NAV

Bismuth subsalicylate

Identification

Summary

Bismuth subsalicylate is an antidiarrheal and anti-inflammatory agent used for symptomatic treatment of nausea, indigestion, upset stomach, diarrhea, and other temporary discomforts of the stomach and gastrointestinal tract.

Brand Names
Diphen, Kaopectate Reformulated Aug 2006, Kola-pectin, Pepto-bismol, Percy Medicine
Generic Name
Bismuth subsalicylate
DrugBank Accession Number
DB01294
Background

Bismuth subsalicylate is an antacid and anti-diarrheal agent. Exhibiting antibacterial and gastroprotective properties, bismuth subsalicylate is an insoluble salt of salicylic acid linked to trivalent bismuth cation. Each molecule of bismuth subsalicylate contains 58% bismuth and 42% salicylate by weight.3 Bismuth subsalicylate has been around for over 100 years: it was originally developed in 1901 for hygienic use and sanitation for cholera infection.2,7

Bismuth subsalicylate was first approved by the FDA in 1939 and is now mainly used to relieve nausea, diarrhea, and gastrointestinal discomfort.2 It is an active ingredient found in Pepto-Bismol, a common over-the-counter medication that is used to temporarily treat discomforts of the stomach and gastrointestinal tract.10 Bismuth subsalicylate is a component of HELIDAC Therapy (bismuth subsalicylate, metronidazole, and tetracycline), which is a treatment regimen indicated for the eradication of H. pylori for treatment of patients with H. pylori infection and duodenal ulcer disease.13

Type
Small Molecule
Groups
Approved, Vet approved
Structure
Similar Structures
Weight
Average: 362.0926
Monoisotopic: 361.999166889
Chemical Formula
C7H5BiO4
Synonyms
  • 2-Hydroxy-benzo[1,3,2]dioxabismin-4-one
  • Basic bismuth salicylate
  • Bismuth oxide salicylate
  • Bismuth oxysalicylate
  • Bismuth subsalicylate
  • Pink bismuth
  • Wismutsubsalicylat

Pharmacology

Indication

Bismuth subsalicylate is indicated to temporarily relieve diarrhea, travelers' diarrhea, and upset stomach due to overindulgence in food and drink, including heartburn, indigestion, nausea, gas, belching, and fullness.10

Bismuth subsalicylate is a component of HELIDAC Therapy (bismuth subsalicylate, metronidazole, and tetracycline), which is a treatment regimen indicated for the eradication of H. pylori for treatment of patients with H. pylori infection and duodenal ulcer disease.13

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Associated Conditions
Contraindications & Blackbox Warnings
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Pharmacodynamics

Bismuth subsalicylate is an antacid and antimicrobial, gastroprotective, anti-secretory, and anti-inflammatory actions.1,2,4 It works to reduce the severity and incidence of flatulence and diarrhea, and consequently relieving gastrointestinal discomfort.2 In one study, bismuth subsalicylate was prevented traveler's diarrhea with a protection rate >60%.8

Organobismuth compounds, formed by the breakdown of bismuth subsalicylate in the gastrointestinal tract, inhibit the growth of Helicobacter pylori and other bacteria implicated in gastrointestinal disorders, and some fungi.5 In one study, bismuth subsalicylate was shown to eradicate up to 90% of H. pylori infection when used as part of a quadruple therapy regimen containing a proton pump inhibitor, tetracycline, and metronidazole.2,6 Bismuth subsalicylate exhibited antimicrobial activity against Clostridium difficile, enterotoxigenic Escherichia coli O157:H7, norovirus, and other common enteric pathogens such as Salmonella and Shigella.8

Mechanism of action

The exact mechanism of bismuth subsalicylate is not fully understood. Bismuth subsalicylate is an insoluble complex that constitutes salicylic acid and trivalent bismuth. Once orally administered, bismuth subsalicylate hydrolyzes in the stomach into bismuth oxychloride, which is minimally absorbed into the bloodstream, and salicylic acid, which is almost completely absorbed. Bismuth interacts with other anions and compounds, such as hydrochloric acid, bicarbonate, phosphate, and hydrogen sulfide, in the gastrointestinal tract to form bismuth salts such as bismuth oxychloride, bismuth subcarbonate, bismuth phosphate, and bismuth sulfide.2,3 Bismuth salts possess bactericidal and antimicrobial activity, mainly by preventing bacteria from binding and growing on the mucosal cells of the stomach. It has no effects on normal gut flora. By preventing bacteria from binding to mucosal cells, bismuth subsalicylate prevents intestinal secretion and fluid loss, promotes fluid and electrolyte reabsorption, reduces gastrointestinal inflammation, and promotes the healing of pre-existing ulcer in the stomach. Salicylic acid from dissociated bismuth subsalicylate adds to the anti-inflammatory actions of bismuth salts by inhibiting the cyclooxygenase enzyme and limiting the formation of prostaglandin, a pro-inflammatory mediator. Bismuth subsalicylate exhibits cytoprotective and demulcent activity, which makes it an effective drug in peptic ulcer disease. It blocks the adhesion of H. pylori to the gastric epithelial cells and blocks the bacteria's enzyme activities, including phospholipase, protease, and urease.2

