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]

Structure

Similar Structures

Synonyms

Oxpentifylline
Pentoxifilina
Pentoxifyllin
Pentoxifylline
Pentoxifyllinum

External IDs

BL 191 / BL-191 / C04AD03 / PTX

Product Images

Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
Pentoxifylline SR	Tablet, extended release	400 mg	Oral	Aa Pharma Inc	1997-01-14	Not applicable
Trental	Tablet, extended release	400 mg	Oral	Sanofi Aventis	1996-10-23	2013-03-01
Trental	Tablet, film coated, extended release	400 mg/1	Oral	Sanofi Aventis	1984-08-30	2013-12-31
Trental	Tablet, film coated	400 mg/1	Oral	Physicians Total Care, Inc.	1984-08-30	2011-09-30
Trental Srt 400mg	Tablet, extended release	400 mg	Oral	Hoechst Roussel Canada Inc.	1993-12-31	1998-08-12
Trental Tab 400mg	Tablet, extended release	400 mg	Oral	Hoechst Canada Inc.	1984-12-31	1996-08-29

Generic Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
Nu-pentoxifylline-SR 400 mg	Tablet, extended release	400 mg	Oral	Nu Pharm Inc	1998-03-18	2012-09-04
Pentoxifylline	Tablet, film coated, extended release	400 mg/1	Oral	Mylan Pharmaceuticals Inc.	1997-07-08	2019-05-31
Pentoxifylline	Tablet, extended release	400 mg/1	Oral	Nucare Pharmaceuticals, Inc.	1999-06-10	Not applicable
Pentoxifylline	Tablet, extended release	400 mg/1	Oral	A-S Medication Solutions	1998-07-31	Not applicable
Pentoxifylline	Tablet, extended release	400 mg/1	Oral	Apotex Corp.	1999-06-10	Not applicable
Pentoxifylline	Tablet, film coated, extended release	400 mg/1	Oral	State of Florida DOH Central Pharmacy	2009-07-01	Not applicable
Pentoxifylline	Tablet, extended release	400 mg/1	Oral	Cardinal Health	2004-02-16	2011-03-31
Pentoxifylline	Tablet, extended release	400 mg/1	Oral	Golden State Medical Supply, Inc.	2001-06-18	Not applicable
Pentoxifylline	Tablet, extended release	400 mg/1	Oral	Physicians Total Care, Inc.	2003-03-25	Not applicable
Pentoxifylline	Tablet, film coated, extended release	400 mg/1	Oral	Mc Kesson Contract Packaging	1997-07-08	2017-09-30

Unapproved/Other Products

Name	Ingredients	Dosage	Route	Labeller	Marketing Start	Marketing End
Gapeam Budibac	Pentoxifylline (1 g/1g) + Amantadine hydrochloride (1 g/1g) + Baclofen (1 g/1g) + Bupivacaine hydrochloride (1 g/1g) + Cyclobenzaprine hydrochloride (1 g/1g) + Diclofenac sodium (1 g/1g) + Gabapentin (1 g/1g)	Kit	Topical	Alvix Laboratories	2014-12-05	2018-03-08

International/Other Brands

Agapurin (Zentiva) / Agapurin SR (Zentiva) / An Ruo Ning (Nanjing Yaoda Bio-Pharmaceutical) / Angiopent (Helcor) / Ao Le Ni (C & O Pharmaceuticals) / Ao Nuo Hong (AosaiKang Pharmaceutical) / Aotong (Treeful Pharmaceutical) / Azupentat / Behrifil (Sanofi-Aventis) / Bo Shu Te (Jisheng Pharmaceutical) / Claudicat (Nycomed) / Durapental (Mylan dura) / Elorgan (Sanofi Aventis) / Endopentoksas (Endokriniai) / Pentilin (Krka) / Pentilin Retard (Krka) / Pentoflux (Bouchara-Recordati) / Pentofyllin (Sopharma) / Pentoksifilin (Panfarma) / Pentolab (Lamsa) / Pentomer (ratiopharm) / Rentylin (Amdipharm) / Torental (Sanofi-Aventis) / Trentilin Retard (Santa-Farma)

Categories

UNII

SD6QCT3TSU

CAS number

6493-05-6

Weight

Average: 278.307
Monoisotopic: 278.137890462

Chemical Formula

C₁₃H₁₈N₄O₃

InChI Key

BYPFEZZEUUWMEJ-UHFFFAOYSA-N

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

IUPAC Name

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

SMILES

CN1C=NC2=C1C(=O)N(CCCCC(C)=O)C(=O)N2C

Pharmacology

Indication

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

Associated Conditions

Pharmacodynamics

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.

