pentoxifylline ๐Ÿถ Veterinary Use | Indications/Contra | FAERs-F | FAERs-M | Orange Bk | 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 ยตM/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

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 144.05 18.10 32 4984 1295 50598813
Infection susceptibility increased 122.85 18.10 32 4984 2552 50597556
Inhibitory drug interaction 122.52 18.10 31 4985 2202 50597906
Glucose tolerance impaired 101.23 18.10 32 4984 5086 50595022
Impaired quality of life 95.93 18.10 32 4984 6024 50594084
Purpura 91.16 18.10 35 4981 9876 50590232
Femoral neck fracture 78.11 18.10 29 4987 7461 50592647
Bone density decreased 77.11 18.10 32 4984 11043 50589065
Poor quality sleep 70.63 18.10 34 4982 16612 50583496
Hyperlipidaemia 66.06 18.10 33 4983 17457 50582651
Impaired work ability 64.42 18.10 30 4986 13610 50586498
Oral herpes 58.01 18.10 32 4984 20693 50579415
Skin disorder 53.60 18.10 32 4984 23998 50576110
Cellulitis 49.56 18.10 47 4969 70751 50529357
Cataract 42.17 18.10 36 4980 47264 50552844
Herpes zoster 36.75 18.10 40 4976 70746 50529362
International normalised ratio increased 34.75 18.10 31 4985 43121 50556987
Deafness bilateral 25.63 18.10 8 5008 1218 50598890
Peripheral ischaemia 25.25 18.10 11 5005 4265 50595843
Pseudomonas infection 24.84 18.10 14 5002 9416 50590692
Insomnia 24.83 18.10 54 4962 174811 50425297
Hypertension 24.26 18.10 60 4956 211143 50388965
Prerenal failure 24.08 18.10 8 5008 1485 50598623
Stevens-Johnson syndrome 22.38 18.10 18 4998 21734 50578374
Allodynia 20.90 18.10 6 5010 686 50599422
Drug interaction 20.12 18.10 54 4962 199567 50400541
Renal failure 20.00 18.10 37 4979 106596 50493512
Contusion 19.89 18.10 38 4978 112145 50487963
Necrotising myositis 19.48 18.10 5 5011 375 50599733
Corneal leukoma 19.46 18.10 3 5013 14 50600094
Melaena 19.08 18.10 18 4998 26846 50573262
Delirium 18.80 18.10 21 4995 38171 50561937
Drug ineffective for unapproved indication 18.55 18.10 16 5000 21265 50578843
Skin ulcer 18.38 18.10 20 4996 35298 50564810

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
Acute kidney injury 48.33 17.84 105 3672 265162 29305588
Pleural mass 39.46 17.84 7 3770 65 29570685
Blood lactic acid 38.90 17.84 9 3768 337 29570413
Hyperkalaemia 38.19 17.84 43 3734 61349 29509401
Peripheral artery occlusion 38.16 17.84 12 3765 1450 29569300
Skin hyperpigmentation 37.42 17.84 14 3763 2850 29567900
Drug dependence 33.58 17.84 25 3752 20956 29549794
Biopsy lymph gland 33.51 17.84 6 3771 59 29570691
Mitral valve prolapse 29.65 17.84 8 3769 564 29570186
Peripheral ischaemia 29.58 17.84 14 3763 5105 29565645
Radiotherapy to brain 28.85 17.84 5 3772 40 29570710
Paraesthesia 24.16 17.84 32 3745 53813 29516937
Endarterectomy 22.88 17.84 5 3772 144 29570606
Metabolic syndrome 22.20 17.84 8 3769 1465 29569285
Hilar lymphadenopathy 22.14 17.84 7 3770 860 29569890
Hypomagnesaemia 21.85 17.84 18 3759 17450 29553300
Extremity necrosis 21.54 17.84 8 3769 1595 29569155
International normalised ratio increased 20.88 17.84 27 3750 44345 29526405
Anaemia 19.43 17.84 63 3714 200888 29369862
Gingival disorder 19.33 17.84 7 3770 1299 29569451
Penile pain 18.74 17.84 7 3770 1417 29569333
Therapeutic response decreased 18.30 17.84 19 3758 24692 29546058

