Guaifenesin

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Structural formula
Structure of guaifenesin
( R ) -isomer (top) and ( S ) -isomer (bottom)
1: 1 mixture of stereoisomers
General
Non-proprietary name Guaifenesin
other names
  • ( RS ) -3- (2-methoxyphenoxy) propane-1,2-diol
  • Guaiacol glycerol ether
Molecular formula C 10 H 14 O 4
External identifiers / databases
CAS number 93-14-1
EC number 202-222-5
ECHA InfoCard 100.002.021
PubChem 3516
ChemSpider 3396
DrugBank DB00874
Wikidata Q420682
Drug information
ATC code

R05 CA03

Drug class

Expectorans

properties
Molar mass 198.22 g · mol -1
Physical state

firmly

Melting point

78-81 ° C

boiling point

215 ° C (at 25 h Pa )

solubility

in water (50 g l −1 at 25 ° C)

safety instructions
Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed
GHS labeling of hazardous substances
07 - Warning

Caution

H and P phrases H: 302
P: no P-phrases
Toxicological data

1510 mg kg −1 ( LD 50 ,  rat ,  oral )

As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Guaifenesin is a drug from the chemical group of guaiacol derivatives and is used to dissolve bronchial secretions ( expectorant ) z. B. used in respiratory infections .

history

The precursor to guaifenesin, creosote , was used as an expectorant and deodorant as early as the 19th century . It consisted of guaiacol and creosol .

Since some patients reacted to treatment with this mixture with gastrointestinal complaints, guaifenesin was developed in 1954, which was now the pure guaiacol glycerol ether. In 1959 it was launched in America under the name "Robitussin" and since 1982 in Germany too.

Various combination preparations followed as capsules and juices.

Pharmacological properties

Guaifenesin has a liquefying effect; the effect is supposed to come about as a reflex by irritating the gastric mucosa , which leads to a parasympathetic stimulation of the bronchial glands.

In higher doses, guaifenesin relaxes muscles . In the event of a severe overdose , nausea and vomiting may occur, and muscle relaxation may occur which requires immediate medical attention.

Clinical information

Application areas (indications)

Guaifenesin is indicated for dissolving mucus in the bronchial area, for example in the case of colds , flu-like infections and bronchitis . Guaifenesin is effective orally .

In veterinary medicine , guaifenesin, along with ketamine and xylazine, is part of the popular triple drip for intravenous anesthesia .

Contraindications (contraindications)

Drug interactions

Guaifenesin enhances the effects of sedatives and muscle relaxants . The simultaneous use of cough suppressants ( antitussives ) poses a risk of congestion of secretions.

Adverse effects (side effects)

Other Information

Guaifenesin was approved as an expectorant by the US Food and Drug Administration (FDA) in 1952 , where it is considered the only expectorant that has been assessed as effective by the FDA. In the German-speaking countries, its therapeutic significance is questionable, especially since expectorant drugs with a more favorable risk-benefit ratio are available.

There are anecdotal reports about the use of guaifenesin in the treatment of fibromyalgia , which goes back to an alternative medical treatment concept of an American doctor. A therapeutic efficacy could not be proven in controlled studies .

literature

Trade names

Monopreparations
Fagusan ("beech tar") (D), Longtussin (D), Myoscain (A), Resyl (A, CH), Vicks cough solver (CH), Wick cough solver (D); Kirkland Signature Mucus Relief Chest (USA), Mucinex (USA), Perrigo Guaifenesin 600 mg Extended Release (generic Mucinex) (USA)
Combination preparations
Bricanyl compositum (A), Bronchostop (A), Demo Cough Elixir (CH), Escotussin (CH), Pecto-Baby (CH), Pectocalmine (CH), Resyl with Codeine (A), Resyl plus (A, CH), Sano Tuss (CH), Tuscalman (CH), Wick DayMed cold drink (D)

Individual evidence

  1. ↑ a b c d e data sheet guaiacol glycerol ether (PDF) from Merck , accessed on April 3, 2011.
  2. ↑ Guaifenesin data sheet from Acros, accessed on February 26, 2010.
  3. ^ A b Wolf-Dieter Müller-Jahncke , Christoph Friedrich , Ulrich Meyer: Medicinal history . Wissenschaftliche Verlagsgesellschaft mbH, Stuttgart 2005, ISBN 978-3-8047-2113-5 , p. 184 .
  4. ↑ a b K. Hardtke et al. (Ed.): Commentary on the European Pharmacopoeia Ph. Eur. 4.05, Guaifenesin. Loose-leaf collection, 19th delivery 2005, Wissenschaftliche Verlagsgesellschaft Stuttgart.
  5. ↑ entry to guaifenesin in Vetpharm, accessed on 3 December 2011th
  6. ↑ akdae.de: Drug Ordinance in Practice, Volume 38, Issue 5, September 2011 (PDF; 352 kB).
  7. ↑ RM Bennett, P. De Garmo, SR Clark (1996): A Randomized, Prospective, 12 Month Study To Compare The Efficacy Of Guaifenesin Versus Placebo In The Management Of Fibromyalgia (reprint). Arthritis and Rheumatism 39 (10): p. 212, doi: 10.1002 / art.1780391402 .