page_title: Metolazone
section_title: Chemistry
hierarchical_section_title: Metolazone / Chemistry
caption_attribution_description: English: Chemical structure of Metolazone
context_page_description: Metolazone is a thiazide-like diuretic marketed under the brand names Zytanix, Metoz, Zaroxolyn, and Mykrox. It is primarily used to treat congestive heart failure and high blood pressure. Metolazone indirectly decreases the amount of water reabsorbed into the bloodstream by the kidney, so that blood volume decreases and urine volume increases. This lowers blood pressure and prevents excess fluid accumulation in heart failure. Metolazone is sometimes used together with loop diuretics such as furosemide or bumetanide, but these highly effective combinations can lead to dehydration and electrolyte abnormalities.
  It was patented in 1966 and approved for medical use in 1974.
context_section_description: The use of activated anthranilic acid derivatives facilitates the preparation of the
  amides in those cases where the amines are either unreactive or difficult to obtain.
  Thus, reaction of (1) with phosgene gives the reactive the isatoic anhydride (2). Condensation of that with ortho-toluidine leads to the acylation product (3) formed with a simultaneous loss of carbon dioxide. This is then converted to the quinazolone (4) by heating with acetic anhydride. Reaction with sodium borohydride in the presence of aluminum chloride selectively reduces the double bond to yield the diuretic agent metolazone (5).
caption: Metolazone center:[5]
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