Merbromin
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| Names |
| IUPAC name
dibromohydroxymercurifluorescein
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| Identifiers |
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CAS Registry Number
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129-16-8 Y |
| ATC code |
D08AK04 |
| ChEMBL |
ChEMBL2097077 N |
| ChemSpider |
10808965 Y |
| EC number |
204-933-6 |
InChI
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InChI=1S/C20H9Br2O5.Hg.2Na.H2O/c21-13-5-11-17(7-15(13)23)27-18-8-16(24)14(22)6-12(18)19(11)9-3-1-2-4-10(9)20(25)26;;;;/h1-7,24H,(H,25,26);;;;1H2/q;3*+1;/p-3 Y
Key: SQFDQLBYJKFDDO-UHFFFAOYSA-K Y
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InChI=1/C20H9Br2O5.Hg.2Na.H2O/c21-13-5-11-17(7-15(13)23)27-18-8-16(24)14(22)6-12(18)19(11)9-3-1-2-4-10(9)20(25)26;;;;/h1-7,24H,(H,25,26);;;;1H2/q;3*+1;/p-3/rC20H10Br2HgO6.2Na/c21-12-5-10-15(7-14(12)24)29-19-11(6-13(22)18(25)17(19)23-28)16(10)8-3-1-2-4-9(8)20(26)27;;/h1-7,25,28H,(H,26,27);;/q;2*+1/p-2
Key: SQFDQLBYJKFDDO-ISOIBTJNAR
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| Jmol-3D images |
Image |
| KEGG |
D00861 Y |
SMILES
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[Na+].[Na+].[O-]C(=O)c4ccccc4C=1c3cc(Br)c([O-])c([Hg]O)c3O/C/2=C/C(=O)C(/Br)=C\C=1\2
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| UNII |
M0T18YH28D Y |
| Properties |
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Chemical formula
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C20H8Br2HgNa2O6 |
| Molar mass |
750.66 g·mol−1 |
| Appearance |
dark green solid |
| Hazards |
| Main hazards |
Toxic, dangerous for the environment |
| R-phrases |
R26 R27 R28 R33 R50 R53 |
| S-phrases |
S13 S28 S36 S45 S60 S61 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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| N verify (what is: Y/N?) |
| Infobox references |
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Merbromin (marketed as Mercurochrome, Merbromine, Sodium mercurescein, Asceptichrome, Supercrome, Brocasept and Cinfacromin) is a topical antiseptic used for minor cuts and scrapes. Merbromin is an organomercuric disodium salt compound and a fluorescein. It is readily available in most countries but, because of its mercury content, it is no longer sold in France, Germany, or the United States.[1][2][3]
Contents
- 1 Uses
- 2 Mercurochrome
- 3 See also
- 4 References
Uses
Merbromin's best-known use is as a topical antiseptic. When applied on a wound, it stains the skin bright red. In the United States, its use has been superseded by other agents (e.g., povidone iodine, benzalkonium chloride, chloroxylenol). It is still an important antiseptic, particularly in developing nations, due to its “unbelievably low cost.”[4]
Merbromin is also used as a biological dye to mark tissue margins and as a metal dye in industrial dye penetrant inspection to detect metal fractures.
Mercurochrome
Mercurochrome is a trade name of merbromin. The name is also commonly used for over-the-counter antiseptic solutions consisting of merbromin (typically at 2% concentration) dissolved in either ethyl alcohol (tincture) or water (aqueous).
Its antiseptic qualities were discovered by Hugh H. Young in 1918, while working at Johns Hopkins Hospital as a physician.[5] The chemical soon became popular among parents and physicians for everyday antiseptic uses, and it was commonly used for minor injuries in the schoolyard.
The United States Food and Drug Administration (FDA) moved it from the “generally recognized as safe” classification into the “untested” classification to effectively halt its distribution in the United States on October 19, 1998 over fears of potential mercury poisoning.[1] Sales were halted in Germany in 2003,[2] and in France in 2006.[3] It is readily available in most other countries.[citation needed]
Within the United States, products such as Humco Mercuroclear play on the brand recognition history of Mercurochrome, but substitute other ingredients with similar properties (Mercuroclear: "Aqueous solution of benzalkonium chloride and lidocaine hydrochloride").[6]
See also
- Thiomersal, also known as Thimerosal or Merthiolate
References
- ^ a b "Quantitative and Qualitative Analysis of Mercury Compounds in the List". Federal Food, Drug, and Cosmetic Act (FD&C Act). U.S. Food and Drug Administration. 2009-04-30.
- ^ a b de:Merbromin
- ^ a b fr:Merbromine
- ^ Mohite, P. N.; Bhatnagar, A. M. (2009). "Mercurochrome 1% as an Antiseptic for Burns: Economical - but is it Efficacious and Safe?". The Internet Journal of Surgery 21 (2). ISSN 1528-8242.
