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

Molecular Formula C12H11N7
Molecular Weight 253.2626
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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
Irreversible renal failure associated with triamterene.
1991
[Urinary lithiasis of medical origin].
2001 Nov-Dec
In vitro antioxidant and photo-oxidant properties of dipyridamole.
2001 Nov-Dec
Determination of hydrochlorothiazide, triamterene and propranolol hydrochloride by the spectrophotometric method and high-performance liquid chromatography (HPLC).
2001 Sep-Oct
Effects of anion and cation inhibitors and carbonic anhydrase inhibitors upon the activity of the gypsy moth (Lepidoptera: Lymantriidae) nucleo-polyhedrovirus.
2002 Apr
Use of the trispan device to assist coil embolization of high-flow arteriovenous fistulas.
2002 Aug
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
Determination of triamterene by transitory retention in a continuous flow solid phase system with fluorimetric transduction.
2002 May 15
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
Potentially significant drug interactions of class III antiarrhythmic drugs.
2003
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
Drug-induced myopia.
2003 Feb
Restoration of arterial baroreflex function contributes to organ protection in spontaneously hypertensive rats treated with long-term hydrochlorothiazide mixture.
2003 Jan-Feb
Pharmacological characterization of unique prazosin-binding sites in human kidney.
2003 Jul
Photostability studies on the furosemide-triamterene drug association.
2003 Sep
Treatment of congenital nephrogenic diabetes insipidus with hydrochlorothiazide and amiloride in an adult patient.
2004
[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
Triamterene-beta-cyclodextrin systems: preparation, characterization and in vivo evaluation.
2004 Mar 29
Dermatological conditions during TNF-alpha-blocking therapy in patients with rheumatoid arthritis: a prospective study.
2005
Differing effects of mineralocorticoid receptor-dependent and -independent potassium-sparing diuretics on fibrinolytic balance.
2005 Aug
Attenuation of the kaluretic properties of furosemide by triamterene (Dyrenium) in healthy volunteers.
2005 Feb
[Capillary electrophoresis with end-column electrochemical detection for hydrochlorothiazide and triamterene diuretics].
2005 Jan
[A case of Gitelman's syndrome presenting with severe hypocalcaemia and hypokalemic periodic paralysis].
2005 Jul
Prediction of genotoxicity of chemical compounds by statistical learning methods.
2005 Jun
Capillary electrophoretic determination of triamterene, methotrexate, and creatinine in human urine.
2005 May
Drug-induced megaloblastic anemia.
2005 Oct
Hydrochlorothiazide-induced noncardiogenic pulmonary edema: an underrecognized yet serious adverse drug reaction.
2005 Sep
High-speed gas chromatography in doping control: fast-GC and fast-GC/MS determination of beta-adrenoceptor ligands and diuretics.
2006 Dec
[Liddle syndrome: Pathogenesis, pathophysiology, and therapy].
2006 Feb
Potassium-sparing diuretics.
2006 Jul 11-17
[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
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
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
Evaluation of a neck-bridge device to assist endovascular treatment of wide-neck aneurysms of the anterior circulation.
2008 Jan
Acute bilateral simultaneous angle closure glaucoma after topiramate administration: a case report.
2008 Jan 8
Responses to diuretic treatment in gene-targeted mice lacking serum- and glucocorticoid-inducible kinase 1.
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.
Substance Class Chemical
Created
by admin
on Thu Jul 06 10:38:19 UTC 2023
Edited
by admin
on Thu Jul 06 10:38:19 UTC 2023
Record UNII
WS821Z52LQ
Record Status Validated (UNII)
Record Version
  • Download
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
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
ChEMBL
CHEMBL585
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
CAS
396-01-0
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
PUBCHEM
5546
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 BANK
DB00384
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
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
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
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
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
RXCUI
10763
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 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
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
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
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
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
Related Record Type Details
BASIS OF STRENGTH->SUBSTANCE
ASSAY (TITRATION)
EP
BINDER->LIGAND
BASIS OF STRENGTH->SUBSTANCE
ASSAY (TITRATION)
USP
Related Record Type Details
METABOLITE ACTIVE -> PARENT
METABOLITE ACTIVE -> PARENT
Related Record Type Details
IMPURITY -> PARENT
For the calculation of contents, multiply the peak areas by 1.5
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
For the calculation of contents, multiply the peak areas by 1.8
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (GC)
EP
Related Record Type Details
ACTIVE MOIETY