Pentoxifylline (CED0002703)

Record Information
Version1.0
Creation Date2016-05-22 03:44:49 UTC
Update Date2026-05-14 16:49:28 UTC
Accession NumberCHEM016826
Identification
Common NamePentoxifylline
ClassSmall Molecule
Description
Pentoxifylline is an organic compound with the formula C13H18N4O3 and an average molecular weight of 278.31 g/mol. Pentoxifylline belongs to the purines and purine derivatives, a subclass of imidazopyrimidines within the organic compounds. This compound acts as a biological antioxidant (PMC8614781). Its recorded protein targets include 5'-nucleotidase (NT5E), Tumor necrosis factor (TNF), Adenosine receptor A1 (ADORA1), and Adenosine receptor A2a (ADORA2A), where it may function as an agonist, antagonist, inhibitor, or other. Pentoxifylline is utilized in healthcare, pharmaceuticals, and veterinary products as peripheral vasodilators and drugs for obstructive airway diseases. It is also used in food preservation. The compound is found in 14 recorded sources, including household cleaning and consumer products such as perfumes within detergents and soaps, tobacco smoke filters, cigar cigarettes, non electric simulated smoking devices, and other smoking requisites. It is also associated with electrical and electronic equipment, including antennas, conductors or conductive bodies characterised by the conductive materials, electrodes, hybrid capacitors, and electrically stimulated smoking devices. Recorded exposure routes include topical and oral administration. Regarding health effects, pentoxifylline is used as a treatment for pain (PMC9022185), peripheral vascular disease (PMC10855613), and rheumatoid arthritis (PMC1010320). Additionally, it has a therapeutic effect on proteinuria (PMC8614781).
Contaminant TypeNot Available
Chemical Structure
Synonyms
ValueSource
PentoxilKegg
TrentalKegg
EHT0201HMDB
AgapurinHMDB
TorentalHMDB
OxpentifyllineHMDB
Chemical FormulaC13H18N4O3
Average Molecular Mass278.307 g/mol
Monoisotopic Mass278.138 g/mol
CAS Registry Number6493-05-6
IUPAC Name3,7-dimethyl-1-(5-oxohexyl)-2,3,6,7-tetrahydro-1H-purine-2,6-dione
Traditional Namepentoxifylline
SMILESCN1C=NC2=C1C(=O)N(CCCCC(C)=O)C(=O)N2C
InChI IdentifierInChI=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
InChI KeyBYPFEZZEUUWMEJ-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as xanthines. These are purine derivatives with a ketone group conjugated at carbons 2 and 6 of the purine moiety.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassImidazopyrimidines
Sub ClassPurines and purine derivatives
Direct ParentXanthines
Alternative Parents
Substituents
  • Xanthine
  • 6-oxopurine
  • Purinone
  • Alkaloid or derivatives
  • Pyrimidone
  • N-substituted imidazole
  • Pyrimidine
  • Azole
  • Imidazole
  • Heteroaromatic compound
  • Vinylogous amide
  • Lactam
  • Ketone
  • Urea
  • Azacycle
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Carbonyl group
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
ApplicationsNot Available
Biological Roles
Chemical RolesNot Available
Organoleptic EffectsNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility5.17 g/LALOGPS
logP0.08ALOGPS
logP0.23ChemAxon
logS-1.7ALOGPS
pKa (Strongest Acidic)19.64ChemAxon
pKa (Strongest Basic)-0.93ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area75.51 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity73.52 m³·mol⁻¹ChemAxon
Polarizability29.27 