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Pentoxifylline

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Pentoxifylline Basic information
Product Name:Pentoxifylline
Synonyms:3,7-DIHYDRO-3,7-DIMETHYL-1-(5-OXOHEXYL)-1H-PURINE-2,6-DIONE;PENTOXIFYLLINE;PENTOXYIFYLLINE;PENTOXYPHYLINE;1-(5-Oxohexyl)-3,7-dimethylxanthine;bl191;Dimethyloxohexylxanthine;Durapental
CAS:6493-05-6
MF:C13H18N4O3
MW:278.31
EINECS:229-374-5
Product Categories:Inhibitors;Intermediates & Fine Chemicals;Pharmaceuticals;Cyclic Nucleotide related;All Inhibitors;pentoxifylline;6493-05-6
Mol File:6493-05-6.mol
Pentoxifylline Structure
Pentoxifylline Chemical Properties
Melting point 98-100°C
Boiling point 421.13°C (rough estimate)
density 1.1713 (rough estimate)
refractive index 1.6000 (estimate)
storage temp. Sealed in dry,Room Temperature
solubility H2O: ≥43 mg/mL
form solid
pka0.50±0.70(Predicted)
color white
λmax276nm(lit.)
Merck 14,7136
CAS DataBase Reference6493-05-6(CAS DataBase Reference)
NIST Chemistry ReferencePentoxifylline(6493-05-6)
EPA Substance Registry System1H-Purine-2,6-dione, 3,7-dihydro-3,7-dimethyl-1-(5-oxohexyl)- (6493-05-6)
Safety Information
Hazard Codes Xn
Risk Statements 22
Safety Statements 36
WGK Germany 3
RTECS XH2475000
HS Code 2939590000
ToxicityLD50 orally in mice: 1385 mg/kg (Popendiker)
MSDS Information
ProviderLanguage
SigmaAldrich English
Pentoxifylline Usage And Synthesis
Chemical PropertiesWhite to Off-White Solid
OriginatorTrental,Albert Roussel ,W. Germany ,1972
UsesPentoxifylline is a methylxanthine phospho-diesterase inhibitor with favorable antiinflammatory effects and immunoregulatory properties.
A metabolite of Pentifylline. Methylxanthine derivative that improves blood flow by decreasing blood viscosity. Phosphodiesterase inhibitor. Inhibits the synthesis of tumor necrosis factor a (TNF-a).
UsesPentoxifylline can increase red blood cell deformability, reduce blood viscosity, and decrease platelet aggregation and thrombus formation. Pentoxifylline is an oral agent that improves perfusion of occluded vessels and is used to treat systemic vascular diseases. The retinal flow velocity in patients with RVO treated with pentoxifylline improved compared with placebo, but the study had a small number of patients (n = 8) and short follow-up (4 weeks), and no visual outcome data were reported.
UsesPentoxifylline has been used:
  • used in the combinatorial treatment with itraconazole for paracoccidioidomycosis (PCM)
  • to treat harvested sperms to check the effect of ′pentoxifylline exposed sperms′ in the contribution of embryonic growth
  • to intrathecally inject female and male mice to investigate whether astrocytes and microglia could be causally involved in the maintenance of pain-like behaviour

DefinitionChEBI: Pentoxifylline is an oxopurine.
IndicationsPentoxifylline at a dose of 400 mg three times a day after meals was reported to alleviate the symptoms in a small open trial.
Manufacturing ProcessA solution of 35.4 g of 1-bromohexanone-5 in 200 ml of ethanol was gradually mixed at the reflux temperature with vigorous stirring with 39.7 g of theobromine-sodium in 100 ml of water. After 3 hours reflux the unreacted theobromine was filtered off with suction, the filtrate was evaporated to dryness, the residue was dissolved in water and the solution was extracted with chloroform. The chloroform was distilled off and 1-(5'-oxohexyl)-3,7 Pentoxifylline dimethylxanthine was obtained as residue; after recrystallization from isopropanol, it melted at 102°C to 103°C (about 25% yield, calculated on the reacted theobromine).
Brand namePentoxil (Upsher Smith); Trental (Sanofi Aventis).
Therapeutic FunctionVasodilator
Biological ActivityPhosphodiesterase inhibitor that blocks production of TNF- α and other cytokines. Displays antinociceptive activity.
Biochem/physiol ActionsPentoxifylline?(PTX) is considered as a nonspecific phosphodiesterase inhibitor. It possesses rheologic properties. Pentoxifylline?is used to treat peripheral vascular disease. It has the ability to block the phosphorylation of I kappa B-alpha (I?Bα) in serines 32 and 36.
Veterinary Drugs and TreatmentsIn horses, pentoxifylline has been used as adjunctive therapy for cutaneous, vasculitis, endotoxemia and for the treatment of navicular disease.
Pentoxifylline has been used in dogs to treat immune-mediated dermatologic conditions, enhance healing, and reduce inflammation caused by ulcerative dermatosis in Shelties and Collies and for other conditions where improved microcirculation may be of benefit. It is being investigated for adjunctive therapy for dilated cardiomyopathy in Doberman pinschers.
Pentoxifylline has been tried in conjunction with prednisolone to decrease vasculitis associated with FIP in cats.
Pentoxifylline’s major indications for humans include symptomatic treatment of peripheral vascular disease (e.g., intermittent claudication, sickle cell disease, Raynaud’s, etc.) and cerebrovascular diseases where blood flow may be impaired in the microvasculature.
Pentoxifylline Preparation Products And Raw materials
Raw materialsEthyl acetoacetate-->1-Bromo-3-chloropropane-->Theobromine-->1-Bromo-5-hexanone
Tag:Pentoxifylline(6493-05-6) Related Product Information
Dehydroepiandrosterone Epiandrosterone acetate Tetrahydro-4H-pyran-4-one N,N-Dimethylformamide Purine Naringin dihydrochalcone Dimethyl fumarate Acetone oxime Dimethyl sulfate Poly(dimethylsiloxane) ETHANE Dimethyl ether Theobromine Dimethyl sulfoxide Dimethyl carbonate Pentoxifylline Impurity 8(Pentoxifylline EP Impurity H) 3,7-Dihydro-3,7-diMethyl-6-[(5-oxohexyl)oxy]-2H-purin-2-one 1,1'-[(5E)-5-Methyl-7-oxo-5-undecene-1,11-diyl] Bis