PENTOXIFYLLINE

Search structure
Trade Names:
Synonyms:
Status: Approved (1984)
Entry Type: Small molecule
Molecule Category: Parent
ATC: C04AD03
UNII: SD6QCT3TSU

Structure
InChI Key BYPFEZZEUUWMEJ-UHFFFAOYSA-N
Smile CC(=O)CCCCn1c(=O)c2c(ncn2C)n(C)c1=O
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

Physicochemical Descriptors

Property Name Value
Molecular Formula C13H18N4O3
Molecular Weight 278.31
AlogP 0.19
Hydrogen Bond Acceptor 7.0
Hydrogen Bond Donor 0.0
Number of Rotational Bond 5.0
Polar Surface Area 78.89
Molecular species NEUTRAL
Aromatic Rings 2.0
Heavy Atoms 20.0

Pharmacology

Action Mechanism of Action Reference
INHIBITOR 3',5'-cyclic phosphodiesterase inhibitor FDA PubMed PubMed Wikipedia
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Enzyme Hydrolase
- 6600 - - -
Enzyme Phosphodiesterase Phosphodiesterase 4 Phosphodiesterase 4A
- - - 37700 -
Enzyme Phosphodiesterase Phosphodiesterase 4 Phosphodiesterase 4B
- - - 37700 -
Enzyme Phosphodiesterase Phosphodiesterase 4 Phosphodiesterase 4C
- - - 37700 -
Enzyme Phosphodiesterase Phosphodiesterase 4 Phosphodiesterase 4D
- - - 37700 -
Membrane receptor Family A G protein-coupled receptor Small molecule receptor (family A GPCR) Nucleotide-like receptor (family A GPCR) Adenosine receptor
- - - 5180 -
Secreted protein
- 85000 - - -
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC21/SLCO family of organic anion transporting polypeptides
- - - - 77

Metabolites

visNetwork

Indications

Mesh Heading Maximum Phase Mesh ID Reference
Nephrotic Syndrome 3 D009404 ClinicalTrials
Liver Failure 3 D017093 ClinicalTrials
Liver Cirrhosis 3 D008103 ClinicalTrials
Hepatitis, Alcoholic 3 D006519 ClinicalTrials
Osteonecrosis 3 D010020 ClinicalTrials
Brachial Plexus Neuropathies 3 D020516 ClinicalTrials
Endometriosis 3 D004715 ClinicalTrials
Glomerulonephritis 3 D005921 ClinicalTrials
Neonatal Sepsis 3 D000071074 ClinicalTrials
Renal Insufficiency, Chronic 3 D051436 ClinicalTrials
Breast Neoplasms 2 D001943 ClinicalTrials
Head and Neck Neoplasms 2 D006258 ClinicalTrials
Leishmaniasis 2 D007896 ClinicalTrials
Brain Diseases 2 D001927 ClinicalTrials
Fibrosis 2 D005355 ClinicalTrials
Malaria, Falciparum 2 D016778 ClinicalTrials
Non-alcoholic Fatty Liver Disease 2 D065626 ClinicalTrials
Liver Cirrhosis, Biliary 2 D008105 ClinicalTrials
Wounds and Injuries 2 D014947 ClinicalTrials
Carcinoma, Non-Small-Cell Lung 2 D002289 ClinicalTrials
Biliary Atresia 2 D001656 ClinicalTrials
Leishmaniasis, Cutaneous 2 D016773 ClinicalTrials
Enterocolitis, Necrotizing 2 D020345 ClinicalTrials
Acute Kidney Injury 2 D058186 ClinicalTrials
Fatty Liver 2 D005234 ClinicalTrials
Sarcoidosis, Pulmonary 2 D017565 ClinicalTrials
Precursor Cell Lymphoblastic Leukemia-Lymphoma 2 D054198 ClinicalTrials
Neoplasms 2 D009369 ClinicalTrials
Diabetic Nephropathies 2 D003928 ClinicalTrials
Ductus Arteriosus, Patent 2 D004374 ClinicalTrials
Behcet Syndrome 2 D001528 ClinicalTrials
Acute Coronary Syndrome 2 D054058 ClinicalTrials
Depressive Disorder, Major 2 D003865 ClinicalTrials
Coronary Disease 2 D003327 ClinicalTrials
HIV Infections 1 D015658 ClinicalTrials
Central Nervous System Neoplasms 1 D016543 ClinicalTrials
Muscular Dystrophy, Duchenne 1 D020388 ClinicalTrials
Hepatopulmonary Syndrome 1 D020065 ClinicalTrials
Schizophrenia 1 D012559 ClinicalTrials
Severe Acute Respiratory Syndrome 1 D045169 ClinicalTrials
Bipolar Disorder 0 D001714 ClinicalTrials
Infertility 0 D007246 ClinicalTrials
Pancreatitis 0 D010195 ClinicalTrials
Pancreatitis 0 D010195 ClinicalTrials
Anemia 0 D000740 ClinicalTrials
Crohn Disease 0 D003424 ClinicalTrials

