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6493-05-6 molecular structure
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3,7-dimethyl-1-(5-oxohexyl)-2,3,6,7-tetrahydro-1H-purine-2,6-dione

ChemBase ID: 685
Molecular Formular: C13H18N4O3
Molecular Mass: 278.30702
Monoisotopic Mass: 278.13789046
SMILES and InChIs

SMILES:
O=c1n(CCCCC(=O)C)c(=O)n(c2ncn(c12)C)C
Canonical SMILES:
CC(=O)CCCCn1c(=O)c2n(C)cnc2n(c1=O)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
InChIKey:
BYPFEZZEUUWMEJ-UHFFFAOYSA-N

Cite this record

CBID:685 http://www.chembase.cn/molecule-685.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
3,7-dimethyl-1-(5-oxohexyl)-2,3,6,7-tetrahydro-1H-purine-2,6-dione
IUPAC Traditional name
pentoxifylline
3,7-dimethyl-1-(5-oxohexyl)purine-2,6-dione
3,7-dimethyl-1-(5-oxohexyl)-2,3,6,7-tetrahydro-1H-purine-2,6-dione
Brand Name
Azupentat
Dimethyloxohexylxanthine
Durapental
Oxpentifylline
PENTOXYPHYLINE
Pentoxifyllin
Pentoxil
Pentoxiphyllium
Pentoxyfylline
Pentoxyphylline
Rentylin
Torental
Trental
Vazofirin
Synonyms
pentoxifylline
EHT0201
Pentoxifylline
cis-9-Octadecenoyl coenzyme A
OLEOYL COENZYME A DIPOTASSIUM SALT
3,7-dimethyl-1-(5-oxohexyl)-1H-purine-2,6(3H,7H)-dione
3,7-Dihydro-3,7-dimethyl-1-(5-oxohexyl)-1H-purine-2,6-dione
1-(5-Oxohexyl)-3,7-dimethylxanthine
1-(5-Oxohexyl)Theobromine
Oxpentifylline
Vasotal
Vazofirin
Torental
Pentoxyphyllin
Pexal
Agapurin
Azupentat
Pentoflux
Pentoxifylline
Trental
CAS Number
6493-05-6
EC Number
229-374-5
PubChem SID
160964148
46505940
PubChem CID
4740

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
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 cm3 Polarizability 27.121319 Å3
Polar Surface Area 75.51 Å2 Rotatable Bonds
Lipinski's Rule of Five true 
Log P 0.08  LOG S -1.73 
Solubility (Water) 5.17e+00 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Solubility
77 mg/mL expand Show data source
Chloroform expand Show data source
Methanol expand Show data source
Water expand Show data source
Apperance
White to Off-White Solid expand Show data source
Melting Point
104-106°C expand Show data source
98-100°C expand Show data source
Hydrophobicity(logP)
0 expand Show data source
Storage Condition
0°C expand Show data source
Refrigerator expand Show data source
Room Temperature (15-30°C) expand Show data source
RTECS
XH2475000 expand Show data source
European Hazard Symbols
Harmful Harmful (Xn) expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
Download expand Show data source
Risk Statements
R:22 expand Show data source
Safety Statements
S:36/37/39 expand Show data source
Target
Others expand Show data source
Mechanism of Action
Along with erythrocyte activity, pentoxifylline also decreases blood viscosity by reducing plasma fibrinogen concentrations and increasing fibrinolytic activity expand Show data source
Inhibits erythrocyte phosphodiesterase, resulting in an increase in erythrocyte cAMP activity. Subsequently, the erythrocyte membrane becomes more resistant to deformity expand Show data source
Purity
90-95% expand Show data source
Salt Data
Free Base expand Show data source
Certificate of Analysis
Download expand Show data source
Download expand Show data source
Download expand Show data source
Application(s)
It also helps prevent strokes, can be used in managing sickle cell disease and improves blood flow to the brain expand Show data source
It is used to treat intermittent claudication resulting from obstructed arteries in the limbs, and vascular dementia expand Show data source
Pentoxifylline has also been used to treat nausea and headaches in the mountains (altitude sickness). expand Show data source
Pentoxifylline improves blood flow through blood vessels and therefore helps with blood circulation in the arms and legs (e.g. intermittent claudication) expand Show data source

DETAILS

DETAILS

MP Biomedicals MP Biomedicals DrugBank DrugBank TRC TRC
MP Biomedicals - 02156107 external link
Phosphodiesterase inhibitor. Also blocks synthesis of Tumor Necrosis Factor-α.
MP Biomedicals - 02100904 external link
Potassium Salt
Purity: 90-95%
DrugBank - DB00806 external link
Item Information
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
Toronto Research Chemicals - P276500 external link
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).

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • Reuter, et al.: Am J. Physiol., 277, 854 (1999)
  • • Poulakis, et al.: Respir. Med., 93, 52 (1999)
  • • : European Pentoxifylline Multi-Infarct Dementia Study. Eur Neurol. 1996;36(5):315-21. Pubmed
  • • Mohler, W. et al., Arzneim.-Forsch., 1971, 21, 1159, (synth, props)
  • • Popendiker, K. et al., Arzneim.-Forsch., 1971, 21, 1160; 1171, (pharmacol)
  • • Hinze, H.J., Arzneim.-Forsch., 1971, 21, 1456, (uv, ir, pmr, ms)
  • • Mueller, R. et al., Curr. Med. Res. Opin., 1981, 7, 253, (rev)
  • • Conde, L.A., Khim.-Farm. Zh., 1986, 20, 493, (rev, pharmacol)
  • • Cadis, E. et al., Rev. Chim. (Bucharest), 1986, 37, 335, (synth)
  • • Negwer, M., Organic-Chemical Drugs and their Synonyms, 7th edn., Akademie-Verlag, 1994, 3582, (synonyms)
  • • Indrayanto, G. et al., Anal. Profiles Drug Subst., 1998, 25, 295-339, (rev, pharmacol)
  • • Martindale, The Extra Pharmacopoeia, 32nd edn., Pharmaceutical Press, 1999, 925
  • • Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, PBU100
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PATENTS

PATENTS

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