PENTOXIFYLLINE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C13H18N4O3
Molecular Weight	278.307
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

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

InChI

InChIKey=BYPFEZZEUUWMEJ-UHFFFAOYSA-N

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

HIDE SMILES / InChI

Molecular Formula	C13H18N4O3
Molecular Weight	278.307
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=ff7c9b1c-4192-4d09-a2ab-b80ec14cd424

Pentoxil (Pentoxifylline Extended-release Tablets, USP) is indicated for the treatment of patients with intermittent claudication based on chronic occlusive arterial disease of the limbs. Pentoxil can improve function and symptoms but is not intended to replace more definitive therapy, such as surgical bypass, or removal of arterial obstructions when treating peripheral vascular disease. Pentoxifylline and its metabolites improve the flow properties of blood by decreasing its viscosity. In patients with chronic peripheral arterial disease, this increases blood flow to the affected microcirculation and enhances tissue oxygenation. The precise mode of action of pentoxifylline and the sequence of events leading to clinical improvement are still to be defined. 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. Pentoxifylline administration has been shown to produce dose-related hemorrheologic effects, lowering blood viscosity, and improving erythrocyte flexibility. Pentoxifylline has been shown to increase leukocyte deformability and to inhibit neutrophil adhesion and activation. Tissue oxygen levels have been shown to be significantly increased by therapeutic doses of pentoxifylline in patients with peripheral arterial disease. Clinical trials were conducted using either extended-release pentoxifylline tablets for up to 60 weeks or immediate-release pentoxifylline capsules for up to 24 weeks. Dosage ranges in the tablet studies were 400 mg bid to tid and in the capsule studies, 200-400 mg tid. The incidence of adverse reactions was higher in the capsule studies (where dose related increases were seen in digestive and nervous system side effects) than in the tablet studies. Studies with the capsule include domestic experience, whereas studies with the extended-release tablets were conducted outside the U.S.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Adenosine A2 receptor 9 Target ID: CHEMBL2094257 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19997047	Antagonist 2849
3',5'-cyclic phosphodiesterase 5 Target ID: CHEMBL2363066 Sources: https://www.ncbi.nlm.nih.gov/pubmed/?term=11692087	Inhibitor 8504

Conditions

Condition	Modality	Targets	Highest Phase	Product
Intermittent claudication 12 Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=ff7c9b1c-4192-4d09-a2ab-b80ec14cd424	Primary		Approved 8583	PENTOXIL Approved Use INDICATIONS & USAGE Pentoxifylline extended-release tablets are indicated for the treatment of patients with intermittent claudication on the basis of chronic occlusive arterial disease of the limbs. Pentoxifylline can improve function and symptoms but is not intended to replace more definitive therapy, such as surgical bypass, or removal of arterial obstructions when treating peripheral vascular disease. Launch Date 1999

C_max

Value	Dose	Analyte	Population
719 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/23400743	600 mg single, oral dose: 600 mg route of administration: Oral experiment type: SINGLE co-administered:	PENTOXIFYLLINE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
272 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3958905	100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered:	PENTOXIFYLLINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
683 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3958905	200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered:	PENTOXIFYLLINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
1607 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3958905	400 mg single, oral dose: 400 mg route of administration: Oral experiment type: SINGLE co-administered:	PENTOXIFYLLINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

AUC

Value	Dose	Analyte	Population
4842 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/23400743	600 mg single, oral dose: 600 mg route of administration: Oral experiment type: SINGLE co-administered:	PENTOXIFYLLINE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
193 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3958905	100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered:	PENTOXIFYLLINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
380 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3958905	200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered:	PENTOXIFYLLINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
1228 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3958905	400 mg single, oral dose: 400 mg route of administration: Oral experiment type: SINGLE co-administered:	PENTOXIFYLLINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

T_1/2

Value	Dose	Analyte	Population
0.48 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3958905	100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered:	PENTOXIFYLLINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
0.39 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3958905	200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered:	PENTOXIFYLLINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
0.84 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3958905	400 mg single, oral dose: 400 mg route of administration: Oral experiment type: SINGLE co-administered:	PENTOXIFYLLINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

Overview

CYP3A4	CYP2C9	CYP2D6	hERG

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
	CYP1A2 1197

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
CYP1A2 1197	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/15194011/ Page: 7.0	yes		likely (co-administration study) Comment: Concomitant administration of strong CYP1A2 inhibitors (including e.g. ciprofloxacin or fluvoxamine) may increase the exposure to pentoxifylline Sources: https://pubmed.ncbi.nlm.nih.gov/15194011/ Page: 7.0

