3,7-dimethyl-1-(5-oxohexyl)-2,3,6,7-tetrahydro-1H-purine-2,6-dione

• ChemBase ID: 685
• Molecular Formular: C13H18N4O3
• Molecular Mass: 278.30702
• Monoisotopic Mass: 278.13789046
• SMILES: O=c1n(CCCCC(=O)C)c(=O)n(c2ncn(c12)C)C
• Canonical SMILES: CC(=O)CCCCn1c(=O)c2n(C)cnc2n(c1=O)C
• InChI: InChI=1S/C13H18N4O3/c1-9(18)6-4-5-7-17-12(19)10-11(14-8-15(10)2)16(3)13(17)20/h8H,4-7H2,1-3H3
• InChIKey: BYPFEZZEUUWMEJ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3,7-dimethyl-1-(5-oxohexyl)-2,3,6,7-tetrahydro-1H-purine-2,6-dione
• IUPAC Traditional name: pentoxifylline; 3,7-dimethyl-1-(5-oxohexyl)purine-2,6-dione; 3,7-dimethyl-1-(5-oxohexyl)-2,3,6,7-tetrahydro-1H-purine-2,6-dione
• Brand Name: Azupentat; Dimethyloxohexylxanthine; Durapental; Oxpentifylline; PENTOXYPHYLINE; Pentoxifyllin; Pentoxil; Pentoxiphyllium; Pentoxyfylline; Pentoxyphylline; Rentylin; Torental; Trental; Vazofirin
• Synonyms: pentoxifylline; EHT0201; Pentoxifylline; 3,7-dimethyl-1-(5-oxohexyl)-1H-purine-2,6(3H,7H)-dione; Trental; cis-9-Octadecenoyl coenzyme A; OLEOYL COENZYME A DIPOTASSIUM SALT; 3,7-Dihydro-3,7-dimethyl-1-(5-oxohexyl)-1H-purine-2,6-dione; 1-(5-Oxohexyl)-3,7-dimethylxanthine; 1-(5-Oxohexyl)Theobromine; Oxpentifylline; Vasotal; Vazofirin; Torental; Pentoxyphyllin; Pexal; Agapurin; Azupentat; Pentoflux; Pentoxifylline

Database IDs

• CAS Number: 6493-05-6
• EC Number: 229-374-5
• PubChem SID: 46505940; 160964148
• PubChem CID: 4740

CALCULATED PROPERTIES

JChem

• Acid pKa: 19.642868
• H Acceptors: 4
• H Donor: 0
• LogD (pH = 5.5): 0.23220569
• LogD (pH = 7.4): 0.23220584
• Log P: 0.23220585
• Molar Refractivity: 73.5223 cm^3
• Polarizability: 27.121319 Å^3
• Polar Surface Area: 75.51 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 0.08
• LOG S: -1.73
• Solubility (Water): 5.17e+00 g/l

PROPERTIES

Physical Property

• Solubility: 77 mg/mL; Chloroform; Methanol; Water
• Apperance: White to Off-White Solid
• Melting Point: 104-106°C; 98-100°C
• Hydrophobicity(logP): 0

Safety Information

• Storage Condition: 0°C; Refrigerator; Room Temperature (15-30°C)
• RTECS: XH2475000
• European Hazard Symbols: Harmful (Xn)
• Risk Statements: R:22
• Safety Statements: S:36/37/39

Pharmacology Properties

• Target: Others
• Mechanism of Action: Along with erythrocyte activity, pentoxifylline also decreases blood viscosity by reducing plasma fibrinogen concentrations and increasing fibrinolytic activity; Inhibits erythrocyte phosphodiesterase, resulting in an increase in erythrocyte cAMP activity. Subsequently, the erythrocyte membrane becomes more resistant to deformity

Product Information

• Purity: 90-95%
• Salt Data: Free Base
• Application(s): It also helps prevent strokes, can be used in managing sickle cell disease and improves blood flow to the brain; It is used to treat intermittent claudication resulting from obstructed arteries in the limbs, and vascular dementia; Pentoxifylline has also been used to treat nausea and headaches in the mountains (altitude sickness).; Pentoxifylline improves blood flow through blood vessels and therefore helps with blood circulation in the arms and legs (e.g. intermittent claudication)

DETAILS

MP Biomedicals - 02156107

Phosphodiesterase inhibitor. Also blocks synthesis of Tumor Necrosis Factor-α.

MP Biomedicals - 02100904

Potassium Salt
Purity: 90-95%

DrugBank - DB00806

• Drug Groups: approved; investigational
• Description: A methylxanthine derivative that inhibits phosphodiesterase and affects blood rheology. It improves blood flow by increasing erythrocyte and leukocyte flexibility. It also inhibits platelet aggregation. Pentoxifylline modulates immunologic activity by stimulating cytokine production. [PubChem]
• Indication: For the treatment of patients with intermittent lameness or immobility arising from chronic occlusive arterial disease of the limbs.
• Pharmacology: Pentoxifylline, a synthetic dimethylxanthine derivative structurally related to theophylline and caffeine, is used in the treatment of peripheral vascular diseases and in the management of cerebrovascular insufficiency, sickle cell disease, and diabetic neuropathy.
• Toxicity: LD₅₀=1385 mg/kg(orally in mice)
• Affected Organisms: Humans and other mammals
• Half Life: 0.4-0.8 hours
• Protein Binding: 70%
• Elimination: Excretion is almost totally urinary; the main biotransformation product is Metabolite V. Essentially no parent drug is found in the urine.
• References: : European Pentoxifylline Multi-Infarct Dementia Study. Eur Neurol. 1996;36(5):315-21. [Pubmed]
• External Links: Wikipedia; RxList; Drugs.com

Toronto Research Chemicals - P276500

A metabolite of Pentifylline. Methylxanthine derivative that improves blood flow by decreasing blood viscosity. Phosphodiesterase inhibitor. Inhibits the synthesis of tumor necrosis factor α (TNF-α).

REFERENCES

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