Amiloride

Amiloride

Systematic (IUPAC) name
3,5-diamino-6-chloro-N-(diaminomethylene)pyrazine-2-carboxamide
Clinical data
Trade names	Midamor
AHFS/Drugs.com	monograph
Pregnancy cat.	B(US)
Legal status	℞-only (US)
Routes	oral
Pharmacokinetic data
Bioavailability	Readily absorbed
Metabolism	none
Half-life	6 to 9 hours
Excretion	unchanged in urine
Identifiers
CAS number	2016-88-8 Y
ATC code	C03DB01
PubChem	CID 16231
IUPHAR ligand	2421
DrugBank	APRD00790
ChemSpider	15403 Y
UNII	7M458Q65S3 Y
KEGG	D07447 Y
ChEBI	CHEBI:2639 Y
ChEMBL	CHEMBL945 Y
Chemical data
Formula	C6H8ClN7O
Mol. mass	229.627 g/mol
SMILES	eMolecules & PubChem
InChI InChI=1S/C6H8ClN7O/c7-2-4(9)13-3(8)1(12-2)5(15)14-6(10)11/h(H4,8,9,13)(H4,10,11,14,15) Y Key:XSDQTOBWRPYKKA-UHFFFAOYSA-N Y
N(what is this?)  (verify)

Amiloride is a potassium-sparing diuretic, first approved for use in 1967 (then known as MK 870), used in the management of hypertension and congestive heart failure. Amiloride was also tested as treatment of cystic fibrosis, but it was revealed inefficient in vivo due to it's short time of action, therefore longer-acting ENaC inhibitors may prove more effective, e.g. Benzamil.^[1]

Structure

Amiloride is a guanidinium group containing pyrazine derivative.

Mechanism of action

Amiloride works by directly blocking the epithelial sodium channel (ENaC) thereby inhibiting sodium reabsorption in the late distal convoluted tubules, connecting tubules, and collecting ducts in the kidneys (this mechanism is the same for triamterene).^[2] This promotes the loss of sodium and water from the body, but without depleting potassium. The drug is often used in conjunction with thiazide (e.g. co-amilozide) or loop diuretics (e.g. co-amilofruse). Due to its potassium-sparing capacities, hyperkalemia (high blood potassium levels) is occasionally observed in patients taking amiloride. The risk is high in concurrent use of ACE inhibitors or spironolactone. Patients are also advised not to use potassium-containing salt replacements.^[3] Amiloride also carries the risk of developing an acidosis.

A fraction of the effects of amiloride is inhibition of cyclic GMP-gated cation channels in the inner medullary collecting duct.^[4]

Amiloride has a second action on the heart, blocking Na+/H+ exchangers Sodium-hydrogen antiporter 1 or NHE-1. This minimizes reperfusion injury in ischemic attacks.

Acid-sensing ion channels (ASICs) are also sensitive to inhibition by amiloride. ASICs are involved in nociceptor responses to pH ^[5].

Formulations and trade names

• amiloride hydrochloride
  • Midamor (U.S.)

• co-amilozide (amiloride hydrochloride with hydrochlorothiazide)

See also

• Benzamil

References

1. ^ (Review)Pharmacological treatment of the biochemical defect in cystic fibrosis airways, H.C. Rodgers, A.J. Knoxhttp://erj.ersjournals.com/content/17/6/1314.full.pdf+html
2. ^ Loffing, Johannes and Kaissling, Brigitte (2003). "Sodium and calcium transport pathways along the mammalian distal nephron: from rabbit to human". Am J Physiol Renal Physiol 284: F628-F643. PMID 12620920. 
3. ^ LoSalt Advisory Statement (PDF)
4. ^ Walter F., PhD. Boron. Medical Physiology: A Cellular And Molecular Approaoch. Elsevier/Saunders. ISBN 1-4160-2328-3.  page 875
5. ^ Hunt and Koltzenburg 2005 'The neurobiology of pain'

This drug article relating to the cardiovascular system is a stub. You can help Wikipedia by expanding it.v · Categories: Potassium-sparing diuretics Aminopyrazines Guanidines World Health Organization essential medicines Cardiovascular system drug stubs Wikimedia Foundation. 2010. Игры ⚽ Нужен реферат? Crime Stoppers Australia 2-Pentanone Look at other dictionaries: Amiloride — structure et représentation de l amiloride Général Nom IUPAC 3,5 diamino 6 chloro N (diaminomet …   Wikipédia en Français amiloride — amil·o·ride ə mil ə .rīd n a diuretic C6H8ClN7O that promotes sodium excretion and potassium retention * * * n. a potassium sparing diuretic that causes the increased excretion of sodium and chloride; it is often combined with a thiazide or loop… …   Medical dictionary amiloride — n. a potassium sparing diuretic that causes the increased excretion of sodium and chloride; it is often combined with a thiazide or loop diuretic (e.g. hydrochlorothiazide as co amilozide) to reduce the potassium loss that occurs with these drugs …   The new mediacal dictionary amiloride — Drug that blocks sodium/proton antiport; used clinically as a potassium sparing diuretic …   Dictionary of molecular biology amiloride — /euh mil euh ruyd /, n. Pharm. a potassium sparing diuretic, C6H8ClN7O, used in the treatment of hypertension. [perh. (di)ami(no 6 ch)lor(opyrazinam)ide, part of its chemical name] * * * …   Universalium amiloride — noun A particular pyrazine guanidinium compound that is used as a diuretic …   Wiktionary amiloride — amil·o·ride …   English syllables amiloride — aˈmilōrīd, ȯ noun ( s) Etymology: amidino + chlor + amide : a diuretic C6H8ClN7O that promotes sodium excretion and potassium retention * * * /euh mil euh ruyd /, n. Pharm. a potassium sparing diuretic, C6H8ClN7O, used in the treatment of… …   Useful english dictionary amiloride hydrochloride — A nonsteroidal compound exerting an effect similar to that of an aldosterone inhibitor, i.e., urinary sodium excretion is enhanced and potassium excretion is reduced; a potassium sparing diuretic. * * * amil·o·ride …   Medical dictionary amiloride-sensitive sodium channel — epithelial sodium c …   Medical dictionary 18+ © Academic, 2000-2024 Contact us: Technical Support, Advertising Dictionaries export, created on PHP, Joomla, Drupal, WordPress, MODx. Mark and share Search through all dictionaries Translate… Search Internet Share the article and excerpts Direct link … Do a right-click on the link above and select “Copy Link”