Absorption

Following oral administration, bismuth subsalicylate hydrolyzes into bismuth and salicylic acid in the stomach. Salicylic acid is almost completely absorbed in the small intestine and reaches plasma peak levels one to two hours after dosing. In one study involving healthy male subjects, oral administration of 60 mL Pepto-Bismol, a common over-the-counter product of bismuth subsalicylate, equivalent to 1050 mg of bismuth subsalicylate, resulted in the peak plasma concentration of salicylate of 40.1 μg/mL, with a time to peak concentration (Tmax) of 1.8 hours.3

Less than 1% of bismuth from bismuth subsalicylate is absorbed from the gastrointestinal tract into the systemic circulation. In one study, oral administration of 787 mg bismuth subsalicylate in the chewable tablet form for two weeks resulted in the mean trough blood bismuth concentration was 5.1 ± 3.1 ng/mL. In another study, the mean trough blood bismuth concentration ranged from five to 32 ng/mL following oral administration of 525 mg bismuth subsalicylate in the liquid suspension form.13

Volume of distribution

There is no information available.

Protein binding

Salicylic acid is about 90% plasma protein bound. Bismuth is about >90% bound to plasma proteins.13

Metabolism

Bismuth subsalicylate undergo hydrolysis at pH levels lesser than three. It is largely hydrolyzed in the stomach to bismuth oxychloride and salicylic acid. In the small intestine, unchanged bismuth subsalicylate reacts with other anions such as bicarbonate and phosphate to form insoluble bismuth salts. In the colon, unchanged bismuth subsalicylate and other bismuth salts react with hydrogen sulfide produced by anaerobic bacteria to form bismuth sulfide, a highly insoluble black salt responsible for the darkening of the stools.3

Hover over products below to view reaction partners

Route of elimination

Following oral administration, salicylate dissociated from bismuth subsalicylate is excreted in the urine.3 Bismuth is primarily eliminated via urinary and biliary routes.13

Half-life

The terminal half-life of salicylic acid following a single oral dose of 525 mg bismuth subsalicylate is ranges from two to five hours. Bismuth has an intermediate half-life of 5 to 11 days and a terminal half-life of 21 to 72 days.13

Clearance

The renal clearance of bismuth is 50 ± 18 mL/min.13

Adverse Effects
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Toxicity

Lowest Lethal Dose (LDLo) in humans is 700 mg/kg. LD50 in rats is 1200 mg/kg via oral route, 542 mg/kg via intraperitoneal route, and 980 mg/kg via subcutaneous route.11

Overdose of bismuth subsalicylate over an extended period of time and consequently, bismuth toxicity, can lead to blackening of the tongue and teeth, fatigue, mood changes, deterioration of mental status, and neurotoxicity. Other signs and symptoms include impaired cognition, tremors, lethargy, somnolence, insomnia, delirium, myoclonus, seizures, depressed mood, anxiety, and a depressed mood.2 Salicylate toxicity can occur from chronic bismuth subsalicylate use 9: it mostly occurs from ingestion of more than 150 mg/kg of salicylates (or >6.5 g of aspirin equivalent).2 As there are no specific antidotes for bismuth salicylate toxicity, overdose should be managed with supportive care, with or without decontamination with activated charcoal. Hemodialysis may be considered in more severe cases and with the presence of altered mental status and metabolic acidosis.2

