Identification

Logo pink
Are you a
new drug developer?
Contact us to learn more about our customized products and solutions.
Logo pink
Stay in the know!
As part of our commitment to providing the most up-to-date drug information, we will be releasing #DrugBankUpdates with our newly added curated drug pages.
#DrugBankUpdates
Name
Triamterene
Accession Number
DB00384  (APRD00079)
Type
Small Molecule
Groups
Approved
Description

Triamterene (2,4,7-triamino-6-phenylpteridine) is a potassium-sparing diuretic that is used in the management of hypertension. It works by promoting the excretion of sodium ions and water while decreasing the potassium excretion in the distal part of the nephron in the kidneys by working on the lumenal side.2 Since it acts on the distal nephron where only a small fraction of sodium ion reabsorption occurs, triamterene is reported to have limited diuretic efficacy.11 Due to its effects on increased serum potassium levels, triamterene is associated with a risk of producing hyperkalemia. Triamterene is a weak antagonist of folic acid, and a photosensitizing drug.12

Triamterene was approved by the Food and Drug Administration in the U.S. in 1964.12 Currently, triamterene is used in the treatment of edema associated with various conditions as monotherapy and is approved for use with other diuretics to enhance diuretic and potassium-sparing effects.Label It is also found in a combination product with hydrochlorothiazide that is used for the management of hypertension or treatment of edema in patients who develop hypokalemia on hydrochlorothiazide alone.

Structure
Thumb
Synonyms
  • 6-phenylpteridine-2,4,7-triamine
  • Teridin
  • Triamteren
  • Triamterena
  • Triamtérène
  • Triamterene
  • Triamtereno
  • Triamterenum
External IDs
NSC-77625 / SK&F 8542 / SK&F-8542
Product Images
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
DyreniumCapsule50 mg/1OralWell Spring Pharmaceutical Corporation1999-10-012019-12-31Us
DyreniumCapsule100 mg/1OralConcordia Pharmaceuticals Inc.1999-01-01Not applicableUs
DyreniumCapsule100 mg/1OralPhysicians Total Care, Inc.2004-06-152011-06-30Us
DyreniumCapsule50 mg/1OralConcordia Pharmaceuticals Inc.1999-10-01Not applicableUs
DyreniumCapsule50 mg/1OralCarilion Materials Management1999-10-01Not applicableUs65197 0002 01 nlmimage10 3315999c
DyreniumCapsule100 mg/1OralWell Spring Pharmaceutical Corporation1999-01-012020-01-31Us65197 0003 01 nlmimage10 2e45975c
Dyrenium 100TabletOralGlaxosmithkline Inc1992-12-312002-07-03Canada
Dyrenium 50TabletOralGlaxosmithkline Inc1992-12-312002-07-03Canada
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

    Learn more
  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

    Learn more
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
TriamtereneCapsule100 mg/1OralPrasco Laboratories2019-08-13Not applicableUs
TriamtereneCapsule50 mg/1OralPrasco Laboratories2019-08-13Not applicableUs
TriamtereneCapsule100 mg/1OralTruPharma LLC2018-12-12Not applicableUs
TriamtereneCapsule50 mg/1OralTruPharma LLC2018-12-12Not applicableUs
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