Mechanism of action

Pentoxifylline 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. It is also a non selective adenosine receptor antagonist.

Target	Actions	Organism
AcAMP-specific 3',5'-cyclic phosphodiesterase 4B	inhibitor	Humans
AAdenosine receptor A1	antagonist	Humans
AcGMP-specific 3',5'-cyclic phosphodiesterase	inhibitor	Humans
AcAMP-specific 3',5'-cyclic phosphodiesterase 4A	inhibitor	Humans
AAdenosine receptor A2a	antagonist	Humans
U5'-nucleotidase	inhibitor	Humans

Absorption

Not Available

Volume of distribution

Not Available

Protein binding

70%

Metabolism

Not Available

Route of elimination

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

Half life

0.4-0.8 hours

Clearance

Not Available

Toxicity

LD₅₀=1385 mg/kg(orally in mice)

Affected organisms

Humans and other mammals

Pathways

Not Available

Pharmacogenomic Effects/ADRs

Not Available

Interactions

Drug Interactions

Drug	Interaction
(R)-warfarin	The therapeutic efficacy of (R)-warfarin can be increased when used in combination with Pentoxifylline.
(S)-Warfarin	The therapeutic efficacy of (S)-Warfarin can be increased when used in combination with Pentoxifylline.
1-(3-Mercapto-2-Methyl-Propionyl)-Pyrrolidine-2-Carboxylic Acid	Pentoxifylline may increase the hypotensive activities of 1-(3-Mercapto-2-Methyl-Propionyl)-Pyrrolidine-2-Carboxylic Acid.
2,5-Dimethoxy-4-ethylamphetamine	The risk or severity of adverse effects can be increased when 2,5-Dimethoxy-4-ethylamphetamine is combined with Pentoxifylline.
2,5-Dimethoxy-4-ethylthioamphetamine	The risk or severity of adverse effects can be increased when 2,5-Dimethoxy-4-ethylthioamphetamine is combined with Pentoxifylline.
3-isobutyl-1-methyl-7H-xanthine	The serum concentration of 3-isobutyl-1-methyl-7H-xanthine can be increased when it is combined with Pentoxifylline.
3,5-diiodothyropropionic acid	The serum concentration of Pentoxifylline can be increased when it is combined with 3,5-diiodothyropropionic acid.
4-Bromo-2,5-dimethoxyamphetamine	The risk or severity of adverse effects can be increased when 4-Bromo-2,5-dimethoxyamphetamine is combined with Pentoxifylline.
4-hydroxycoumarin	The therapeutic efficacy of 4-hydroxycoumarin can be increased when used in combination with Pentoxifylline.
6-Deoxyerythronolide B	The metabolism of Pentoxifylline can be decreased when combined with 6-Deoxyerythronolide B.

Food Interactions

Take with food to reduce irritation. Limit caffeine intake.

References

General References

Authors unspecified: European Pentoxifylline Multi-Infarct Dementia Study. Eur Neurol. 1996;36(5):315-21. [PubMed:8864715]

External Links

Human Metabolome Database: HMDB0014944
KEGG Drug: D00501
KEGG Compound: C07424
PubChem Compound: 4740
PubChem Substance: 46505940
ChemSpider: 4578
BindingDB: 10850
ChEBI: 7986
ChEMBL: CHEMBL628
Therapeutic Targets Database: DAP000048
PharmGKB: PA450864
HET: PNX
RxList: RxList Drug Page
Drugs.com: Drugs.com Drug Page
Wikipedia: Pentoxifylline

ATC Codes

C04AD03 — Pentoxifylline

R03DA20 — Combinations of xanthines

AHFS Codes

20:24.00 — Hemorrheologic Agents

PDB Entries

2a3c / 3arr / 3aru / 3tvx

FDA label

Download (51.7 KB)

