mg) + Calcium Carbonate (350 mg)TabletOralTechnilab Pharma Inc.1993-12-311998-09-14Canada
Bismuth + Antacid (chewable Tablets)Bismuth Subsalicylate (262 mg) + Calcium Carbonate (675 mg)TabletOralPerrigo International2000-09-27Not applicableCanada
Bismuth Chewable TabletsBismuth Subsalicylate (262 mg) + Calcium Carbonate (308 mg)TabletOralVita Health Products Inc2001-04-012004-07-26Canada
Bismuth Tablets With Calcium CarbonateBismuth Subsalicylate (262 mg) + Calcium Carbonate (350 mg)Tablet, chewableOralTanta Pharmaceuticals IncNot applicableNot applicableCanada
Cherry Flavour Pepto-bismol TabBismuth Subsalicylate (262 mg) + Calcium Carbonate (350 mg)TabletOralProcter And Gamble1992-12-311997-10-31Canada
Chewable Bismuth Tablets With Calcium CarbonateBismuth Subsalicylate (262 mg) + Calcium Carbonate (350 mg)Tablet, chewableOralPharmetics (2011) Inc.2009-09-24Not applicableCanada
Pepto-bismol ChewablesBismuth Subsalicylate (262 mg) + Calcium Carbonate (350 mg)TabletOralProcter And Gamble2000-02-18Not applicableCanada
Pepto-bismol TabBismuth Subsalicylate (262 mg) + Calcium Carbonate (350 mg)TabletOralRichardson Vicks, Division Of The Procter & Gamble Company1991-12-311996-09-16Canada
Pepto-bismol TabletsBismuth Subsalicylate (262 mg) + Calcium Carbonate (350 mg)TabletOralProcter And Gamble1996-12-312000-02-18Canada
Pink Bismuth Plus Antacid Relief TabletsBismuth Subsalicylate (262 mg) + Calcium Carbonate (495 mg)TabletOralPerrigo International1997-09-292000-10-10Canada
Categories
UNII
62TEY51RR1
CAS number
14882-18-9
Weight
Average: 362.0926
Monoisotopic: 361.999166889
Chemical Formula
C7H5BiO4
InChI Key
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
IUPAC Name
2-hydroxy-2H,4H-benzo[d]1,3-dioxa-2-bismacyclohexan-4-one
SMILES
O[Bi]1OC(=O)C2=CC=CC=C2O1

Pharmacology

Indication

Used to treat nausea, heartburn, indigestion, upset stomach, diarrhea, and other temporary discomforts of the stomach and gastrointestinal tract.