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
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AbciximabThe risk or severity of bleeding can be increased when Bismuth subsalicylate is combined with Abciximab.
AcarboseBismuth subsalicylate may increase the hypoglycemic activities of Acarbose.
AceclofenacThe therapeutic efficacy of Bismuth subsalicylate can be decreased when used in combination with Aceclofenac.
AcenocoumarolBismuth subsalicylate may increase the anticoagulant activities of Acenocoumarol.
AcetaminophenThe risk or severity of adverse effects can be increased when Acetaminophen is combined with Bismuth subsalicylate.
AcetazolamideThe risk or severity of adverse effects can be increased when Bismuth subsalicylate is combined with Acetazolamide.
AcetohexamideBismuth subsalicylate may increase the hypoglycemic activities of Acetohexamide.
AcetyldigitoxinThe serum concentration of Acetyldigitoxin can be decreased when it is combined with Bismuth subsalicylate.
Acetylsalicylic acidThe therapeutic efficacy of Bismuth subsalicylate can be decreased when used in combination with Acetylsalicylic acid.
AlbiglutideBismuth subsalicylate may increase the hypoglycemic activities of Albiglutide.
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Food Interactions
No interactions found.

Products

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Active Moieties
NameKindUNIICASInChI Key
Salicylic acidunknownO414PZ4LPZ69-72-7YGSDEFSMJLZEOE-UHFFFAOYSA-N
Bismuth cationionicZS9CD1I8YE23713-46-4JDIBGQFKXXXXPN-UHFFFAOYSA-N
International/Other Brands
Maalox Multi-Action
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
7 Select Pink BismuthSuspension1050 mg/30mLOral7-Eleven2014-04-172019-10-31US flag
7-Select Pepto BismolTablet, chewable262 mg/1OralLil' Drug Store Products, Inc.2011-08-012017-12-31US flag
Anti-DiarrhealTablet262 mg/1OralLil' Drug Store Products, Inc.2019-02-21Not applicableUS flag
Anti-Diarrheal Maximum StrengthTablet525 mg/1OralWAL-MART STORES INC2020-04-06Not applicableUS flag
Basic Care Stomach ReliefTablet, chewable262 mg/1OralL. Perrigo Company2019-01-11Not applicableUS flag
Being Well stomach relief original strengthSuspension525 mg/30mLOralSave-A-Lot Food Stores Ltd2006-02-252019-08-01US flag
BismatrolLiquid262 mg/15mLOralAidarex Pharmaceuticals LLC2008-05-30Not applicableUS flag
BismatrolTablet, chewable262 mg/1OralMajor Pharmaceuticals2003-01-03Not applicableUS flag
BismatrolTablet, chewable262 mg/1OralPreferred Pharmaceuticals Inc.2018-04-19Not applicableUS flag
BismatrolLiquid262 mg/15mLOralProficient Rx LP2008-05-30Not applicableUS flag
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
Bismed Chewable TabletsBismuth subsalicylate (300 mg) + Calcium carbonate (350 mg)TabletOralTechnilab Pharma Inc.1993-12-311998-09-14Canada flag
Bismuth + Antacid (chewable Tablets)Bismuth subsalicylate (262 mg) + Calcium carbonate (675 mg)Tablet, chewableOralPerrigo International2000-09-272021-07-22Canada flag
Bismuth Chewable TabletsBismuth subsalicylate (262 mg) + Calcium carbonate (308 mg)TabletOralVita Health Products Inc2001-04-012004-07-26Canada flag
Bismuth Subsalicylate/Metronidazole/Tetracycline HydrochlorideBismuth subsalicylate (262.4 mg/1) + Metronidazole (250 mg/1) + Tetracycline hydrochloride (500 mg/1)KitOralAilex Pharmaceuticals, Llc2018-11-30Not applicableUS flag
Bismuth Tablets With Calcium CarbonateBismuth subsalicylate (262 mg) + Calcium carbonate (350 mg)Tablet, chewableOralTanta Pharmaceuticals IncNot applicableNot applicableCanada flag
Cherry Flavour Pepto-bismol TabBismuth subsalicylate (262 mg / tab) + Calcium carbonate (350 mg / tab)TabletOralProcter And Gamble1992-12-311997-10-31Canada flag
Chewable Bismuth Tablets With Calcium CarbonateBismuth subsalicylate (262 mg) + Calcium carbonate (350 mg)Tablet, chewableOralCellchem Pharmaceuticals Inc.2009-09-24Not applicableCanada flag
DiphenBismuth subsalicylate (262 mg/1) + Acetaminophen (325 mg/1) + Acetaminophen (500 mg/1) + Bacitracin zinc (400 [USP'U]/1g) + Benzalkonium chloride (1.3 mg/1g) + Benzocaine (200 mg/1g) + Calcium carbonate (420 mg/1) + Calcium carbonate (27 mg/1) + Dextromethorphan hydrobromide monohydrate (15 mg/1) + Diphenhydramine hydrochloride (25 mg/1) + Guaifenesin (200 mg/1) + Hydrocortisone acetate (10 mg/1g) + Ibuprofen (200 mg/1) + Lidocaine hydrochloride (5 mg/1g) + Loratadine (10 mg/1) + Magnesium oxide (20 mg/1) + Meclizine hydrochloride (25 mg/1) + Neomycin sulfate (3.5 mg/1g) + Phenylephrine hydrochloride (5 mg/1) + Polymyxin B sulfate (5000 [USP'U]/1g) + Potassium chloride (80 mg/1)Cream; Kit; Liquid; Ointment; Tablet; Tablet, chewable; Tablet, film coatedOral; TopicalRemedy Pack LLC2022-05-10Not applicableUS flag
HELIDAC TherapyBismuth subsalicylate (262.4 mg/1) + Metronidazole (250 mg/1) + Tetracycline hydrochloride (500 mg/1)KitOralCasper Pharma Llc2020-06-11Not applicableUS flag
HELIDAC TherapyBismuth subsalicylate (262.4 mg/1) + Metronidazole (250 mg/1) + Tetracycline hydrochloride (500 mg/1)KitOralPrometheus Laboratories1996-08-152014-02-01US flag