MSDS

Download (73.9 KB)

Clinical Trials

Clinical Trials

Phase	Status	Purpose	Conditions	Count
0	Active Not Recruiting	Treatment	Crohn's Disease (CD)	1
0	Completed	Treatment	Acute Pancreatitis (AP)	1
0	Not Yet Recruiting	Treatment	Anemia Renal	1
0	Recruiting	Prevention	Pancreatitis	1
1	Completed	Treatment	Brain and Central Nervous System Tumors	1
1	Completed	Treatment	Human Immunodeficiency Virus (HIV) Infections	1
1	Terminated	Treatment	Alcoholic Hepatitis (AH)	1
1	Terminated	Treatment	Hepatopulmonary Syndrome	1
1, 2	Completed	Treatment	Muscular Dystrophy, Duchenne	2
2	Active Not Recruiting	Treatment	Long-term Adverse Effects of Radiotherapy for Pelvic Cancer	1
2	Completed	Prevention	Colorectal Cancers / Hepatic Metastases / Irradiation Damage / Radiation Induced Liver Disease	1
2	Completed	Prevention	Fibrosis	1
2	Completed	Prevention	Neoplasms, Head and Neck	1
2	Completed	Supportive Care	Cancer, Breast / Lymphedema of the extremities	1
2	Completed	Treatment	Anemia of Chronic Kidney Disease	1
2	Completed	Treatment	Atherosclerosis / Cardiovascular Disease (CVD) / Human Immunodeficiency Virus (HIV)	1
2	Completed	Treatment	Atherosclerosis / Cardiovascular Disease (CVD) / Human Immunodeficiency Virus (HIV) / Human Immunodeficiency Virus (HIV) Infections / Vascular Diseases	1
2	Completed	Treatment	Cardiovascular Disease (CVD) / Coronary Artery Disease / Depression / Depressive Symptoms / Heart Diseases / Major Depressive Disorder (MDD)	1
2	Completed	Treatment	Fatty Liver	1
2	Completed	Treatment	Fibrosis / Radiation Injuries	1
2	Completed	Treatment	Nonalcoholic Steatohepatitis	1
2	Completed	Treatment	Primary Biliary Cholangitis	1
2	Completed	Treatment	Sarcoidosis, Pulmonary	1
2	Not Yet Recruiting	Treatment	Adenocarcinoma, Prostate / Erectile Dysfunction (ED) / Erectile Dysfunction, CTCAE	1
2	Not Yet Recruiting	Treatment	Behçet Disease Affecting Oral Mucosa	1
2	Recruiting	Prevention	Brain Metastasis	1
2	Recruiting	Treatment	Biliary Atresia	1
2	Recruiting	Treatment	Leishmaniasis	1
2	Recruiting	Treatment	Lung Cancer Non-Small Cell Cancer (NSCLC)	1
2	Terminated	Treatment	End Stage Renal Disease (ESRD)	1
2	Terminated	Treatment	Neoplasms, Breast	1
2	Terminated	Treatment	Plasmodium Falciparum Malaria	1
2	Terminated	Treatment	Wounds and Injuries	1
2	Unknown Status	Treatment	Fibrosis	1
2	Unknown Status	Treatment	Necrotizing Enterocolitis	1
2	Unknown Status	Treatment	Patent Ductus Arteriosus (PDA)	1
2, 3	Completed	Treatment	Acute Alcoholic Hepatitis	1
2, 3	Completed	Treatment	Diabetic Nephropathies	1
2, 3	Completed	Treatment	Leishmaniasis, Cutaneous	2
2, 3	Completed	Treatment	Liver Diseases / Nonalcoholic Steatohepatitis	1
2, 3	Not Yet Recruiting	Treatment	Acute Kidney Injury (AKI) / Pentoxifylline	1
2, 3	Recruiting	Treatment	Acute Lymphoblastic Leukaemias (ALL)	1
3	Active Not Recruiting	Treatment	Cancer, Breast	1
3	Active Not Recruiting	Treatment	Infection, Human Immunodeficiency Virus I	1
3	Completed	Treatment	Acute on Chronic Pancreatitis / Acute Pancreatitis (AP) / Autoimmune Pancreatitis / Cancer Acute Pancreatitis / Drug Induced AP / Gallstone Pancreatitis / Hypertriglyceridemia Acute Pancreatitis / Hypertriglyceridemia AP / Idiopathic (Unknown) Acute Pancreatitis / Medication Induced Acute Pancreatitis / Miscellaneous (i.e. Acute on Chronic Pancreatitis) / Pancreatitis, Alcoholic / Post-ERCP AP / Post-ERCP/Post-procedural Pancreatitis / Trauma Acute Pancreatitis / Trauma AP	1
