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2-Hydroxybenzoic Acid Bismuth (3+) Salt, Basic

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Also known as: 14882-18-9, Bismuth oxysalicylate, Bismuth oxide salicylate, Wismutsubsalicylat, Basic bismuth salicylate, Bismuthi subsalicylas

Molecular Formula

C₇H₆BiO₄

Molecular Weight

363.10 g/mol

InChI Key

QBWLKDFBINPHFT-UHFFFAOYSA-L

Bismuth Subsalicylate is a bismuth salt of salicylic acid. Little absorbed from the gastrointestinal tract, bismuth subsalicylate exerts a local effect on the gastric mucosa, coating it and protecting it from the corrosive effects of acid and pepsin. This agent also has local antimicrobial properties. (NCI04)

1 2D Structure

Bismuth Subsalicylate

2 Identification

2.1 Computed Descriptors

2.1.1 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;+2;/p-2

2.1.2 InChI Key

QBWLKDFBINPHFT-UHFFFAOYSA-L

2.1.3 Canonical SMILES

C1=CC=C2C(=C1)C(=O)O[Bi]O2.O

2.2 Synonyms

2.2.1 MeSH Synonyms

1. Helidac

2. Kaopectate

3. Pepto-bismol

4. Subsalicylate Bismuth

5. Trigastronol

2.2.2 Depositor-Supplied Synonyms

1. 14882-18-9

2. Bismuth Oxysalicylate

3. Bismuth Oxide Salicylate

4. Wismutsubsalicylat

5. Basic Bismuth Salicylate

6. Bismuthi Subsalicylas

7. 4h-1,3,2-benzodioxabismin-4-one, 2-hydroxy-

8. Bismutum Subsalicylicum

9. Bismuth(iii) Subsalicylate

10. Pink Bismuth

11. Bismuth, (2-hydroxybenzoato-o1,o2)oxo-

12. Stabisol

13. Vismut

14. Spiromak Forte

15. Ncgc00166299-01

16. Trigastronol

17. 2-hydroxy-benzo[1,3,2]dioxabismin-4-one

18. Bismuth Oxysalicylate;bismuth(iii) Salicylate Basic

19. 2-hydroxy-2h,4h-benzo[d]1,3-dioxa-2-bismacyclohexan-4-one

20. Bismuth Salicylate, Basic

21. Wismutsalicylat, Basisches

22. Bismuth, Oxo(salicylato)-

23. Bismogenol Tosse Inj

24. Ccris 4751

25. Hsdb 332

26. Salicylic Acid Basic Bismuth Salt

27. Salicylic Acid, Bismuth Basic Salt

28. Einecs 238-953-1

29. Unii-62tey51rr1

30. Bismuth, (2-hydroxybenzoato-o(1),o(2))oxo-

31. Wismutoxidsalicylat

32. 2-hydroxybenzoic Acid Bismuth (3+) Salt, Basic

33. Bismuth-subsalicylate

34. Mfcd00085368

35. Pepto-bismol (tn)

36. Bismuth Subsalicylate [usan:usp:jan]

37. Dsstox_cid_4622

38. 2-hydroxy-4h-1,3,2-benzodioxabismin-4-one

39. Ec 238-953-1

40. Dsstox_rid_77471

41. Dsstox_gsid_24622

42. Mls000069654

43. Dtxsid6024622

44. Bismuth Subsalicylate (jan/usp)

45. Chebi:261649

46. Hms2093h13

47. Pharmakon1600-01505412

48. Hy-b0550

49. Tox21_112398

50. Nsc759117

51. Akos015888405

52. Ccg-213424

53. Db01294

54. Nsc 759117

55. Ncgc00166299-03

56. 2-hydroxy-1,3,2-benzodioxabismin-4-one

57. As-65783

58. Smr000059234

59. Sbi-0206855.p001

60. Cas-14882-18-9

61. C07870

62. D00728

63. Ab00489978_02

64. 2-hydroxy-4h-benzo[d][1,3,2]dioxabismin-4-one

65. Sr-05000001933

66. J-008518

67. Sr-05000001933-1

68. Bismuth(iii) Subsalicylate, 99.9% Trace Metals Basis

69. Bismuth(iii) Salicylate Basic, Purum, >=97.0% (kt)

70. Bismuth Oxysalicylate, Bismuth Subsalicylate, Bismuth(iii) Salicylate Basic

71. Bismuth Subsalicylate, United States Pharmacopeia (usp) Reference Standard

72. 87-27-4

2.3 Create Date

2007-08-23

3 Chemical and Physical Properties

Molecular Formula	C₇H₆BiO₄
Molecular Weight	363.10 g/mol
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	4
Rotatable Bond Count	0
Exact Mass	363.00701 g/mol
Monoisotopic Mass	363.00701 g/mol
Topological Polar Surface Area	36.5 Å²
Heavy Atom Count	12
Formal Charge	0
Complexity	173
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	2

4 Drug and Medication Information

4.1 Therapeutic Uses

USED MEDICINALLY AS INTESTINAL ABSORBENT.