Sourcing

Vendor/Aggregator	ID	URL
3B Scientific (Wuhan) Corp	3B1-00326	http://www.3bsc.com/index/pro_info.php?id=20538
3B Scientific (Wuhan) Corp	3B2-0680	http://www.3bsc.com/index/pro_info.php?id=20036
abcr GmbH	AB379899	http://www.abcr.com/shop/en/AB379899
AbMole Bioscience	M2923	http://www.abmole.com/products/pentoxifylline.html
Acadechem	ACDS-027148	http://www.acadechemical.com/product/101847
AHH Chemical co.,ltd	API-1650	http://www.ahhchemical.com/product/API-1650.html
AK Scientific, Inc. (AKSCI)	J10071	http://www.aksci.com/item_detail.php?cat=J10071
AK Scientific, Inc. (AKSCI)	V0152	http://www.aksci.com/item_detail.php?cat=V0152
Alfa Aesar	B24600	https://www.alfa.com/en/catalog/B24600/
Alfa Chemistry	1677687	https://www.alfa-chemistry.com/pentoxifylline-cas-6493-05-6-item-293156.htm
Alfa Chemistry	AP6493056-A	https://reagents.alfa-chemistry.com/product/pentoxifylline-cas-6493-05-6-14615.html
Alfa Chemistry	AP6493056-B	https://reagents.alfa-chemistry.com/product/pentoxifylline-cas-6493-05-6-14616.html
Ambeed	A646154	https://www.ambeed.com/products/6493-05-6.html
Ambinter	Amb19133613	http://www.ambinter.com/reference/19133613
Aurum Pharmatech LLC	H3041	http://www.Aurumpharmatech.com/Product/ProductDetails/H3041
Avantor Inc	101095-756	https://us.vwr.com/store/catalog/product.jsp?catalog_number=101095-756
Avantor Inc	TCP2050-25G	https://us.vwr.com/store/product/16814128/pentoxifylline-98-0-by-hplc-titration-analysis
Avantor Inc	TCP2050-5G	https://us.vwr.com/store/product/16814128/pentoxifylline-98-0-by-hplc-titration-analysis
Axon MedChem	3179	https://www.axonmedchem.com/product/3179
BioChemPartner	BCP29306	http://www.biochempartner.com/6493-05-6-BCP29306
BLD Pharm	BD105907	http://www.bldpharm.com/products/6493-05-6.html
Calbiochem	516354	http://www.emdbiosciences.com/product/516354
Chem Scene	CS-2954	http://www.chemscene.com/6493-05-6.html
ChemMol	30113430	http://www.chemmol.com/chemmol/30113430.html
ChemMol	49402479	http://www.chemmol.com/chemmol/49402479.html
ChemMol	97900367	http://www.chemmol.com/chemmol/97900367.html
ChemMol	99137774	http://www.chemmol.com/chemmol/99137774.html
Chemspace	CSSB00020615131	https://chem-space.com/CSSB00020615131
Clearsynth	CS-T-38995	https://www.clearsynth.com/en/CST38995.html
Clearsynth	CS-T-60258	https://www.clearsynth.com/en/CST60258.html
CSNpharm	CSN10102	https://www.csnpharm.com/products/pentoxifylline.html
EMD Millipore	516354	http://www.emdbiosciences.com/product/516354
eNovation Chemicals	D675472	https://www.enovationchem.com/ProductDetails.asp?ProductID=D675472
Finetech	FT-0603570	http://www.finetechnology-ind.com/prod/detail/pub/6493-05-6.html
Finetech	FT-0657886	http://www.finetechnology-ind.com/prod/detail/pub/6493-05-6.html
Finetech	FT-0673610	http://www.finetechnology-ind.com/prod/detail/pub/1185878-98-1.html
Glentham Life Sciences	GP1948	http://www.glentham.com/products/product/GP1948/
Lab Network	LN00832312	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN00832312
LGC Standards	DRE-C15981800	https://www.lgcstandards.com/US/en/p/DRE-C15981800
LGC Standards	LGCFOR0761.00	https://www.lgcstandards.com/US/en/p/LGCFOR0761.00
LGC Standards	MM0761.00	https://www.lgcstandards.com/US/en/p/MM0761.00
mcule	MCULE-9951939936	https://mcule.com/MCULE-9951939936/
MedChem Express	HY-B0715	https://www.medchemexpress.com/Pentoxifylline.html
Sinfoo Biotech	S011491	http://www.sinfoobiotech.com/product/1014889
Smolecule	S538998	http://www.smolecule.com/products/s538998
TCI (Tokyo Chemical Industry)	P2050	http://www.tcichemicals.com/eshop/en/us/commodity/P2050/index.html
THE BioTek	bt-278531	https://www.thebiotek.com/product/inhibitors/bt-278531
Tocris	3056	https://www.tocris.com/products/pentoxifylline_3056
Vesino Industrial Co Ltd	VZ33607	http://www.vsnchem.com/goto/product/34351/

