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

Stem definitionDrug idCAS RN
anticoagulants, dicoumarol derivatives 2138 435-97-2

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • phenprocoumon
  • fencumar
  • marcoumar
  • phenprocoumarol
  • phenprocoumarole
  • liquamar
Coumarin derivative that acts as a long acting oral anticoagulant.
  • Molecular weight: 280.32
  • Formula: C18H16O3
  • CLOGP: 4.71
  • LIPINSKI: 0
  • HAC: 3
  • HDO: 1
  • TPSA: 46.53
  • ALOGS: -3.76
  • ROTB: 3

  • Status: OFM

  • Legend:
    OFP - off patent
    OFM - off market
    ONP - on patent

Drug dosage:

DoseUnitRoute
3 mg O

ADMET properties:

PropertyValueReference
MRTD (Maximum Recommended Therapeutic Daily Dose) 1.43 ยตM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
Vd (Volume of distribution) 0.20 L/kg Lombardo F, Berellini G, Obach RS
CL (Clearance) 0.02 mL/min/kg Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma) 0.57 % Lombardo F, Berellini G, Obach RS
t_half (Half-life) 126 hours Lombardo F, Berellini G, Obach RS
S (Water solubility) 0.01 mg/mL Bocci G, Oprea TI, Benet LZ
BDDCS (Biopharmaceutical Drug Disposition Classification System) 1 Bocci G, Oprea TI, Benet LZ

Approvals:

DateAgencyCompanyOrphan
Dec. 30, 1957 FDA ORGANON USA INC

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
General physical health deterioration 282.35 26.97 205 6534 201197 63281086
Product monitoring error 250.01 26.97 64 6675 4452 63477831
Product prescribing error 240.02 26.97 94 6645 26195 63456088
Haematochezia 127.13 26.97 76 6663 53468 63428815
Anaemia 121.19 26.97 152 6587 293278 63189005
Haematoma 119.62 26.97 63 6676 34757 63447526
Acute kidney injury 112.80 26.97 139 6600 263276 63219007
Atrial fibrillation 101.36 26.97 90 6649 116546 63365737
Labelled drug-drug interaction medication error 98.35 26.97 41 6698 13358 63468925
Cardiac failure 87.98 26.97 74 6665 89068 63393215
Drug interaction 83.94 26.97 112 6627 229019 63253264
International normalised ratio increased 78.00 26.97 53 6686 46372 63435911
Drug ineffective 70.75 26.97 13 6726 1044752 62437531
Therapeutic drug monitoring analysis not performed 69.14 26.97 18 6721 1334 63480949
Fall 66.07 26.97 135 6604 392199 63090084
Pallor 63.82 26.97 40 6699 30528 63451755
Electrocardiogram abnormal 63.72 26.97 27 6712 9152 63473131
Prothrombin time prolonged 62.65 26.97 27 6712 9537 63472746
Bradycardia 56.67 26.97 53 6686 73174 63409109
Device stimulation issue 55.17 26.97 9 6730 59 63482224
Arrhythmia 49.00 26.97 37 6702 38103 63444180
Systemic infection 47.22 26.97 18 6721 4642 63477641
Dehydration 46.22 26.97 73 6666 173281 63309002
Skin haemorrhage 45.59 26.97 22 6717 10072 63472211
Gastrointestinal haemorrhage 43.17 26.97 48 6691 81128 63401155
Painful respiration 40.37 26.97 14 6725 2760 63479523
Shock haemorrhagic 40.01 26.97 20 6719 9875 63472408
Foetal chromosome abnormality 39.89 26.97 6 6733 21 63482262
Syncope 37.78 26.97 54 6685 117331 63364952
Upper gastrointestinal haemorrhage 37.66 26.97 24 6715 18828 63463455
Eosinophilic granulomatosis with polyangiitis 35.56 26.97 12 6727 2180 63480103
Dyspnoea 35.35 26.97 151 6588 661162 62821121
Faecaloma 34.93 26.97 17 6722 7924 63474359
Vitamin K deficiency 33.20 26.97 8 6731 432 63481851
Circulatory collapse 32.04 26.97 23 6716 21915 63460368
Epistaxis 31.97 26.97 39 6700 72686 63409597
Rash 31.88 26.97 10 6729 560861 62921422
Pulmonary vein occlusion 31.41 26.97 6 6733 105 63482178
Urogenital haemorrhage 31.34 26.97 7 6732 270 63482013
Cerebral haemorrhage 31.27 26.97 26 6713 30703 63451580
Coagulopathy 31.06 26.97 22 6717 20522 63461761
International normalised ratio abnormal 30.75 26.97 12 6727 3292 63478991
Lactic acidosis 30.15 26.97 28 6711 38259 63444024
Vascular graft infection 29.05 26.97 5 6734 47 63482236
Dizziness 28.40 26.97 105 6634 429820 63052463
Labelled drug-food interaction medication error 28.39 26.97 6 6733 178 63482105
Tachycardia 27.72 26.97 47 6692 118109 63364174
Angina pectoris 27.64 26.97 24 6715 30054 63452229
Dysmorphism 27.39 26.97 10 6729 2286 63479997
Fracture 27.38 26.97 20 6719 19564 63462719
International normalised ratio decreased 27.17 26.97 12 6727 4489 63477794