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
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
Aromatic heteropolycyclic compound / Benzenoid / Carboxylic acid derivative / Carboxylic acid salt / Hydrocarbon derivative / Metalloheterocycle / Monocarboxylic acid or derivatives / Organic metal salt / Organic oxide / Organic oxygen compound
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
salicylates, bismuth coordination entity (CHEBI:261649)
Affected organisms
  • Humans and other mammals
  • Enteric bacteria and other eubacteria
  • Bacteria
  • Helicobacter pylori
  • Shigella
  • Escherichia coli O157:H7
  • Clostridium difficile (strain 630)
  • Salmonella spp.

Chemical Identifiers

UNII
62TEY51RR1
CAS number
14882-18-9
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

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. [Article]
  2. Budisak P, Abbas M: Bismuth Subsalicylate . [Article]
  3. Bierer DW: Bismuth subsalicylate: history, chemistry, and safety. Rev Infect Dis. 1990 Jan-Feb;12 Suppl 1:S3-8. doi: 10.1093/clinids/12.supplement_1.s3. [Article]
  4. DuPont HL: Bismuth subsalicylate in the treatment and prevention of diarrheal disease. Drug Intell Clin Pharm. 1987 Sep;21(9):687-93. doi: 10.1177/106002808702100901. [Article]
  5. Dodge AG, Wackett LP: Metabolism of bismuth subsalicylate and intracellular accumulation of bismuth by Fusarium sp. strain BI. Appl Environ Microbiol. 2005 Feb;71(2):876-82. doi: 10.1128/AEM.71.2.876-882.2005. [Article]
  6. Graham DY, Hoffman J, el-Zimaity HM, Graham DP, Osato M: Twice a day quadruple therapy (bismuth subsalicylate, tetracycline, metronidazole plus lansoprazole) for treatment of Helicobacter pylori infection. Aliment Pharmacol Ther. 1997 Oct;11(5):935-8. doi: 10.1046/j.1365-2036.1997.00219.x. [Article]
  7. Keogan DM, Griffith DM: Current and potential applications of bismuth-based drugs. Molecules. 2014 Sep 23;19(9):15258-97. doi: 10.3390/molecules190915258. [Article]
  8. Pitz AM, Park GW, Lee D, Boissy YL, Vinje J: Antimicrobial activity of bismuth subsalicylate on Clostridium difficile, Escherichia coli O157:H7, norovirus, and other common enteric pathogens. Gut Microbes. 2015;6(2):93-100. doi: 10.1080/19490976.2015.1008336. [Article]
  9. Halani S, Wu PE: Salicylate toxicity from chronic bismuth subsalicylate use. BMJ Case Rep. 2020 Nov 30;13(11). pii: 13/11/e236929. doi: 10.1136/bcr-2020-236929. [Article]
  10. DailyMed Label: PEPTO-BISMOL (bismuth subsalicylate) kit, for oral use [Link]
  11. Santa Cruz Biotechnology: Bismuth(III) subsalicylate Safety Data Sheet [Link]
  12. Spectrum Chemical: Bismuth salicylate Safety Data Sheet [Link]
  13. FDA Approved Drug Products: HELIDAC Therapy (bismuth subsalicylate, metronidazole, and tetracycline) [Link]
Human Metabolome Database
HMDB0015408
KEGG Drug
D00728
KEGG Compound
C07870
PubChem Compound
16682734
PubChem Substance
46507128
ChemSpider
17215772
RxNav
19478
ChEBI
261649
ChEMBL
CHEMBL1120
PharmGKB
PA164774805
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Bismuth_subsalicylate
MSDS
Download (73.6 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4CompletedPreventionHelicobacter Pylori Infection / Obesity, Morbid1