3	Completed	Treatment	Alcoholic Hepatitis (AH) / Severe alcoholic liver disease	1
3	Completed	Treatment	Chronic Renal Failure (CRF)	1
3	Completed	Treatment	Endometriosis-Associated Infertility	1
3	Completed	Treatment	Glomerulonephritis minimal lesion	1
3	Completed	Treatment	HTLV-1 / Immune System Diseases / Pentoxifylline / Physical Disability / Tropical Spastic Paraparesis	1
3	Completed	Treatment	Hepatic Failure / Liver Cirrhosis	1
3	Completed	Treatment	Intermittent Claudication Fontaine Stage II PAOD / Stage II Peripheral Arterial Occlusive Disease	1
3	Completed	Treatment	Neonatal Late Onset Sepsis	1
3	Completed	Treatment	Radiation Induced Brachial Plexopathy	1
3	Not Yet Recruiting	Supportive Care	Carcinoma, Breast / Fibrosis	1
3	Not Yet Recruiting	Treatment	Non-Squamous Cell Non-small Cell Lung Cancer	1
3	Recruiting	Treatment	Acute Kidney Injury (AKI)	1
3	Recruiting	Treatment	Avascular Necrosis / Bisphosphonate-related Osteonecrosis of the Jaw / Medication-related Osteonecrosis of the Jaw	1
3	Recruiting	Treatment	Erectile Dysfunction (ED) / Prostate Cancer	1
3	Terminated	Treatment	Glomerulonephritis	1
3	Unknown Status	Treatment	Alcoholic Hepatitis (AH)	1
4	Active Not Recruiting	Treatment	Lumbar Disc Disease / Lumbar Radiculopathy / Prolapsed Lumbar Disc	1
4	Completed	Prevention	Diabetic Nephropathies	1
4	Completed	Treatment	BMI >30 kg/m2	1
4	Completed	Treatment	Chronic Kidney Disease (CKD)	1
4	Completed	Treatment	End-Stage Renal Disease (ESRD) / Hemodialysis Treatment / Inflammatory Reaction	1
4	Completed	Treatment	Osteoradionecrosis	1
4	Not Yet Recruiting	Treatment	Diabetic Kidney Disease	1
4	Not Yet Recruiting	Treatment	Nephritis, Lupus	1
4	Recruiting	Treatment	Chronic Kidney Disease stage3 and 4 / Type 2 Diabetes Mellitus	1
4	Recruiting	Treatment	Chronic Renal Failure (CRF)	1
4	Unknown Status	Treatment	Hepacivirus / Human Immunodeficiency Virus (HIV) Infections	1
4	Unknown Status	Treatment	Irritable Bowel Syndrome (IBS)	1
4	Unknown Status	Treatment	Sepsis of the Newborn	1
4	Unknown Status	Treatment	Type 2 Diabetes Mellitus	1
Not Available	Completed	Not Available	Alcoholic Hepatitis (AH) / Severe alcoholic liver disease	1
Not Available	Completed	Treatment	Human Immunodeficiency Virus (HIV) Infections	1
Not Available	Completed	Treatment	Primary Glomerulonephritis	1
Not Available	Completed	Treatment	Recurrent Aphthous Stomatitis	1
Not Available	Enrolling by Invitation	Treatment	Dizziness / Vertigo	1
Not Available	No Longer Available	Not Available	Diabetes, Diabetes Mellitus Type 1	1
Not Available	Not Yet Recruiting	Treatment	Advanced Gastric Cancer Adenocarcinoma of Esophagogastric Junction	1
Not Available	Terminated	Treatment	Graves Ophthalmopathy	1
Not Available	Unknown Status	Prevention	Capsular Contractures	1
Not Available	Unknown Status	Prevention	Renal Dysfunction	1
Not Available	Unknown Status	Treatment	Congestive Heart Failure (CHF)	1
Not Available	Unknown Status	Treatment	Hepatopulmonary Syndrome	1
Not Available	Unknown Status	Treatment	Metabolic Parameters and Liver Histology	1
Not Available	Unknown Status	Treatment	Non-Alcoholic Steatohepatitis	1
Not Available	Withdrawn	Prevention	Contrast Induced Nephropathy (CIN) / Diabetes Mellitus (DM)	1