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
Product prescribing error 197.48 21.16 105 9475 22822 34924529
General physical health deterioration 158.56 21.16 185 9395 128084 34819267
Product monitoring error 149.08 21.16 53 9527 4328 34943023
International normalised ratio abnormal 127.47 21.16 44 9536 3291 34944060
Contraindicated product administered 92.39 21.16 63 9517 21418 34925933
Rectal prolapse 90.24 21.16 22 9558 470 34946881
Renal cyst haemorrhage 84.53 21.16 22 9558 617 34946734
Intestinal haemorrhage 81.28 21.16 32 9548 3464 34943887
Intraductal papillary mucinous neoplasm 78.48 21.16 20 9560 515 34946836
Haematoma 69.55 21.16 57 9523 25548 34921803
SARS-CoV-2 antibody test positive 67.89 21.16 17 9563 407 34946944
Dizziness 66.84 21.16 169 9411 218352 34728999
Vena cava injury 66.44 21.16 16 9564 324 34947027
Abdominal wall haemorrhage 65.45 21.16 17 9563 473 34946878
Carotid arteriosclerosis 61.39 21.16 22 9558 1836 34945515
Blood glucose fluctuation 60.36 21.16 27 9553 4017 34943334
Vascular anastomotic haemorrhage 58.63 21.16 14 9566 273 34947078
International normalised ratio increased 57.80 21.16 68 9512 47259 34900092
Delayed graft function 57.56 21.16 22 9558 2199 34945152
Oedema peripheral 57.36 21.16 111 9469 119701 34827650
Aortic dilatation 55.53 21.16 19 9561 1382 34945969
Haematochezia 55.40 21.16 66 9514 46468 34900883
Perineal cyst 54.18 21.16 13 9567 259 34947092
Spinal stenosis 53.55 21.16 27 9553 5242 34942109
Actinic keratosis 51.14 21.16 25 9555 4542 34942809
Blood glucose abnormal 50.44 21.16 27 9553 5925 34941426
Vascular compression 50 21.16 13 9567 363 34946988
Mean cell volume increased 50.00 21.16 22 9558 3147 34944204
Hyperparathyroidism secondary 49.68 21.16 18 9562 1550 34945801
Respiratory tract haemorrhage 49.47 21.16 17 9563 1253 34946098
Cardiac failure 49.21 21.16 89 9491 91159 34856192
Platelet dysfunction 48.63 21.16 12 9568 270 34947081
Aortic arteriosclerosis 47.83 21.16 24 9556 4612 34942739
Renal artery stenosis 46.68 21.16 19 9561 2242 34945109
Dyspnoea 46.60 21.16 215 9365 376567 34570784
Electrolyte imbalance 45.36 21.16 35 9545 14377 34932974
Diverticulum intestinal 44.99 21.16 22 9558 3999 34943352
Hepatosplenomegaly 44.24 21.16 22 9558 4147 34943204
Abnormal clotting factor 44.23 21.16 9 9571 80 34947271
Syncope 42.84 21.16 84 9496 91367 34855984
Drug ineffective 41.09 21.16 39 9541 456712 34490639
