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Record Information
Version3.6
Creation Date2006-05-18 09:06:02 UTC
Update Date2013-02-09 00:11:04 UTC
HMDB IDHMDB01940
Secondary Accession NumbersNone
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
  1. 6-Phenyl-2,4,7-triaminopteridine
  2. Ademin
  3. Ademine
  4. Diren
  5. Ditak
  6. Diurene
  7. Dyren
  8. Dyrenium
  9. Dytac
  10. Jatropur
  11. Noridil
  12. Noridyl
  13. Pterofen
  14. Pterophene
  15. Taturil
  16. Teriam
  17. Teridin
  18. Tri-Span
  19. Triampur
  20. Triamteren
  21. Triamterene
  22. Triamteril
  23. Triamteril complex
  24. Trispan
  25. Triteren
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
KingdomOrganic Compounds
Super ClassAromatic Heteropolycyclic Compounds
ClassPteridines and Derivatives
Sub ClassN/A
Other Descriptors
  • Aromatic Heteropolycyclic Compounds
Substituents
  • Aminopyrazine
  • Aminopyrimidine
  • Polyamine
  • Pyrazine
  • Pyrimidine
Direct ParentPteridines and Derivatives
Ontology
StatusExpected and Not Quantified
Origin
  • Drug
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm (predicted from logP)
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 Solubility0.96ALOGPS
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
Spectra
SpectraMS/MS1D NMR2D NMR
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biofluid LocationsNot Available
Tissue LocationNot Available
PathwaysNot Available
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
NuGOwiki LinkHMDB01940
Metagene LinkHMDB01940
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