    Learn more
  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

    Learn more
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Apo TriazideTriamterene (50 mg) + Hydrochlorothiazide (25 mg)TabletOralApotex Corporation1984-12-31Not applicableCanada
DyazideTriamterene (37.5 mg/1) + Hydrochlorothiazide (25 mg/1)CapsuleOralMckesson Rxpak Inc1994-03-30Not applicableUs
DyazideTriamterene (37.5 mg/1) + Hydrochlorothiazide (25 mg/1)CapsuleOralGlaxoSmithKline LLC1994-03-30Not applicableUs0007 365020180810 16125 1bkzpqu
DyazideTriamterene (37.5 mg/1) + Hydrochlorothiazide (25 mg/1)CapsuleOralPhysicians Total Care, Inc.2003-09-092011-06-30Us
DyazideTriamterene (37.5 mg/1) + Hydrochlorothiazide (25 mg/1)CapsuleOralGlaxosmithkline Inc1994-03-302018-02-23Us
DyazideTriamterene (37.5 mg/1) + Hydrochlorothiazide (25 mg/1)CapsuleOralCardinal Health1994-03-30Not applicableUs00007 3650 22 nlmimage10 4c192669
Dyazide TabTriamterene (50 mg) + Hydrochlorothiazide (25 mg)TabletOralSmithkline Beecham Pharma Division Of Smithkline Beecham Inc1992-12-312001-03-05Canada
MaxzideTriamterene (75 mg/1) + Hydrochlorothiazide (50 mg/1)TabletOralPhysicians Total Care, Inc.1988-05-132012-06-30Us
MaxzideTriamterene (75 mg/1) + Hydrochlorothiazide (50 mg/1)TabletOralMylan Pharmaceuticals Inc.1988-05-13Not applicableUs
Maxzide-25Triamterene (37.5 mg/1) + Hydrochlorothiazide (25 mg/1)TabletOralPhysicians Total Care, Inc.1988-05-132012-06-30Us
International/Other Brands
Diuteren (Kotobuki Seiyaku) / Dytac (Mercury) / Riyazine (Ciiphar) / Triteren (Kyoto Yakuhin) / Urinis (Ying Yuan)
Categories
UNII
WS821Z52LQ
CAS number
396-01-0
Weight
Average: 253.2626
Monoisotopic: 253.107593387
Chemical Formula
C12H11N7
InChI Key
FNYLWPVRPXGIIP-UHFFFAOYSA-N
InChI
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)
IUPAC Name
6-phenylpteridine-2,4,7-triamine
SMILES
NC1=NC(N)=C2N=C(C(N)=NC2=N1)C1=CC=CC=C1

Pharmacology

Indication

Triamterene is indicated 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.Label

Triamterene in combination with hydrochlorothiazide is indicated for the managment of hypertension or treatment of edema in patients who develop hypokalemia following hydrochlorothiazide monotherapy, and in patients who require thiazide diuretic and in whom the development of hypokalemia cannot be risked.13 Triamterene allows the maintenance of potassium balance when given in combination with loop diuretics and thiazides.11

Associated Conditions
Pharmacodynamics

Triamterene, a relatively weak, potassium-sparing diuretic and antihypertensive, is used in the management of hypertension and edema. It primarily works on the distal nephron in the kidneys; it acts from the late distal tubule to the collecting duct to inhibit Na+ reabsorption and decreasing K+ excretion.11 As triamterene tends to conserve potassium more strongly than promoting Na+ excretion, it can cause an increase in serum potassium, which may result in hyperkalemia potentially associated with cardiac irregularities.Label In healthy volunteers administered with oral triamterene, there was an increase in the renal clearnace of sodium and magnesium, and a decrease in the clearance of uric acid and creatinine5 due to its effect of reducing glomerular filtration renal plasma flow.13 Triamterene does not affect calcium excretion.13 In clinical trials, the use of triamterene in combination with hydrochlorothiazide resulted an enhanced blood pressure-lowering effects of hydrochlorothiazide.7

Mechanism of action

Triamterene inhibits the epithelial sodium channels (ENaC) located on the lumenal side in the late distal convoluted tubule and collecting tubule 6, which are transmembrane channels that normally promotes sodium uptake and potassium secretion.7 In the late distal tubule to the collecting duct, sodium ions are actively reabsorbed via ENaC on the lumnial membrane and are extruded out of the cell into the peritubular medium by a sodium-potassium exchange pump, the Na-K-ATPase,8 with water following passively.11 Triamterene exerts a diuretic effect on the distal renal tubule to inhibit the reabsorption of sodium ions in exchange for potassium and hydrogen ions and its natriuretic activity is limited by the amount of sodium reaching its site of action.13 Its action is antagonistic to that of adrenal mineralocorticoids, such as aldosterone, but it is not an inhibitor or antagonist of aldosterone.Label Triamterene maintains or increases the sodium excretionm, thereby increasing the excretion of water, and reduces the excess loss of potassium, hydrogen and chloride ions by inhibiting the distal tubular exchange mechanism.13 Due to its diuretic effect, triamterene rapidly and reversibly reduces the lumen-negative transepithelial potential difference by almost complete abolition of Na+ conductance without altering K+ conductance.3 This reduces the driving force for potassium movement into the tubular lumen and thus decreases potassium excretion. 8 Triamterene is similar in action to amiloride but, unlike amiloride, increases the urinary excretion of magnesium.5