PubMed

Title	Date	PubMed
Management of patients with severe oral mucosal disease.	2001-08-02	11480183
Administration of pentoxifylline during allergen sensitization dissociates pulmonary allergic inflammation from airway hyperresponsiveness.	2001-08-01	11466394
A pilot study of pentoxifylline in the treatment of radiation-induced trismus.	2001-08	11474263
Pentoxifylline improves in vitro fertilization and subsequent development of bovine oocytes.	2001-07-15	11480615
The role of glucose in supporting motility and capacitation in human spermatozoa.	2001-07-14	11451366
A redox-regulated tyrosine phosphorylation cascade in rat spermatozoa.	2001-07-14	11451358
Effect of pentoxifylline on nitrogen balance and 3-methylhistidine excretion in parenterally fed endotoxemic rats.	2001-07-13	11448584
In vivo downregulation of T helper cell 1 immune responses reduces atherogenesis in apolipoprotein E-knockout mice.	2001-07-10	11447086
Intravenous pentoxifylline does not enhance the pulmonary haemodynamic efficacy of frusemide in strenuously exercising thoroughbred horses.	2001-07	11469767
Integrating anti-tumor necrosis factor therapy in inflammatory bowel disease: current and future perspectives.	2001-07	11467623
Ibudilast attenuates astrocyte apoptosis via cyclic GMP signalling pathway in an in vitro reperfusion model.	2001-07	11454657
Oral pentoxifylline inhibits release of tumor necrosis factor-alpha from human peripheral blood monocytes : a potential treatment for aseptic loosening of total joint components.	2001-07	11451976
Renal failure, anaemia, cytokines and inflammation.	2001-07	11427669
Analysis of the cilostazol safety database.	2001-06-28	11434897
Comparative effects of cilostazol and other therapies for intermittent claudication.	2001-06-28	11434896
Intermittent claudication: effective medical management of a common circulatory problem.	2001-06-28	11434895
Medical management of peripheral arterial disease.	2001-06-19	11405904
[Acute alcoholic hepatitis: treatments].	2001-06-09	11433695
[Beneficial effects of pentoxifylline in patients with idiopathic dilated cardiomyopathy treated with angiotensin-converting enzyme inhibitors and carvedilol. Results of a randomised study].	2001-06	11460849
The effect of tumour necrosis factor (TNF) inhibitors in Clostridium difficile toxin-induced paw oedema and neutrophil migration.	2001-06	11453371
Improved response of colon cancer xenografts to radioimmunotherapy with pentoxifylline treatment.	2001-06	11440036
[Effect of pentoxifylline on the healing of experimental anastomosis of the left colon in rats].	2001-06	11432172
Pentoxifylline rescue preserves lung function in isolated canine lungs injured with phorbol myristate acetate.	2001-06	11399720
Pentoxifylline effects on acute and late complications after radiotherapy in rabbit.	2001-06	11391259
Therapeutic effects of Vascupump treatment patients with Fontaine Stage II B arteriopathy.	2001-06	11382835
Countervailing influence of tumor necrosis factor-alpha and nitric oxide in endotoxemia.	2001-06	11373343
Use of pentoxifylline in membranous nephropathy.	2001-05-26	11425374
Pentoxifylline: wonder drug?	2001-05-22	11361111
The role of cGMP hydrolysing phosphodiesterases 1 and 5 in cerebral artery dilatation.	2001-05-18	11412839
[Pentoxifylline: is it useful in multiple sclerosis?].	2001-05-17	11353990
Preventive effect of inhaled nitric oxide and pentoxifylline on ischemia/reperfusion injury after lung transplantation.	2001-05-15	11397965
Pentoxifylline inhibits the synthesis and IFN-gamma-inducing activity of IL-18.	2001-05	11422205
Controlled perfusion of the transplanted lung.	2001-05	11383858
Prophylactic use of pentoxifylline on inflammation in elderly cardiac surgery patients.	2001-05	11383794
Influence of prophylactic use of pentoxifylline on postoperative organ function in elderly cardiac surgery patients.	2001-05	11378603
Modulation of human peripheral blood mononuclear cell activation by the combination of leflunomide and pentoxifylline.	2001-05	11377478
A toast to pentoxifylline.	2001-05	11374714
Inhibitory effects of cyclic AMP elevating agents on lipopolysaccharide (LPS)-induced microvascular permeability change in mouse skin.	2001-05	11350859
New treatment options in intermittent claudication: the US experience.	2001-04	11355276
Cilostazol: a novel treatment option in intermittent claudication.	2001-04	11355274
[Effect of pentoxifylline on promoter activity of human alpha 1(I) procollagen gene].	2001-04	11350679
The effects of pentoxifylline treatment on bacterial translocation after hemorrhagic shock in rats.	2001-03	11467403
Inhibition of human CYP1A2 activity in vitro by methylxanthines: potent competitive inhibition by 8-phenyltheophylline.	2001-03	11465391
Time-dependent influence of pentoxifylline on the pharmacokinetics of orally administered carbamazepine in human subjects.	2001-03	11401423
The effect of pentoxifylline on intestinal ischemia/reperfusion injury.	2001-02	11468009
[Disturbances of rhythm and atrio-ventricular conduction in digitalis overdose. Case reports].	2001	11450159
Immunotherapy of inflammatory demyelinating diseases of the central nervous system.	2001	11444389
Indobufen: an updated review of its use in the management of atherothrombosis.	2001	11392445
Microvascular endothelial dysfunction: a renewed appreciation of sepsis pathophysiology.	2001	11379985
The alveolar septal thickness and type II pneumocytes number in irradiated lungs, time expression and the effect of pentoxifylline.	2001	11367886

