pentoxifylline 🐶 Veterinary Use | Indications/Contra | FAERs-F | FAERs-M | Orange Bk | PK/Tox | Related Drugs | BioActivity |

Stem definitionDrug idCAS RN
N-methylated xanthine derivatives 2099 6493-05-6

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • pentoxifylline
  • azupentat
  • dimethyloxohexylxanthine
  • oxpentifylline
  • pentoxifyllin
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.
  • Molecular weight: 278.31
  • Formula: C13H18N4O3
  • CLOGP: 0.12
  • LIPINSKI: 0
  • HAC: 7
  • HDO: 0
  • TPSA: 75.51
  • ALOGS: -1.73
  • ROTB: 5
  • Status: OFP
    • Legend:
    OFP - off patent
    OFM - off market
    ONP - on patent

Drug dosage:

DoseUnitRoute
1 g O
0.30 g P

ADMET properties:

PropertyValueReference
BDDCS (Biopharmaceutical Drug Disposition Classification System) 1 Benet LZ, Broccatelli F, Oprea TI
S (Water solubility) 191 mg/mL Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine) 0 % Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose) 71.86 µM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BA (Bioavailability) 25 % Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
Vd (Volume of distribution) 1.80 L/kg Lombardo F, Berellini G, Obach RS
CL (Clearance) 39 mL/min/kg Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma) 0.51 % Lombardo F, Berellini G, Obach RS
t_half (Half-life) 1.20 hours Lombardo F, Berellini G, Obach RS

Predicted pharmacokinetic/toxicological properties (PK-AZ):

PropertyDescriptionValueUnitConfidenceSimilarity
pfas-class PFAS structural alert (1 = True, 0 = False) 0

Approvals:

DateAgencyCompanyOrphan
Aug. 30, 1984 FDA

FDA Adverse Event Reporting System (Female)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Body tinea 210.42 18.95 45 6507 2103 90619792
Inhibitory drug interaction 187.80 18.95 44 6508 3119 90618776
Infection susceptibility increased 183.41 18.95 45 6507 3881 90618014
Poor quality sleep 156.47 18.95 61 6491 24632 90597263
Glucose tolerance impaired 151.75 18.95 45 6507 7940 90613955
Purpura 135.88 18.95 48 6504 14730 90607165
Impaired quality of life 128.57 18.95 52 6500 23092 90598803
Impaired work ability 126.88 18.95 49 6503 19277 90602618
Bone density decreased 117.52 18.95 45 6507 17300 90604595
Hyperlipidaemia 108.70 18.95 46 6506 22870 90599025
Oral herpes 89.03 18.95 45 6507 33479 90588416
Skin disorder 88.02 18.95 46 6506 36660 90585235
Femoral neck fracture 81.88 18.95 30 6522 10203 90611692
Cataract 80.00 18.95 55 6497 72037 90549858
Cellulitis 79.23 18.95 60 6492 91277 90530618
Herpes zoster 66.65 18.95 55 6497 94589 90527306
International normalised ratio increased 47.57 18.95 34 6518 47282 90574613
Insomnia 43.99 18.95 83 6469 333391 90288504
Ischaemic stroke 42.60 18.95 24 6528 22142 90599753
Drug ineffective for unapproved indication 37.32 18.95 34 6518 66610 90555285
Drug ineffective 35.18 18.95 194 6358 1384104 89237791
Drug interaction 31.80 18.95 65 6487 276388 90345507
Peripheral ischaemia 25.61 18.95 11 6541 5656 90616239
Deafness bilateral 25.47 18.95 8 6544 1705 90620190
Stevens-Johnson syndrome 24.78 18.95 19 6533 29357 90592538
Insulin resistance 24.07 18.95 7 6545 1151 90620744
Prerenal failure 23.82 18.95 8 6544 2107 90619788
Skin ulcer 23.18 18.95 23 6529 50052 90571843
Pseudomonas infection 23.03 18.95 14 6538 14851 90607044
Renal failure 22.95 18.95 37 6515 130970 90490925
Contusion 22.02 18.95 53 6499 251163 90370732
Melaena 21.95 18.95 19 6533 34778 90587117
Allodynia 20.45 18.95 6 6546 1018 90620877
Hypertension 20.44 18.95 76 6476 457456 90164439
Infusion related reaction 20.27 18.95 3 6549 416777 90205118
Osteonecrosis 20.03 18.95 16 6536 26225 90595670
Clostridium test positive 19.64 18.95 9 6543 5392 90616503

