Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C13H18N4O3 |
| Molecular Weight | 278.307 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CN1C=NC2=C1C(=O)N(CCCCC(C)=O)C(=O)N2C
InChI
InChIKey=BYPFEZZEUUWMEJ-UHFFFAOYSA-N
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
Pentoxil (Pentoxifylline Extended-release Tablets, USP) is indicated for the treatment of patients with intermittent claudication based on chronic occlusive arterial disease of the limbs. Pentoxil can improve function and symptoms but is not intended to replace more definitive therapy, such as surgical bypass, or removal of arterial obstructions when treating peripheral vascular disease. Pentoxifylline and its metabolites improve the flow properties of blood by decreasing its viscosity. In patients with chronic peripheral arterial disease, this increases blood flow to the affected microcirculation and enhances tissue oxygenation. The precise mode of action of pentoxifylline and the sequence of events leading to clinical improvement are still to be defined. Pentoxifylline inhibits erythrocyte phosphodiesterase, resulting in an increase in erythrocyte cAMP activity. Subsequently, the erythrocyte membrane becomes more resistant to deformity. Along with erythrocyte activity, pentoxifylline also decreases blood viscosity by reducing plasma fibrinogen concentrations and increasing fibrinolytic activity. It is also a non-selective adenosine receptor antagonist. Pentoxifylline administration has been shown to produce dose-related hemorrheologic effects, lowering blood viscosity, and improving erythrocyte flexibility. Pentoxifylline has been shown to increase leukocyte deformability and to inhibit neutrophil adhesion and activation. Tissue oxygen levels have been shown to be significantly increased by therapeutic doses of pentoxifylline in patients with peripheral arterial disease. Clinical trials were conducted using either extended-release pentoxifylline tablets for up to 60 weeks or immediate-release pentoxifylline capsules for up to 24 weeks. Dosage ranges in the tablet studies were 400 mg bid to tid and in the capsule studies, 200-400 mg tid. The incidence of adverse reactions was higher in the capsule studies (where dose related increases were seen in digestive and nervous system side effects) than in the tablet studies. Studies with the capsule include domestic experience, whereas studies with the extended-release tablets were conducted outside the U.S.
Originator
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL2094257 |
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Target ID: CHEMBL2363066 |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | PENTOXIL Approved UseINDICATIONS & USAGE Pentoxifylline extended-release tablets are indicated for the treatment of patients with intermittent claudication on the basis of chronic occlusive arterial disease of the limbs. Pentoxifylline can improve function and symptoms but is not intended to replace more definitive therapy, such as surgical bypass, or removal of arterial obstructions when treating peripheral vascular disease. Launch Date9.2283837E11 |
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
1607 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3958905 |
400 mg single, oral dose: 400 mg route of administration: Oral experiment type: SINGLE co-administered: |
PENTOXIFYLLINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
272 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3958905 |
100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered: |
PENTOXIFYLLINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
683 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3958905 |
200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered: |
PENTOXIFYLLINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
719 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/23400743 |
600 mg single, oral dose: 600 mg route of administration: Oral experiment type: SINGLE co-administered: |
PENTOXIFYLLINE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
AUC
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
1228 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3958905 |
400 mg single, oral dose: 400 mg route of administration: Oral experiment type: SINGLE co-administered: |
PENTOXIFYLLINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