Gosselin, R.E., H.C. Hodge, R.P. Smith, and M.N. Gleason. Clinical Toxicology of Commercial Products. 4th ed. Baltimore: Williams and Wilkins, 1976., p. II-93

MEDICATION (VET): ANTIDIARRHEAL. WEAK INTESTINAL ANTISEPTIC DUE TO LIBERATION OF SALICYLIC ACID. USUALLY COMBINED WITH CARBONATES TO MINIMIZE IRRITANT EFFECTS OF FREE ACID WHILE UTILIZING PROTECTIVE EFFECT OF BISMUTH.

Rossoff, I.S. Handbook of Veterinary Drugs. New York: Springer Publishing Company, 1974., p. 48

THE CMPD IS SOMETIMES USED ORALLY TO ALLAY DIARRHEA OR TO SOOTHE GASTRITIS OR PEPTIC ULCER. ... BEFORE THE ADVENT OF PENICILLIN, BISMUTH SUBSALICYLATE WAS MUCH USED IN THE TREATMENT OF SYPHILIS...

Hayes, W.J., Jr., E.R. Laws, Jr., (eds.). Handbook of Pesticide Toxicology. Volume 2. Classes of Pesticides. New York, NY: Academic Press, Inc., 1991., p. 542

/SRP: FORMER/ TREATMENT OF VINCENT'S ANGINA, SYPHILIS

American Hospital Formulary Service. Volumes I and II. Washington, DC: American Society of Hospital Pharmacists, to 1984., p. 8:28

For more Therapeutic Uses (Complete) data for BISMUTH SUBSALICYLATE (7 total), please visit the HSDB record page.

4.2 Drug Warning

EVEN WHEN ITS USE WAS EXTENSIVE, THE GRADUAL IM INJECTION USED AGAINST SYPHILIS RARELY LED TO SERIOUS POISONING. IT WAS CUSTOMARY TO STOP TREATMENT IF GINGIVITIS, ALBUMINURIA, CUTANEOUS ERUPTIONS, OR MARKED DIARRHEA APPEARED.

Hayes, W.J., Jr., E.R. Laws, Jr., (eds.). Handbook of Pesticide Toxicology. Volume 2. Classes of Pesticides. New York, NY: Academic Press, Inc., 1991., p. 543

BIOAVAILABILITY OF DOXYCYCLINE WAS SIGNIFICANTLY REDUCED BY 37% & 51%, RESPECTIVELY, WHEN SUBSALICYLATE BISMUTH WAS GIVEN SIMULTANEOUSLY & AS A MULTIPLE-DOSE REGIMEN BEFORE DOXYCYCLINE. SUBSALICYLATE BISMUTH SHOULD NOT BE TAKEN WHEN DOXYCYCLINE IS USED FOR THERAPEUTIC PURPOSES. AUTHORS SUGGEST TRAVELERS SHOULD NOT TAKE THE AGENTS TOGETHER IN AN EFFORT TO PREVENT DIARRHEA.

PMID:7040708 ERICSSON CD ET AL; JAMA 247 (16): 2266 (1982)

The excretion of large amounts of bismuth obtained from bismuth subsalicylate into breast milk is not expected because of the poor absorption of bismuth into the systemic circulation. Salicylates, however, are excreted in milk and are eliminated more slowly from milk than from plasma with milk:plasma ratios, rising from 0.03-0.08 at 3 hours to 0.34 at 12 hours. Due to the potential for adverse effects in the nursing infant, the American Academy of Pediatrics recommends that salicylates should be used cautiously during breast feeding. A recent review also states that bismuth subsalicylate should be avoided during lactation because of systemic salicylate absorption.

Briggs, G.G, R.K. Freeman, S.J. Yaffe. A Reference Guide to Fetal and Neonatal Risk. Drugs in Pregnancy and Lactation. 4th ed. Baltimore, MD: Williams & Wilkins 1994., p. 96

Although the risk for toxicity may be small, significant fetal adverse effects have resulted from chronic exposure to salicylates Because of this, the use of bismuth subsalicyate during gestation should be restricted to the first half of pregnancy and then only in amounts that do not exceed the recommended doses.