FDA Adverse Event Reporting System (Male)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Sedation complication 57.21 18.50 19 5109 2900 42613307
Akathisia 54.07 18.50 26 5102 10425 42605782
Arrhythmia 41.10 18.50 36 5092 40281 42575926
Peripheral artery occlusion 40.28 18.50 13 5115 1813 42614394
Blood lactic acid 39.44 18.50 9 5119 337 42615870
Hyperkalaemia 38.68 18.50 48 5080 80410 42535797
Pleural mass 38.39 18.50 7 5121 82 42616125
Acute kidney injury 36.80 18.50 112 5016 367225 42248982
Biopsy lymph gland 33.42 18.50 6 5122 64 42616143
Peripheral ischaemia 33.14 18.50 16 5112 6469 42609738
Skin hyperpigmentation 33.09 18.50 14 5114 4167 42612040
Heart valve stenosis 32.70 18.50 6 5122 73 42616134
Mitral valve prolapse 28.55 18.50 8 5120 689 42615518
Radiotherapy to brain 27.88 18.50 5 5123 53 42616154
Drug dependence 27.70 18.50 25 5103 29069 42587138
Aortic bruit 26.05 18.50 6 5122 234 42615973
Intentional product misuse 25.15 18.50 34 5094 61866 42554341
Myocardial necrosis 25.05 18.50 6 5122 278 42615929
Basal cell carcinoma 24.57 18.50 21 5107 22712 42593495
Agitation 24.13 18.50 34 5094 64280 42551927
Endarterectomy 22.58 18.50 5 5123 163 42616044
Penile pain 21.15 18.50 8 5120 1780 42614427
Oesophageal dilatation 20.50 18.50 5 5123 250 42615957
International normalised ratio increased 20.39 18.50 27 5101 48141 42568066
Metabolic syndrome 20.34 18.50 8 5120 1975 42614232
Hilar lymphadenopathy 20.06 18.50 7 5121 1239 42614968
Ventricular enlargement 19.83 18.50 6 5122 677 42615530
Atrial enlargement 19.44 18.50 6 5122 723 42615484
Paraesthesia 19.37 18.50 33 5095 73426 42542781
Extremity necrosis 19.13 18.50 8 5120 2311 42613896
Skin squamous cell carcinoma recurrent 18.65 18.50 4 5124 112 42616095

