2-hydroxy-2H,4H-benzo[d]1,3-dioxa-2-bismacyclohexan-4-one

• ChemBase ID: 1146
• Molecular Formular: C7H5BiO4
• Molecular Mass: 362.0926
• Monoisotopic Mass: 361.99918164
• SMILES: c12c(O[Bi](OC1=O)O)cccc2
• Canonical SMILES: O[Bi]1OC(=O)c2c(O1)cccc2
• 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
• InChIKey: ZREIPSZUJIFJNP-UHFFFAOYSA-K

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-hydroxy-2H,4H-benzo[d]1,3-dioxa-2-bismacyclohexan-4-one
• IUPAC Traditional name: pepto-bismol; @bismuth subsalicylate
• Brand Name: Maalox multi action; Pepto-bismol and others; Extra strength bismuth; Extra-strength bismuth; PMS-bismuth subsalicylate; Pepto-bismol; Spiromak forte; Stabisol; Vismut; Wismutsubsalicylat; Bismuth chewables; Bismuth caplets; Bismed; Bismatrol
• Synonyms: Bismuth subsalicylate; Bismuth(III) salicylate basic; Bismuth(III) subsalicylate; Bismuth(III) salicylate basic; Bismutum subsalicylicum; Bismuthi subsalicylas; Bismuth(III) subsalicylate; Bismuth oxysalicylate; Bismuth oxide salicylate; Bismuth; Bismuth Subsalicylate; 水杨酸铋(III) 碱性; 次水杨酸铋(III); 碱式水杨酸铋(III)

Database IDs

• CAS Number: 14882-18-9
• EC Number: 238-953-1
• MDL Number: MFCD00085368
• Beilstein Number: 9170211
• PubChem SID: 46507128; 160964609; 24890149; 24871718
• PubChem CID: 16682734
• CHEBI ID: 261649
• CHEMBL: 1120
• Chemspider ID: 17215772
• DrugBank ID: DB01294
• KEGG ID: D00728
• Unique Ingredient Identifier: 62TEY51RR1
• Wikipedia Title: Bismuth_subsalicylate
• Medline Plus: a607040

CALCULATED PROPERTIES

JChem

• Acid pKa: 14.301071
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 1.1143
• LogD (pH = 7.4): 1.1142999
• Log P: 1.1143
• Molar Refractivity: 35.7177 cm^3
• Polarizability: 21.77017 Å^3
• Polar Surface Area: 55.76 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 0.37
• LOG S: -0.78
• Solubility (Water): 5.97e+01 g/l

PROPERTIES

Physical Property

• Melting Point: >350 °C(lit.)

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Pharmacology Properties

• Admin Routes: Oral
• Legal Status: OTC (US)

Product Information

• Purity: ≥97.0% (KT); 99.9% trace metals basis
• Grade: purum
• Linear Formula: HOC6H4COOBiO

DETAILS

DrugBank - DB01294

• Drug 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.
• Indication: Used to treat nausea, heartburn, indigestion, upset stomach, diarrhea, and other temporary discomforts of the stomach and gastrointestinal tract.
• Pharmacology: 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.
• Biotransformation: 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.
• Absorption: Following oral administration, absorption of the salicylate component from the small intestine is generally rapid and complete (>90%).
• References: 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: Wikipedia; RxList; Drugs.com

Sigma Aldrich - 480789

Application
A drug used to treat temporary discomforts of the stomach and gastrointestinal tract, such as diarrhea, heartburn and nausea.
Packaging
100, 500 g in poly bottle

REFERENCES

• 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