Briggs, G.G, R.K. Freeman, S.J. Yaffe. A Reference Guide to Fetal and Neonatal Risk. Drugs in Pregnancy and Lactation. 4th ed. Baltimore, MD: Williams & Wilkins 1994., p. 96

4.3 Minimum/Potential Fatal Human Dose

3(?). 3= MODERATELY TOXIC: PROBABLE ORAL LETHAL DOSE (HUMAN) 0.5-5 G/KG, BETWEEN 1 OZ & 1 PINT FOR 70 KG PERSON (150 LB).

Gosselin, R.E., H.C. Hodge, R.P. Smith, and M.N. Gleason. Clinical Toxicology of Commercial Products. 4th ed. Baltimore: Williams and Wilkins, 1976., p. II-93

4.4 Drug 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. 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.

5 Pharmacology and Biochemistry

5.1 Pharmacology

Bismuth subsalicylate is an antacid and antimicrobial, gastroprotective, anti-secretory, and anti-inflammatory actions. It works to reduce the severity and incidence of flatulence and diarrhea, and consequently relieving gastrointestinal discomfort. In one study, bismuth subsalicylate was prevented traveler's diarrhea with a protection rate >60%. 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. 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. Bismuth subsalicylate exhibited antimicrobial activity against _Clostridium difficile_, enterotoxigenic _Escherichia coli_ O157:H7, _norovirus_, and other common enteric pathogens such as _Salmonella_ and _Shigella_.

5.2 MeSH Pharmacological Classification

Antidiarrheals

Miscellaneous agents found useful in the symptomatic treatment of diarrhea. They have no effect on the agent(s) that cause diarrhea, but merely alleviate the condition. (See all compounds classified as Antidiarrheals.)

5.3 FDA Pharmacological Classification

5.3.1 Pharmacological Classes

Bismuth [EPC]; Bismuth [CS]

5.4 Absorption, Distribution and Excretion

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 g/mL, with a time to peak concentration (T_max) of 1.8 hours. 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.

Route of Elimination

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

Volume of Distribution

There is no information available.

Clearance

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

THE AUTOPSY DISTRIBUTION OF BISMUTH IN 22 PATIENTS WHO RECEIVED THERAPEUTIC IM INJECTIONS (MAINLY BISMUTH SALICYLATE) WAS AS FOLLOWS (MEDIAN VALUES, MG/KG, WET WEIGHT): KIDNEY 33.3; LIVER 6.8; SPLEEN 1.6; COLON 1.2; LUNG 0.9; BRAIN 0.6 & BLOOD 0.5.

Friberg, L., Nordberg, G.F., Kessler, E. and Vouk, V.B. (eds). Handbook of the Toxicology of Metals. 2nd ed. Vols I, II.: Amsterdam: Elsevier Science Publishers B.V., 1986., p. 121

In the gastrointestinal tract, bismuth subsalicylate is converted to salicylic acid and insoluble bismuth salts. The salicylate portion of bismuth subsalicylate is extensively absorbed (greater than 90%) and excreted in urine.

Clayton, G.D., F.E. Clayton (eds.) Patty's Industrial Hygiene and Toxicology. Volumes 2A, 2B, 2C, 2D, 2E, 2F: Toxicology. 4th ed. New York, NY: John Wiley & Sons Inc., 1993-1994., p. 1951

Bismuth subsalicylate (bismuth salicylate) is hydrolyzed in the gastrointestinal tract to bismuth salts and sodium salicylate. Two tablets or 30 ml suspension of the compound yields 204 mg and 258 mg, respectively, of salicylate. Inorganic bismuth salts, in contrast to organic complexes of bismuth, are relatively water-insoluble and poorly absorbed systemically, but significant absorption of salicylate does occur. A brief 1992 study found minimal absorption of bismuth (exact serum concentrations not specified) from bismuth subsalicylate in 12 healthy subjects, as opposed to a peak serum level of 0.050 ug/ml after a dose of 216 mg of colloidal bismuth subcitrate in a single patient. Some bismuth absorption was documented across the normal gastric mucosa, but the primary absorption occurred from the duodenum.

Briggs, G.G, R.K. Freeman, S.J. Yaffe. A Reference Guide to Fetal and Neonatal Risk. Drugs in Pregnancy and Lactation. 4th ed. Baltimore, MD: Williams & Wilkins 1994., p. 95

5.5 Metabolism/Metabolites

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.

