Details
Stereochemistry | ACHIRAL |
Molecular Formula | C12H11N7 |
Molecular Weight | 253.2626 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
NC1=NC2=C(N=C(C3=CC=CC=C3)C(N)=N2)C(N)=N1
InChI
InChIKey=FNYLWPVRPXGIIP-UHFFFAOYSA-N
InChI=1S/C12H11N7/c13-9-7(6-4-2-1-3-5-6)16-8-10(14)18-12(15)19-11(8)17-9/h1-5H,(H6,13,14,15,17,18,19)
DescriptionSources: http://www.drugbank.ca/drugs/DB00384Curator's Comment: Description was created based on several sources, including
https://www.drugs.com/triamterene.html
Sources: http://www.drugbank.ca/drugs/DB00384
Curator's Comment: Description was created based on several sources, including
https://www.drugs.com/triamterene.html
Triamterene, a relatively weak, potassium-sparing diuretic and antihypertensive, is used in the management of hypokalemia. Triamterene inhibits the epithelial sodium channels on principal cells in the late distal convoluted tubule and collecting tubule, which are responsible for 1-2% of total sodium reabsorption. As sodium reabsorption is inhibited, this increases the osmolarity in the nephron lumen and decreases the osmolarity of the interstitium. Since sodium concentration is the main driving force for water reabsorption, triamterene can achieve a modest amount of diuresis by decreasing the osmotic gradient necessary for water reabsorption from lumen to interstitium. Triamterene also has a potassium-sparing effect. Normally, the process of potassium excretion is driven by the electrochemical gradient produced by sodium reabsorption. As sodium is reabsorbed, it leaves a negative potential in the lumen, while producing a positive potential in the principal cell. This potential promotes potassium excretion through apical potassium channels. By inhibiting sodium reabsorption, triamterene also inhibits potassium excretion.Triamterene is used for the treatment of edema associated with congestive heart failure, cirrhosis of the liver, and the nephrotic syndrome; also in steroid-induced edema, idiopathic edema, and edema due to secondary hyperaldosteronism. Triamterene is maeketed under the trade name Dyrenium.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
5.0 µM [IC50] | |||
Target ID: CHEMBL2111408 Sources: https://www.ncbi.nlm.nih.gov/pubmed/6321204 |
127.0 µM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | DYRENIUM Approved UseEdema: For the treatment of edema associated with congestive heart failure, cirrhosis of the liver and the nephrotic syndrome; also in steroid-induced edema, idiopathic edema and edema due to secondary hyperaldosteronism. Launch Date-1.70294395E11 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
46.4 ng/mL |
37.5 mg 1 times / day multiple, oral dose: 37.5 mg route of administration: Oral experiment type: MULTIPLE co-administered: HYDROCHLOROTHIAZIDE |
TRIAMTERENE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
125.1 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7166735 |
100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered: |
TRIAMTERENE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
44.77 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/21193005 |
50 mg single, oral dose: 50 mg route of administration: Oral experiment type: SINGLE co-administered: |
TRIAMTERENE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
148.7 ng × h/mL |
37.5 mg 1 times / day multiple, oral dose: 37.5 mg route of administration: Oral experiment type: MULTIPLE co-administered: HYDROCHLOROTHIAZIDE |
TRIAMTERENE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
488.4 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7166735 |
100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered: |
TRIAMTERENE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
190.69 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/21193005 |
50 mg single, oral dose: 50 mg route of administration: Oral experiment type: SINGLE co-administered: |
TRIAMTERENE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
1.75 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/21193005 |
50 mg single, oral dose: 50 mg route of administration: Oral experiment type: SINGLE co-administered: |
TRIAMTERENE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
2 h |
unknown |
TRIAMTERENE plasma | Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
Funbound
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
33% |
37.5 mg 1 times / day multiple, oral dose: 37.5 mg route of administration: Oral experiment type: MULTIPLE co-administered: HYDROCHLOROTHIAZIDE |
