Acetazolamide

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Structural formula
Structure of acetazolamide
General
Non-proprietary name Acetazolamide
other names

N - (5- (aminosulfonyl) -1,3,4-thiadiazol-2-yl) acetamide ( IUPAC )

Molecular formula C 4 H 6 N 4 O 3 S 2
Brief description

White to almost white, crystalline powder

External identifiers / databases
CAS number 59-66-5
EC number 200-440-5
ECHA InfoCard 100,000,400
PubChem 1986
DrugBank DB00819
Wikidata Q413690
Drug information
ATC code

S01 EC01

Drug class

Carbonic anhydrase inhibitors

properties
Molar mass 222,25 g · mol -1
Physical state

firmly

Melting point

260.5 ° C

pK s value

7.2

solubility
  • very sparingly soluble in water (980 mg l −1 at 30 ° C)
  • hardly soluble in ethanol 96%
  • readily soluble in 1 M NH 4 OH (50 g · l −1 ), soluble in DMSO , slightly soluble in methanol and ethanol
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: 315-319
P: 305 + 351 + 338
Toxicological data

1175 mg kg −1 ( LD 50 ,  mouse ,  ip )

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

Acetazolamide is a carbonic anhydrase inhibitor from the sulfonamide class of substances . It is a diuretic and inhibits the absorption of bicarbonate . It can lower intraocular pressure , intracranial pressure, and blood pressure. Acetazolamide leads to increased excretion of potassium with the urine, so that if it is used over a long period, care should be taken to increase the intake of potassium with the food.

Clinical information

Application areas (indications)

Acetazolamide is used in particular for increased eye pressure (glaucoma or "glaucoma") or for edema of various origins (including pseudotumor cerebri or cystoid macular edema ). Acetazolamide can also be used to treat respiratory insufficiency with respiratory alkalosis , pancreatitis or pancreatic fistulas, as well as in epilepsy or Meniere's disease . A study from 2014 aimed to investigate the use of acetazolamide to reduce intracranial pressure in idiopathic normal pressure hydrocephalus.

It is also approved for the preventive treatment of altitude sickness . It works by increasing the ventilation of the lungs when breathing - similar to what is genetically determined in Tibetans - which also makes breathing less effective.

At high altitudes with low oxygen partial pressure, humans breathe faster, which leads to respiratory alkalosis. This is prevented with carbonic anhydrase inhibitors. This reduces the excretion of hydronium ions in the urine in the cells of the proximal tubules of the kidneys.

Acetazolamide also relieves symptoms of certain types of myotonia congenita . However, there is no approval for this area of ​​application.

In the context of cerebral perfusion scintigraphy , acetazolamide is used ( off-label use ) to distinguish areas with normal reserve capacity from areas whose vessels are already maximally dilated to compensate for upstream vasoconstriction.

Side effects

With intravenous use, dizziness , tinnitus , paresthesia around the mouth, nausea and a drop in blood pressure occur. The symptoms are usually mild and go away on their own.

Contraindications

Absolute contraindications are allergies to sulfonamides and the subacute stage of stroke . The relative contraindications are migraines , renal insufficiency and liver insufficiency .

Trade names

Monopreparations

Acemit (D), Diamox (D, A, CH), Glaupax (D, CH)

In Germany, an injection solution for intramuscular or intravenous use is available for acute treatment ( Diamox parenteral ).

Individual evidence

  1. ↑ a b European Pharmacopoeia 6.2.
  2. ↑ a b c d Entry on acetazolamide in the ChemIDplus database of the United States National Library of Medicine (NLM) .
  3. ↑ a b c data sheet Acetazolamide from Sigma-Aldrich , accessed on March 20, 2011 ( PDF ).
  4. ^ H. Knauf and Ernst Mutschler : "Diuretika", Urban & Schwarzenberg , Munich, Vienna, Baltimore 1986, ISBN 3-541-11391-X , page 7.
  5. ↑ a b Heinz Lüllmann , Klaus Mohr, Lutz Hein : Pharmakologie und Toxikologie. Understand the effects of drugs - use drugs in a targeted manner. A textbook for students of medicine, pharmacy and life sciences, a source of information for doctors, pharmacists and health policymakers. 17th, completely revised edition. Thieme, Stuttgart et al. 2010, ISBN 978-3-13-368517-7 , p. 226, ( limited preview in the Google book search).
  6. ↑ clinicaltrials.gov
  7. ↑ Treatment of acute altitude sickness. (No longer available online.) In: arznei-telegram . June 1995, p. 66 , archived from the original on April 13, 2015 ; Retrieved June 17, 2010 .
  8. ↑ Michael Lange: Natural gene doping in Tibet - the Tibetan genetic makeup has adapted to the oxygen-poor air. (No longer available online.) In: WDR 5 , Leonardo - Wissenschaft und mehr, broadcast on May 14, 2010. Archived from the original on December 8, 2015 ; accessed on July 28, 2010 : "Geneticists from the USA and China have discovered two gene variants that enable Tibetans to live in thin mountain air" .
  9. ↑ “ … acetazolamide improved submaximal exercise SaO2 while reducing breathing efficiency through an increase in ventilation… ” Sophie Lalande, Eric M. Snyder, Thomas P. Olson, Minelle L. Hulsebus, Marek Orban, Virend K. Somers, Bruce D. Johnson, Robert P. Frantz: The effects of sildenafil and acetazolamide on breathing efficiency and ventilatory control during hypoxic exercise. In: European Journal of Applied Physiology. Volume 106, No. 4, 2009, pp. 509-515, doi: 10.1007 / s00421-009-1042-5 , PMID 19337745 , PMC 2732568 (free full text, PDF).
  10. ↑ Randall G. Trudell, Kenneth K. Kaiser, Robert C. Griggs: Acetazolamide-responsive myotonia congenita. In: Neurology . Volume 37, No. 3, 1987, pp. 488-491, doi: 10.1212 / WNL.37.3.488 , PMID 3822145 .
  11. ↑ a b c Torsten Kuwert: Brain. In: Torsten Kuwert, Frank Grünwald , Uwe Haberkorn , Thomas Krause : Nuclear Medicine . 4th, newly created and expanded edition. Thieme, Stuttgart et al. 2008, ISBN 978-3-13-118504-4 , p. 231-257 .
  12. ↑ ROTE LISTE 2017, Verlag Rote Liste Service GmbH, Frankfurt am Main, ISBN 978-3-946057-10-9 , p. 157.