Triamterene Chemical Properties
- Melting point:316°C
- Boiling point:386.46°C (rough estimate)
- Density 1.3215 (rough estimate)
- refractive index 1.8260 (estimate)
- Flash point:11 °C
- storage temp. 2-8°C
- solubility formic acid: soluble200 mg + 4 mL warm Formic Acid, clear, yellow-green
- pka6.2(at 25℃)
- form neat
- Water Solubility <0.1 G/100 ML AT 20 ºC
- Merck 14,9599
- BRN 266723
- CAS DataBase Reference396-01-0(CAS DataBase Reference)
- NIST Chemistry ReferenceTriamterene(396-01-0)
- IARC2B (Vol. 108) 2016
- EPA Substance Registry SystemTriamterene (396-01-0)
Triamterene Usage And Synthesis
- Chemical PropertiesYellow Solid
- OriginatorJatropur,Rohm,W. Germany,1962
- UsesTriamterene is a potassium-sparing diuretic ie, it inhibits the urinary excretion of potassium
- UsesThis drug is recommended in combination with other diuretics for treating edema caused by usual reasons such as circulatory insufficiency, cirrhosis of the liver, and nephrotic syndrome.
- UsesTriamterene is a weak diuretic with potassium sparing properties; blocks Na+ reuptake in the kidneys.
- Manufacturing ProcessTo a solution of 9 grams of 5-nitroso-2,4,6-triaminopyrimidine in 500 mi of
refluxing dimethylformamide is added 9 grams of phenylacetonitrile and the
refluxing is stopped. The 3 grams of anhydrous sodium methoxide is added
and the mixture is refluxed for 15 minutes. The mixture is chilled and the
solid is filtered and washed several times with warm water until the washings
are neutral. Drying gives yellow crystals which are recrystallized with a Darco
treatment from formamide-water heating the solution no hotter than 125°C.
This product is then suspended in filtered deionized water and warmed for 15 minutes. This yields the 2,4,7-triamino-6-phenylpteridine as yellow crystals with a MP of 314° to 317°C.
- Therapeutic FunctionDiuretic
- Biological FunctionsTriamterene (Dyrenium) results in changes in urinary electrolyte patterns that are qualitatively similar to those produced by spironolactone. The mechanism by which this agents bring about the alterations in electrolyte loss, however, is quite different. Triamterene produces this effects whether or not aldosterone or any other mineralocorticoid is present. The action of this drug is clearly unrelated to endogenous mineralocorticoid activity, and this drug is effective in adrenalectomized patients.
- General DescriptionOdorless yellow powder or crystalline solid. Melting point 316°C. Almost tasteless at first and with a slightly bitter aftertaste. Acidified solutions give a blue fluorescence. Used as a diuretic drug.
- Air & Water ReactionsSensitive to light; slowly oxidized upon exposure to air. Insoluble in water.
- Reactivity Profile2,4,7-Triamino-6-phenylpteridine neutralizes acids in exothermic reactions to form salts plus water. May be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. Flammable gaseous hydrogen may be generated in combination with strong reducing agents, such as hydrides.
- Fire HazardFlash point data for 2,4,7-Triamino-6-phenylpteridine are not available; however, 2,4,7-Triamino-6-phenylpteridine is probably combustible.
- Mechanism of actionTriamterene is a pyrazine derivative that inhibits reabsorption of sodium ions without
increasing excretion of potassium ions. It exhibits the same approximate effect as spironolactone;
however, it does not competitively bind with aldosterone receptors. Its action does
not have an effect on secretion of aldosterone or its antagonists, which are a result of direct
action on renal tubules.
This potassium sparing diuretic causes a moderate increase in excretion of sodium and bicarbonate ions in urine, and it raises excretion of potassium and ammonia ions. It has little effect on urine volume.
- Clinical UseTriamterene can be used in the treatment of congestive
heart failure, cirrhosis, and the edema caused by
secondary hyperaldosteronism. It is frequently used in
combination with other diuretics except spironolactone.
Amiloride, but not triamterene, possesses antihypertensive
effects that can add to those of the thiazides.
These K+-sparing diuretics have low efficacy when
used alone, since only a small amount of total Na reabsorption
occurs at more distal sites of the nephron.
These compounds are used primarily in combination with other diuretics, such as the thiazides and loop diuretics, to prevent or correct hypokalemia. The availability of fixed-dose mixtures of thiazides with nonsteroidal K+-sparing compounds has proved a rational form of drug therapy. Both triamterene and amiloride are available alone or in combination with hydrochlorothiazide.
- Side effectsBecause the actions of triamterene and amiloride are independent of plasma aldosterone levels, their prolonged administration is likely to result in hyperkalemia. Both amiloride and triamterene are contraindicated in patients with hyperkalemia.Triamterene should not be given to patients with impaired renal function. Potassium intake must be reduced, especially in outpatients.A folic acid deficiency has been reported to occur occasionally following the use of triamterene.
- Chemical SynthesisTriamterene, 2,4,7-triamino-6-phenylpteridine (21.5.13), is synthesized in by
the following scheme. Reacting guanidine with malonodinitrile gives 2,4,6-triaminopyrimidine
(21.5.11). This undergoes nitrosation by reacting it with nitric acid, which results in the formation of 5-nitroso-2,4,6-triaminopyrimidine (21.5.12), which upon condensation with
benzyl cyanide in the presence of sodium methoxide cyclizes into triamterene (21.5.13).
- Veterinary Drugs and TreatmentsTriamterene is a potassium-sparing diuretic that potentially could be used as an alternative to spironolactone for the adjunctive treatment of congestive heart failure in dogs, however, there is little experience associated with its use in dogs or cats.
Triamterene Preparation Products And Raw materials
- Trimethoprim Clarithromycin Docetaxel TRIAMTERENE-D5 Amiloride hydrochloride Bumetanide Entacapone Rivaroxaban Carvedilol β-ESTRADIOL Glibenclamide 2,4-Diamino-6-(p-methoxyphenyl)pteridine hydrochloride N,N',N''-(6-Phenyl-2,4,7-pteridinetriyl)tris-acetamide BIBW 22 Triamterene P-HYDROXY TRIAMTERENE SULFATE 4-hydroxytriamterene propyl 5-[4-(2,4,7-triaminopteridin-6-yl)phenoxy]pentanoate
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