Intervertebral disc space narrowing 40.62 21.16 14 9566 1041 34946310
Gastrointestinal haemorrhage 39.91 21.16 80 9500 88397 34858954
Blood 25-hydroxycholecalciferol decreased 39.18 21.16 10 9570 259 34947092
Gamma-glutamyltransferase increased 39.03 21.16 44 9536 29187 34918164
Spinal osteoarthritis 38.99 21.16 25 9555 7658 34939693
Swelling of eyelid 36.12 21.16 13 9567 1098 34946253
Arrhythmia 34.95 21.16 46 9534 35762 34911589
Restless legs syndrome 34.71 21.16 24 9556 8330 34939021
Basal cell carcinoma 34.07 21.16 34 9546 19624 34927727
Activated partial thromboplastin time prolonged 33.84 21.16 24 9556 8671 34938680
Squamous cell carcinoma of skin 33.31 21.16 26 9554 10855 34936496
Fall 32.94 21.16 126 9454 202759 34744592
Renal failure 32.75 21.16 94 9486 130463 34816888
Benign prostatic hyperplasia 32.66 21.16 29 9551 14466 34932885
Therapeutic drug monitoring analysis not performed 31.84 21.16 10 9570 555 34946796
Urinary incontinence 31.53 21.16 32 9548 18842 34928509
Left ventricular hypertrophy 30.63 21.16 22 9558 8108 34939243
JC virus CSF test positive 30.28 21.16 7 9573 118 34947233
Vitamin D decreased 30.10 21.16 16 9564 3460 34943891
Prothrombin time abnormal 29.08 21.16 10 9570 738 34946613
Spontaneous haemorrhage 28.20 21.16 8 9572 312 34947039
Glycosylated haemoglobin increased 28.15 21.16 24 9556 11336 34936015
Language disorder 27.22 21.16 13 9567 2243 34945108
C-reactive protein increased 26.90 21.16 51 9529 54047 34893304
Bradycardia 26.87 21.16 62 9518 75356 34871995
Large intestine polyp 26.62 21.16 20 9560 7894 34939457
Nocturia 26.18 21.16 22 9558 10188 34937163
Implant site inflammation 25.63 21.16 6 9574 107 34947244
Dyspnoea exertional 25.60 21.16 44 9536 43235 34904116
Vertigo 25.21 21.16 33 9547 25503 34921848
Cognitive disorder 25.16 21.16 35 9545 28658 34918693
Anaemia 24.99 21.16 128 9452 233207 34714144
Mean cell haemoglobin concentration 24.93 21.16 5 9575 41 34947310
Febrile neutropenia 24.61 21.16 4 9576 136845 34810506
Off label use 24.41 21.16 49 9531 419475 34527876
Soft tissue haemorrhage 23.98 21.16 6 9574 143 34947208
Haemorrhoids 23.05 21.16 24 9556 14551 34932800
Nail bed inflammation 22.92 21.16 6 9574 172 34947179
Contusion 22.87 21.16 38 9542 36326 34911025
Circulatory collapse 22.04 21.16 28 9552 21010 34926341
Prothrombin level decreased 21.65 21.16 9 9571 1119 34946232
Haemorrhage 21.42 21.16 45 9535 51325 34896026
Arteriosclerosis 21.29 21.16 21 9559 11947 34935404