Pharmacoeconomics

Manufacturers

Actavis elizabeth llc
Apotex inc
Biovail laboratories inc
Heritage pharmaceuticals inc
Impax laboratories inc
Mylan pharmaceuticals inc
Pliva inc
Teva pharmaceuticals usa inc
Watson laboratories inc
Upsher smith laboratories inc
Sanofi aventis us llc

Packagers

Amerisource Health Services Corp.
Amneal Pharmaceuticals
Apotex Inc.
A-S Medication Solutions LLC
Atlantic Biologicals Corporation
Biovail Pharmaceuticals
Cardinal Health
Dept Health Central Pharmacy
Dispensing Solutions
Diversified Healthcare Services Inc.
Gallipot
Golden State Medical Supply Inc.
Heartland Repack Services LLC
Lake Erie Medical and Surgical Supply
Major Pharmaceuticals
Mckesson Corp.
Merrell Pharmaceuticals Inc.
Murfreesboro Pharmaceutical Nursing Supply
Mylan
Nucare Pharmaceuticals Inc.
Pharmedix
Physicians Total Care Inc.
Pliva Inc.
Prepak Systems Inc.
Remedy Repack
Sandhills Packaging Inc.
Sanofi-Aventis Inc.
Southwood Pharmaceuticals
Teva Pharmaceutical Industries Ltd.
Torpharm Inc.
Tya Pharmaceuticals
UDL Laboratories
Upsher Smith Laboratories
Va Cmop Dallas
Vangard Labs Inc.
Zoetica Pharmaceutical Corp.

Dosage forms

Form	Route	Strength
Kit	Topical
Tablet, extended release	Oral	400 mg/1
Tablet, film coated, extended release	Oral	400 mg/1
Tablet, extended release	Oral	400 mg
Tablet, film coated	Oral	400 mg/1

Prices

Unit description	Cost	Unit
TRENtal 400 mg Controlled Release Tabs	1.4USD	tab
Trental er 400 mg tablet	1.27USD	tablet
Pentoxifylline powder	0.91USD	g
Trental 400 mg Sustained-Release Tablet	0.88USD	tablet
Pentoxifylline 400 mg tablet sa	0.71USD	tablet
Pentoxifylline CR 400 mg Controlled Release Tabs	0.62USD	tab
Pentoxil 400 mg Controlled Release Tabs	0.62USD	tab
Pentoxil er 400 mg tablet	0.62USD	tablet
Pentoxifylline er 400 mg tablet	0.6USD	tablet
Apo-Pentoxifylline Sr 400 mg Sustained-Release Tablet	0.4USD	tablet
Nu-Pentoxifylline-Sr 400 mg Sustained-Release Tablet	0.4USD	tablet

DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.

Patents

Not Available

Properties

State

Solid

Experimental Properties

Property	Value	Source
melting point (°C)	105 °C	Not Available
water solubility	7.7E+004 mg/L (at 25 °C)	MERCK INDEX (1996)
logP	0.29	BIOBYTE (1995)

Predicted Properties

Property	Value	Source
Water Solubility	5.17 mg/mL	ALOGPS
logP	0.08	ALOGPS
logP	0.23	ChemAxon
logS	-1.7	ALOGPS
pKa (Strongest Acidic)	19.64	ChemAxon
pKa (Strongest Basic)	-0.93	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	75.51 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	73.52 m³·mol^-1	ChemAxon
Polarizability	29.27 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted ADMET features