193 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3958905 |
100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered: |
PENTOXIFYLLINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
380 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3958905 |
200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered: |
PENTOXIFYLLINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
4842 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/23400743 |
600 mg single, oral dose: 600 mg route of administration: Oral experiment type: SINGLE co-administered: |
PENTOXIFYLLINE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
T1/2
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
0.84 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3958905 |
400 mg single, oral dose: 400 mg route of administration: Oral experiment type: SINGLE co-administered: |
PENTOXIFYLLINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
0.48 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3958905 |
100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered: |
PENTOXIFYLLINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
0.39 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3958905 |
200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered: |
PENTOXIFYLLINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
Doses
| Dose | Population | Adverse events |
|---|---|---|
80 mg/kg single, oral Overdose Dose: 80 mg/kg Route: oral Route: single Dose: 80 mg/kg Sources: |
unhealthy, adult and children n = 44 Health Status: unhealthy Condition: peripheral vascular disease Age Group: adult and children Sex: unknown Population Size: 44 Sources: |
Disc. AE: Flushing, Hypotension... AEs leading to discontinuation/dose reduction: Flushing (44 patients) Sources: Hypotension (44 patients) Convulsions (44 patients) Somnolence (44 patients) Loss of consciousness (44 patients) Fever (44 patients) Agitation (44 patients) |
AEs
| AE | Significance | Dose | Population |
|---|---|---|---|
| Agitation | 44 patients Disc. AE |
80 mg/kg single, oral Overdose Dose: 80 mg/kg Route: oral Route: single Dose: 80 mg/kg Sources: |
unhealthy, adult and children n = 44 Health Status: unhealthy Condition: peripheral vascular disease Age Group: adult and children Sex: unknown Population Size: 44 Sources: |
| Convulsions | 44 patients Disc. AE |
80 mg/kg single, oral Overdose Dose: 80 mg/kg Route: oral Route: single Dose: 80 mg/kg Sources: |
unhealthy, adult and children n = 44 Health Status: unhealthy Condition: peripheral vascular disease Age Group: adult and children Sex: unknown Population Size: 44 Sources: |
| Fever | 44 patients Disc. AE |
80 mg/kg single, oral Overdose Dose: 80 mg/kg Route: oral Route: single Dose: 80 mg/kg Sources: |
unhealthy, adult and children n = 44 Health Status: unhealthy Condition: peripheral vascular disease Age Group: adult and children Sex: unknown Population Size: 44 Sources: |
| Flushing | 44 patients Disc. AE |
80 mg/kg single, oral Overdose Dose: 80 mg/kg Route: oral Route: single Dose: 80 mg/kg Sources: |
unhealthy, adult and children n = 44 Health Status: unhealthy Condition: peripheral vascular disease Age Group: adult and children Sex: unknown Population Size: 44 Sources: |
| Hypotension | 44 patients Disc. AE |
80 mg/kg single, oral Overdose Dose: 80 mg/kg Route: oral Route: single Dose: 80 mg/kg Sources: |
unhealthy, adult and children n = 44 Health Status: unhealthy Condition: peripheral vascular disease Age Group: adult and children Sex: unknown Population Size: 44 Sources: |
| Loss of consciousness | 44 patients Disc. AE |
80 mg/kg single, oral Overdose Dose: 80 mg/kg Route: oral Route: single Dose: 80 mg/kg Sources: |
unhealthy, adult and children n = 44 Health Status: unhealthy Condition: peripheral vascular disease Age Group: adult and children Sex: unknown Population Size: 44 Sources: |
| Somnolence | 44 patients Disc. AE |
80 mg/kg single, oral Overdose Dose: 80 mg/kg Route: oral Route: single Dose: 80 mg/kg Sources: |
unhealthy, adult and children n = 44 Health Status: unhealthy Condition: peripheral vascular disease Age Group: adult and children Sex: unknown Population Size: 44 Sources: |
Overview
| CYP3A4 | CYP2C9 | CYP2D6 | hERG |
|---|---|---|---|
OverviewOther
| Other Inhibitor | Other Substrate | Other Inducer |
|---|---|---|
Drug as victim
| Target | Modality | Activity | Metabolite | Clinical evidence |
|---|---|---|---|---|
