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

pka

0.50±0.70(Predicted)

color 

white

λmax

276nm(lit.)

Merck 

14,7136

CAS DataBase Reference

6493-05-6(CAS DataBase Reference)

NIST Chemistry Reference

Pentoxifylline(6493-05-6)

EPA Substance Registry System

1H-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

Toxicity

LD50 orally in mice: 1385 mg/kg (Popendiker)

MSDS

• Language:English Provider:SigmaAldrich

Pentoxifylline Usage And Synthesis

Chemical Properties

White to Off-White Solid

Originator

Trental,Albert Roussel ,W. Germany ,1972

Uses

Pentoxifylline 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

Uses

Pentoxifylline 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).

Uses

Pentoxifylline 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.

Indications

Pentoxifylline at a dose of 400 mg three times a day after meals was reported to alleviate the symptoms in a small open trial.

Definition

ChEBI: Pentoxifylline is an oxopurine.

Manufacturing Process

A 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 name

Pentoxil (Upsher Smith); Trental (Sanofi Aventis).

Therapeutic Function

Vasodilator

Biological Activity

Phosphodiesterase inhibitor that blocks production of TNF- α and other cytokines. Displays antinociceptive activity.

Biochem/physiol Actions

Pentoxifylline?(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 Treatments

In 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(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