Property	Value	Probability
Human Intestinal Absorption	+	1.0
Blood Brain Barrier	+	0.9851
Caco-2 permeable	-	0.5056
P-glycoprotein substrate	Substrate	0.595
P-glycoprotein inhibitor I	Non-inhibitor	0.6905
P-glycoprotein inhibitor II	Inhibitor	0.7157
Renal organic cation transporter	Non-inhibitor	0.7023
CYP450 2C9 substrate	Non-substrate	0.7897
CYP450 2D6 substrate	Non-substrate	0.9117
CYP450 3A4 substrate	Substrate	0.6511
CYP450 1A2 substrate	Inhibitor	0.9107
CYP450 2C9 inhibitor	Non-inhibitor	0.9518
CYP450 2D6 inhibitor	Non-inhibitor	0.943
CYP450 2C19 inhibitor	Non-inhibitor	0.9313
CYP450 3A4 inhibitor	Non-inhibitor	0.9827
CYP450 inhibitory promiscuity	Low CYP Inhibitory Promiscuity	0.901
Ames test	Non AMES toxic	0.7131
Carcinogenicity	Non-carcinogens	0.8965
Biodegradation	Not ready biodegradable	0.7457
Rat acute toxicity	2.4070 LD50, mol/kg	Not applicable
hERG inhibition (predictor I)	Weak inhibitor	0.6463
hERG inhibition (predictor II)	Non-inhibitor	0.8734

ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)

Not Available

Spectra

Spectrum	Spectrum Type	Splash Key
Predicted GC-MS Spectrum - GC-MS	Predicted GC-MS	Not Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
LC-MS/MS Spectrum - LC-ESI-qTof , Positive	LC-MS/MS	Not Available
MS/MS Spectrum - , positive	LC-MS/MS	splash10-0059-1890000000-c9be2fe26b2862cba4f5
MS/MS Spectrum - , positive	LC-MS/MS	splash10-001r-2900000000-d54457aaede5317cef72
LC-MS/MS Spectrum - LC-ESI-QFT , positive	LC-MS/MS	splash10-0059-2970000000-95d1edcd63b61b13b22e

Taxonomy

Description: This compound belongs to the class of organic compounds known as xanthines. These are purine derivatives with a ketone group conjugated at carbons 2 and 6 of the purine moiety.
Kingdom: Organic compounds
Super Class: Organoheterocyclic compounds
Class: Imidazopyrimidines
Sub Class: Purines and purine derivatives
Direct Parent: Xanthines
Alternative Parents: 6-oxopurines / Alkaloids and derivatives / Pyrimidones / N-substituted imidazoles / Vinylogous amides / Heteroaromatic compounds / Ureas / Lactams / Ketones / Azacyclic compounds
show 4 more
Substituents: Xanthine / 6-oxopurine / Purinone / Alkaloid or derivatives / Pyrimidone / N-substituted imidazole / Pyrimidine / Azole / Imidazole / Heteroaromatic compound
show 14 more
Molecular Framework: Aromatic heteropolycyclic compounds
External Descriptors: oxopurine (CHEBI:7986)

Targets

Details1. cAMP-specific 3',5'-cyclic phosphodiesterase 4B

Kind: Protein
Organism: Humans
Pharmacological action: Yes
Actions: Inhibitor

General Function: Metal ion binding
Specific Function: Hydrolyzes the second messenger cAMP, which is a key regulator of many important physiological processes. May be involved in mediating central nervous system effects of therapeutic agents ranging f...
Gene Name: PDE4B
Uniprot ID: Q07343
Uniprot Name: cAMP-specific 3',5'-cyclic phosphodiesterase 4B
Molecular Weight: 83342.695 Da

References

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]

Property	Measurement	pH	Temperature (°C)	References
Ki (nM)	180000	N/A	N/A	8496906

Details2. Adenosine receptor A1

Kind: Protein
Organism: Humans
Pharmacological action: Yes
Actions: Antagonist

General Function: Purine nucleoside binding
Specific Function: Receptor for adenosine. The activity of this receptor is mediated by G proteins which inhibit adenylyl cyclase.
Gene Name: ADORA1
Uniprot ID: P30542
Uniprot Name: Adenosine receptor A1
Molecular Weight: 36511.325 Da