TargetActionsOrganism
AAmiloride-sensitive sodium channel subunit gamma
inhibitor
Humans
AAmiloride-sensitive sodium channel subunit alpha
inhibitor
Humans
AAmiloride-sensitive sodium channel subunit beta
inhibitor
Humans
UAmiloride-sensitive sodium channel subunit delta
inhibitor
Humans
Additional Data Available
Adverse Effects

Comprehensive structured data on known drug adverse effects with statistical prevalence. MedDRA and ICD10 ids are provided for adverse effect conditions and symptoms.

Learn more
Additional Data Available
Contraindications

Structured data covering drug contraindications. Each contraindication describes a scenario in which the drug is not to be used. Includes restrictions on co-administration, contraindicated populations, and more.

Learn more
Additional Data Available
Blackbox Warnings

Structured data representing warnings from the black box section of drug labels. These warnings cover important and dangerous risks, contraindications, or adverse effects.

Learn more
Absorption

Triamterene is shown to be rapidly absorbed in the gastrointestinal tract 11 Label Its onset of action achiveved within 2 to 4 hours after oral ingestion Label and its duration of action is 12-16 hours.11 It is reported that the diuretic effect of triamterene may not be observed for several days after administration.Label In a pharmacokinetic study, the oral bioavailability of triamterene was determined to be 52%.4 Following administration of a single oral dose to fasted healthy male volunteers, the mean AUC of triamterene was about 148.7 ng*hr/mL 13 and the mean peak plasma concentrations (Cmax) were 46.4 ng/mL reached at 1.1 hour after administration.13 In a limited study, administration of triamterene in combination with hydrochlorothiazide resulted in an increased bioavailability of triamterene by about 67% and a delay of up to 2 hours in the absorption of the drug.13 It is advised that triamterene is administered after meals; in a limited study, combination use of triamterene and hydrochlorothiazide with the consumption of a high-fat meal resulted in an increase in the mean bioavailability and peak serum concentrations of triamterene and its active sulfate metabolite, as well as a delay of up to 2 hours in the absorption of the active constituents.13

Volume of distribution

In a pharmacolinetic study involving healthy volunteers receiving triamterene intravenously, the volumes of distribution of the central compartment of triamterene and its hydroxylated ester metabolite were 1.49 L/kg and 0.11 L/kg, respectively.1 Triamterene was found to cross the placental barrier and appear in the cord blood of animals.Label

Protein binding

67% bound to proteins. Label

Metabolism

Triamterene undergoes phase I metabolism involving hydroxylation, via CYP1A2 activity, to form 4'-hydroxytriamterene. 4'-Hydroxytriamterene is further transformed in phase II metabolism mediated by cytosolic sulfotransferases to form the major metabolite, 4′-hydroxytriamterene sulfate, which retains a diuretic activity. 10,12 Both the plasma and urine levels of this metabolite greatly exceed triamterene levels Label while the renal clearance of the sulfate conjugate was les than that of triamterene; this low renal clearance of the sulfate conjugate as compared with triamterene may be explained by the low unbound fraction of the metabolite in plasma.9

Route of elimination

Triamterene and its metabolites are excreted by the kidney by filtration and tubular secretion.14 Upon oral ingestion, somewhat less than 50% of the oral dose reaches the urine. Label About 20% of an oral dose appears unchanged in the urine, 70% as the sulphate ester of hydroxytriamterene and 10% as free hydroxytriamterene and triamterene glucuronide. 14

