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Record Information
Version4.0
Creation Date2006-05-18 09:06:02 UTC
Update Date2017-10-23 19:03:55 UTC
HMDB IDHMDB0001940
Secondary Accession Numbers
  • HMDB01940
Metabolite Identification
Common NameTriamterene
DescriptionPteridine. A pteridine that is used as a mild diuretic. -- Pubchem; Triamterene is a potassium-sparing diuretic used in combination with thiazide diuretics for the treatment of hypertension. -- Wikipedia.
Structure
Thumb
Synonyms
ValueSource
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 triamtereneMeSH
SmithKline beecham brand OF triamtereneMeSH
Wellspring brand OF triamtereneMeSH
UrocaudalMeSH
Goldshield brand OF triamtereneMeSH
Chemical FormulaC12H11N7
Average Molecular Weight253.2626
Monoisotopic Molecular Weight253.107593387
IUPAC Name6-phenylpteridine-2,4,7-triamine
Traditional Nametriamterene
CAS Registry Number396-01-0
SMILES
NC1=NC(N)=C2N=C(C(N)=NC2=N1)C1=CC=CC=C1
InChI Identifier
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)
InChI KeyFNYLWPVRPXGIIP-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis 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.
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
Ontology
Disposition

Biological Location:

  Subcellular:

Process

Naturally occurring process:

  Biological process:

    Biochemical pathway:

Role

Industrial application:

  Pharmaceutical industry:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point316 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP0.98HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility0.96 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity75.13 m³·mol⁻¹ChemAxon
Polarizability25.9 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - CI-B (Non-derivatized)splash10-0udi-0090000000-c8bbcf103f5a3fdfebb5View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0w29-1290000000-6c14e74eed7c6b52485aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - CI-B (Unknown) , Positivesplash10-0udi-0090000000-c8bbcf103f5a3fdfebb5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0udr-0090000000-007b38b2c4832f349909View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-000i-0590000000-b0551f41584c039101f6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-00kf-0910000000-6428faa965a39a470ea5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0udi-0090000000-c1e38db82ca2bfb168b7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0udi-0090000000-e0b752d624dade8793efView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0udi-0090000000-4c12cffcdf72d196b590View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0f79-0190000000-e63d14e64b8206d5c635View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0f79-0970000000-a69efa072a4b5fca0463View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0uxu-0910000000-f8ece9e1491b71df0c70View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0uxu-3900000000-946796a2530a51263ccdView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0f79-9600000000-59b671ef134dd8106331View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0gw0-9200000000-3451a9c6dc2b3f4b6e3bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0udi-0190000000-425707e7729440a5bdb4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0udi-0190000000-32f8b6872d5877d00316View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0090000000-3a67cf224a0c9bef9905View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0090000000-fbfd0aa98b13bc4d5b0aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-6970000000-fb2ed0e5293d1d61d1efView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0090000000-38d6dd3df3067f42a151View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-2890000000-a521342894e2932298e5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0903-7960000000-6787f453927715d187d7View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biofluid LocationsNot Available
Tissue LocationNot Available
Pathways
NameSMPDB/PathwhizKEGG
Triamterene PathwayPw000341Pw000341 greyscalePw000341 simpleNot Available
Displaying 1 entry
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB022755
KNApSAcK IDNot Available
Chemspider ID5345
KEGG Compound IDD00386
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkTriamterene
METLIN ID2908
PubChem Compound5546
PDB IDDX2
ChEBI ID117411
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
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. [PubMed:15090352 ]
  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. [PubMed:12169472 ]
  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. [PubMed:20557801 ]
  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. [PubMed:22189288 ]
  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. [PubMed:14605114 ]
  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. [PubMed:11157188 ]
  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. [PubMed:15103433 ]
  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. [PubMed:17216530 ]
  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. [PubMed:15593430 ]
  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. [PubMed:12111055 ]
  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. [PubMed:14740272 ]

Enzymes

General function:
Involved in 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 membrane of epithelial cells. Controls the reabsorption of sodium in kidney, colon, lung and sweat glands. Also plays a role in taste perception
Gene Name:
SCNN1A
Uniprot ID:
P37088
Molecular weight:
75703.1
General function:
Involved in 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 membrane of epithelial cells. Controls the reabsorption of sodium in kidney, colon, lung and sweat glands. Also plays a role in taste perception
Gene Name:
SCNN1G
Uniprot ID:
P51170
Molecular weight:
74269.6
General function:
Involved in 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 membrane of epithelial cells. Controls the reabsorption of sodium in kidney, colon, lung and sweat glands. Also plays a role in taste perception
Gene Name:
SCNN1B
Uniprot ID:
P51168
Molecular weight:
72658.5
General function:
Involved in 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 membrane of epithelial cells. Controls the reabsorption of sodium in kidney, colon, lung and sweat glands. Also plays a role in taste perception
Gene Name:
SCNN1D
Uniprot ID:
P51172
Molecular weight:
70214.2