5.6 Biological 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.

5.7 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. 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.

IN THE Y-1 ADRENAL CELL TISSUE CULTURE SYSTEM, A PREPN CONTAINING BISMUTH SUBSALICYLATE REDUCED THE ACTIVITY OF CRUDE TOXIN FROM VIBRIO CHOLERAE BY 104-FOLD AS COMPARED WITH THE ACTIVITY OF CONTROLS. SIMILAR RESULTS WERE OBTAINED USING THE ADULT RABBIT LIGATED INTESTINAL LOOP MODEL. THE PREPN FAILED TO AFFECT CRUDE ESCHERICHIA COLI OR CHOLERA TOXIN ACTIVITY ONCE THESE TOXINS HAD BECOME BOUND TO INTESTINAL MUCOSA.

PMID:335003 ERICSSON CD ET AL; J INFECT DIS 136 (5): 693 (1977)

ATTAPULGITE & PEPTO-BISMOL WERE EFFECTIVE IN REDUCING FLUID ACCUMULATION IN LIGATED SEGMENTS OF PIG INTESTINE INFECTED WITH ENTEROPATHOGENIC ESCHERICHIA COLI. FOR PEPTO-BISMOL THIS EFFECT WAS ASSOCIATED WITH AN ANTIBACTERIAL AS WELL AS AN ANTITOXIC EFFECT, PROBABLY DUE TO ITS ABSORBENT PROPERTIES. AN ASPIRIN-LIKE EFFECT IN THE GUT DUE TO THE ACTIVE INGREDIENT BISMUTH SUBSALICYLATE MAY HAVE CONTRIBUTED TO THE EFFECTIVENESS OF PEPTO-BISMOL.

PMID:356940 Full text: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1277637 GYLES CL, ZIGLER M; CAN J COMP MED 42 (3): 260 (1978)

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Find Bismuth Subsalicylate manufacturers, exporters & distributors on PharmaCompass

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CHEMISTRY

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ACTIVE PHARMA INGREDIENTS

10 API Suppliers

7 USDMF

8 NDC API

4 Listed Suppliers

$ API Reference Price

DEVELOPMENTS

1 Drugs in Development

FINISHED DOSAGE FORMULATIONS

21 FDF Dossiers

2 FDA Orange Book

14 Canada

5 Listed Dossiers

RELATED EXCIPIENT COMPANIES

10 Rochem International Inc

26 SPI Pharma

11 DKSH

2 Pharm-RX Chemical

9 Faran Shimi Pharmaceutical

1 Boai NKY Pharmaceuticals Ltd

14 Gangwal Healthcare

3 Nanjing Well Pharmaceutical

2 Pfanstiehl

1 Capital Farma

1 ACG Worldwide

7 Actylis

4 Aeon Procare

8 Anhui Sunhere Pharmaceutical Excipients Co.,Ltd

20 BASF

1 Bioplus Life Sciences

10 Corel Pharma Chem

4 DFE Pharma

1 Finar

10 Gangwal Chemicals

5 Ideal Cures Pvt Ltd

5 Ingredion Pharma Solutions

17 Kerry

4 Kima Chemical

6 Lonza Capsugel

17 Microlex e.U

1 Nanjing Bold Chemical

2 Novo Excipients

3 Pharmatrans-Sanaq

11 Pluviaendo

4 Prachin Chemical

1 Qianhao Chemical (Hebei) Co., Ltd

1 Qualicaps

35 Roquette

13 Seppic

6 Shanghai Shenmei Pharmaceutical Technology Co., Ltd

2 Shijiazhuang Huaxu Pharmaceutical

11 Sigachi Industries

3 The Dow Chemical Company

1 Valens Pharmachem

4 Vasa Pharmachem

1 Zhejiang Huakang Pharmaceutical

EXCIPIENTS BY APPLICATIONS

75 Fillers, Diluents & Binders

51 Coating Systems & Additives

42 Direct Compression

37 Thickeners and Stabilizers

31 Disintegrants & Superdisintegrants

30 Taste Masking

26 Granulation

26 Solubilizers

26 Controlled & Modified Release

22 Film Formers & Plasticizers

21 Chewable & Orodispersible Aids

20 Lubricants & Glidants

19 Parenteral

17 Co-Processed Excipients

15 Topical

12 Rheology Modifiers

11 API Stability Enhancers

9 Emulsifying Agents