Patents

Sample Use Guides

In Vivo Use Guide

The usual dosage of Pentoxil (Pentoxifylline Extended-release Tablets, USP) in extended-release tablet form is one tablet (400 mg) three times a day with meals. While the effect of Pentoxil may be seen within 2 to 4 weeks, it is recommended that treatment be continued for at least 8 weeks. Efficacy has been demonstrated in double-blind clinical studies of 6 months duration.

Route of Administration: Oral

In Vitro Use Guide

The proliferation rate of the cells treated with 1 mM Pentoxifylline (PTX) significantly decreased compared with that of the control in T6 cells (78.3 ± 6.03% at 12 h, 61.0 ± 7.55% at 24 h, and 44.7 ± 2.08% at 48 h, p < 0.05). PTX (1 mM) also decreased the fraction of the hepatic stellate cells (HSC) population in the S and G2/M-phases of the cell cycle in primary activated rat HSCs. The Raf-1 inhibitor GW5074 and the ERK inhibitor U0126 had inhibitory effects that were similar to those of PTX on HSC proliferation. In addition, PTX inhibited the phosphorylation of Raf-1 (p-Raf-1) and ERK (p-ERK) in a dose- and time-dependent manner in HSCs.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:01:22 GMT 2025` Edited by `admin` on `Mon Mar 31 18:01:22 GMT 2025`
Record UNII	SD6QCT3TSU
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

C04AD03

Preferred Name

English

PENTOXIFYLLINE

Official Name

English

PENTOXIFYLLINE [ORANGE BOOK]

Common Name

English

PENTOXIFYLLINE [MART.]

Common Name

English

NSC-637086

Code

English

OXYPENTIFYLLINE

Common Name

English

BL-191

Code

English

TRENTAL

Brand Name

English

PENTOXIFYLLINE [EP MONOGRAPH]

Common Name

English

PENTOXIFYLLINE [VANDF]

Common Name

English

PENTOXIFYLLINE [JAN]

Common Name

English

PENTOXIL

Brand Name

English

PENTOXIFYLLINE [USP-RS]

Common Name

English

pentoxifylline [INN]

Common Name

English

1H-PURINE-2,6-DIONE, 3,7-DIHYDRO-3,7-DIMETHYL-1-(5-OXOHEXYL)-

Systematic Name

English

NSC-758481

Code

English

PENTOXIPHYLLIN

Common Name

English

PENTOXIFYLLINE [USP MONOGRAPH]

Common Name

English

Pentoxifylline [WHO-DD]

Common Name

English

PENTOXIFYLLINE [MI]

Common Name

English

BL 191

Code

English

1-(5-Oxohexyl)theobromine

Systematic Name

English

PENTOXIFYLLINE [USAN]

Common Name

English

Classification Tree Code System Code

FDA ORPHAN DRUG

369712