TRIAMTERENE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
38.7% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7166735 |
100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered: |
TRIAMTERENE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
Doses
Dose | Population | Adverse events |
---|---|---|
100 mg 2 times / day multiple, oral Dose: 100 mg, 2 times / day Route: oral Route: multiple Dose: 100 mg, 2 times / day Co-administed with:: hydrochlorothiazide(50 mg twice daily; 28 days) Sources: |
unhealthy, 54 ± 3 years n = 9 Health Status: unhealthy Condition: hypokalemia Age Group: 54 ± 3 years Population Size: 9 Sources: |
Other AEs: Kidney failure... |
37.5 mg 1 times / day single, oral Dose: 37.5 mg, 1 times / day Route: oral Route: single Dose: 37.5 mg, 1 times / day Co-administed with:: hydrochlorothiazide(25 mg) Sources: |
unhealthy Health Status: unhealthy Sources: |
Disc. AE: Hyperkalemia... AEs leading to discontinuation/dose reduction: Hyperkalemia Sources: |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Kidney failure | acute | 100 mg 2 times / day multiple, oral Dose: 100 mg, 2 times / day Route: oral Route: multiple Dose: 100 mg, 2 times / day Co-administed with:: hydrochlorothiazide(50 mg twice daily; 28 days) Sources: |
unhealthy, 54 ± 3 years n = 9 Health Status: unhealthy Condition: hypokalemia Age Group: 54 ± 3 years Population Size: 9 Sources: |
Hyperkalemia | Disc. AE | 37.5 mg 1 times / day single, oral Dose: 37.5 mg, 1 times / day Route: oral Route: single Dose: 37.5 mg, 1 times / day Co-administed with:: hydrochlorothiazide(25 mg) Sources: |
unhealthy Health Status: unhealthy Sources: |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Sources: https://dmd.aspetjournals.org/content/36/6/995 Page: 3.0 |
yes | |||
yes |
PubMed
Title | Date | PubMed |
---|---|---|
Screening for 18 diuretics and probenecid in doping analysis by liquid chromatography-tandem mass spectrometry. | 2002 Dec |
|
Liddle's syndrome associated with a point mutation in the extracellular domain of the epithelial sodium channel gamma subunit. | 2002 Dec |
|
Non-traumatic neurological emergencies: emergency neuroradiological interventions. | 2002 Jul |
|
Micellar electrokinetic capillary chromatography analysis of diuretics in pharmaceutical formulations. | 2002 May 16 |
|
[Liddle's syndrome: late diagnosis of a rare cause of arterial hypertension]. | 2002 May-Jun |
|
Thiazide-induced lichenoid photosensitivity. | 2002 Nov |
|
Acetazolamide-induced muscle weakness in hypokalemic periodic paralysis. | 2002 Sep |
|
Rational diuretic management in congestive heart failure: a case-based review. | 2003 Dec |
|
Direct determination of triamterene by potentiometry using a coated wire selective electrode. | 2003 Dec 4 |
|
Restoration of arterial baroreflex function contributes to organ protection in spontaneously hypertensive rats treated with long-term hydrochlorothiazide mixture. | 2003 Jan-Feb |
|
Kinetic modeling of triamterene intestinal absorption and its inhibition by folic acid and methotrexate. | 2003 May |
|
Endovascular treatment of a wide-neck renal artery bifurcation aneurysm. | 2003 Nov |
|
Mutations in the epithelial Na+ channel ENaC outer pore disrupt amiloride block by increasing its dissociation rate. | 2003 Oct |
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Drug-induced renal calculi: epidemiology, prevention and management. | 2004 |
|
Treatment of congenital nephrogenic diabetes insipidus with hydrochlorothiazide and amiloride in an adult patient. | 2004 |
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Transvenous coil treatment of a type a carotid cavernous fistula in association with transarterial trispan coil protection. | 2004 Apr |
|
[Determination of five components in compound hypotensive tablet by HPLC]. | 2004 Aug |
|
Application of PLS regression to fluorimetric data for the determination of furosemide and triamterene in pharmaceutical preparations and triamterene in urine. | 2004 Feb 6 |
|
Application of a fluorescence sensor for miniscale on-line monitoring of powder mixing kinetics. | 2004 Jan |
|
Effects of pH and the presence of micelles on the resolution of diuretics by reversed-phase liquid chromatography. | 2004 Jan 2 |
|
[Circadian rhythm of the renin-angiotensin-aldosterone system: a summary of our research studies]. | 2004 Jul-Aug |
|
Coil treatment of a fusiform upper basilar trunk aneurysm with a combination of "kissing" neuroform stents, TriSpan-, 3D- and fibered coils, and permanent implantation of the microguidewires. | 2004 Jun |
