Chemical Component Summary

Name3,7-DIMETHYL-1-(5-OXOHEXYL)-3,7-DIHYDRO-1H-PURINE-2,6-DIONE
SynonymsPENTOXIFYLLINE
Identifiers3,7-dimethyl-1-(5-oxohexyl)purine-2,6-dione
FormulaC13 H18 N4 O3
Molecular Weight278.307
TypeNON-POLYMER
Isomeric SMILESCC(=O)CCCCN1C(=O)c2c(ncn2C)N(C1=O)C
InChIInChI=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
InChIKeyBYPFEZZEUUWMEJ-UHFFFAOYSA-N

Chemical Details

Formal Charge0
Atom Count38
Chiral Atom Count0
Bond Count39
Aromatic Bond Count10

Drug Info: DrugBank

DrugBank IDDB00806 
NamePentoxifylline
Groups
  • approved
  • investigational
DescriptionPentoxifylline (PTX) is a synthetic dimethylxanthine derivative that modulates the rheological properties of blood and also has both anti-oxidant and anti-inflammatory properties.[A226415, L30300] Although originally developed to treat intermittent claudication, a form of exertion-induced leg pain common in patients with peripheral arterial disease, PTX has been investigated for its possible use in diverse conditions, including osteoradionecrosis, diabetic kidney disease, and generally any condition associated with fibrosis.[A226410, A226415, A226455] More recently, PTX has been suggested as a possible treatment for COVID-19-induced pulmonary complications due to its ability to regulate the production of inflammatory cytokines.[A226608] Pentoxifylline has been marketed in Europe since 1972; PTX extended-release tablets sold under the trade name TRENTAL by US Pharm Holdings were first approved by the FDA on Aug 30, 1984, but have since been discontinued. A branded product, PENTOXIL, marketed by Upsher-Smith Laboratories, and generic forms marketed by Valeant Pharmaceuticals and APOTEX have been available since the late 1990s.[L30300]
Synonyms
  • Oxpentifylline
  • Pentoxifyllin
  • Pentoxifilina
  • Pentoxifyllinum
  • Pentoxifylline
Brand Names
  • Pentoxifylline 0.5% / Triamcinolone Acetonide 0.1%
  • Pentoxil
  • Trental
  • Trental Tab 400mg
  • Truemed Group LLC
IndicationPentoxifylline is indicated for the treatment of intermittent claudication in patients with chronic occlusive arterial disease. Pentoxifylline may improve limb function and reduce symptoms but cannot replace other therapies such as surgical bypass or removal of vascular obstructions.[L30300]
Categories
  • Alkaloids
  • Antioxidants
  • Antiplatelet agents
  • Blood Viscosity Reducer
  • Cardiovascular Agents
ATC-Code
  • C04AD03
  • R03DA20
CAS number6493-05-6

Drug Targets

NameTarget SequencePharmacological ActionActions
Adenosine receptor A2aMPIMGSSVYITVELAIAVLAILGNVLVCWAVWLNSNLQNVTNYFVVSLAA...unknownagonist
Phosphodiesterase enzymes-unknowninhibitor
Adenosine receptor A1MPPSISAFQAAYIGIEVLIALVSVPGNVLVIWAVKVNQALRDATFCFIVS...unknown
5'-nucleotidaseMCPRAARAPATLLLALGAVLWPAAGAWELTILHTNDVHSRLEQTSEDSSK...unknowninhibitor
Cytochrome P450 1A2MALSQSVPFSATELLLASAIFCLVFWVLKGLRPRVPKGLKSPPEPWGWPL...unknownsubstrate
Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682

Related Resource References

Resource NameReference
Pharos CHEMBL628
PubChem 4740
ChEMBL CHEMBL628
ChEBI CHEBI:7986
CCDC/CSD JAKGEH, WEDXEL, WEDXIP, FEFYIA, JAKGEH01, HUNJEH, DUKJUR, FEFYAS, HUNJIL, HUNJOR, FEFYEW, IXUCEM
COD 7228842, 7228844, 2232472