Page: 7.0 |
yes | likely (co-administration study) Comment: Concomitant administration of strong CYP1A2 inhibitors (including e.g. ciprofloxacin or fluvoxamine) may increase the exposure to pentoxifylline Page: 7.0 |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Immunotherapy of inflammatory demyelinating diseases of the central nervous system. | 2001 |
|
| The alveolar septal thickness and type II pneumocytes number in irradiated lungs, time expression and the effect of pentoxifylline. | 2001 |
|
| Managing cancer-related anorexia/cachexia. | 2001 |
|
| The efficacy of medication on tinnitus due to acute acoustic trauma. | 2001 |
|
| New treatment options in intermittent claudication: the US experience. | 2001 Apr |
|
| Cilostazol: a novel treatment option in intermittent claudication. | 2001 Apr |
|
| A new treatment for peripheral arterial disease. | 2001 Apr |
|
| Methylxanthine sensitization of human colon cancer cells to 186Re-labeled monoclonal antibody. | 2001 Apr |
|
| Pentoxifylline reduces coronary leukocyte accumulation early in reperfusion after cold ischemia. | 2001 Apr |
|
| Value of the hamster oocyte test and computerised measurements of sperm motility in predicting if four or more viable embryos will be obtained in an IVF cycle. | 2001 Apr |
|
| Matrix metalloproteinase inhibitors cause cell cycle arrest and apoptosis in glomerular mesangial cells. | 2001 Apr |
|
| Prevention of compartment syndrome in dorsal root ganglia caused by exposure to nucleus pulposus. | 2001 Apr 15 |
|
| Intracellular pool of IL-10 receptors in specific granules of human neutrophils: differential mobilization by proinflammatory mediators. | 2001 Apr 15 |
|
| Administration of pentoxifylline during allergen sensitization dissociates pulmonary allergic inflammation from airway hyperresponsiveness. | 2001 Aug 1 |
|
| Pentoxifylline treatment of mice with chronic pulmonary tuberculosis accelerates the development of destructive pathology. | 2001 Feb |
|
| Is cilostazol more effective than pentoxifylline in the treatment of symptoms of intermittent claudication? | 2001 Feb |
|
| [Infusion therapy with pentoxifylline and/or hydroxyethyl starch]. | 2001 Feb 23 |
|
| Beneficial effects of pentoxifylline in patients with idiopathic dilated cardiomyopathy treated with angiotensin-converting enzyme inhibitors and carvedilol: results of a randomized study. | 2001 Feb 27 |
|
| Cytokine-mediated suppression of cytochrome P450 1A1 in Hepa-1c1c7 cells by pokeweed mitogen. | 2001 Feb 28 |
|
| May pentoxifylline improve lung function after one-lung flooding? | 2001 Jan |
|
| [Parkinsonism or Parkinson's disease unmasked by pentoxifylline?]. | 2001 Jan |
|
| Integrating anti-tumor necrosis factor therapy in inflammatory bowel disease: current and future perspectives. | 2001 Jul |
|
| Ibudilast attenuates astrocyte apoptosis via cyclic GMP signalling pathway in an in vitro reperfusion model. | 2001 Jul |
|
| Renal failure, anaemia, cytokines and inflammation. | 2001 Jul |
|
| In vivo downregulation of T helper cell 1 immune responses reduces atherogenesis in apolipoprotein E-knockout mice. | 2001 Jul 10 |
|
| Pentoxifylline improves in vitro fertilization and subsequent development of bovine oocytes. | 2001 Jul 15 |
|
| Management of patients with severe oral mucosal disease. | 2001 Jul-Aug |
|
| A redox-regulated tyrosine phosphorylation cascade in rat spermatozoa. | 2001 Jul-Aug |
|
| Effect of pentoxifylline on nitrogen balance and 3-methylhistidine excretion in parenterally fed endotoxemic rats. | 2001 Jul-Aug |
|
| Medical management of peripheral arterial disease. | 2001 Jul-Aug |
|
| [Beneficial effects of pentoxifylline in patients with idiopathic dilated cardiomyopathy treated with angiotensin-converting enzyme inhibitors and carvedilol. Results of a randomised study]. | 2001 Jun |
|
| Improved response of colon cancer xenografts to radioimmunotherapy with pentoxifylline treatment. | 2001 Jun |
|
| Pentoxifylline rescue preserves lung function in isolated canine lungs injured with phorbol myristate acetate. | 2001 Jun |
|
| Therapeutic effects of Vascupump treatment patients with Fontaine Stage II B arteriopathy. | 2001 Jun |
|
| Countervailing influence of tumor necrosis factor-alpha and nitric oxide in endotoxemia. | 2001 Jun |
|
| Analysis of the cilostazol safety database. | 2001 Jun 28 |
|