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrumsplash10-0006-9480000000-5858a0a94add96d62994Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-001r-2900000000-d54457aaede5317cef72Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0059-1890000000-c9be2fe26b2862cba4f5Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-001r-2900000000-d54457aaede5317cef72Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0059-2970000000-95d1edcd63b61b13b22eNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0059-2970000000-0c35991320854cec88ddNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0019-0900000000-dd015a4509f33caa03c0Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-001r-0900000000-65fb6e1754eabaf86ab4Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-001r-3910000000-848959253dccbbc260a7Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-004i-0090000000-4f61bb0b4f8342199149Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-001i-0900000000-79465a5f4259ad7a5fd7Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-001i-0940000000-a097189c3d45a68b6674Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-01t9-0090000000-e92064736a2f3e194af7Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03fr-1590000000-3aa22ac7d56a3f0cb967Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-001i-9300000000-9e889c5028746f141557Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-004i-0390000000-a66c81c066b3055aee27Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-004i-2790000000-10e4eef90ade382bc5f4Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-052f-9500000000-23bd0511497da2b1fc18Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-004i-0390000000-3e633d64da435129d91bNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-001i-0910000000-285222c9846c41ea2ed2Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03di-3900000000-3902c6584393e2a548edNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-004i-0290000000-2d198d549fd71c261d88Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-004i-1930000000-cbb2368f24d9797f040aNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-056r-5950000000-89a80796e36b81a0c4a3Not AvailableView Spectrum
1D NMR13C NMR Spectrum (1D, D2O, predicted)Not AvailableNot AvailableView Spectrum
1D NMR1H NMR Spectrum (1D, D2O, predicted)Not AvailableNot AvailableView Spectrum
Toxicity Profile
Mechanism of ToxicityNot Available
Carcinogenicity (IARC Classification)Not Available
Minimum Risk LevelNot Available
SymptomsNot Available
TreatmentNot Available
Toxicity Values
Toxicity ValueUnitValue RangeOrganismDose DescriptorRoute of ExposurePredicted or ExperimentalReference
1049.0Log mg/kg[590:1900]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
rheumatoid arthritisis_treatment_forNot AvailablePMC1010320
painis_treatment_forNot AvailablePMC9022185
proteinuriahas_therapeutic_effect_onNot AvailablePMC8614781
peripheral vascular diseaseis_treatment_forNot AvailablePMC10855613
osteonecrosisis_treatment_forNot AvailablePMC7578793
alcoholic hepatitishas_therapeutic_effect_onNot AvailablePMC1492602
Exposure Sources
Source IDSourceSectorReference
10InsecticidesAgriculture & land managementNot Available
291Peripheral vasodilatorsHealthcare, pharmaceuticals & veterinary productsNot Available
391Drugs for obstructive airway diseasesHealthcare, pharmaceuticals & veterinary productsNot Available
506AntennasElectrical & Electronic EquipmentNot Available
511Conductors Or Conductive Bodies Characterised By The Conductive MaterialsElectrical & Electronic EquipmentNot Available
518Electrically Stimulated Smoking DevicesElectrical & Electronic EquipmentNot Available
519ElectrodesElectrical & Electronic EquipmentNot Available
524Hybrid CapacitorsElectrical & Electronic EquipmentNot Available
527MagnetsElectrical & Electronic EquipmentNot Available
545Food PreservationFood, food processing & cookwareNot Available
556Cigar CigarettesHousehold cleaning & consumer productsNot Available
559Non Electric Simulated Smoking DevicesHousehold cleaning & consumer productsNot Available
560Other Smoking RequisitesHousehold cleaning & consumer productsNot Available
561Perfumes Within Detergents And SoapsHousehold cleaning & consumer productsNot Available
569Tobacco Smoke FiltersHousehold cleaning & consumer productsNot Available
580Manufacture Preparation Of Tobacco ProductsIndustrial manufacturing & chemical processingNot Available
596AcaricidesAgriculture & land managementNot Available
602MolluscicidesAgriculture & land managementNot Available
603NematocidesAgriculture & land managementNot Available
