U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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

Description
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

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
DYRENIUM

Approved Use

Edema: 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

Cmax

ValueDoseCo-administeredAnalytePopulation
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
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
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

AUC

ValueDoseCo-administeredAnalytePopulation
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
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
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

T1/2

ValueDoseCo-administeredAnalytePopulation
1.75 h
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

Funbound

ValueDoseCo-administeredAnalytePopulation
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%
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

Doses

DosePopulationAdverse 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...
Other AEs:
Kidney failure (acute)
Sources:
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
Disc. AE: Hyperkalemia...
AEs leading to
discontinuation/dose reduction:
Hyperkalemia
Sources:
AEs

AEs

AESignificanceDosePopulation
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
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer


Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
yes
yes
PubMed

PubMed

TitleDatePubMed
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
Drug-induced renal calculi: epidemiology, prevention and management.
2004
Treatment of congenital nephrogenic diabetes insipidus with hydrochlorothiazide and amiloride in an adult patient.
2004
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
[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
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
Responses to diuretic treatment in gene-targeted mice lacking serum- and glucocorticoid-inducible kinase 1.
2009
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
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.
Name Type Language
TRIAMTERENE
EP   HSDB   INN   MART.   MI   ORANGE BOOK   USAN   USP   USP-RS   VANDF   WHO-DD  
INN   USAN  
Official Name English
DYAZIDE COMPONENT TRIAMTERENE
Common Name English
SK&F 8542
Code English
TRIAMTERENE [USP MONOGRAPH]
Common Name English
2,4,7-PTERIDINETRIAMINE, 6-PHENYL-
Systematic Name English
TRIAMTERENE COMPONENT OF DYAZIDE
Common Name English
NSC-639359
Code English
TRIAMTERENE [ORANGE BOOK]
Common Name English
TRIAMTERENE [JAN]
Common Name English
TRIAMTERENE [USAN]
Common Name English
TRIAMTERENE [IARC]
Common Name English
TRIAMTERENE [USP IMPURITY]
Common Name English
TRIAMTERENE [USP-RS]
Common Name English
TRIAMTERENE [MART.]
Common Name English
triamterene [INN]
Common Name English
SK-8542
Code English
MAXZIDE COMPONENT TRIAMTERENE
Common Name English
2,4,7-Triamino-6-phenylpteridine
Systematic Name English
NSC-77625
Code English
TRIAMTERENE [HSDB]
Common Name English
SK&F-8542
Code English
TRIAMTERENE [MI]
Common Name English
TRIAMTERENE [VANDF]
Common Name English
TRIAMTERENE COMPONENT OF MAXZIDE
Common Name English
TRIAMTERENE [EP MONOGRAPH]
Common Name English
Triamterene [WHO-DD]
Common Name English
Classification Tree Code System Code
WHO-ATC C03DB02
Created by admin on Thu Jul 06 10:38:19 UTC 2023 , Edited by admin on Thu Jul 06 10:38:19 UTC 2023
NDF-RT N0000175418
Created by admin on Thu Jul 06 10:38:19 UTC 2023 , Edited by admin on Thu Jul 06 10:38:19 UTC 2023
NCI_THESAURUS C49186
Created by admin on Thu Jul 06 10:38:19 UTC 2023 , Edited by admin on Thu Jul 06 10:38:19 UTC 2023
LIVERTOX NBK547859
Created by admin on Thu Jul 06 10:38:19 UTC 2023 , Edited by admin on Thu Jul 06 10:38:19 UTC 2023
NDF-RT N0000175359
Created by admin on Thu Jul 06 10:38:19 UTC 2023 , Edited by admin on Thu Jul 06 10:38:19 UTC 2023
WHO-VATC QC03DB02
Created by admin on Thu Jul 06 10:38:19 UTC 2023 , Edited by admin on Thu Jul 06 10:38:19 UTC 2023
NDF-RT N0000008859
Created by admin on Thu Jul 06 10:38:19 UTC 2023 , Edited by admin on Thu Jul 06 10:38:19 UTC 2023
Code System Code Type Description
NSC
77625
Created by admin on Thu Jul 06 10:38:19 UTC 2023 , Edited by admin on Thu Jul 06 10:38:19 UTC 2023
PRIMARY
RS_ITEM_NUM
1680007
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PRIMARY
ChEMBL
CHEMBL585
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PRIMARY
CAS
396-01-0
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PRIMARY
PUBCHEM
5546
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PRIMARY
DRUG BANK
DB00384
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PRIMARY
LACTMED
Triamterene
Created by admin on Thu Jul 06 10:38:19 UTC 2023 , Edited by admin on Thu Jul 06 10:38:19 UTC 2023
PRIMARY
SMS_ID
100000092570
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PRIMARY
WIKIPEDIA
TRIAMTERENE
Created by admin on Thu Jul 06 10:38:19 UTC 2023 , Edited by admin on Thu Jul 06 10:38:19 UTC 2023
PRIMARY
NCI_THESAURUS
C29519
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PRIMARY
RXCUI
10763
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PRIMARY RxNorm
NSC
639359
Created by admin on Thu Jul 06 10:38:19 UTC 2023 , Edited by admin on Thu Jul 06 10:38:19 UTC 2023
PRIMARY
HSDB
3405
Created by admin on Thu Jul 06 10:38:19 UTC 2023 , Edited by admin on Thu Jul 06 10:38:19 UTC 2023
PRIMARY
EVMPD
SUB11256MIG
Created by admin on Thu Jul 06 10:38:19 UTC 2023 , Edited by admin on Thu Jul 06 10:38:19 UTC 2023
PRIMARY
DRUG CENTRAL
2728
Created by admin on Thu Jul 06 10:38:19 UTC 2023 , Edited by admin on Thu Jul 06 10:38:19 UTC 2023
PRIMARY
EPA CompTox
DTXSID6021373
Created by admin on Thu Jul 06 10:38:19 UTC 2023 , Edited by admin on Thu Jul 06 10:38:19 UTC 2023
PRIMARY
MESH
D014223
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PRIMARY
MERCK INDEX
M11030
Created by admin on Thu Jul 06 10:38:19 UTC 2023 , Edited by admin on Thu Jul 06 10:38:19 UTC 2023
PRIMARY Merck Index
IUPHAR
4329
Created by admin on Thu Jul 06 10:38:19 UTC 2023 , Edited by admin on Thu Jul 06 10:38:19 UTC 2023
PRIMARY
INN
1266
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PRIMARY
ECHA (EC/EINECS)
206-904-3
Created by admin on Thu Jul 06 10:38:19 UTC 2023 , Edited by admin on Thu Jul 06 10:38:19 UTC 2023
PRIMARY
DAILYMED
WS821Z52LQ
Created by admin on Thu Jul 06 10:38:19 UTC 2023 , Edited by admin on Thu Jul 06 10:38:19 UTC 2023
PRIMARY
CHEBI
9671
Created by admin on Thu Jul 06 10:38:19 UTC 2023 , Edited by admin on Thu Jul 06 10:38:19 UTC 2023
PRIMARY
FDA UNII
WS821Z52LQ
Created by admin on Thu Jul 06 10:38:19 UTC 2023 , Edited by admin on Thu Jul 06 10:38:19 UTC 2023
PRIMARY