References

Daly JW, Jacobson KA, Ukena D: Adenosine receptors: development of selective agonists and antagonists. Prog Clin Biol Res. 1987;230:41-63. [PubMed:3588607]

Details3. cGMP-specific 3',5'-cyclic phosphodiesterase

Kind: Protein
Organism: Humans
Pharmacological action: Yes
Actions: Inhibitor

General Function: Metal ion binding
Specific Function: Plays a role in signal transduction by regulating the intracellular concentration of cyclic nucleotides. This phosphodiesterase catalyzes the specific hydrolysis of cGMP to 5'-GMP (PubMed:9714779, ...
Gene Name: PDE5A
Uniprot ID: O76074
Uniprot Name: cGMP-specific 3',5'-cyclic phosphodiesterase
Molecular Weight: 99984.14 Da

References

Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]

Details4. cAMP-specific 3',5'-cyclic phosphodiesterase 4A

Kind: Protein
Organism: Humans
Pharmacological action: Yes
Actions: Inhibitor

General Function: Metal ion binding
Specific Function: Hydrolyzes the second messenger cAMP, which is a key regulator of many important physiological processes.
Gene Name: PDE4A
Uniprot ID: P27815
Uniprot Name: cAMP-specific 3',5'-cyclic phosphodiesterase 4A
Molecular Weight: 98142.155 Da

References

Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]

Details5. Adenosine receptor A2a

Kind: Protein
Organism: Humans
Pharmacological action: Yes
Actions: Antagonist

General Function: Identical protein binding
Specific Function: Receptor for adenosine. The activity of this receptor is mediated by G proteins which activate adenylyl cyclase.
Gene Name: ADORA2A
Uniprot ID: P29274
Uniprot Name: Adenosine receptor A2a
Molecular Weight: 44706.925 Da

References

Kreth S, Ledderose C, Luchting B, Weis F, Thiel M: Immunomodulatory properties of pentoxifylline are mediated via adenosine-dependent pathways. Shock. 2010 Jul;34(1):10-6. doi: 10.1097/SHK.0b013e3181cdc3e2. [PubMed:19997047]

Details6. 5'-nucleotidase

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Inhibitor

General Function: Nucleotide binding
Specific Function: Hydrolyzes extracellular nucleotides into membrane permeable nucleosides. Exhibits AMP-, NAD-, and NMN-nucleosidase activities.
Gene Name: NT5E
Uniprot ID: P21589
Uniprot Name: 5'-nucleotidase
Molecular Weight: 63367.255 Da

References

Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
Ustunsoy H, Sivrikoz MC, Tarakcioglu M, Bakir K, Guldur E, Celkan MA: The effects of pentoxifylline on the myocardial inflammation and ischemia-reperfusion injury during cardiopulmonary bypass. J Card Surg. 2006 Jan-Feb;21(1):57-61. [PubMed:16426349]

Enzymes

Details1. Cytochrome P450 1A2

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Substrate

General Function: Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen
Specific Function: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name: CYP1A2
Uniprot ID: P05177
Uniprot Name: Cytochrome P450 1A2
Molecular Weight: 58293.76 Da

References

Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
Lee SH, Slattery JT: Cytochrome P450 isozymes involved in lisofylline metabolism to pentoxifylline in human liver microsomes. Drug Metab Dispos. 1997 Dec;25(12):1354-8. [PubMed:9394024]
Zhou SF, Yang LP, Zhou ZW, Liu YH, Chan E: Insights into the substrate specificity, inhibitors, regulation, and polymorphisms and the clinical impact of human cytochrome P450 1A2. AAPS J. 2009 Sep;11(3):481-94. doi: 10.1208/s12248-009-9127-y. Epub 2009 Jul 10. [PubMed:19590965]

Drug created on June 13, 2005 07:24 / Updated on April 23, 2019 12:19

Pentoxifylline

Identification

Structure for Pentoxifylline (DB00806)

Pharmacology

Interactions

References

Clinical Trials

Pharmacoeconomics

Properties

Spectra

Taxonomy

Targets

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Enzymes

References