Related Entries

MCS

Scaffolds

Side Effects from Label

Side effects Relative Frequency (%) Labels
Gastrointestinal disorders Nausea 28.8
Gastrointestinal disorders Nausea 14.0
Cardiac disorders Dizziness 11.9
Gastrointestinal disorders Dyspepsia 9.6
Cardiac disorders Dizziness 9.4
Gastrointestinal disorders Abdominal distension 9.0
Gastrointestinal disorders Eructation 9.0
Gastrointestinal disorders Flatulence 9.0
Gastrointestinal disorders Nausea
Nervous system disorders Headache 6.2
Nervous system disorders Headache
Nervous system disorders Somnolence
Nervous system disorders Headache 4.9
Gastrointestinal disorders Dyspepsia
Gastrointestinal disorders Vomiting 4.5
Cardiac disorders Dizziness
Gastrointestinal disorders Abdominal discomfort 4.0
Gastrointestinal disorders Abdominal distension
Gastrointestinal disorders Eructation
Gastrointestinal disorders Flatulence
Gastrointestinal disorders Diarrhoea 3.4
Gastrointestinal disorders Vomiting 3.4
Cardiac disorders Dizziness
Gastrointestinal disorders Diarrhoea
Gastrointestinal disorders Dyspepsia
Gastrointestinal disorders Dyspepsia 2.8
General disorders and administration site conditions Flushing 2.3
Nervous system disorders Insomnia 2.3
Eye disorders Vision blurred 2.3
Cardiac disorders Angina pectoris
Cardiac disorders Chest pain
Nervous system disorders Insomnia
Gastrointestinal disorders Nausea 2.2
Cardiac disorders Dizziness 1.9
Nervous system disorders Agitation 1.7
Cardiac disorders Arrhythmia 1.7
Psychiatric disorders Nervousness 1.7
Cardiac disorders Palpitations 1.7
Psychiatric disorders Tension 1.7
Nervous system disorders Headache
Gastrointestinal disorders Abdominal discomfort
Eye disorders Vision blurred
Nervous system disorders Headache 1.2
Gastrointestinal disorders Vomiting 1.2
Cardiac disorders Angina pectoris 1.1
Cardiac disorders Chest pain 1.1
Nervous system disorders Somnolence 1.1
Gastrointestinal disorders Nausea
Nervous system disorders Tremor
Nervous system disorders Agitation
Cardiac disorders Arrhythmia
General disorders and administration site conditions Flushing
Psychiatric disorders Nervousness
Cardiac disorders Palpitations
Psychiatric disorders Tension
Gastrointestinal disorders Vomiting
Gastrointestinal disorders Abdominal distension 0.6
Gastrointestinal disorders Eructation 0.6
Gastrointestinal disorders Flatulence 0.6
Cardiac disorders Angina pectoris 0.3
Cardiac disorders Chest pain 0.3
Nervous system disorders Tremor 0.3

Adverse Reactions

SOC By Demographic Distribution
System Organ Classification (SOC)
Relative Frequency (%)
Vascular disorders
13.64
Nervous system disorders
12.77
General disorders and administration site conditions
11.76
Gastrointestinal disorders
7.63
Cardiac disorders
7.13
Injury, poisoning and procedural complications
6.88
Skin and subcutaneous tissue disorders
5.26
Investigations
4.76
Eye disorders
4.51
Psychiatric disorders
4.26
Respiratory, thoracic and mediastinal disorders
3.63
Metabolism and nutrition disorders
3.0
Immune system disorders
2.5
Infections and infestations
2.38

Cross References

Resources Reference
CAS NUMBER 6493-05-6
ChEBI 7986
ChEMBL CHEMBL628
DrugBank DB00806
DrugCentral 2099
EPA CompTox DTXSID7023437
FDA SRS SD6QCT3TSU
Human Metabolome Database HMDB0014944
Guide to Pharmacology 7095
KEGG C07424
PDB PNX
PharmGKB PA450864
PubChem 4740
SureChEMBL SCHEMBL34039
ZINC ZINC000001530776
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