Triamterene

Base Information

• Chemical Name: Triamterene
• CAS No.: 396-01-0
• Molecular Formula: C12H11N7
• Molecular Weight: 253.266
• Hs Code.: 2933997500
• European Community (EC) Number: 206-904-3
• NSC Number: 757367,77625
• UNII: WS821Z52LQ
• DSSTox Substance ID: DTXSID6021373
• Nikkaji Number: J2.040K
• Wikipedia: Triamterene
• Wikidata: Q221520
• NCI Thesaurus Code: C29519
• RXCUI: 10763
• Pharos Ligand ID: HVBUKXJVYVL3
• Metabolomics Workbench ID: 37945
• ChEMBL ID: CHEMBL585
• Mol file: 396-01-0.mol

Synonyms:Dyrenium;Dytac;Triamterene;Urocaudal

Chemical Property of Triamterene

Chemical Property:

• Appearance/Colour: Yellow solid
• Melting Point: 316 °C
• Refractive Index: 1.8260 (estimate)
• Boiling Point: 573.4 °C at 760 mmHg
• PKA: 6.2(at 25℃)
• Flash Point: 335.5 °C
• PSA: 129.62000
• Density: 1.502 g/cm³
• LogP: 2.57700
• Storage Temp.: 2-8°C
• Solubility.: formic acid: soluble200 mg + 4 mL warm Formic Acid, clear, yello
• Water Solubility.: <0.1 g/100 mL at 20℃
• XLogP3: 1
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 1
• Exact Mass: 253.10759338
• Heavy Atom Count: 19
• Complexity: 307

Purity/Quality:

99% ^*data from raw suppliers

Triamterene ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn, T, F
• Hazard Codes: Xn,T,F
• 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

MSDS Files:

SDS file from LookChem

Useful:

• Drug Classes: Diuretics
• Canonical SMILES: C1=CC=C(C=C1)C2=NC3=C(N=C(N=C3N=C2N)N)N
• Recent ClinicalTrials: Data Analysis for Drug Repurposing for Effective Alzheimer's Medicines (DREAM)- Amiloride vs Triamterene
• 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 .
• Uses: Triamterene is a potassium-sparing diuretic ie, it inhibits the urinary excretion of potassium Triamterene is a weak diuretic with potassium sparing properties; blocks Na+ reuptake in the kidneys. 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.
• 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.
• 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.
• 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.

Technology Process of Triamterene

There total 4 articles about Triamterene which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 85.7%

5-nitroso-2,4,6-triaminopyrimidine (1006-23-1) + phenylacetonitrile (140-29-4) → triamterene (396-01-0)

Guidance literature:

With sodium ethanolate; sodium hydroxide; In ethanol; N,N-dimethyl acetamide; at 90 - 100 ℃; Reagent/catalyst;

Reference yield:

5-nitroso-2,4,6-triaminopyrimidine (1006-23-1) + dihydrocinnamonitrile (645-59-0) → triamterene (396-01-0)

Guidance literature:

5-nitroso-2,4,6-triaminopyrimidine; With sodium carbonate; sodium hydroxide; In ethanol; at 79 - 83 ℃;

dihydrocinnamonitrile; In ethanol; at 81 - 83 ℃; for 5.8h; Temperature;

Reference yield:

4-chloro-2-furfurylamino-5-sulfamoyl-benzoic acid (54-31-9) → triamterene (396-01-0)

Guidance literature:

upstream raw materials:

5-nitroso-2,4,6-triaminopyrimidine

phenylacetonitrile

4-chloro-2-furfurylamino-5-sulfamoyl-benzoic acid

dihydrocinnamonitrile

Downstream raw materials:

2,7-diamino-6-phenyl-3H-pteridin-4-one

2,4-diamino-6-phenyl-7(8H)-pteridinone

(S)-2-Amino-4-methyl-pentanoic acid (2,4-diamino-6-phenyl-pteridin-7-yl)-amide

(S)-2-Amino-4-methyl-pentanoic acid (4,7-diamino-6-phenyl-pteridin-2-yl)-amide

Refernces

• 1、 -. "Triamterene compound and preparation method thereof". Paragraph 0011; 0013; 0015. . Retrieved 2018/04/02.
• 2、 -. "Potassium-neutral salureticum with anti-hypertensive effect". . . Retrieved 2008/06/13.