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
Product prescribing error 434.87 20.75 198 14941 44615 79684634
General physical health deterioration 405.92 20.75 368 14771 274870 79454379
Product monitoring error 372.39 20.75 115 15024 8791 79720458
Haematochezia 171.07 20.75 138 15001 87507 79641742
Haematoma 157.82 20.75 107 15032 52088 79677161
International normalised ratio abnormal 142.24 20.75 50 15089 5718 79723531
International normalised ratio increased 133.59 20.75 118 15021 84603 79644646
Anaemia 123.51 20.75 265 14874 444750 79284499
Drug ineffective 95.88 20.75 43 15096 1080870 78648379
Labelled drug-drug interaction medication error 93.97 20.75 61 15078 27589 79701660
Renal cyst haemorrhage 90.80 20.75 22 15117 670 79728579
Therapeutic drug monitoring analysis not performed 89.40 20.75 27 15112 1909 79727340
Atrial fibrillation 87.43 20.75 144 14995 197742 79531507
Arrhythmia 84.12 20.75 79 15060 61193 79668056
Drug interaction 83.24 20.75 218 14921 414965 79314284
Cardiac failure 79.88 20.75 121 15018 154721 79574528
Dizziness 78.99 20.75 249 14890 526192 79203057
Bradycardia 78.70 20.75 112 15027 135445 79593804
Intraductal papillary mucinous neoplasm 77.82 20.75 20 15119 778 79728471
Syncope 75.79 20.75 128 15011 179321 79549928
Gastrointestinal haemorrhage 75.58 20.75 115 15024 147604 79581645
Dyspnoea 73.60 20.75 339 14800 856686 78872563
SARS-CoV-2 antibody test positive 73.50 20.75 17 15122 422 79728827
Vena cava injury 71.73 20.75 16 15123 336 79728913
Rectal prolapse 65.86 20.75 22 15117 2156 79727093
Abdominal wall haemorrhage 65.76 20.75 17 15122 677 79728572
Fall 65.31 20.75 222 14917 487407 79241842
Vascular anastomotic haemorrhage 63.75 20.75 14 15125 273 79728976
Actinic keratosis 62.63 20.75 28 15111 6014 79723235
Prothrombin time prolonged 61.67 20.75 39 15100 16860 79712389
Oedema peripheral 61.61 20.75 143 14996 252145 79477104
Carotid arteriosclerosis 61.59 20.75 22 15117 2634 79726615
Electrolyte imbalance 60.96 20.75 49 15090 30832 79698417
Perineal cyst 59.07 20.75 13 15126 256 79728993
Aortic dilatation 57.58 20.75 19 15120 1793 79727456
Delayed graft function 55.63 20.75 22 15117 3485 79725764
Arthralgia 54.98 20.75 20 15119 571783 79157466
Pallor 54.69 20.75 57 15082 50005 79679244
Circulatory collapse 52.51 20.75 49 15090 37619 79691630
Aortic arteriosclerosis 52.28 20.75 28 15111 8890 79720359
Intestinal haemorrhage 51.74 20.75 25 15114 6401 79722848
Respiratory tract haemorrhage 49.56 20.75 17 15122 1806 79727443
Vascular compression 49.28 20.75 13 15126 561 79728688
Renal failure 48.03 20.75 113 15026 200855 79528394
Platelet dysfunction 47.64 20.75 12 15127 430 79728819
Hyperparathyroidism secondary 46.84 20.75 18 15121 2642 79726607
Spinal stenosis 46.80 20.75 32 15107 15759 79713490
Renal artery stenosis 45.48 20.75 19 15120 3463 79725786
Benign prostatic hyperplasia 45.40 20.75 28 15111 11584 79717665
Electrocardiogram abnormal 45.11 20.75 32 15107 16705 79712544
Spontaneous haemorrhage 44.73 20.75 13 15126 804 79728445
Hepatosplenomegaly 44.05 20.75 22 15117 6047 79723202
Mean cell volume increased 43.43 20.75 22 15117 6231 79723018
Haematuria 41.57 20.75 58 15081 68778 79660471
Orthostatic intolerance 41.10 20.75 15 15124 1909 79727340
Gamma-glutamyltransferase increased 40.62 20.75 51 15088 54629 79674620
Activated partial thromboplastin time prolonged 40.20 20.75 28 15111 14200 79715049
Presyncope 40.00 20.75 44 15095 41010 79688239
Diverticulum intestinal 39.48 20.75 23 15116 8582 79720667
Blood 25-hydroxycholecalciferol decreased 39.16 20.75 10 15129 379 79728870
Acute kidney injury 38.97 20.75 198 14941 519206 79210043
Intervertebral disc space narrowing 38.83 20.75 14 15125 1721 79727528
Off label use 38.65 20.75 71 15068 907144 78822105
Dehydration 38.54 20.75 119 15020 248068 79481181
Blood loss anaemia 38.05 20.75 28 15111 15470 79713779
Rash 36.13 20.75 34 15105 578324 79150925