FDA Adverse Event Reporting System (Geriatric)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Body tinea 189.60 15.14 44 11415 2071 110575769
Infection susceptibility increased 157.62 15.14 44 11415 4354 110573486
Glucose tolerance impaired 149.68 15.14 51 11408 9786 110568054
Inhibitory drug interaction 148.06 15.14 43 11416 4904 110572936
Poor quality sleep 118.61 15.14 58 11401 28019 110549821
Purpura 107.89 15.14 52 11407 24336 110553504
Bone density decreased 101.89 15.14 44 11415 15998 110561842
Impaired work ability 92.31 15.14 48 11411 26371 110551469
Impaired quality of life 92.07 15.14 50 11409 29967 110547873
Hyperlipidaemia 73.55 15.14 46 11413 35802 110542038
Femoral neck fracture 68.61 15.14 31 11428 12536 110565304
Oral herpes 68.29 15.14 44 11415 36036 110541804
Skin disorder 63.67 15.14 45 11414 42868 110534972
Cataract 59.68 15.14 56 11403 79429 110498411
Peripheral ischaemia 59.49 15.14 27 11432 11031 110566809
Amaurosis fugax 59.41 15.14 18 11441 2372 110575468
International normalised ratio increased 57.36 15.14 57 11402 86715 110491125
Hyperkalaemia 48.65 15.14 65 11394 135731 110442109
Cellulitis 47.74 15.14 62 11397 125954 110451886
Akathisia 45.62 15.14 26 11433 17087 110560753
Herpes zoster 43.70 15.14 55 11404 108324 110469516
Urinary tract disorder 43.68 15.14 18 11441 5826 110572014
Acute kidney injury 43.04 15.14 154 11305 635276 109942564
Drug ineffective for unapproved indication 39.58 15.14 51 11408 102787 110475053
Pleural mass 38.02 15.14 7 11452 102 110577738
Blood lactic acid 37.88 15.14 9 11450 469 110577371
Arrhythmia 37.53 15.14 41 11418 69534 110508306
Peripheral artery occlusion 36.26 15.14 13 11446 2892 110574948
Drug interaction 35.35 15.14 123 11336 500060 110077780
Drug ineffective 35.21 15.14 273 11186 1520267 109057573
Haemorrhagic stroke 34.22 15.14 20 11439 13769 110564071
Peripheral vascular disorder 34.07 15.14 17 11442 8559 110569281
Biopsy lymph gland 31.50 15.14 6 11453 106 110577734
Ocular discomfort 31.23 15.14 16 11443 8517 110569323
Skin hyperpigmentation 30.94 15.14 16 11443 8680 110569160
Insomnia 30.23 15.14 94 11365 360496 110217344
Joint swelling 29.88 15.14 5 11454 442840 110135000
Drug dependence 29.66 15.14 31 11428 49989 110527851
Extremity necrosis 29.40 15.14 12 11447 3790 110574050
Radiotherapy to brain 29.08 15.14 5 11454 48 110577792
Ischaemic stroke 28.92 15.14 28 11431 41235 110536605
Heart valve stenosis 28.50 15.14 6 11453 179 110577661
Skin ulcer 26.76 15.14 33 11426 63612 110514228
Aortic bruit 26.24 15.14 6 11453 264 110577576
Peripheral coldness 24.21 15.14 18 11441 18522 110559318
Haematuria 24.17 15.14 36 11423 82969 110494871
Sedation complication 23.11 15.14 18 11441 19837 110558003
Myocardial necrosis 21.95 15.14 6 11453 549 110577291
Telangiectasia 21.93 15.14 8 11451 1869 110575971
Generalised oedema 21.83 15.14 21 11438 30683 110547157
Melaena 21.73 15.14 31 11428 68726 110509114
Head discomfort 21.63 15.14 17 11442 18983 110558857
Systemic scleroderma 21.55 15.14 8 11451 1964 110575876
Penile pain 21.43 15.14 7 11452 1177 110576663
Ventricular enlargement 20.37 15.14 6 11453 718 110577122
Mitral valve prolapse 20.09 15.14 8 11451 2370 110575470
Presyncope 19.99 15.14 25 11434 48862 110528978
Arthropathy 19.94 15.14 3 11456 287519 110290321
Intermittent claudication 19.79 15.14 9 11450 3692 110574148
Anaemia 19.73 15.14 110 11349 546976 110030864
Skin squamous cell carcinoma recurrent 19.31 15.14 4 11455 110 110577730
Deafness bilateral 19.10 15.14 8 11451 2696 110575144
Hypersensitivity 19.07 15.14 9 11450 403989 110173851
Endarterectomy 18.99 15.14 5 11454 396 110577444
Cardio-respiratory arrest 18.99 15.14 39 11420 115797 110462043
Rheumatoid arthritis 18.88 15.14 4 11455 299609 110278231
Insulin resistance 18.82 15.14 7 11452 1727 110576113
Synovitis 18.69 15.14 3 11456 274089 110303751
Coma 18.53 15.14 39 11420 117830 110460010
Agitation 18.46 15.14 38 11421 113013 110464827
Haematoma 17.95 15.14 26 11433 58450 110519390
Hepatocellular injury 17.75 15.14 24 11435 50618 110527222
Fall 17.72 15.14 115 11344 603367 109974473
Metabolic syndrome 17.69 15.14 8 11451 3239 110574601
Atrial enlargement 17.63 15.14 6 11453 1145 110576695
Infusion related reaction 17.23 15.14 9 11450 381153 110196687
Contusion 16.98 15.14 58 11401 233303 110344537
Hilar lymphadenopathy 16.90 15.14 7 11452 2295 110575545
Oesophageal dilatation 16.86 15.14 5 11454 612 110577228
Systemic lupus erythematosus 16.86 15.14 3 11456 254335 110323505
Altered state of consciousness 16.79 15.14 25 11434 57601 110520239
Dihydrotestosterone increased 16.41 15.14 3 11456 42 110577798
Haematemesis 16.30 15.14 25 11434 59083 110518757
Drug hypersensitivity 16.13 15.14 14 11445 454076 110123764
Suspected product contamination 15.78 15.14 4 11455 273 110577567
Cardiac failure 15.78 15.14 49 11410 187577 110390263
Penile swelling 15.55 15.14 5 11454 801 110577039
Anticoagulation drug level decreased 15.54 15.14 4 11455 290 110577550
Nasopharyngitis 15.47 15.14 11 11448 394350 110183490
Intentional product misuse 15.40 15.14 39 11420 132865 110444975
Renal failure 15.34 15.14 55 11404 226519 110351321
Mycobacterium abscessus infection 15.33 15.14 6 11453 1700 110576140
Prerenal failure 15.28 15.14 8 11451 4451 110573389

FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

SourceCodeDescription
ATC C04AD03 CARDIOVASCULAR SYSTEM
PERIPHERAL VASODILATORS
PERIPHERAL VASODILATORS
Purine derivatives
FDA PE N0000009065 Hematologic Activity Alteration
MeSH PA D000975 Antioxidants
MeSH PA D002317 Cardiovascular Agents
MeSH PA D004791 Enzyme Inhibitors
MeSH PA D006401 Hematologic Agents
MeSH PA D010726 Phosphodiesterase Inhibitors
MeSH PA D010975 Platelet Aggregation Inhibitors
MeSH PA D011837 Radiation-Protective Agents
MeSH PA D014665 Vasodilator Agents
MeSH PA D016166 Free Radical Scavengers
MeSH PA D020011 Protective Agents
FDA EPC N0000175895 Blood Viscosity Reducer
CHEBI has role CHEBI:22587 antiviral agent
CHEBI has role CHEBI:35469 antidepressant
CHEBI has role CHEBI:35476 antipsychotic agent
CHEBI has role CHEBI:35526 hypoglycemic agent
CHEBI has role CHEBI:35554 cardiovascular drug
CHEBI has role CHEBI:35610 antineoplastic agent
CHEBI has role CHEBI:35623 anticonvulsant
CHEBI has role CHEBI:38068 antimalarial
CHEBI has role CHEBI:48407 antiparkinson drug
CHEBI has role CHEBI:62868 hepatoprotective agent
CHEBI has role CHEBI:64946 anti-HIV agent
CHEBI has role CHEBI:67079 anti-inflammatory agent
CHEBI has role CHEBI:70868 antileishmanial agent
CHEBI has role CHEBI:73336 vulnerary
CHEBI has role CHEBI:75835 anti-anaemic agent
CHEBI has role CHEBI:149553 anticoronaviral agent
CHEBI has role CHEBI:231911 renoprotective agent
CHEBI has role CHEBI:233423 antifibrotic agent

Related Drugs by ATC class:

C04AD Purine derivatives 3 drugs
etofylline nicotinatepentifyllinexantinol

Drug Use | Suggest Off label Use Form| |View source of the data|

DiseaseRelationSNOMED_IDDOID
Peripheral vascular disease indication 400047006
Osteoradionecrosis off-label use 109333005
Alcoholic hepatitis off-label use 235875008
Retinal hemorrhage contraindication 28998008
Blood coagulation disorder contraindication 64779008 DOID:1247
Kidney disease contraindication 90708001 DOID:557
Bleeding contraindication 131148009
Hemorrhagic cerebral infarction contraindication 230706003




🐶 Veterinary Drug Use

None

🐶 Veterinary products

None

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 1.43 Basic

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])		Mechanism
action		Bioact sourceMoA source
Adenosine receptor A2b GPCR ANTAGONIST Ki 5.29 CHEMBL CHEMBL
cAMP-specific 3',5'-cyclic phosphodiesterase 4B Enzyme INHIBITOR WOMBAT-PK CHEMBL
cGMP-specific 3',5'-cyclic phosphodiesterase Enzyme INHIBITOR DRUGBANK CHEMBL
Acetylcholinesterase Enzyme IC50 5.18 CHEMBL

External reference:

IDSource
4018468 VUID
N0000146791 NUI
D00501 KEGG_DRUG
4018468 VANDF
C0030899 UMLSCUI
CHEBI:7986 CHEBI
PNX PDB_CHEM_ID
CHEMBL628 ChEMBL_ID
DB00806 DRUGBANK_ID
D010431 MESH_DESCRIPTOR_UI
4740 PUBCHEM_CID
7095 IUPHAR_LIGAND_ID
3309 INN_ID
SD6QCT3TSU UNII
8013 RXNORM
10203 MMSL
41909 MMSL
5257 MMSL
d00336 MMSL
002098 NDDF
387522004 SNOMEDCT_US
91376007 SNOMEDCT_US

