Amiloride

  • 3,5-diamino- N- carbamimidoyl -6- chloropyrazine -2- carboxamide (IUPAC)
  • N- amidino -3 ,5- diamino-6- chloropyrazine -2-carboxamide

2016-88-8 ( amiloride · hydrochloride)

C03DB01

Pale yellow to greenish yellow powder ( amiloride · hydrochloride)

Diuretic

293 ° C ( amiloride · hydrochloride)

8.7

  • Sparingly soluble in cold water
  • Slightly soluble in anhydrous ethanol
  • Practically insoluble in acetone and ethyl acetate
  • Slightly soluble in DMSO

Risk

Template: Infobox chemical / molecular formula search available

Amiloride is a drug from the group of potassium-sparing diuretics (water resources). It is used in combination with another diuretic substance - used to treat a potassium deficiency as a result of heart failure and for the treatment of high blood pressure - usually hydrochlorothiazide. Amiloride came in 1967 as a drug in the market ( Moduretic ®, MSD Sharp & Dohme ).

Chemically, it is located at an amiloride pyrazine. It also contains a guanidino group. Amiloride is light sensitive.

Operation

The effect of amiloride is based on direct blocking the epithelial sodium channel ( ENaC). This is, among others, in the distal portion of the Tubulussystems a nephron of the kidneys where it leads to the resumption of sodium ions from the primary. Amiloride leads to increase potassium excretion by inhibiting sodium reuptake in increased sodium and water loss without however.

Pharmacological properties

Amiloride is always used together with a thiazide diuretic or loop diuretic. Through the potassium-sparing effect may be an increase of serum potassium up to a hyperkalemia. The risk of this is with concurrent use of ACE inhibitors or spironolactone, an aldosterone antagonist, increased. Contraindications include hyperkalaemia (high blood potassium levels), pregnancy and anuria ( abnormal decreased urine production ).

Pharmacokinetics

After oral intake the maximum blood plasma concentration occurs after about 4 hours. 50 % of the absorbed dose is bioavailable, 50% renally excreted 50 % in the faeces. There is hardly metabolism instead; the majority is eliminated unchanged. Amiloride has a half-life of about 18 hours.

Exploration of other properties

In a mouse model of cystic fibrosis Zhou et al. Showed that in the first days after inhalation administered amiloride prevents the typical symptoms of cystic fibrosis, and training / development of chronic lung disease. The symptoms were, however, already exists, no improvement occurred by the treatment. A chronic lung damage apparently prevents the effect of amiloride. This suggests that the changes that trigger the disease in the lungs, may be irreversible.

Further use

The ability of amiloride to block the epithelial sodium channel is also used in the exploration of taste. ENaC is located in the taste receptor cells on the tongue and in the throat area and is involved in the perception of salt taste.

Commercial preparations

Amiloretik (D, A), Comilorid (CH), Diaphal (D), Diursan (D), Ecodurex (CH), Escoretic (CH), Cold (CH), Loradur (A), Moducrin (D) Moduretic (A, CH ), Rhefluin (CH), Tensoflux (D ), various generics (D, A, CH)

Other properties

Amiloride hydrochloride fluoresces under ultraviolet light ( 365 nm wavelength). That makes you look in the detection of thin-layer chromatographic identity test according to the European Pharmacopoeia to use.

Amiloride hydrochloride contains about 12 % water of crystallization; the water of crystallization when heated has an influence on the melting point.

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