Pentoxifylline

Pentoxifylline

Clinical data
Pronunciation	/ˌpɛntɒkˈsɪfᵻliːn, -ɪn/
Trade names	Many names worldwide
AHFS/Drugs.com	Monograph
MedlinePlus	a685027
License data	US FDA: Pentoxifylline
Pregnancy category	AU: B1 US: C (Risk not ruled out)
Routes of administration	By mouth
ATC code	C04AD03 (WHO)
Legal status
Legal status	AU: S4 (Prescription only) CA: ℞-only UK: POM (Prescription only) US: ℞-only
Pharmacokinetic data
Bioavailability	10–30%
Metabolism	Hepatic and via erythrocytes
Biological half-life	0.4–0.8 hours (1–1.6 hours for active metabolite)
Excretion	Urine (95%), faeces (<4%)
Identifiers
IUPAC name 3,7-Dimethyl-1-(5-oxohexyl)-3,7-dihydro-1H-purine-2,6-dione
CAS Number	6493-05-6 Y
PubChem CID	4740
IUPHAR/BPS	7095
DrugBank	DB00806 Y
ChemSpider	4578 Y
UNII	SD6QCT3TSU
KEGG	D00501 Y
ChEMBL	CHEMBL628 Y
ECHA InfoCard	100.026.704
Chemical and physical data
Formula	C13H18N4O3
Molar mass	278.31 g/mol
3D model (Jmol)	Interactive image
SMILES O=C2N(c1ncn(c1C(=O)N2CCCCC(=O)C)C)C
InChI 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 Y Key:BYPFEZZEUUWMEJ-UHFFFAOYSA-N Y

Pentoxifylline (INN, BAN, USAN) or oxpentifylline (AAN) is a xanthine derivative used as a drug to treat muscle pain in people with peripheral artery disease. It is generic and sold under many brand names worldwide.

Its primary use in medicine is to reduce pain, cramping, numbness, or weakness in the arms or legs which occurs due to intermittent claudication, a form of muscle pain resulting from peripheral artery diseases. This is its only FDA, MHRA and TGA-labelled indication.

Common side effects are belching, bloating, stomach discomfort or upset, nausea, vomiting, indigestion, dizziness, and flushing. Uncommon and rare side effects include angina, palpitations, hypersensitivity, itchiness, rash, hives, bleeding, hallucinations, arrhythmias, and aseptic meningitis.

Contraindications include intolerance to pentoxifylline or other xanthine derivatives, recent retinal or cerebral haemorrhage, and risk factors for haemorrhage.

Co-administration of pentoxifylline and sodium thiopental may cause death by acute pulmonary edema in rats.

Like other methylated xanthine derivatives, pentoxifylline is a competitive nonselective phosphodiesterase inhibitor which raises intracellular cAMP, activates PKA, inhibits TNF and leukotriene synthesis, and reduces inflammation and innate immunity. In addition, pentoxifylline improves red blood cell deformability (known as a haemorrheologic effect), reduces blood viscosity and decreases the potential for platelet aggregation and thrombus formation. Pentoxifylline is also an antagonist at adenosine 2 receptors.