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Pentoxifylline HUMAN PRESCRIPTION DRUG LABEL 1 0615-8511 TABLET, EXTENDED RELEASE 400 mg ORAL ANDA 17 sections
PENTOXIFYLLINE HUMAN PRESCRIPTION DRUG LABEL 1 0904-5448 TABLET, EXTENDED RELEASE 400 mg ORAL ANDA 17 sections
Pentoxifylline HUMAN PRESCRIPTION DRUG LABEL 1 16571-856 TABLET, EXTENDED RELEASE 400 mg ORAL ANDA 17 sections
PENTOXIFYLLINE HUMAN PRESCRIPTION DRUG LABEL 1 16590-856 TABLET, EXTENDED RELEASE 400 mg ORAL ANDA 19 sections
PENTOXIFYLLINE HUMAN PRESCRIPTION DRUG LABEL 1 33261-992 TABLET, EXTENDED RELEASE 400 mg ORAL ANDA 17 sections
Pentoxifylline HUMAN PRESCRIPTION DRUG LABEL 1 43353-123 TABLET, EXTENDED RELEASE 400 mg ORAL ANDA 19 sections
Pentoxifylline HUMAN PRESCRIPTION DRUG LABEL 1 53808-0516 TABLET, FILM COATED, EXTENDED RELEASE 400 mg ORAL ANDA 19 sections
Pentoxifylline HUMAN PRESCRIPTION DRUG LABEL 1 53808-0757 TABLET, EXTENDED RELEASE 400 mg ORAL ANDA 19 sections
Pentoxifylline HUMAN PRESCRIPTION DRUG LABEL 1 53808-0758 TABLET, FILM COATED, EXTENDED RELEASE 400 mg ORAL ANDA 19 sections
Pentoxifylline HUMAN PRESCRIPTION DRUG LABEL 1 54868-4515 TABLET, EXTENDED RELEASE 400 mg ORAL ANDA 19 sections
PENTOXIFYLLINE HUMAN PRESCRIPTION DRUG LABEL 1 60505-0033 TABLET, EXTENDED RELEASE 400 mg ORAL ANDA 17 sections
PENTOXIFYLLINE HUMAN PRESCRIPTION DRUG LABEL 1 63629-2910 TABLET, EXTENDED RELEASE 400 mg ORAL ANDA 16 sections
PENTOXIFYLLINE HUMAN PRESCRIPTION DRUG LABEL 1 67544-252 TABLET, EXTENDED RELEASE 400 mg ORAL ANDA 16 sections
Pentoxifylline HUMAN PRESCRIPTION DRUG LABEL 1 68071-4532 TABLET, EXTENDED RELEASE 400 mg ORAL ANDA 19 sections
Pentoxifylline HUMAN PRESCRIPTION DRUG LABEL 1 70954-668 TABLET, EXTENDED RELEASE 400 mg ORAL ANDA 17 sections
Pentoxifylline HUMAN PRESCRIPTION DRUG LABEL 1 70954-668 TABLET, EXTENDED RELEASE 400 mg ORAL ANDA 17 sections
Pentoxifylline HUMAN PRESCRIPTION DRUG LABEL 1 71335-2586 TABLET, EXTENDED RELEASE 400 mg ORAL ANDA 17 sections
PENTOXIFYLLINE HUMAN PRESCRIPTION DRUG LABEL 1 72162-2113 TABLET, EXTENDED RELEASE 400 mg ORAL ANDA 16 sections
PENTOXIFYLLINE HUMAN PRESCRIPTION DRUG LABEL 1 72189-025 TABLET, EXTENDED RELEASE 400 mg ORAL ANDA 9 sections
PENTOXIFYLLINE HUMAN PRESCRIPTION DRUG LABEL 1 72189-025 TABLET, EXTENDED RELEASE 400 mg ORAL ANDA 9 sections
PENTOXIFYLLINE HUMAN PRESCRIPTION DRUG LABEL 1 72189-025 TABLET, EXTENDED RELEASE 400 mg ORAL ANDA 9 sections
PENTOXIFYLLINE 0.5% / TRIAMCINOLONE ACETONIDE 0.1% HUMAN PRESCRIPTION DRUG LABEL 2 72934-1169 GEL 0.50 g TOPICAL unapproved drug other 4 sections
BETAMETHASONE DIPROPIONATE 0.05% / MINOXIDIL 5% / NIACINAMIDE 2% / PENTOXIFYLLINE 0.5% HUMAN PRESCRIPTION DRUG LABEL 4 72934-4024 SOLUTION 2 g TOPICAL unapproved drug other 4 sections