| Comparative effects of cilostazol and other therapies for intermittent claudication. | 2001 Jun 28 |
|
| Intermittent claudication: effective medical management of a common circulatory problem. | 2001 Jun 28 |
|
| The effects of pentoxifylline treatment on bacterial translocation after hemorrhagic shock in rats. | 2001 Mar |
|
| Inhibition of human CYP1A2 activity in vitro by methylxanthines: potent competitive inhibition by 8-phenyltheophylline. | 2001 Mar |
|
| [The effect of pentoxifylline on the deformability of erythrocytes in erythrocyte concentrates in additive solution]. | 2001 Mar |
|
| Necrobiosis lipoidica. Indolent plaques may signal diabetes. | 2001 Mar |
|
| Pentoxifylline inhibits the synthesis and IFN-gamma-inducing activity of IL-18. | 2001 May |
|
| Controlled perfusion of the transplanted lung. | 2001 May |
|
| Influence of prophylactic use of pentoxifylline on postoperative organ function in elderly cardiac surgery patients. | 2001 May |
|
| Modulation of human peripheral blood mononuclear cell activation by the combination of leflunomide and pentoxifylline. | 2001 May |
|
| A toast to pentoxifylline. | 2001 May |
|
| A comparison of heat-induced hyperactivation in patients' sperm after colloid or pentoxifylline wash methods. | 2001 May |
|
| Regulation of TNFalpha and interleukin-10 production by prostaglandins I(2) and E(2): studies with prostaglandin receptor-deficient mice and prostaglandin E-receptor subtype-selective synthetic agonists. | 2001 May 1 |
|
| Pentoxifylline: wonder drug? | 2001 May-Jun |
Sample Use Guides
The usual dosage of Pentoxil (Pentoxifylline Extended-release Tablets, USP) in extended-release tablet form is one tablet (400 mg) three times a day with meals. While the effect of Pentoxil may be seen within 2 to 4 weeks, it is recommended that treatment be continued for at least 8 weeks. Efficacy has been demonstrated in double-blind clinical studies of 6 months duration.
Route of Administration:
Oral
The proliferation rate of the cells treated with 1 mM Pentoxifylline (PTX) significantly decreased compared with that of the control in T6 cells (78.3 ± 6.03% at 12 h, 61.0 ± 7.55% at 24 h, and 44.7 ± 2.08% at 48 h, p < 0.05). PTX (1 mM) also decreased the fraction of the hepatic stellate cells (HSC) population in the S and G2/M-phases of the cell cycle in primary activated rat HSCs. The Raf-1 inhibitor GW5074 and the ERK inhibitor U0126 had inhibitory effects that were similar to those of PTX on HSC proliferation. In addition, PTX inhibited the phosphorylation of Raf-1 (p-Raf-1) and ERK (p-ERK) in a dose- and time-dependent manner in HSCs.
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| Classification Tree | Code System | Code | ||
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FDA ORPHAN DRUG |
369712
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WHO-VATC |
QC04AD03
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NDF-RT |
N0000009065
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NCI_THESAURUS |
C744
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NCI_THESAURUS |
C1327
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NCI_THESAURUS |
C221
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LIVERTOX |
NBK548672
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NDF-RT |
N0000175895
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WHO-ATC |
C04AD03
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637086
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3309
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Pentoxifylline
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1508901
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m8519
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758481
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D010431
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6493-05-6
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SUB09705MIG
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2099
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DB00806
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CHEMBL628
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C733
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PENTOXIFYLLINE
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100000091628
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ACTIVE MOIETY
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