Merbromin

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Structural formula
Structure of merbromin
General
Non-proprietary name Merbromin
other names

2,7-dibromo-4- (hydroxymercuri) fluorescein

Molecular formula
  • C 20 H 8 Br 2 HgNa 2 O 6 (merbromine disodium salt)
  • C 20 H 10 Br 2 HgO 6 (merbromine)
Brief description

dark green solid

External identifiers / databases
CAS number
  • 129-16-8 (Merbromin Di- sodium salt )
  • 55728-51-3 (Merbromin)
EC number 204-933-6
ECHA InfoCard 100.004.486
PubChem 441373
ChemSpider 10808965
DrugBank DB13392
Wikidata Q419070
Drug information
ATC code

D08 AK04

Drug class

antiseptic

properties
Molar mass
  • 750.66 g mol −1 (merbromine disodium salt)
  • 706.69 g mol −1 (merbromin)
Physical state

firmly

Melting point

> 300 ° C (merbromin disodium salt)

solubility

very light in water (1500 g l −1 at 20 ° C, merbromine disodium salt)

safety instructions
Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed
GHS hazard labeling from  Regulation (EC) No. 1272/2008 (CLP) , expanded if necessary
06 - Toxic or very toxic 08 - Dangerous to health 09 - Dangerous for the environment

danger

H and P phrases H: 300-310-330-373-410
P: 260-264-273-280-284-301 + 310
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Merbromin is a fluorescent triphenylmethane and xanthene dye , similar to eosin and fluorescein .

Tip of a mercurochrome bottle. The intrinsic red color and the greenish fluorescence are clearly visible

use

The mercury-containing dye was sold in Germany until June 30, 2003 in the form of a two percent aqueous solution as an antiseptic (trade name Mercurochrome).

It has long been popular as an antiseptic for treating skin injuries such as cuts and abrasions . However, today it is controversial because of its mercury content ( toxic in the event of absorption , environmental pollution) and is no longer available in Germany as a finished preparation or a recipe.

Medical publications sometimes speak of a rather questionable effect.

However, this is mainly due to the fact that a well-founded and gradually weighed benefit-harm scale was never drawn up and the antiseptic was recently criticized mainly because of its very well adhering but red color. Merbromine is often confused with the alternative antiseptic mercuchrome, which, however, consists of a povidone-iodine solution.

"Mercurochrome" is the US drug name. It continues to be used very successfully around the world, especially in the treatment of open tropical ulcers. In the private sector it still seems to be very popular as a home remedy because of its rapid wound healing. In France, "Mercurochrome" is just a trademark under which other medical devices are sold.

Octenidine is often suggested as a modern alternative, but it is more used for cleaning wounds and was used earlier as an antiseptic anilline dye. Merbromin itself is not a classic Hg salt in the sense of Hg-Br! It is attached to a dense lipophilic molecule with a hydrophilic end. Therefore, it also adheres well to the lipophilic skin and causes it to loosen again when the skin regenerates and flakes. On the whole, it is readily soluble in water and , in contrast to the newer antiseptics , diffuses less into the tissue due to its molecular size, at least not clinically observable. Since Merbromin granulates wounds much better than Octanisept , Mercurochrome was previously used on dry, difficult to heal and well pre-cleaned wounds. In the 1970s, the bromine-iodine sticks , which are much more effective than iodine, were pushed out of households for reasons of profit optimization . Because of the accelerated granulation and healing, merbromine was avoided in split-thickness skin grafts because of the risk of detachment. It was also avoided in the long-term treatment of larger wound areas, which have to granulate from the inside out before a secondary, but more successful wound healing can occur.

The low Hg molecular content, the low concentration, the small amount of surface used and the good surface adhesion suggest concentrations well below the natural Hg exposure. The green fluorescence component is more likely to be triggered by the mesomerism of the anillin-like effective molecular component and is reinforced by detergent surfactants. As with Octanisept, the anillin-like part of the molecule also has a slightly antiseptic effect. The colorless Octanisept can theoretically be changed into any fluorescent red or green color after only a slight chemical change. This seems less useful with mainly cleansing antiseptics than with pure wound tinctures. The practical use of different wound tinctures is still undisputed, as there are the most varied forms of wounds with different degrees of severity and healing tendencies on the most diverse parts of the body. In addition to simplified documentation, the focus should always be on the success of the treatment on the whole person.

Individual evidence

  1. a b c d Entry on Merbromin in the GESTIS substance database of the IFA , accessed on February 11, 2017(JavaScript required) .
  2. Data sheet Mercury dibromofluorescein disodium salt from Sigma-Aldrich , accessed on April 9, 2011 ( PDF ).
  3. Not explicitly listed in Regulation (EC) No. 1272/2008 (CLP) , but with the specified labeling it falls under the group entry organic compounds of mercury with the exception of those specified elsewhere in this Annex in the Classification and Labeling Inventory of the European Chemicals Agency ( ECHA), accessed on February 1, 2016. Manufacturers or distributors can expand the harmonized classification and labeling .
  4. a b Merbromin in the mirror of expert opinions , Pharmazeutische Zeitung , September 22, 2003.
  5. Disinfectant Mercurochrome: We Were the Red Army , Spiegel Online , July 17, 2013.