Pentoxifylline

Base Information

• Chemical Name: Pentoxifylline
• CAS No.: 6493-05-6
• Molecular Formula: C13H18N4O3
• Molecular Weight: 278.311
• Hs Code.: 2939590000
• European Community (EC) Number: 229-374-5
• NSC Number: 758481,637086
• UNII: SD6QCT3TSU
• DSSTox Substance ID: DTXSID7023437
• Nikkaji Number: J3.419C
• Wikipedia: Pentoxifylline
• Wikidata: Q416331
• NCI Thesaurus Code: C733
• RXCUI: 8013
• Pharos Ligand ID: QN7ZYW5JAXF3
• Metabolomics Workbench ID: 43097
• ChEMBL ID: CHEMBL628
• Mol file: 6493-05-6.mol

Synonyms:Agapurin;BL 191;BL-191;BL191;Oxpentifylline;Pentoxifylline;Pentoxil;Torental;Trental

Chemical Property of Pentoxifylline

Chemical Property:

• Appearance/Colour: White to off-white solid
• Melting Point: 98-100°C
• Refractive Index: 1.6000 (estimate)
• Boiling Point: 531.3 °C at 760 mmHg
• PKA: 0.50±0.70(Predicted)
• Flash Point: 275.1 °C
• PSA: 78.89000
• Density: 1.31 g/cm³
• LogP: 0.19300
• Storage Temp.: Store at RT
• Solubility.: H2O: ≥43 mg/mL
• XLogP3: 0.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 278.13789045
• Heavy Atom Count: 20
• Complexity: 426

Purity/Quality:

97%-103%, ^*data from raw suppliers

Pentoxifylline ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22
• Safety Statements: 36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Drug Classes: Intermittent Claudication Agents
• Canonical SMILES: CC(=O)CCCCN1C(=O)C2=C(N=CN2C)N(C1=O)C
• Recent ClinicalTrials: RECLAIM: Recovering From COVID-19 Lingering Symptoms Adaptive Integrative Medicine
• Recent EU Clinical Trials: Feasibility of Aggressive Albuminuria Reduction in Biopsy-Proven Diabetic Nephropathy - A Pilot Study
• 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). 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. 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 growthto intrathecally inject female and male mice to investigate whether astrocytes and microglia could be causally involved in the maintenance of pain-like behaviour
• 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.
• Therapeutic Function: Vasodilator

Technology Process of Pentoxifylline

There total 8 articles about Pentoxifylline which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 91.1%

theobromine / (83-67-0) + (5-oxohexyl) mesylate → pentoxyphylline (6493-05-6)

Guidance literature:

With potassium carbonate; In ethanol; water; at 50 ℃; for 16h;

Reference yield: 76.1%

6-amino-hexan-2-one (26342-06-3) + 4-[(chlorocarbonyl)(methyl)amino]-1-methyl-1H-imidazole-5-carbonyl chloride → pentoxyphylline (6493-05-6)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 5 ℃; for 0.333333h; Reagent/catalyst; Solvent; Temperature;

Reference yield:

theobromine / (83-67-0) + 6-chloro-2-hexanone (10226-30-9) → pentoxyphylline (6493-05-6)

Guidance literature:

With potassium carbonate; In N,N-dimethyl-formamide; at 110 ℃; for 18h;

upstream raw materials:

theobromine /

6-Bromo-2-hexanone

6-chloro-2-hexanone

1-(4-chlorobutyl)-3,7-dimethyl-3,7-dihydro-1H-purine-2,6-dione

Downstream raw materials:

1-(5-hydroxyhexyl)theobromine

(+)-(S)-3,7-dimethyl-1-(5-hydroxyhexyl)-3,7-dihydropurine-2,6-dione

formyl bromide

lisofylline

Refernces

• 1、 Donslund, Aske S.,Pedersen, Simon S.,Gaardbo, Cecilie,Neumann, Karoline T.,Kingston, Lee,Elmore, Charles S.,Skrydstrup, Troels. "Direct Access to Isotopically Labeled Aliphatic Ketones Mediated by Nickel(I) Activation". . p. 8099 - 8103. Retrieved 2020/03/16.
• 2、 -. "COMPOSITIONS AND METHODS FOR THE TREATMENT OF CHRONIC DISEASES AND INFLAMMATORY DISORDERS". Paragraph 0116-0118. . Retrieved 2015/03/31.