605Pest RepellantsAgriculture & land managementNot Available
610Aftersun ProductsPersonal care & cosmeticsNot Available
611Anti Perspirants Or Body DeoderantsPersonal care & cosmeticsNot Available
615Eye Makeup ProductsPersonal care & cosmeticsNot Available
617Lip Care ProductsPersonal care & cosmeticsNot Available
618Lip Makeup ProductsPersonal care & cosmeticsNot Available
619Manicure PedicurePersonal care & cosmeticsNot Available
632ApparelTextiles, leather & furnishingsNot Available
642FootwearTextiles, leather & furnishingsNot Available
650Purses Luggage Hand BagsTextiles, leather & furnishingsNot Available
Pathways
1 pathway
Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Adenosine receptor A2b structureClick to view 3D structureAdenosine receptor A2bP29275HumansPredicted (SEA)6.69503
Endochitinase B1 structureClick to view 3D structureEndochitinase B1Q873X9Neosartorya fumigataPredicted (SEA)0.155698
Click to view 3D structureAdenosine receptor A2aP46616Cavia porcellusPredicted (SEA)4.35956
Click to view 3D structureAdenosine receptor A2aP30543Rattus norvegicusPredicted (SEA)44.919
Click to view 3D structureAdenosine receptor A1P25099Rattus norvegicusPredicted (SEA)47.488
Acetylcholinesterase structureClick to view 3D structureAcetylcholinesteraseP22303HumansPredicted (SEA)51.614
Adenosine receptor A2a structureClick to view 3D structureAdenosine receptor A2aP29274HumansPredicted (SEA)65.0819
Adenosine receptor A3 structureClick to view 3D structureAdenosine receptor A3P0DMS8HumansPredicted (SEA)91.5507
Click to view 3D structureAdenosine receptor A1P47745Cavia porcellusPredicted (SEA)31.6846
Adenosine receptor A1 structureClick to view 3D structureAdenosine receptor A1P30542HumansPredicted (SEA)108.133
Amine oxidase [flavin-containing] B structureClick to view 3D structureAmine oxidase [flavin-containing] BP27338HumansPredicted (SEA)159.202
Click to view 3D structureAdenosine receptor A3P28647Rattus norvegicusPredicted (SEA)56.0514
Amine oxidase [flavin-containing] A structureClick to view 3D structureAmine oxidase [flavin-containing] AP21397HumansPredicted (SEA)111.48
CCR4-NOT transcription complex subunit 7 structureClick to view 3D structureCCR4-NOT transcription complex subunit 7Q9UIV1HumansPredicted (SEA)1.71268
Click to view 3D structureAdenosine receptor A2bP29276Rattus norvegicusPredicted (SEA)13.2344
Short transient receptor potential channel 5 structureClick to view 3D structureShort transient receptor potential channel 5Q9UL62HumansPredicted (SEA)7.55137
Click to view 3D structure5-hydroxytryptamine receptor 1AP19327Rattus norvegicusPredicted (SEA)407.774
5-hydroxytryptamine receptor 7 structureClick to view 3D structure5-hydroxytryptamine receptor 7P34969HumansPredicted (SEA)437.123
Voltage-gated inwardly rectifying potassium channel KCNH2 structureClick to view 3D structureVoltage-gated inwardly rectifying potassium channel KCNH2Q12809HumansPredicted (SEA)1813.96
Click to view 3D structure5-hydroxytryptamine receptor 2AP14842Rattus norvegicusPredicted (SEA)514.505
5'-3' exonuclease PLD3 structureClick to view 3D structure5'-3' exonuclease PLD3Q8IV08HumansPredicted (SEA)11.4438
Click to view 3D structureD(2) dopamine receptorP61169RatPredicted (SEA)784.564
Guanine deaminase structureClick to view 3D structureGuanine deaminaseQ9Y2T3HumansPredicted (SEA)0.0778492
Dipeptidyl peptidase 4 structureClick to view 3D structureDipeptidyl peptidase 4P27487HumansPredicted (SEA)142.62
5-hydroxytryptamine receptor 6 structureClick to view 3D structure5-hydroxytryptamine receptor 6P50406HumansPredicted (SEA)1077.82
Concentrations
Not Available
External Links
DrugBank IDDB00806
HMDB IDHMDB0014944
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDPNX
Wikipedia LinkPentoxifylline
Chemspider ID4578
ChEBI ID127029
PubChem Compound ID4740
Kegg Compound IDC07424
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Authors unspecified: European Pentoxifylline Multi-Infarct Dementia Study. Eur Neurol. 1996;36(5):315-21.