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

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 257.41 25.10 173 5499 142261 50457191
Product prescribing error 198.06 25.10 78 5594 20883 50578569
Product monitoring error 159.76 25.10 41 5631 2723 50596729
Atrial fibrillation 99.65 25.10 86 5586 101659 50497793
Haematochezia 92.82 25.10 57 5615 39825 50559627
Anaemia 86.84 25.10 123 5549 252333 50347119
Haematoma 79.76 25.10 47 5625 30463 50568989
Cardiac failure 75.86 25.10 65 5607 75975 50523477
Drug interaction 75.68 25.10 102 5570 199519 50399933
International normalised ratio increased 71.81 25.10 50 5622 43102 50556350
Labelled drug-drug interaction medication error 65.24 25.10 29 5643 10448 50589004
Fall 62.37 25.10 124 5548 334808 50264644
Bradycardia 60.05 25.10 53 5619 64373 50535079
Acute kidney injury 57.04 25.10 96 5576 227962 50371490
Drug ineffective 55.98 25.10 12 5660 819321 49780131
Device stimulation issue 54.68 25.10 9 5663 59 50599393
Arrhythmia 51.87 25.10 37 5635 33095 50566357
Pallor 51.00 25.10 32 5640 23167 50576285
Painful respiration 41.76 25.10 14 5658 2361 50597091
Foetal chromosome abnormality 39.56 25.10 6 5666 21 50599431
Therapeutic drug monitoring analysis not performed 38.49 25.10 10 5662 695 50598757
Prothrombin time prolonged 38.14 25.10 19 5653 8819 50590633
Electrocardiogram abnormal 37.78 25.10 18 5654 7587 50591865
Syncope 36.45 25.10 51 5621 102951 50496501
Eosinophilic granulomatosis with polyangiitis 36.27 25.10 12 5660 1943 50597509
Gastrointestinal haemorrhage 33.21 25.10 41 5631 73280 50526172
Vitamin K deficiency 33.08 25.10 8 5664 415 50599037
Cerebral haemorrhage 32.95 25.10 26 5646 27026 50572426
Urogenital haemorrhage 31.85 25.10 7 5665 237 50599215
Dyspnoea 31.69 25.10 133 5539 547475 50051977
Dehydration 31.36 25.10 59 5613 152390 50447062
Pulmonary vein occlusion 31.09 25.10 6 5666 105 50599347
Dizziness 30.95 25.10 97 5575 346272 50253180
Systemic infection 30.64 25.10 11 5661 2272 50597180
Tachycardia 30.35 25.10 46 5626 99717 50499735
Angina pectoris 29.41 25.10 24 5648 26164 50573288
Fracture 29.13 25.10 20 5652 16813 50582639
International normalised ratio decreased 27.49 25.10 12 5660 4136 50595316
Dysmorphism 27.43 25.10 10 5662 2157 50597295
Skin haemorrhage 27.30 25.10 14 5658 6904 50592548
Faecaloma 26.94 25.10 14 5658 7094 50592358
Hygroma colli 26.60 25.10 4 5668 13 50599439
Epistaxis 26.16 25.10 34 5638 63920 50535532
Dandy-Walker syndrome 25.62 25.10 5 5667 93 50599359
Blood loss anaemia 25.16 25.10 14 5658 8125 50591327

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
General physical health deterioration 155.48 21.12 164 7862 102693 29463808
Product prescribing error 154.65 21.12 82 7944 17894 29548607
Contraindicated product administered 89.79 21.12 58 7968 18208 29548293
International normalised ratio abnormal 75.83 21.12 29 7997 2934 29563567
Intestinal haemorrhage 71.21 21.12 28 7998 3051 29563450
Product monitoring error 68.09 21.12 26 8000 2619 29563882
Dizziness 64.69 21.12 152 7874 189532 29376969
Haematoma 57.93 21.12 49 7977 23163 29543338
Cardiac failure 56.33 21.12 87 7939 79200 29487301
International normalised ratio increased 55.12 21.12 64 7962 44308 29522193