Structured Indications
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
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteractionDrug group
ChlortetracyclineThe serum concentration of Chlortetracycline can be decreased when it is combined with Bismuth Subsalicylate.Approved, Investigational, Vet Approved
DemeclocyclineThe serum concentration of Demeclocycline can be decreased when it is combined with Bismuth Subsalicylate.Approved
DoxycyclineThe serum concentration of Doxycycline can be decreased when it is combined with Bismuth Subsalicylate.Approved, Investigational, Vet Approved
MinocyclineThe serum concentration of Minocycline can be decreased when it is combined with Bismuth Subsalicylate.Approved, Investigational
Food Interactions
Not 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 References
  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:1158081]
External Links
Human Metabolome Database
HMDB15408
KEGG Drug
D00728
KEGG Compound
C07870
PubChem Compound
16682734
PubChem Substance
46507128
ChemSpider
17215772
ChEBI
261649
ChEMBL
CHEMBL1120
PharmGKB
PA164774805
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Bismuth_subsalicylate
AHFS Codes
  • 56:04.00 — Antacids and Adsorbents
  • 56:08.00 — Antidiarrhea Agents
MSDS
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Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1CompletedTreatmentHealthy Volunteers1
2CompletedTreatmentMalignant Lymphomas1
2, 3CompletedTreatmentFemale Genital Diseases1
4CompletedTreatmentCure Rate of Helicobacter Pylori Infection1
4CompletedTreatmentDry Eye Syndromes1
4CompletedTreatmentFunctional Dyspepsia / Helicobacter Pylori / Peptic Ulcers1
4CompletedTreatmentFunctional Dyspepsia / Peptic Ulcers1
4CompletedTreatmentFunctional Dyspepsia / Scarred Peptic Ulcer1
4CompletedTreatmentGastritis / Indigestion / Peptic Ulcers2
4CompletedTreatmentHelicobacter Infection1
4CompletedTreatmentHelicobacter Pylori Treatment Failure1
4CompletedTreatmentIndigestion / Peptic Ulcers1
4Not Yet RecruitingTreatmentBacterial Infection Due to Helicobacter Pylori (H. Pylori)1
Not AvailableCompletedBasic ScienceDry Eye Syndrome (DES)1
Not AvailableCompletedHealth Services ResearchDiarrhea1
Not AvailableCompletedTreatmentBacterial Infection Due to Helicobacter Pylori (H. Pylori)1
Not AvailableCompletedTreatmentBlood Diseases / Haematological Malignancies / Hematological Diseases / Leukemias / Malignant Lymphomas / Multiple Myeloma (MM)1
Not AvailableRecruitingTreatmentBacterial Infection Due to Helicobacter Pylori (H. Pylori)2
Not AvailableTerminatedTreatmentColitis1
Not AvailableUnknown StatusTreatmentBacterial Infection Due to Helicobacter Pylori (H. Pylori)1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Dosage forms
FormRouteStrength
LiquidOral17.66 mg
TabletOral262 mg/434mg
LiquidOral17.6 mg
SuspensionOral17.5 mg
TabletOral262 mg
LiquidOral17.5 mg
SuspensionOral35.2 mg
Tablet, chewableOral
LiquidOral262 mg/15mL
PowderOral262 mg/1
LiquidOral35 mg
SuspensionOral35 mg
SuspensionOral525 mg/30mL
TabletOral262 mg/1
LiquidOral35 mg/mL
LiquidOral17.47 mg/mL
LiquidOral525 mg/15mL
Tablet, chewableOral524 mg
SuspensionOral17.5 mg/mL
SuspensionOral262 mg/15mL
SuspensionOral525 mg/15mL
Kit
TabletOral525 mg/21
TabletOral
LiquidOral35.2 mg
Tablet, chewableOral262 mg
LiquidOral1050 mg/10mL
SuspensionOral17.6 mg
LiquidOral1.7 %
LiquidOral1050 mg/30mL
LiquidOral262 mg/30mL
Tablet, chewableOral262 mg/1
SuspensionOral1050 mg/30mL
LiquidOral525 mg/30mL
PowderOral525 mg/1
LiquidOral
Prices
Unit descriptionCostUnit
Kaopectate 262 mg caplet0.37USD caplet
Gas-x with maalox chew tablet0.25USD tablet
Bismuth subsalicylate powdr0.17USD g
Jr maalox plus antigas tablet chew0.17USD tablet
Calcium carb 500 mg tablet chew0.14USD tablet
Pepto-bismol caplet0.14USD caplet
Soothe caplets0.12USD caplet
Bismatrol 262 mg tablet0.09USD tablet
Maalox advanced tablet chew0.09USD tablet
Maalox quick dissolve tablet0.09USD tablet
Maalox max quick dissolve tablet0.06USD tablet
Stomach relief tablet0.06USD tablet
Magnesium-aluminum suspension0.03USD ml
Bismuth 262 mg/15ml susp0.02USD ml
Maalox max strength multi symp0.02USD ml
Maalox maximum strength susp0.02USD ml
Pepto-bismol max str susp0.02USD ml
Pub calcium carb 1000 mg tablet0.02USD tablet
Maalox plus x-strength susp0.01USD ml
Maalox total relief (bismuth)0.01USD ml
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
PropertyValueSource
Water Solubility59.7 mg/mLALOGPS
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 Area55.76 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity35.72 m3·mol-1ChemAxon
Polarizability15.67 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9086
Blood Brain Barrier+0.9387
Caco-2 permeable+0.5187
P-glycoprotein substrateNon-substrate0.7003
P-glycoprotein inhibitor INon-inhibitor0.8865
P-glycoprotein inhibitor IINon-inhibitor0.9885
Renal organic cation transporterNon-inhibitor0.9091
CYP450 2C9 substrateNon-substrate0.7983
CYP450 2D6 substrateNon-substrate0.8434
CYP450 3A4 substrateNon-substrate0.6608
CYP450 1A2 substrateNon-inhibitor0.5106
CYP450 2C9 inhibitorNon-inhibitor0.6648
CYP450 2D6 inhibitorNon-inhibitor0.8639
CYP450 2C19 inhibitorNon-inhibitor0.7378
CYP450 3A4 inhibitorNon-inhibitor0.7081
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.887
Ames testNon AMES toxic0.6317
CarcinogenicityNon-carcinogens0.8734
BiodegradationNot ready biodegradable0.8052
Rat acute toxicity2.6494 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.7517
hERG inhibition (predictor II)Non-inhibitor0.9359
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as benzenoids. These are aromatic compounds containing one or more benzene rings.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Not Available
Sub Class
Not Available
Direct Parent
Benzenoids
Alternative Parents
Carboxylic acid salts / Oxacyclic compounds / Organic metal salts / Monocarboxylic acids and derivatives / Metalloheterocyclic compounds / Organooxygen compounds / Organic oxides / Hydrocarbon derivatives
Substituents
Benzenoid / Carboxylic acid salt / Oxacycle / Organic metal salt / Organoheterocyclic compound / Monocarboxylic acid or derivatives / Metalloheterocycle / Carboxylic acid derivative / Organic oxygen compound / Organic oxide
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
salicylates, bismuth coordination entity (CHEBI:261649)

Carriers

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Binder
General Function
Toxic substance binding
Specific Function
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 colloid...
Gene Name
ALB
Uniprot ID
P02768
Uniprot Name
Serum albumin
Molecular Weight
69365.94 Da
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:11110794]
  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:12620681]
  3. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Transferrin receptor binding
Specific Function
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 si...
Gene Name
TF
Uniprot ID
P02787
Uniprot Name
Serotransferrin
Molecular Weight
77063.195 Da
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:11110794]
  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:12620681]
  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:15519234]
  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:15544343]
  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:17330963]

Drug created on June 30, 2007 08:17 / Updated on November 19, 2017 20:34