Drug intolerance 36.10 20.75 4 15135 264115 79465134
Squamous cell carcinoma of skin 35.92 20.75 26 15113 14007 79715242
Coagulopathy 35.79 20.75 39 15100 35967 79693282
Completed suicide 35.49 20.75 3 15136 245764 79483485
Abnormal clotting factor 35.13 20.75 8 15131 185 79729064
Blood glucose fluctuation 33.70 20.75 19 15120 6663 79722586
Shock haemorrhagic 33.70 20.75 29 15110 20031 79709218
Spinal osteoarthritis 33.70 20.75 27 15112 16900 79712349
Disorientation 33.67 20.75 50 15089 62726 79666523
Language disorder 33.65 20.75 15 15124 3199 79726050
Blood glucose abnormal 32.71 20.75 22 15117 10544 79718705
Overdose 32.07 20.75 92 15047 184114 79545135
Left ventricular hypertrophy 31.56 20.75 22 15117 11169 79718080
Abdominal discomfort 31.39 20.75 5 15134 250722 79478527
Anxiety 31.02 20.75 5 15134 248507 79480742
Product dose omission issue 30.85 20.75 5 15134 247532 79481717
Foetal chromosome abnormality 30.68 20.75 5 15134 16 79729233
Coagulation test abnormal 30.65 20.75 11 15128 1334 79727915
JC virus CSF test positive 30.45 20.75 7 15132 169 79729080
Skin haemorrhage 30.21 20.75 22 15117 11959 79717290
Right ventricular failure 29.77 20.75 29 15110 23468 79705781
Painful respiration 29.52 20.75 14 15125 3439 79725810
Tachycardia 29.23 20.75 87 15052 177681 79551568
Product use in unapproved indication 29.17 20.75 6 15133 250353 79478896
Prothrombin time abnormal 28.85 20.75 10 15129 1096 79728153
Upper gastrointestinal haemorrhage 28.22 20.75 37 15102 41343 79687906
Febrile neutropenia 28.05 20.75 5 15134 230994 79498255
Basal cell carcinoma 27.98 20.75 35 15104 37340 79691909
Blood potassium increased 27.86 20.75 31 15108 29244 79700005
Joint swelling 27.85 20.75 10 15129 288636 79440613
Restlessness 27.80 20.75 39 15100 46453 79682796
Hypersensitivity 27.22 20.75 8 15131 262231 79467018
Lactic acidosis 26.80 20.75 48 15091 70311 79658938
Mean cell haemoglobin concentration 26.55 20.75 5 15134 43 79729206
Melaena 26.41 20.75 44 15095 60846 79668403
Chronic kidney disease 26.31 20.75 46 15093 66108 79663141
Pulmonary vein occlusion 26.17 20.75 6 15133 143 79729106
Fracture 25.94 20.75 26 15113 21775 79707474
Restless legs syndrome 25.83 20.75 25 15114 20067 79709182
Nocturia 25.50 20.75 21 15118 13660 79715589
Labelled drug-food interaction medication error 25.32 20.75 6 15133 166 79729083
Swelling of eyelid 25.28 20.75 13 15126 3798 79725451
Hypertensive crisis 25.13 20.75 25 15114 20745 79708504
Prothrombin level decreased 24.99 20.75 10 15129 1634 79727615
Glycosylated haemoglobin increased 24.83 20.75 24 15115 19236 79710013
Systemic infection 24.80 20.75 18 15121 9734 79719515
Large intestine polyp 24.72 20.75 20 15119 12688 79716561
Toxic epidermal necrolysis 24.61 20.75 36 15103 44545 79684704
Vitamin K deficiency 24.61 20.75 8 15131 720 79728529
Hypotension 24.47 20.75 155 14984 440162 79289087
Prothrombin time shortened 24.31 20.75 12 15127 3216 79726033
Sinusitis 24.24 20.75 4 15135 195497 79533752
Pain 24.18 20.75 62 15077 703740 79025509
Stevens-Johnson syndrome 23.64 20.75 33 15106 39133 79690116
Eosinophilic granulomatosis with polyangiitis 22.89 20.75 12 15127 3648 79725601
Urinary incontinence 22.53 20.75 33 15106 40876 79688373
Implant site inflammation 22.46 20.75 6 15133 272 79728977
Small intestine polyp 22.22 20.75 4 15135 26 79729223
Contraindicated product administered 22.11 20.75 73 15066 157465 79571784
Faecaloma 22.08 20.75 18 15121 11546 79717703
Cardiorenal syndrome 21.87 20.75 9 15130 1580 79727669
Epistaxis 21.67 20.75 58 15081 111457 79617792
Complications of transplanted kidney 21.51 20.75 14 15125 6352 79722897
Headache 21.38 20.75 59 15080 653713 79075536
Renal impairment 21.16 20.75 72 15067 157711 79571538
Malaise 21.09 20.75 38 15101 489831 79239418
Febrile infection 21.01 20.75 11 15128 3335 79725914
International normalised ratio decreased 20.76 20.75 15 15124 8055 79721194

FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

SourceCodeDescription
ATC B01AA04 BLOOD AND BLOOD FORMING ORGANS
ANTITHROMBOTIC AGENTS
ANTITHROMBOTIC AGENTS
Vitamin K antagonists
FDA EPC N0000175476 Vitamin K Antagonist
MeSH PA D000925 Anticoagulants
MeSH PA D006401 Hematologic Agents
FDA MoA N0000175964 Vitamin K Inhibitors
CHEBI has role CHEBI:50249 anticoagulants
CHEBI has role CHEBI:50390 NAD(P)H dehydrogenase (quinone) inhibitors

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

DiseaseRelationSNOMED_IDDOID
Myocardial infarction indication 22298006 DOID:5844
Thromboembolic disorder indication 371039008
Thrombosis indication 439127006
Prosthetic replacement of heart valve off-label use 307279007




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 4.51 acidic

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
Vitamin K epoxide reductase complex subunit 1 Enzyme INHIBITOR IC50 5.75 SCIENTIFIC LITERATURE CHEMBL
Pol polyprotein Enzyme Ki 6.10 CHEMBL
Vitamin K epoxide reductase complex subunit 1 Unclassified Ki 6.70 CHEMBL

External reference:

IDSource
4018525 VUID
N0000146847 NUI
D05457 KEGG_DRUG
4018525 VANDF
C0031444 UMLSCUI
CHEBI:50438 CHEBI
CHEMBL1465 ChEMBL_ID
CHEMBL16694 ChEMBL_ID
DB00946 DRUGBANK_ID
D010644 MESH_DESCRIPTOR_UI
54680692 PUBCHEM_CID
6839 IUPHAR_LIGAND_ID
247 INN_ID
Q08SIO485D UNII
8150 RXNORM
002086 NDDF
59488002 SNOMEDCT_US

Pharmaceutical products:

None