Apart from these qualities, still the most important factor for which mercurochrome has remained the favorite of the physicians in the developing countries is its attractive price. The compound is being sold at unbelievably low cost ... the reasons being the low manufacturing cost, longer shelf life, use in diluted form and importantly less propaganda about its medical use.
- ^ Wilner, I. (2006). The Man Time Forgot: A Tale of Genius, Betrayal, and the Creation of Time Magazine. Harper Collins. p. 230. ISBN 0-06-050549-4.
- ^ "Mercuroclear MSDS" (PDF). Humco.
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Mercury compounds
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| Mercury(I) |
- HgH
- Hg2H2
- Hg2Br2
- Hg2Cl2
- Hg2F2
- Hg2I2
- Hg2(NO3)2
- Hg2O
- Hg2CO3
- Hg2SO4
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| Mercury(II) |
- HgH2
- HgNH2Cl
- HgSe
- HgS
- HgTe
- Hg(O2CCH3)2
- HgBr2
- HgCl2
- Hg(CN)2
- HgF2
- Hg(OH)2
- HgI2
- Hg(NO3)2
- HgO
- HgSO4
- Hg(SCN)2
- Hg(CNO)2
- Hg3N2
- Hg(Si(CH3)3)2
- K2HgI4
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Organomercury
compounds
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- Hg(CH3)2
- Hg(C2H5)2
- Hg(C6H5)2
- HgC6H5CH3CO2
- HgC6H5OB(OH)2
- HgClC6H4CO2H
- HgOHCH2CHOCH3CH2(NHCO)2C2H4CO2H
- HgOHCH2CHOCH3CH2NHCOC6H4OCH2CO2H
- Na2HgOHC6HOBrC6H2OBrOCHC6H4CO2
- HgOC6H2CH3NO2
- NaHgC2H5SC6H4CO2
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| Mercury(IV) |
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| Amalgams |
- Na(Hg)
- Al(Hg)
- K(Hg)
- Au(Hg)
- Tl(Hg)
- Sn(Hg)
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| Mercury cations |
- Hg2+
- Hg4+
- Hg22+
- Hg32+
- Hg42+
- Hg34+
- HgCH3+
- HgC2H5+
- HgC6H5+
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Antiseptics and disinfectants (D08)
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| Acridine derivatives |
- Ethacridine lactate
- 9-Aminoacridine
- Euflavine
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| Biguanides and amidines |
- Dibrompropamidine
- Chlorhexidine#
- Propamidine
- Hexamidine
- Polihexanide
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| Phenol and derivatives |
- Hexachlorophene
- Policresulen
- Phenol
- Triclosan
- Chloroxylenol#
- Biphenylol
- Fenticlor
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| Nitrofuran derivatives |
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| Iodine products |
- Iodine/octylphenoxypolyglycolether
- Povidone-iodine#
- Diiodohydroxypropane
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| Quinoline derivatives |
- Dequalinium
- Chlorquinaldol
- Oxyquinoline
- Clioquinol
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| Quaternary ammonium compounds |
- Benzalkonium
- Benzethonium chloride
- Cetrimonium (bromide/chloride)
- Cetylpyridinium
- Cetrimide
- Benzoxonium chloride
- Didecyldimethylammonium chloride
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| Mercurial products |
- Mercuric amidochloride
- Phenylmercuric borate
- Mercuric chloride
- Merbromin
- Thiomersal
- Mercuric iodide
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| Silver compounds |
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| Alcohols |
- Propanol (propyl alcohol)
- Isopropanol (isopropyl alcohol)
- Ethanol (ethyl alcohol)#
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| Other |
- Potassium permanganate
- Sodium hypochlorite
- Hydrogen peroxide
- Eosin
- Tosylchloramide
- Octenidine dihydrochloride
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- #WHO-EM
- ‡Withdrawn from market
- Clinical trials:
- †Phase III
- §Never to phase III
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Index of skin
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| Description |
- Anatomy
- Physiology
- Development
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| Disease |
- Infections
- Vesiculobullous
- Dermatitis and eczema
- Papulosquamous
- Urticaria and erythema
- Radiation-related
- Pigmentation
- Mucinoses
- Keratosis, ulcer, atrophy, and necrobiosis
- Vasculitis
- Fat
- Neutrophilic and eosinophilic
- Congenital
- Neoplasms and cancer
- nevi and melanomas
- epidermis
- dermis
- Symptoms and signs
- Terminology
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| Treatment |
- Procedures
- Drugs
- antibiotics
- disinfectants
- emollients and protectives
- itch
- psoriasis
- other
- Wound and ulcer
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