CAS 6493-05-6|cis-9-Octadecenoyl coenzyme A|3,7-dimethyl-1-(5-oxohexyl)-2,3,6,7-tetrahydro-1H-purine-2,6-dione|3,7-dimethyl-1-(5-oxohexyl)purine-2,6-dione|OLEOYL COENZYME A DIPOTASSIUM SALT|Pentoxif...

General Information

Structure

Molecular Formula

C₁₃H₁₈N₄O₃

Molecular Mass

278.30702

Exact Mass

278.13789046

Charge

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

InChIKey

BYPFEZZEUUWMEJ-UHFFFAOYSA-N

Canonic Smiles

CC(=O)CCCCn1c(=O)c2n(C)cnc2n(c1=O)C

Isomeric Smiles

O=c1n(CCCCC(=O)C)c(=O)n(c2ncn(c12)C)C

Calculated Properties

JChem

Acid pKa

19.642868

H Acceptors

H Donor

LogD (pH = 5.5)

0.23220569

LogD (pH = 7.4)

0.23220584

Log P

0.23220585

Molar Refractivity

73.5223

Polarizability

27.121319

Polar Surface Area

75.51

Rotatable Bonds

Lipinski's Rule of Five

true

ALOGPS 2.1

Log P

0.08

LOG S

-1.73

Solubility (Water)

5.17e+00 g/l

Data Source

Names and Identifiers

IUPAC name

3,7-dimethyl-1-(5-oxohexyl)-2,3,6,7-tetrahydro-1H-purine-2,6-dione

Synonyms

cis-9-Octadecenoyl coenzyme AOLEOYL COENZYME A DIPOTASSIUM SALTPentoxifyllineTrental3,7-dimethyl-1-(5-oxohexyl)-1H-purine-2,6(3H,7H)-dione1-(5-Oxohexyl)Theobromine1-(5-Oxohexyl)-3,7-dimethylxanthinePexalTorentalPentoxyphyllinVasotalVazofirin3,7-Dihydro-3,7-dimethyl-1-(5-oxohexyl)-1H-purine-2,6-dioneOxpentifyllineEHT0201pentoxifyllineAzupentatPentoxifyllinePentofluxAgapurin

IUPAC Traditional name

3,7-dimethyl-1-(5-oxohexyl)purine-2,6-dione pentoxifylline 3,7-dimethyl-1-(5-oxohexyl)-2,3,6,7-tetrahydro-1H-purine-2,6-dione

Brand Name

PentoxiphylliumPentoxyfyllineDurapentalDimethyloxohexylxanthinePentoxyphyllinePentoxilTorentalRentylinVazofirinOxpentifyllineTrentalPentoxifyllinPENTOXYPHYLINEAzupentat

Names and Identifiers

Registration numbers

CAS Number

PubChem SID

PubChem CID

EC Number

Registration numbers

Properties

Product Information

Purity

90-95%

Certificate of Analysis

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Application(s)

Pentoxifylline improves blood flow through blood vessels and therefore helps with blood circulation in the arms and legs (e.g. intermittent claudication)

It is used to treat intermittent claudication resulting from obstructed arteries in the limbs, and vascular dementia

It also helps prevent strokes, can be used in managing sickle cell disease and improves blood flow to the brain

Pentoxifylline has also been used to treat nausea and headaches in the mountains (altitude sickness).

Free Base

Pharmacology Properties

Mechanism of Action

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

Target

Others

Properties

Related Proteins

No Data Available

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Molecular Spectra

No Data Available

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Molecule Details

DrugBank

DB00806

Drug Groups

approved; investigational

Description

A methylxanthine derivative that inhibits phosphodiesterase and affects blood rheology. It improves blood flow by increasing erythrocyte and leukocyte flexibility. It also inhibits platelet aggregation. Pentoxifylline modulates immunologic activity by stimulating cytokine production. [PubChem]

Indication

For the treatment of patients with intermittent lameness or immobility arising from chronic occlusive arterial disease of the limbs.

Pharmacology

Pentoxifylline, a synthetic dimethylxanthine derivative structurally related to theophylline and caffeine, is used in the treatment of peripheral vascular diseases and in the management of cerebrovascular insufficiency, sickle cell disease, and diabetic neuropathy.

Toxicity

LD₅₀=1385 mg/kg(orally in mice)

Affected Organisms

Humans and other mammals

Half Life

0.4-0.8 hours

Protein Binding

70%

Elimination

Excretion is almost totally urinary; the main biotransformation product is Metabolite V. Essentially no parent drug is found in the urine.

References

• : European Pentoxifylline Multi-Infarct Dementia Study. Eur Neurol. 1996;36(5):315-21. [Pubmed]

External Links

• [Wikipedia]

• [RxList]

• [Drugs.com]

MP Biomedicals

02100904

Potassium Salt
Purity: 90-95%

02156107

Phosphodiesterase inhibitor. Also blocks synthesis of Tumor Necrosis Factor-α.

TRC

P276500

A metabolite of Pentifylline. Methylxanthine derivative that improves blood flow by decreasing blood viscosity. Phosphodiesterase inhibitor. Inhibits the synthesis of tumor necrosis factor α (TNF-α).

Molecule Details

References

PubChem Literature

From Data Sources

• : European Pentoxifylline Multi-Infarct Dementia Study. Eur Neurol. 1996;36(5):315-21. Pubmed

• Reuter, et al.: Am J. Physiol., 277, 854 (1999)

• Poulakis, et al.: Respir. Med., 93, 52 (1999)

• Indrayanto, G. et al., Anal. Profiles Drug Subst., 1998, 25, 295-339, (rev, pharmacol)

• Conde, L.A., Khim.-Farm. Zh., 1986, 20, 493, (rev, pharmacol)

• Mueller, R. et al., Curr. Med. Res. Opin., 1981, 7, 253, (rev)

• Negwer, M., Organic-Chemical Drugs and their Synonyms, 7th edn., Akademie-Verlag, 1994, 3582, (synonyms)

• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, PBU100

• Hinze, H.J., Arzneim.-Forsch., 1971, 21, 1456, (uv, ir, pmr, ms)

• Mohler, W. et al., Arzneim.-Forsch., 1971, 21, 1159, (synth, props)

• Cadis, E. et al., Rev. Chim. (Bucharest), 1986, 37, 335, (synth)

• Martindale, The Extra Pharmacopoeia, 32nd edn., Pharmaceutical Press, 1999, 925

• Popendiker, K. et al., Arzneim.-Forsch., 1971, 21, 1160; 1171, (pharmacol)

References

Bioactivity

PubChem BioAssay

Bioactivity