Half life

The half-life of the drug in plasma ranges from 1.5 to 2 hours.14 In a pharmacokinetic study involving healthy volunteers, the terminal half-lives for triamterene and 4′-hydroxytriamterene sulfate were 255 ± 42 and 188 ± 70 minutes, respectively, after intravenous infusion of the parent drug.1,12

Clearance

The total plasma clearance was 4.5 l/min and renal plasma clearance was 0.22 l/kg following intravenous administration of triamterene in healthy volunteers.1

Toxicity

Acute oral LD50 of triamterene in rats is 400 mg/kg and 285-380 mg/kg in mice.Label,MSDS There has been a case of reversible acute renal failure following ingestion of 50 combination pills containing 50 mg triamterene and 25 mg hydrochlorothiazide. Label Symptoms of overdose, such as nausea, vomiting, gastrointestinal disturbances, weakness, and hypotension, are related to electrolyte imbalances, such as hyperkalemia.Label As there is no specific antidote, emesis and gastric lavage should be use to induce immediate evacuation of the stomach and careful evaluation of the electrolyte pattern and fluid balance should be made.Label Dialysis may be somewhat effective in case of an overdosage.Label

In a carciongenicity study in male and female mice administered with triamterene at the highst dosage level, there was an increased incidence of hepatocellular neoplasia, primarily adenomas. However, this was not a dose-dependent phenomenon and there was no statistically significant difference from control incidence at any dose level.Label In bacterial assays, there was no demonstrated mutagenic potential of triamterene. In in vitro assay using Chinese hamster ovary (CHO) cells with or without metabolic activation, there were no chromosomal aberrations.Label Studies evaluating the effects of triamterene on reproductive system or fertility have not been conducted. It is advised that the use of triamterene is avoided during pregnancy. As triamterene has been detected in human breast milk, triamterene should be used when nursing is ceased.Label

Affected organisms
  • Humans and other mammals
Pathways
PathwayCategory
Triamterene Action PathwayDrug action
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
(R)-warfarinThe metabolism of (R)-warfarin can be decreased when combined with Triamterene.
6-O-benzylguanineThe metabolism of 6-O-benzylguanine can be decreased when combined with Triamterene.
7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline may increase the orthostatic hypotensive activities of Triamterene.
8-azaguanineThe metabolism of 8-azaguanine can be decreased when combined with Triamterene.
8-chlorotheophyllineThe metabolism of 8-chlorotheophylline can be decreased when combined with Triamterene.
9-DeazaguanineThe metabolism of 9-Deazaguanine can be decreased when combined with Triamterene.
9-MethylguanineThe metabolism of 9-Methylguanine can be decreased when combined with Triamterene.
AbacavirTriamterene may decrease the excretion rate of Abacavir which could result in a higher serum level.
AbataceptThe metabolism of Triamterene can be increased when combined with Abatacept.
AbirateroneThe serum concentration of Triamterene can be increased when it is combined with Abiraterone.
Additional Data Available
  • Extended Description
    Extended Description

    Extended description of the mechanism of action and particular properties of each drug interaction.

    Learn more
  • Severity
    Severity

    A severity rating for each drug interaction, from minor to major.

    Learn more
  • Evidence Level
    Evidence Level

    A rating for the strength of the evidence supporting each drug interaction.

    Learn more
  • Action
    Action

    An effect category for each drug interaction. Know how this interaction affects the subject drug.

    Learn more
Food Interactions
Not Available

References

Synthesis Reference

Frederic J. Nugent, John K. C. Yen, "Process for preparing the combination products of triamterene and hydrochlorothiazide." U.S. Patent US4804540, issued July, 1987.