|
Triamterene-beta-cyclodextrin systems: preparation, characterization and in vivo evaluation. | 2004 Mar 29 |
|
Rate-limiting biotransformation of triamterene is mediated by CYP1A2. | 2005 Jul |
|
Prediction of genotoxicity of chemical compounds by statistical learning methods. | 2005 Jun |
|
Multicommuted flow-through fluorescence optosensor for determination of furosemide and triamterene. | 2005 Nov |
|
Drug-induced megaloblastic anemia. | 2005 Oct |
|
[Differential diagnosis of a macrocytic, hyperchromic anemia following alcohol abuse and simultaneous therapy with triamterene and cotrimoxazole]. | 2005 Sep 23 |
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[Drug-induced renal calculi]. | 2006 Apr |
|
High-speed gas chromatography in doping control: fast-GC and fast-GC/MS determination of beta-adrenoceptor ligands and diuretics. | 2006 Dec |
|
[Diuretic therapy in heart failure]. | 2006 Jan-Feb |
|
[Influence of diuretics on occupationally important qualities of engine drivers]. | 2007 |
|
Stereoselective syntheses of the 2-Isopropenyl-2,3-dihydrobenzofuran nucleus: potential chiral building blocks for the syntheses of tremetone, hydroxytremetone, and rotenone. | 2007 Apr 13 |
|
Fast quantitative determination of diuretic drugs in tablets and human urine by microchip electrophoresis with native fluorescence detection. | 2007 Aug |
|
Naturalised Vitis rootstocks in Europe and consequences to native wild grapevine. | 2007 Jun 13 |
|
Update of diuretics in the treatment of hypertension. | 2007 Mar-Apr |
|
A study of western pharmaceuticals contained within samples of Chinese herbal/patent medicines collected from New York City's Chinatown. | 2007 Sep |
|
Determination of norfloxacin in rat liver perfusate using capillary electrophoresis with laser-induced fluorescence detection. | 2007 Sep 1 |
|
Determination of losartan and triamterene in pharmaceutical compounds and urine using cathodic adsorptive stripping voltammetry. | 2008 |
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Practical aspects in the management of hypokalemic periodic paralysis. | 2008 Apr 21 |
|
Development of a vessel-simulating flow-through cell method for the in vitro evaluation of release and distribution from drug-eluting stents. | 2008 Aug 25 |
|
Chemical and genetic validation of dihydrofolate reductase-thymidylate synthase as a drug target in African trypanosomes. | 2008 Jul |
|
Quantitative investigation of the role of breast cancer resistance protein (Bcrp/Abcg2) in limiting brain and testis penetration of xenobiotic compounds. | 2008 Jun |
|
The prince and the pauper. A tale of anticancer targeted agents. | 2008 Oct 23 |
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Responses to diuretic treatment in gene-targeted mice lacking serum- and glucocorticoid-inducible kinase 1. | 2009 |
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Update on the treatment of ocular toxoplasmosis. | 2009 |
|
Graz Endocrine Causes of Hypertension (GECOH) study: a diagnostic accuracy study of aldosterone to active renin ratio in screening for primary aldosteronism. | 2009 Apr 7 |
|
Consensus guidelines for oral dosing of primarily renally cleared medications in older adults. | 2009 Feb |
|
[Asynchronous lumbar synovial cysts after surgical resection: a case report]. | 2009 Mar-Apr |
|
Heritable forms of hypertension. | 2009 Oct |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.drugs.com/ppa/triamterene.html
Edema: Oral: 100 to 300 mg daily in 1 to 2 divided doses; maximum dose: 300 mg daily
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/6129855
Triamterene in the concentration range from 8X10(-13) mol/l to 8X10(-3) mol/l exerted a dose-dependent inhibitory effect of the rat kidney plasma membrane Na-K-Mg-ATPase and Na-K-ATPase activities--estimated IC50 values lay at about 8X10(-3) mol/l and 8X10(-7) mol/l, respectively.
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C49186
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LIVERTOX |
NBK547859
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N0000008859
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DB00384
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Triamterene
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100000092570
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TRIAMTERENE
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C29519
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ACTIVE MOIETY
METABOLITE ACTIVE (PARENT)
METABOLITE ACTIVE (PARENT)