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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
Structure of TRIAMTERENE

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)

HIDE SMILES / InChI

Molecular Formula C12H11N7
Molecular Weight 253.2626
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

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.

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
5.0 µM [IC50]
127.0 µM [IC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
DYRENIUM

Cmax

ValueDoseCo-administeredAnalytePopulation
44.77 ng/mL
50 mg single, oral
TRIAMTERENE plasma
Homo sapiens
125.1 ng/mL
100 mg single, oral
TRIAMTERENE plasma
Homo sapiens
46.4 ng/mL
37.5 mg 1 times / day multiple, oral
TRIAMTERENE plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
190.69 ng × h/mL
50 mg single, oral
TRIAMTERENE plasma
Homo sapiens
488.4 ng × h/mL
100 mg single, oral
TRIAMTERENE plasma
Homo sapiens
148.7 ng × h/mL
37.5 mg 1 times / day multiple, oral
TRIAMTERENE plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
1.75 h
50 mg single, oral
TRIAMTERENE plasma
Homo sapiens
2 h
unknown
TRIAMTERENE plasma
Homo sapiens

Funbound

ValueDoseCo-administeredAnalytePopulation
38.7%
100 mg single, oral
TRIAMTERENE plasma
Homo sapiens
33%
37.5 mg 1 times / day multiple, oral
TRIAMTERENE plasma
Homo sapiens

Doses

AEs

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer


Drug as victim

PubMed

Sample Use Guides

In Vivo Use Guide
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
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.
Substance Class Chemical
Record UNII
WS821Z52LQ
Record Status Validated (UNII)
Record Version