US4804540
General References
  1. Gilfrich HJ, Kremer G, Mohrke W, Mutschler E, Volger KD: Pharmacokinetics of triamterene after i.v. administration to man: determination of bioavailability. Eur J Clin Pharmacol. 1983;25(2):237-41. [PubMed:6628507]
  2. BABA WI, TUDHOPE GR, WILSON GM: Triamterene, a new diuretic drug. I. Studies in normal men and in adrenalectomized rats. Br Med J. 1962 Sep 22;2(5307):756-60. doi: 10.1136/bmj.2.5307.756. [PubMed:13863613]
  3. Knauf H, Wais U, Lubcke R, Albiez G: On the mechanism of action of triamterene: effects on transport of Na+, K+, and H+/HCO3- -ions. Eur J Clin Invest. 1976 Jan 30;6(1):43-50. [PubMed:130243]
  4. Mutschler E, Gilfrich HJ, Knauf H, Mohrke W, Volger KD: Pharmacokinetics of triamterene. Clin Exp Hypertens A. 1983;5(2):249-69. [PubMed:6831748]
  5. Walker BR, Hoppe RC, Alexander F: Effect of triamterene on the renal clearance of calcium, magnesium, phosphate, and uric acid in man. Clin Pharmacol Ther. 1972 Mar-Apr;13(2):245-50. [PubMed:4552822]
  6. Knauf H, Wais U, Albiez G, Lubcke R: [Inhibition of the exchange of Na+ for K+ and and H+ by triamterene (in epithelia)(author's transl)]. Arzneimittelforschung. 1976 Apr;26(4):484-6. [PubMed:133688]
  7. Tu W, Decker BS, He Z, Erdel BL, Eckert GJ, Hellman RN, Murray MD, Oates JA, Pratt JH: Triamterene Enhances the Blood Pressure Lowering Effect of Hydrochlorothiazide in Patients with Hypertension. J Gen Intern Med. 2016 Jan;31(1):30-6. doi: 10.1007/s11606-015-3469-1. [PubMed:26194642]
  8. Horisberger JD, Giebisch G: Potassium-sparing diuretics. Ren Physiol. 1987;10(3-4):198-220. [PubMed:2455308]
  9. Hasegawa J, Lin ET, Williams RL, Sorgel F, Benet LZ: Pharmacokinetics of triamterene and its metabolite in man. J Pharmacokinet Biopharm. 1982 Oct;10(5):507-23. [PubMed:7166735]
  10. Fuhr U, Kober S, Zaigler M, Mutschler E, Spahn-Langguth H: Rate-limiting biotransformation of triamterene is mediated by CYP1A2. Int J Clin Pharmacol Ther. 2005 Jul;43(7):327-34. [PubMed:16035375]
  11. 28. (2012). In Rang and Dale's Pharmacology (7th ed., pp. 352-353, 356). Edinburgh: Elsevier/Churchill Livingstone. [ISBN:978-0-7020-3471-8]
  12. Triamterene - International Agency for Research on Cancer (IARC) Monographs [Link]
  13. DYAZIDE (hydrochlorothiazide and triamterene) - FDA Label [Link]
  14. PRO-TRIAZIDE (Triamterene 50 mg and Hydrochlorothiazide 25 mg) - Product Monograph [Link]
External Links
Human Metabolome Database
HMDB0001940
KEGG Drug
D00386
PubChem Compound
5546
PubChem Substance
46507623
ChemSpider
5345
BindingDB
6644
ChEBI
9671
ChEMBL
CHEMBL585
Therapeutic Targets Database
DAP000575
PharmGKB
PA451752
Guide to Pharmacology
GtP Drug Page
HET
DX2
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Triamterene
ATC Codes
C03DB02 — Triamterene
AHFS Codes
  • 40:28.16 — Potassium-sparing Diuretics
PDB Entries
3jq7
FDA label
Download (248 KB)
MSDS
Download (73.5 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
3CompletedNot AvailableCardiovascular Disease (CVD) / Death, Sudden,Cardiac / Heart Arrest / Heart Diseases / High Blood Pressure (Hypertension)1
3CompletedPreventionAtherosclerosis / Cardiovascular Disease (CVD) / Coronary Heart Disease (CHD) / Diabetes Mellitus (DM) / High Blood Pressure (Hypertension) / High Cholesterol / Type 2 Diabetes Mellitus1
4RecruitingTreatmentProteinuria1
Not AvailableUnknown StatusBasic ScienceDiabetic Nephropathies / High Blood Pressure (Hypertension)1