Respiratory tract haemorrhage 54.24 21.12 17 8009 947 29565554
Dyspnoea 53.80 21.12 202 7824 326530 29239971
Electrolyte imbalance 53.42 21.12 35 7991 11239 29555262
Platelet dysfunction 51.93 21.12 12 8014 204 29566297
Blood glucose fluctuation 50.68 21.12 23 8003 3574 29562927
Syncope 49.21 21.12 83 7943 81288 29485213
Oedema peripheral 47.87 21.12 94 7932 103463 29463038
Drug ineffective 45.47 21.12 21 8005 363149 29203352
Rectal prolapse 44.17 21.12 11 8015 260 29566241
Blood glucose abnormal 43.13 21.12 23 8003 5060 29561441
Intraductal papillary mucinous neoplasm 41.69 21.12 11 8015 329 29566172
Vena cava injury 41.37 21.12 10 8016 208 29566293
SARS-CoV-2 antibody test positive 40.71 21.12 10 8016 223 29566278
Haematochezia 40.43 21.12 50 7976 36933 29529568
Renal cyst haemorrhage 39.78 21.12 11 8015 394 29566107
Gastrointestinal haemorrhage 36.48 21.12 72 7954 79461 29487040
Fall 35.42 21.12 117 7909 177061 29389440
Arrhythmia 32.09 21.12 41 7985 31272 29535229
Renal failure 31.89 21.12 87 7939 118512 29447989
Spontaneous haemorrhage 31.85 21.12 8 8018 196 29566305
Dyspnoea exertional 31.60 21.12 44 7982 36446 29530055
Gamma-glutamyltransferase increased 30.59 21.12 37 7989 26700 29539801
JC virus CSF test positive 30.34 21.12 7 8019 118 29566383
Language disorder 29.10 21.12 13 8013 1946 29564555
Anaemia 27.09 21.12 117 7909 200834 29365667
Spinal stenosis 26.86 21.12 16 8010 4347 29562154
Carotid arteriosclerosis 26.13 21.12 11 8015 1427 29565074
Urinary incontinence 26.05 21.12 27 7999 16454 29550047
Drug interaction 25.90 21.12 114 7912 197271 29369230
Implant site inflammation 25.74 21.12 6 8020 106 29566395
Mean cell haemoglobin concentration 25.43 21.12 5 8021 37 29566464
Abdominal wall haemorrhage 25.36 21.12 7 8019 249 29566252
Soft tissue haemorrhage 24.59 21.12 6 8020 130 29566371
Cognitive disorder 24.43 21.12 31 7995 23468 29543033
Actinic keratosis 23.61 21.12 14 8012 3772 29562729
Circulatory collapse 23.27 21.12 27 7999 18646 29547855
Nail bed inflammation 23.26 21.12 6 8020 164 29566337
Delayed graft function 23.04 21.12 11 8015 1916 29564585
Orthostatic intolerance 22.55 21.12 8 8018 654 29565847
Prothrombin level decreased 22.30 21.12 9 8017 1049 29565452
Basophil count decreased 21.63 21.12 5 8021 85 29566416
Nocturia 21.56 21.12 18 8008 8344 29558157
Congestive hepatopathy 21.15 21.12 10 8016 1704 29564797

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
General physical health deterioration 375.14 19.80 314 12346 204111 64281961
Product prescribing error 347.16 19.80 159 12501 35110 64450962
Product monitoring error 211.39 19.80 67 12593 5387 64480685
Haematochezia 125.40 19.80 104 12556 66269 64419803
International normalised ratio increased 123.15 19.80 111 12549 79056 64407016
Haematoma 114.43 19.80 85 12575 46165 64439907
Anaemia 105.10 19.80 230 12430 378450 64107622
Drug ineffective 93.54 19.80 25 12635 840222 63645850
Dizziness 83.75 19.80 228 12432 429935 64056137
Cardiac failure 82.36 19.80 115 12545 132258 64353814
Drug interaction 80.76 19.80 202 12458 361881 64124191
Arrhythmia 79.86 19.80 73 12587 52871 64433201
Syncope 79.42 19.80 124 12536 157511 64328561
Atrial fibrillation 78.56 19.80 129 12531 170960 64315112
Dyspnoea 75.49 19.80 309 12351 718365 63767707
