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Triamterene

CAS No.
396-01-0
Chemical Name:
Triamterene
Synonyms
triamteren;ADEMINE;dyrenium;Ademine(Triamterene);ditak;diren;dytac;dyren;teriam;diurene
CBNumber:
CB0663775
Molecular Formula:
C12H11N7
Molecular Weight:
253.26
MDL Number:
MFCD00006708
MOL File:
396-01-0.mol
MSDS File:
SDS
Last updated:2024-03-16 07:03:48

Triamterene 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
pka 6.2(at 25℃)
color Pale Yellow to Yellow
Water Solubility <0.1 G/100 ML AT 20 ºC
Merck 14,9599
BRN 266723
InChIKey FNYLWPVRPXGIIP-UHFFFAOYSA-N
CAS DataBase Reference 396-01-0(CAS DataBase Reference)
FDA UNII WS821Z52LQ
Proposition 65 List Triamterene
ATC code C03DB02
NIST Chemistry Reference Triamterene(396-01-0)
IARC 2B (Vol. 108) 2016
EPA Substance Registry System Triamterene (396-01-0)

Pharmacokinetic data

Protein binding 60%
Excreted unchanged in urine 5-10%
Volume of distribution 2.2-3.7(L/kg)
Biological half-life 2 / 10

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictograms
GHS07
Signal word  Warning
Hazard statements  H302-H315-H319-H335
Precautionary statements  P261-P264-P270-P301+P312-P302+P352-P305+P351+P338
Hazard Codes  Xn,T,F
Risk Statements  22-36/37/38-36/38-23/25-39/23/24/25-23/24/25-11
Safety Statements  26-36/37/39-45-33-24-16-7-36/37
RIDADR  2811
WGK Germany  3
RTECS  UO3470000
HazardClass  6.1(b)
PackingGroup  III
HS Code  2933997500
NFPA 704
0
2 0

Triamterene price More Price(30)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich PHR1722 Triamterene Pharmaceutical Secondary Standard; Certified Reference Material 396-01-0 400mg $179 2024-03-01 Buy
Sigma-Aldrich BP340 Triamterene British Pharmacopoeia (BP) Reference Standard 396-01-0 100MG $244 2024-03-01 Buy
Sigma-Aldrich 1680007 Triamterene United States Pharmacopeia (USP) Reference Standard 396-01-0 200mg $436 2024-03-01 Buy
Alfa Aesar B20044 2,4,7-Triamino-6-phenylpteridine, 98% 396-01-0 5g $37.65 2024-03-01 Buy
Alfa Aesar B20044 2,4,7-Triamino-6-phenylpteridine, 98% 396-01-0 25g $76.65 2024-03-01 Buy
Product number Packaging Price Buy
PHR1722 400mg $179 Buy
BP340 100MG $244 Buy
1680007 200mg $436 Buy
B20044 5g $37.65 Buy
B20044 25g $76.65 Buy

Triamterene Chemical Properties,Uses,Production

Description

Triamterene is an inhibitor of the epithelial sodium channel (ENaC; IC50 = 4.5 μM for the rat channel). In vivo, triamterene (0.5-32 mg/animal) enhances sodium secretion and decreases potassium secretion in adrenalectomized rats. Formulations containing triamterene have been used in the treatment of edema. This product is also available as an analytical reference standard .

Chemical Properties

Yellow Solid

Originator

Jatropur,Rohm,W. Germany,1962

Uses

This 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.

Uses

Triamterene is a potassium-sparing diuretic ie, it inhibits the urinary excretion of potassium

Uses

Triamterene is a weak diuretic with potassium sparing properties; blocks Na+ reuptake in the kidneys.

Definition

ChEBI: Triamterene is pteridine substituted at positions 2, 4 and 7 with amino groups and at position 6 with a phenyl group. A sodium channel blocker, it is used as a diuretic in the treatment of hypertension and oedema. It has a role as a diuretic and a sodium channel blocker.

Manufacturing Process

To 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 Function

Diuretic

Biological Functions

Triamterene (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 Description

Odorless 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 Reactions

Sensitive to light; slowly oxidized upon exposure to air. Insoluble in water.

Reactivity Profile

2,4,7-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 Hazard

Flash point data for 2,4,7-Triamino-6-phenylpteridine are not available; however, 2,4,7-Triamino-6-phenylpteridine is probably combustible.

Mechanism of action

Triamterene 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 Use

Triamterene 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 effects

Because 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.

Synthesis

Triamterene, 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).

Synthesis_396-01-0

Veterinary Drugs and Treatments

Triamterene 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.

Drug interactions

Potentially hazardous interactions with other drugs
ACE inhibitors and angiotensin-II antagonists: enhanced hypotensive effect (risk of severe hyperkalaemia).
Analgesics: increased risk of nephrotoxicity with NSAIDs; increased risk of hyperkalaemia, especially with indometacin; antagonism of hypotensive effect.
Antibacterials: avoid concomitant use with lymecycline.
Antidepressants: enhanced hypotensive effect with MAOIs; increased risk of postural hypotension with tricyclics.
Antipsychotics: enhanced hypotensive effect with phenothiazines.
Antihypertensives: enhanced hypotensive effect; increased risk of first dose hypotensive effect of postsynaptic alpha-blockers, e.g. prazosin.
Ciclosporin: increased risk of hyperkalaemia.
Cytotoxics: increased risk of nephrotoxicity and ototoxicity with platinum compounds.
Lithium: reduced excretion of lithium (risk of lithium toxicity).
Potassium salts: increased risk of hyperkalaemia.
Tacrolimus: increased risk of hyperkalaemia.

Metabolism

Triamterene is extensively metabolised apparently via the cytochrome P450 isoenzyme CYP1A2. It is mainly excreted in the urine in the form of metabolites with some unchanged triamterene; variable amounts are also excreted in the bile.

1006-23-1
140-29-4
396-01-0
Synthesis of Triamterene from 5-Nitroso-2,4,6-triaminopyrimidine and Benzeneacetonitrile
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View Lastest Price from Triamterene manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
Triamterene pictures 2024-03-16 Triamterene
396-01-0
US $0.00-0.00 / g 1g 99.9% 20 tons airuikechemical co., ltd.
Triamterene pictures 2024-03-16 Triamterene
396-01-0
US $0.00 / KG 100g 98%+ 100kg WUHAN CIRCLE POWDER TECHNOLOGY CO.,LTD
Triamterene pictures 2023-08-16 Triamterene
396-01-0
US $0.00 / KG 1KG 99% 50000KG/month Hebei Mojin Biotechnology Co., Ltd
  • Triamterene pictures
  • Triamterene
    396-01-0
  • US $0.00-0.00 / g
  • 99.9%
  • airuikechemical co., ltd.
  • Triamterene pictures
  • Triamterene
    396-01-0
  • US $0.00 / KG
  • 98%+
  • WUHAN CIRCLE POWDER TECHNOLOGY CO.,LTD
  • Triamterene pictures
  • Triamterene
    396-01-0
  • US $0.00 / KG
  • 99%
  • Hebei Mojin Biotechnology Co., Ltd
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