Pharmacoeconomics

Manufacturers
  • Wellspring pharmaceutical corp
Packagers
  • Advanced Pharmaceutical Services Inc.
  • Amerisource Health Services Corp.
  • Apotex Inc.
  • Apotheca Inc.
  • A-S Medication Solutions LLC
  • Atlantic Biologicals Corporation
  • Barr Pharmaceuticals
  • Bryant Ranch Prepack
  • Cardinal Health
  • Central Texas Community Health Centers
  • Comprehensive Consultant Services Inc.
  • Corepharma LLC
  • Dept Health Central Pharmacy
  • DHHS Program Support Center Supply Service Center
  • Direct Dispensing Inc.
  • Dispensing Solutions
  • Diversified Healthcare Services Inc.
  • Duramed
  • GlaxoSmithKline Inc.
  • Golden State Medical Supply Inc.
  • Group Health Cooperative
  • H.J. Harkins Co. Inc.
  • Heartland Repack Services LLC
  • Ivax Pharmaceuticals
  • Kaiser Foundation Hospital
  • Liberty Pharmaceuticals
  • Major Pharmaceuticals
  • Medvantx Inc.
  • Murfreesboro Pharmaceutical Nursing Supply
  • Mylan
  • Neuman Distributors Inc.
  • Nucare Pharmaceuticals Inc.
  • Palmetto Pharmaceuticals Inc.
  • PCA LLC
  • PD-Rx Pharmaceuticals Inc.
  • Pharmaceutical Utilization Management Program VA Inc.
  • Pharmacy Service Center
  • Physicians Total Care Inc.
  • Pliva Inc.
  • Preferred Pharmaceuticals Inc.
  • Prepackage Specialists
  • Prepak Systems Inc.
  • Qualitest
  • Rebel Distributors Corp.
  • Remedy Repack
  • Resource Optimization and Innovation LLC
  • Sandhills Packaging Inc.
  • Sandoz
  • Southwood Pharmaceuticals
  • Stat Scripts LLC
  • Tya Pharmaceuticals
  • UDL Laboratories
  • Va Cmop Dallas
  • Vangard Labs Inc.
  • Watson Pharmaceuticals
  • Wellspring Pharmaceutical
Dosage forms
FormRouteStrength
CapsuleOral100 mg/1
CapsuleOral50 mg/1
TabletOral
CapsuleOral
TabletOral
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)316 °CPhysProp
water solubilityVery slightly soluble in water (<0.1%)IARC monograph, DYAZIDE (hydrochlorothiazide and triamterene) Label
logP0.98HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility0.963 mg/mLALOGPS
logP1.21ALOGPS
logP1.11ChemAxon
logS-2.4ALOGPS
pKa (Strongest Acidic)15.88ChemAxon
pKa (Strongest Basic)3.11ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area129.62 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity75.13 m3·mol-1ChemAxon
Polarizability25.9 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.8735
Caco-2 permeable+0.7017
P-glycoprotein substrateNon-substrate0.6269
P-glycoprotein inhibitor INon-inhibitor0.8782
P-glycoprotein inhibitor IINon-inhibitor0.8814
Renal organic cation transporterNon-inhibitor0.8437
CYP450 2C9 substrateNon-substrate0.8949
CYP450 2D6 substrateNon-substrate0.8892
CYP450 3A4 substrateNon-substrate0.7542
CYP450 1A2 substrateInhibitor0.9107
CYP450 2C9 inhibitorNon-inhibitor0.907
CYP450 2D6 inhibitorNon-inhibitor0.9231
CYP450 2C19 inhibitorNon-inhibitor0.9025
CYP450 3A4 inhibitorNon-inhibitor0.831
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.6161
Ames testNon AMES toxic0.8934
CarcinogenicityNon-carcinogens0.9092
BiodegradationNot ready biodegradable0.9959
Rat acute toxicity2.7706 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9604
hERG inhibition (predictor II)Non-inhibitor0.6829
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
GC-MS Spectrum - CI-BGC-MSsplash10-0udi-0090000000-c8bbcf103f5a3fdfebb5
MS/MS Spectrum - CI-B (Unknown) , PositiveLC-MS/MSsplash10-0udi-0090000000-c8bbcf103f5a3fdfebb5
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0udr-0090000000-007b38b2c4832f349909
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-000i-0590000000-b0551f41584c039101f6
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-00kf-0910000000-6428faa965a39a470ea5
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0udi-0090000000-c1e38db82ca2bfb168b7
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0udi-0090000000-e0b752d624dade8793ef
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0udi-0090000000-4c12cffcdf72d196b590
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0f79-0190000000-e63d14e64b8206d5c635
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0f79-0970000000-a69efa072a4b5fca0463
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0uxu-0910000000-f8ece9e1491b71df0c70
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0uxu-3900000000-946796a2530a51263ccd
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0f79-9600000000-59b671ef134dd8106331
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0gw0-9200000000-3451a9c6dc2b3f4b6e3b
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0udi-0190000000-425707e7729440a5bdb4
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0udi-0190000000-32f8b6872d5877d00316
1H NMR Spectrum1D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable

