Triamterene (CHEM016063)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-20 16:13:03 UTC
Update Date2016-11-09 01:15:19 UTC
Accession NumberCHEM016063
Identification
Common NameTriamterene
ClassSmall Molecule
DescriptionTriamterene (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. 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. 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. Triamterene was approved by the Food and Drug Administration in the U.S. in 1964. 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. 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.
Contaminant Sources
  • FooDB Chemicals
  • IARC Carcinogens Group 2B
  • STOFF IDENT Compounds
  • Suspected Compounds
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
TriamterenaChEBI
TriamterenumChEBI
DyreniumKegg
6-Phenyl-2,4,7-triaminopteridineHMDB
AdeminHMDB
AdemineHMDB
DirenHMDB
DitakHMDB
DiureneHMDB
DyrenHMDB
DytacHMDB
JatropurHMDB
NoridilHMDB
NoridylHMDB
PterofenHMDB
PteropheneHMDB
TaturilHMDB
TeriamHMDB
TeridinHMDB
Tri-spanHMDB
TriampurHMDB
TriamterenHMDB
TriamterilHMDB
Triamteril complexHMDB
TrispanHMDB
TriterenHMDB
Jorba brand OF triamtereneHMDB
SmithKline beecham brand OF triamtereneHMDB
Wellspring brand OF triamtereneHMDB
UrocaudalHMDB
Goldshield brand OF triamtereneHMDB
Chemical FormulaC12H11N7
Average Molecular Mass253.263 g/mol
Monoisotopic Mass253.108 g/mol
CAS Registry Number396-01-0
IUPAC Name6-phenylpteridine-2,4,7-triamine
Traditional Nametriamterene
SMILESNC1=NC(N)=C2N=C(C(N)=NC2=N1)C1=CC=CC=C1
InChI IdentifierInChI=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)
InChI KeyFNYLWPVRPXGIIP-UHFFFAOYSA-N
Chemical Taxonomy
Description 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.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassPteridines and derivatives
Sub ClassNot Available
Direct ParentPteridines and derivatives
Alternative Parents
Substituents
  • Pteridine
  • Aminopyrazine
  • Aminopyrimidine
  • Monocyclic benzene moiety
  • Pyrazine
  • Pyrimidine
  • Benzenoid
  • Imidolactam
  • Heteroaromatic compound
  • Azacycle
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Primary amine
  • Organonitrogen compound
  • Organopnictogen compound
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.96 g/LALOGPS
logP1.21ALOGPS
logP1.11ChemAxon
logS-2.4ALOGPS
pKa (Strongest Acidic)15.88ChemAxon
pKa (Strongest Basic)1.86ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area129.62 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity75.13 m³·mol⁻¹ChemAxon
Polarizability25.9 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - CI-B (Non-derivatized)splash10-0udi-0090000000-c8bbcf103f5a3fdfebb5Spectrum
GC-MSGC-MS Spectrum - CI-B (Non-derivatized)splash10-0udi-0090000000-c8bbcf103f5a3fdfebb5Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0w29-1290000000-6c14e74eed7c6b52485aSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - CI-B (Unknown) , Positivesplash10-0udi-0090000000-c8bbcf103f5a3fdfebb5Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0udr-0090000000-007b38b2c4832f349909Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-000i-0590000000-b0551f41584c039101f6Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-00kf-0910000000-6428faa965a39a470ea5Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0udi-0090000000-c1e38db82ca2bfb168b7Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0udi-0090000000-e0b752d624dade8793efSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0udi-0090000000-4c12cffcdf72d196b590Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0f79-0190000000-e63d14e64b8206d5c635Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0f79-0970000000-a69efa072a4b5fca0463Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0uxu-0910000000-f8ece9e1491b71df0c70Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0uxu-3900000000-946796a2530a51263ccdSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0f79-9600000000-59b671ef134dd8106331Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0gw0-9200000000-3451a9c6dc2b3f4b6e3bSpectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0udi-0190000000-425707e7729440a5bdb4Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0udi-0190000000-32f8b6872d5877d00316Spectrum
LC-MS/MSLC-MS/MS Spectrum - 45V, Positivesplash10-0udi-0090000000-a14c539f152a7ab67875Spectrum
LC-MS/MSLC-MS/MS Spectrum - 75V, Positivesplash10-0f79-0970000000-fe05b51d696f50542dc0Spectrum
LC-MS/MSLC-MS/MS Spectrum - 60V, Positivesplash10-0f79-0190000000-11a49ba5bf0ceb455fe2Spectrum
LC-MS/MSLC-MS/MS Spectrum - 90V, Positivesplash10-0uxu-0910000000-68e1cc4a9e81f92b16e2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0090000000-3a67cf224a0c9bef9905Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0090000000-fbfd0aa98b13bc4d5b0aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-6970000000-fb2ed0e5293d1d61d1efSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0090000000-38d6dd3df3067f42a151Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-2890000000-a521342894e2932298e5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0903-7960000000-6787f453927715d187d7Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB00384
HMDB IDHMDB0001940
FooDB IDFDB022755
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN ID2908
PDB IDNot Available
Wikipedia LinkTriamterene
Chemspider ID5345
ChEBI ID9671
PubChem Compound ID5546
Kegg Compound IDD00386
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Remonda L, Frigerio SB, Buhler R, Schroth G: Transvenous coil treatment of a type a carotid cavernous fistula in association with transarterial trispan coil protection. AJNR Am J Neuroradiol. 2004 Apr;25(4):611-3.