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 131.89 15.83 31 8106 1262 64489333
Glucose tolerance impaired 109.00 15.83 38 8099 6405 64484190
Infection susceptibility increased 108.94 15.83 31 8106 2695 64487900
Inhibitory drug interaction 96.00 15.83 30 8107 3597 64486998
Impaired quality of life 82.62 15.83 31 8106 6440 64484155
Purpura 75.82 15.83 39 8098 17207 64473388
Bone density decreased 69.71 15.83 31 8106 9921 64480674
Femoral neck fracture 67.02 15.83 29 8108 8695 64481900
Peripheral ischaemia 55.18 15.83 25 8112 8353 64482242
Impaired work ability 54.44 15.83 30 8107 15189 64475406
Poor quality sleep 53.46 15.83 32 8105 18919 64471676
Hyperlipidaemia 50.22 15.83 33 8104 22943 64467652
Acute kidney injury 49.33 15.83 146 7991 449094 64041501
International normalised ratio increased 47.24 15.83 54 8083 79113 64411482
Oral herpes 46.44 15.83 31 8106 22121 64468474
Hyperkalaemia 44.24 15.83 59 8078 101070 64389525
Skin disorder 40.23 15.83 31 8106 27649 64462946
Pleural mass 38.98 15.83 7 8130 71 64490524
Blood lactic acid 36.40 15.83 9 8128 454 64490141
Peripheral artery occlusion 33.82 15.83 12 8125 2126 64488469
Drug dependence 33.21 15.83 30 8107 33282 64457313
Cellulitis 32.60 15.83 49 8088 93608 64396987
Cataract 32.33 15.83 36 8101 51226 64439369
Skin hyperpigmentation 32.25 15.83 16 8121 6535 64484060
Biopsy lymph gland 30.88 15.83 6 8131 96 64490499
Peripheral vascular disorder 30.70 15.83 16 8121 7245 64483350
Radiotherapy to brain 28.69 15.83 5 8132 42 64490553
Extremity necrosis 27.44 15.83 11 8126 2723 64487872
Herpes zoster 26.94 15.83 41 8096 79146 64411449
Peripheral coldness 26.06 15.83 18 8119 13566 64477029
Deafness bilateral 20.41 15.83 8 8129 1868 64488727
Drug interaction 20.39 15.83 95 8042 361988 64128607
Mitral valve prolapse 20.20 15.83 8 8129 1919 64488676
Hypertension 19.23 15.83 74 8063 259187 64231408
Endarterectomy 19.03 15.83 5 8132 322 64490273
Anaemia 18.91 15.83 96 8041 378584 64112011
Haematoma 18.71 15.83 26 8111 46224 64444371
Metabolic syndrome 18.67 15.83 8 8129 2340 64488255
Melaena 18.60 15.83 28 8109 53520 64437075
Hilar lymphadenopathy 18.23 15.83 7 8130 1546 64489049
Penile pain 17.95 15.83 6 8131 889 64489706
Contusion 17.45 15.83 42 8095 113923 64376672
Mycobacterium abscessus infection 17.22 15.83 6 8131 1008 64489587
Skin ulcer 16.72 15.83 24 8113 43950 64446645
Hypomagnesaemia 16.62 15.83 22 8115 37354 64453241
Mucosa vesicle 16.57 15.83 3 8134 32 64490563
Prerenal failure 16.25 15.83 8 8129 3214 64487381
Hepatocellular injury 16.20 15.83 24 8113 45211 64445384
Chillblains 15.97 15.83 4 8133 213 64490382
Allodynia 15.84 15.83 6 8131 1277 64489318

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 D016166 Free Radical Scavengers
MeSH PA D006401 Hematologic Agents
MeSH PA D010726 Phosphodiesterase Inhibitors
MeSH PA D010975 Platelet Aggregation Inhibitors
MeSH PA D020011 Protective Agents
MeSH PA D011837 Radiation-Protective Agents
MeSH PA D014665 Vasodilator Agents
FDA EPC N0000175895 Blood Viscosity Reducer

Drug Use (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




๐Ÿถ Veterinary Drug Use

None

๐Ÿถ 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 0615-8305 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 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 68682-101 TABLET, EXTENDED RELEASE 400 mg ORAL ANDA 20 sections
Pentoxifylline HUMAN PRESCRIPTION DRUG LABEL 1 68682-101 TABLET, EXTENDED RELEASE 400 mg ORAL ANDA 20 sections
PENTOXIFYLLINE HUMAN PRESCRIPTION DRUG LABEL 1 70518-1285 TABLET, EXTENDED RELEASE 400 mg ORAL ANDA 17 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