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14882-18-9 molecular structure
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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 and InChIs

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

Cite this record

CBID:1146 http://www.chembase.cn/molecule-1146.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
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)
CAS Number
14882-18-9
EC Number
238-953-1
MDL Number
MFCD00085368
Beilstein Number
9170211
PubChem SID
160964609
46507128
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

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 14.301071  H Acceptors
H Donor LogD (pH = 5.5) 1.1143 
LogD (pH = 7.4) 1.1142999  Log P 1.1143 
Molar Refractivity 35.7177 cm3 Polarizability 21.77017 Å3
Polar Surface Area 55.76 Å2 Rotatable Bonds
Lipinski's Rule of Five true 
Log P 0.37  LOG S -0.78 
Solubility (Water) 5.97e+01 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Melting Point
>350 °C(lit.) expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
German water hazard class
3 expand Show data source
Personal Protective Equipment
Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter expand Show data source
Admin Routes
Oral expand Show data source
Legal Status
OTC (US) expand Show data source
Purity
≥97.0% (KT) expand Show data source
99.9% trace metals basis expand Show data source
Grade
purum expand Show data source
Linear Formula
HOC6H4COOBiO expand Show data source

DETAILS

DETAILS

DrugBank DrugBank Wikipedia Wikipedia Sigma Aldrich Sigma Aldrich
DrugBank - DB01294 external link
Item Information
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 external link
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

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • 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
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PATENTS

PATENTS

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