2. Weill A, Roy D, Georganos SA, Guilbert F, Raymond J: Use of the trispan device to assist coil embolization of high-flow arteriovenous fistulas. AJNR Am J Neuroradiol. 2002 Aug;23(7):1149-52.
3. Yang TH, Wong HF, Yang MS, Ou CH, Ho TL: "Waffle cone"technique for intra/extra-aneurysmal stent placement for the treatment of complex and wide-necked bifurcation aneurysm. Interv Neuroradiol. 2008 Nov 11;14 Suppl 2:49-52. Epub 2009 Jan 2.
4. Nakiri GS, Bravo E, Al-Khawaldeh M, Rivera R, Badilla L, Mounayer C: Endovascular treatment of aneurysm arising from fenestration of the supraclinoid internal carotid artery--two case reports. J Neuroradiol. 2012 Jul;39(3):195-9. doi: 10.1016/j.neurad.2011.10.001. Epub 2011 Dec 19.
5. Dib M, Sedat J, Raffaelli C, Petit I, Robertson WG, Jaeger P: Endovascular treatment of a wide-neck renal artery bifurcation aneurysm. J Vasc Interv Radiol. 2003 Nov;14(11):1461-4.
6. Turk AS, Rappe AH, Villar F, Virmani R, Strother CM: Evaluation of the TriSpan neck bridge device for the treatment of wide-necked aneurysms: an experimental study in canines. Stroke. 2001 Feb;32(2):492-7.
7. Henkes H, Kirsch M, Mariushi W, Miloslavski E, Brew S, Kuhne D: 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. Neuroradiology. 2004 Jun;46(6):464-8. Epub 2004 Apr 22.
8. Bradac GB, Bergui M, Stura G, Fontanella M, Daniele D, Gozzoli L, Berardino M, Ducati A: Periprocedural morbidity and mortality by endovascular treatment of cerebral aneurysms with GDC: a retrospective 12-year experience of a single center. Neurosurg Rev. 2007 Apr;30(2):117-25; discussion 125-6. Epub 2007 Jan 11.
9. Cil BE, Erdogan C, Akmangit I, Cekirge S, Balkanci F: Use of the TriSpan coil to facilitate the transcatheter occlusion of pulmonary arteriovenous malformation. Cardiovasc Intervent Radiol. 2004 Nov-Dec;27(6):655-8.
10. Schroth G, Lovblad KO, Ozdoba C, Remonda L: Non-traumatic neurological emergencies: emergency neuroradiological interventions. Eur Radiol. 2002 Jul;12(7):1648-62. Epub 2002 May 18.
11. Chan DT, Boet R, Yu S, Poon WS: Trispan-assisted coiling of a wide-necked Persistent Trigeminal Artery aneurysm. Acta Neurochir (Wien). 2004 Jan;146(1):87-8; discussion 88. Epub 2003 Dec 15.
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=26194642
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=26385116
14. https://www.ncbi.nlm.nih.gov/pubmed/?term=27913567
15. https://www.ncbi.nlm.nih.gov/pubmed/?term=28166217
16. https://www.ncbi.nlm.nih.gov/pubmed/?term=28435224
17. https://www.ncbi.nlm.nih.gov/pubmed/?term=28588673