Taxonomy

Description
This compound belongs to the class of organic compounds known as pteridines and derivatives. These are polycyclic aromatic compounds containing a pteridine moiety, which consists of a pyrimidine fused to a pyrazine ring to form pyrimido(4,5-b)pyrazine.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Pteridines and derivatives
Sub Class
Not Available
Direct Parent
Pteridines and derivatives
Alternative Parents
Aminopyrimidines and derivatives / Aminopyrazines / Imidolactams / Benzene and substituted derivatives / Heteroaromatic compounds / Azacyclic compounds / Primary amines / Organopnictogen compounds / Hydrocarbon derivatives
Substituents
Pteridine / Aminopyrazine / Aminopyrimidine / Monocyclic benzene moiety / Pyrazine / Pyrimidine / Benzenoid / Imidolactam / Heteroaromatic compound / Azacycle
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available

Targets

Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Inhibitor
General Function
Ww domain binding
Specific Function
Sodium permeable non-voltage-sensitive ion channel inhibited by the diuretic amiloride. Mediates the electrodiffusion of the luminal sodium (and water, which follows osmotically) through the apical...
Gene Name
SCNN1G
Uniprot ID
P51170
Uniprot Name
Amiloride-sensitive sodium channel subunit gamma
Molecular Weight
74269.62 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
  3. Hiraoka Y, Taniguchi T, Tanaka T, Okada K, Kanamaru H, Muramatsu I: Pharmacological characterization of unique prazosin-binding sites in human kidney. Naunyn Schmiedebergs Arch Pharmacol. 2003 Jul;368(1):49-56. Epub 2003 Jun 25. [PubMed:12827214]
  4. Busch AE, Suessbrich H, Kunzelmann K, Hipper A, Greger R, Waldegger S, Mutschler E, Lindemann B, Lang F: Blockade of epithelial Na+ channels by triamterenes - underlying mechanisms and molecular basis. Pflugers Arch. 1996 Sep;432(5):760-6. [PubMed:8772124]
  5. Wagner CA, Ott M, Klingel K, Beck S, Melzig J, Friedrich B, Wild KN, Broer S, Moschen I, Albers A, Waldegger S, Tummler B, Egan ME, Geibel JP, Kandolf R, Lang F: Effects of the serine/threonine kinase SGK1 on the epithelial Na(+) channel (ENaC) and CFTR: implications for cystic fibrosis. Cell Physiol Biochem. 2001;11(4):209-18. [PubMed:11509829]
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Inhibitor
General Function
Ww domain binding
Specific Function
Sodium permeable non-voltage-sensitive ion channel inhibited by the diuretic amiloride. Mediates the electrodiffusion of the luminal sodium (and water, which follows osmotically) through the apical...
Gene Name
SCNN1A
Uniprot ID
P37088
Uniprot Name
Amiloride-sensitive sodium channel subunit alpha
Molecular Weight
75703.08 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
  3. Busch AE, Suessbrich H, Kunzelmann K, Hipper A, Greger R, Waldegger S, Mutschler E, Lindemann B, Lang F: Blockade of epithelial Na+ channels by triamterenes - underlying mechanisms and molecular basis. Pflugers Arch. 1996 Sep;432(5):760-6. [PubMed:8772124]