4CompletedTreatmentCure Rate of Helicobacter Pylori Infection1
4CompletedTreatmentHelicobacter Pylori Infection1
4RecruitingTreatmentCoronavirus Disease 2019 (COVID‑19) / Diarrhea1
4WithdrawnTreatmentClostridium Difficile Infection (CDI)1
3CompletedTreatmentOptimization of Second Line Treatment Protocol for H Pylori Eradication1
3RecruitingPreventionAntibiotic Resistant Infection / Traveler's Diarrhea1
2CompletedTreatmentMalignant Lymphomas1
2, 3CompletedTreatmentGenital Diseases, Female1
1CompletedTreatmentHealthy Subjects (HS)1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
  • Amend
  • Chattem Chemicals Inc.
  • Dispensing Solutions
  • Kroger Co.
  • Major Pharmaceuticals
  • Novartis AG
  • Pharma Pac LLC
  • Procter & Gamble
  • Publix Super Markets
  • Walgreen Co.
Dosage Forms
FormRouteStrength
SuspensionOral1.7 g
Tablet, chewableBuccal262 mg
SuspensionOral1750 mg
TabletOral
LiquidOral17.66 mg / mL
TabletOral262 mg/434mg
SuspensionOral1.747 g
SuspensionOral17.6 mg / mL
TabletOral262 mg
LiquidOral17.5 mg / mL
LiquidOral17.6 mg / mL
Capsule, gelatin coatedOral262 mg/1
SuspensionOral17.5 mg / mL
Tablet, chewableOral
Tablet, chewableOral262 mg/1
Cream; kit; liquid; ointment; tablet; tablet, chewable; tablet, film coatedOral; Topical
Tablet, chewableBuccal262.5 mg
PowderOral262 mg/1
LiquidOral35 mg / mL
SuspensionOral35 mg / mL
LiquidOral1050 mg/30mL
KitOral
Tablet, coatedOral262 mg/1
LiquidOral35.0 mg/1mL
LiquidOral17.47 mg/1mL
LiquidOral525 mg/15mL
SyrupOral525 mg/15mL
SuspensionOral1050 mg/30mL
Tablet, film coatedOral
TabletOral125 MG
SuspensionOral17.5 mg/1mL
SuspensionOral262 mg/15mL
TabletOral262 mg/1
SuspensionOral525 mg/15mL
SuspensionOral1.75 g
CapsuleOral262 mg
Capsule, liquid filledOral262 mg/1
Kit; suspension; tabletOral
Kit; suspension; tablet, chewableOral
LiquidOral525 mg/30mL
TabletOral525 mg/21
Tablet, chewableOral
SuspensionOral35.2 mg / mL
TabletOral262.4 mg
TabletOral525 mg/1
LiquidOral1050 mg/10mL
LiquidOral262 mg/15mL
LiquidOral1.7 %
Tablet, film coatedOral262 mg/1
TabletOral375 MG
LiquidOral262 mg/30mL
SuspensionOral525 mg/30mL
PowderOral525 mg/1
LiquidOral
Tablet, chewableOral262 mg/1g
Tablet, chewableOral262 mg
TabletOral524 mg
SuspensionOral524 mg/15ml
Tablet, chewableOral524 mg
TabletOral1048 mg
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
PropertyValueSource
melting point (°C)>350Spectrum Chemical Safety Data Sheet
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
Polarizability15.66 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

Carriers

Details1. Serum albumin
Kind
Protein
Organism
Humans
Pharmacological action
No
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. [Article]
  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. [Article]
  3. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
  4. Sox TE, Olson CA: Binding and killing of bacteria by bismuth subsalicylate. Antimicrob Agents Chemother. 1989 Dec;33(12):2075-82. doi: 10.1128/aac.33.12.2075. [Article]
Details2. Serotransferrin
Kind
Protein
Organism
Humans
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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]

Drug created at June 30, 2007 14:17 / Updated at September 29, 2022 07:52