6-phenylpteridine-2,4,7-triamine

• ChemBase ID: 268
• Molecular Formular: C12H11N7
• Molecular Mass: 253.26264
• Monoisotopic Mass: 253.10759339
• SMILES: n1c(c2ccccc2)c(nc2nc(nc(N)c12)N)N
• Canonical SMILES: Nc1nc(N)c2c(n1)nc(c(n2)c1ccccc1)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)
• InChIKey: FNYLWPVRPXGIIP-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 6-phenylpteridine-2,4,7-triamine
• IUPAC Traditional name: triamterene; 6-phenylpteridine-2,4,7-triamine
• Brand Name: Ademin; Ademine; Diren; Ditak; Diucelpin; Diurene; Dyazide; Dyren; Dyrenium; Dytac; Jatropur; Maxzide; Maxzide-25; Noridil; Noridyl; Pterofen; Pterophene; Taturil; Teriam; Teridin; Tri-Span; Triampur; Triamteril; Triamteril Complex; Trispan; Triteren; Urocaudal
• Synonyms: 6-PHENYL-2,4,7-TRIAMINO PTERIDINE; 6-Phenyl-2,4,7-pteridinetriamine; Triamterene; 6-Phenyl-2,4,7-triaminopteridine; Ademin; Ademine; Diren; Ditak; Diurene; NSC 77625; Noridil; Triamterene; 2,4,7-Triamino-6-phenylpteridine; Triamteren; Triamterene; 6-Phenyl-2,4,7-pteridinetriamine; 2,4,7-Triamino-6-phenylpteridine; urocaudal; Dytac; Dyrenium; Jatropur; Triampur; Tri-Span; Adernine; Pterofen; Pterophene; Triteren; 6-phenylpteridine-2,4,7-triamine; 2,4,7-三氨基-6-苯基蝶啶

Database IDs

• CAS Number: 396-01-0
• EC Number: 200-659-6; 206-904-3
• MDL Number: MFCD00006708
• Beilstein Number: 266723
• Merck Index: 149599
• PubChem SID: 46507623; 24277877; 160963731
• PubChem CID: 5546

CALCULATED PROPERTIES

JChem

• Acid pKa: 15.8762245
• H Acceptors: 7
• H Donor: 3
• LogD (pH = 5.5): 1.114474
• LogD (pH = 7.4): 1.1145703
• Log P: 1.1145715
• Molar Refractivity: 75.1259 cm^3
• Polarizability: 27.961065 Å^3
• Polar Surface Area: 129.62 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 1.21
• LOG S: -2.42
• Solubility (Water): 9.63e-01 g/l

PROPERTIES

Physical Property

• Solubility: 48.2 mg/L; DMSO
• Apperance: Yellow Solid
• Melting Point: >300°C; >300°C (dec.); 316°C
• Flash Point: 11 °C; 51.8 °F
• Hydrophobicity(logP): -0.247; 0.3

Safety Information

• Storage Condition: -20°C Freezer; Room Temperature (15-30°C)
• Storage Warning: IRRITANT
• RTECS: UO3470000
• European Hazard Symbols: Flammable (F); Toxic (T); X; Harmful (Xn)
• UN Number: 1230
• German water hazard class: 1; 3
• Hazard Class: 3
• Packing Group: 2
• Risk Statements: 11-23/24/25-39/23/24/25; 22-36/37/38; R:22
• Safety Statements: 26-36/37; 26-36/37/39; 7-16-36/37-45; S:36/37/39
• TSCA Listed: false; 否
• GHS Pictograms: GHS02; GHS06; GHS07; GHS08
• GHS Signal Word: Danger; Warning
• GHS Hazard statements: H225-H301-H311-H331-H370; H301-H315-H319-H335; H302-H315-H319-H335
• GHS Precautionary statements: P210-P260-P280-P301 + P310-P311; P261-P301+P310-P305+P351+P338-P302+P352-P405-P501A; P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Faceshields, Gloves; Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US)
• RID/ADR: UN 1230 3/PG 2

Pharmacology Properties

• Target: Sodium Channel
• Mechanism of Action: Potassium transport inhibitor; Sodium reabsorption inhibitor; Sodium transport inhibitor

Product Information

• Purity: ≥99%; 95%; 98%
• Salt Data: Free Base
• Application(s): Antimalarial agent; Diuretic

DETAILS

MP Biomedicals - 05221529

MP Biomedicals Rare Chemical collection

MP Biomedicals - 02156960

Purity: 98%
Sodium channel blocker.

DrugBank - DB00384

• Drug Groups: approved
• Description: A pteridine that is used as a mild diuretic. [PubChem]
• Indication: 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.
• Pharmacology: Triamterene, a relatively weak, potassium-sparing diuretic and antihypertensive, is used in the management of hypokalemia. Triamterene is similar in action to amiloride but, unlike amiloride, increases the urinary excretion of magnesium.
• Toxicity: In the event of overdosage it can be theorized that electrolyte imbalance would be the major concern, with particular attention to possible hyperkalemia. Other symptoms that might be seen would be nausea and vomiting, other G.I. disturbances, and weakness. It is conceivable that some hypotension could occur. The oral LD₅₀ in mice is 380 mg/kg.
• Affected Organisms: Humans and other mammals
• Biotransformation: Triamterene is primarily metabolized to the sulfate conjugate of hydroxytriamterene. Both the plasma and urine levels of this metabolite greatly exceed triamterene levels.
• Absorption: Rapidly absorbed, with somewhat less than 50% of the oral dose reaching the urine.
• Half Life: 255 minutes (188 minutes for OH-TA-ester metabolite) after IV administration.
• Protein Binding: 55-67% (93% for the OH-TA-ester metabolite)
• Clearance: * 4.5 l/min [total plasma clearance]; * 0.22 l/kg [renal plasma clearance]
• References: WellSpring Pharmaceutical Corporation. Dyrenium (triamterene) capsules prescribing information. Neptune, NJ; 2001 June.; 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]
• External Links: Wikipedia; RxList; Drugs.com

Sigma Aldrich - T4143

Biochem/physiol Actions
Weak diuretic with potassium sparing properties; blocks Na+ reuptake in the kidneys.

Toronto Research Chemicals - T767325

Triamterene is a weak diuretic with potassium sparing properties; blocks Na+ reuptake in the kidneys.

REFERENCES

• WellSpring Pharmaceutical Corporation. Dyrenium (triamterene) capsules prescribing information. Neptune, NJ; 2001 June.
• 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
• Osdene, et al.: J. Med. Chem., 10, 431 (1967)
• Kapoor, V.K., et al.: Anal. Profiles Drug Subs. Excip., 23, 571 (1967)
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• Osdene, T.S. et al., J. Med. Chem., 1967, 10, 431, (synth, pharmacol)
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• Schwalbe, C.H. et al., Acta Cryst. C, 1987, 43, 1097, (cryst struct)
• Negwer, M., Organic-Chemical Drugs and their Synonyms, 6th edn., Akademie-Verlag, 1987, 2248
• Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 829
• Kapoor, V.K., Anal. Profiles Drug Subst., 1994, 23, 571, (rev)
• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, UVJ450