  4. Wagner CA, Ott M, Klingel K, Beck S, Melzig J, Friedrich B, Wild KN, Broer S, Moschen I, Albers A, Waldegger S, Tummler B, Egan ME, Geibel JP, Kandolf R, Lang F: Effects of the serine/threonine kinase SGK1 on the epithelial Na(+) channel (ENaC) and CFTR: implications for cystic fibrosis. Cell Physiol Biochem. 2001;11(4):209-18. [PubMed:11509829]
  5. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Inhibitor
General Function
Ww domain binding
Specific Function
Sodium permeable non-voltage-sensitive ion channel inhibited by the diuretic amiloride. Mediates the electrodiffusion of the luminal sodium (and water, which follows osmotically) through the apical...
Gene Name
SCNN1B
Uniprot ID
P51168
Uniprot Name
Amiloride-sensitive sodium channel subunit beta
Molecular Weight
72658.485 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
  3. Busch AE, Suessbrich H, Kunzelmann K, Hipper A, Greger R, Waldegger S, Mutschler E, Lindemann B, Lang F: Blockade of epithelial Na+ channels by triamterenes - underlying mechanisms and molecular basis. Pflugers Arch. 1996 Sep;432(5):760-6. [PubMed:8772124]
  4. Wagner CA, Ott M, Klingel K, Beck S, Melzig J, Friedrich B, Wild KN, Broer S, Moschen I, Albers A, Waldegger S, Tummler B, Egan ME, Geibel JP, Kandolf R, Lang F: Effects of the serine/threonine kinase SGK1 on the epithelial Na(+) channel (ENaC) and CFTR: implications for cystic fibrosis. Cell Physiol Biochem. 2001;11(4):209-18. [PubMed:11509829]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Ligand-gated sodium channel activity
Specific Function
Sodium permeable non-voltage-sensitive ion channel inhibited by the diuretic amiloride. Mediates the electrodiffusion of the luminal sodium (and water, which follows osmotically) through the apical...
Gene Name
SCNN1D
Uniprot ID
P51172
Uniprot Name
Amiloride-sensitive sodium channel subunit delta
Molecular Weight
70214.195 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
  3. Wagner CA, Ott M, Klingel K, Beck S, Melzig J, Friedrich B, Wild KN, Broer S, Moschen I, Albers A, Waldegger S, Tummler B, Egan ME, Geibel JP, Kandolf R, Lang F: Effects of the serine/threonine kinase SGK1 on the epithelial Na(+) channel (ENaC) and CFTR: implications for cystic fibrosis. Cell Physiol Biochem. 2001;11(4):209-18. [PubMed:11509829]

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
Curator comments
Data supported only by in vitro studies.
General Function
Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP1A2
Uniprot ID
P05177
Uniprot Name
Cytochrome P450 1A2
Molecular Weight
58293.76 Da
References
  1. Fuhr U, Kober S, Zaigler M, Mutschler E, Spahn-Langguth H: Rate-limiting biotransformation of triamterene is mediated by CYP1A2. Int J Clin Pharmacol Ther. 2005 Jul;43(7):327-34. [PubMed:16035375]

Drug created on June 13, 2005 07:24 / Updated on November 22, 2019 04:04