International normalised ratio abnormal 73.68 19.80 30 12630 4958 64481114
Bradycardia 70.99 19.80 101 12559 118118 64367954
Fall 68.53 19.80 208 12452 416618 64069454
Electrolyte imbalance 68.31 19.80 49 12611 25194 64460878
Gastrointestinal haemorrhage 62.37 19.80 101 12559 132211 64353861
Labelled drug-drug interaction medication error 53.31 19.80 40 12620 22022 64464050
Respiratory tract haemorrhage 52.44 19.80 17 12643 1467 64484605
Spontaneous haemorrhage 52.40 19.80 13 12647 423 64485649
Therapeutic drug monitoring analysis not performed 51.58 19.80 16 12644 1196 64484876
Pallor 49.92 19.80 49 12611 38732 64447340
Platelet dysfunction 49.53 19.80 12 12648 353 64485719
Oedema peripheral 48.51 19.80 119 12541 210198 64275874
Circulatory collapse 44.12 19.80 43 12617 33689 64452383
Vena cava injury 44.05 19.80 10 12650 220 64485852
Prothrombin time prolonged 43.60 19.80 31 12629 15710 64470362
SARS-CoV-2 antibody test positive 43.26 19.80 10 12650 239 64485833
Intestinal haemorrhage 42.37 19.80 21 12639 5493 64480579
Arthralgia 42.28 19.80 17 12643 442243 64043829
Renal cyst haemorrhage 41.88 19.80 11 12649 451 64485621
Renal failure 41.03 19.80 102 12558 181586 64304486
Intraductal papillary mucinous neoplasm 39.08 19.80 11 12649 586 64485486
Blood loss anaemia 37.65 19.80 27 12633 13865 64472207
Disorientation 36.92 19.80 50 12610 55778 64430294
Language disorder 35.59 19.80 15 12645 2702 64483370
Completed suicide 33.06 19.80 3 12657 224411 64261661
Coagulation test abnormal 32.27 19.80 11 12649 1108 64484964
Foetal chromosome abnormality 32.19 19.80 5 12655 10 64486062
Actinic keratosis 31.96 19.80 17 12643 5148 64480924
Right ventricular failure 31.17 19.80 29 12631 21442 64464630
JC virus CSF test positive 30.88 19.80 7 12653 153 64485919
Painful respiration 30.60 19.80 14 12646 3067 64483005
Electrocardiogram abnormal 29.40 19.80 23 12637 13458 64472614
Contraindicated product administered 29.17 19.80 65 12595 107764 64378308
Dehydration 29.00 19.80 101 12559 216662 64269410
Fracture 28.53 19.80 26 12634 18729 64467343
Overdose 28.34 19.80 82 12578 159484 64326588
Tachycardia 27.67 19.80 78 12582 149501 64336571
Rectal prolapse 27.63 19.80 11 12649 1715 64484357
Mean cell haemoglobin concentration 27.55 19.80 5 12655 33 64486039
Gamma-glutamyltransferase increased 26.97 19.80 40 12620 48470 64437602
Pulmonary vein occlusion 26.48 19.80 6 12654 131 64485941
Aortic arteriosclerosis 26.12 19.80 17 12643 7459 64478613
Blood glucose abnormal 25.72 19.80 18 12642 8895 64477177
Carotid arteriosclerosis 25.65 19.80 11 12649 2068 64484004
Prothrombin level decreased 25.64 19.80 10 12650 1476 64484596
Presyncope 25.62 19.80 33 12627 35056 64451016
Haematuria 25.56 19.80 44 12616 60427 64425645
Prothrombin time shortened 25.36 19.80 12 12648 2837 64483235
Eosinophilic granulomatosis with polyangiitis 25.23 19.80 12 12648 2870 64483202
Rash 25.05 19.80 32 12628 458517 64027555
Vitamin K deficiency 24.89 19.80 8 12652 671 64485401
Spinal stenosis 24.56 19.80 21 12639 13910 64472162
Blood glucose fluctuation 24.46 19.80 15 12645 5940 64480132
Anxiety 24.46 19.80 5 12655 202644 64283428
Epistaxis 24.16 19.80 57 12603 98074 64387998
Abdominal wall haemorrhage 24.09 19.80 7 12653 418 64485654
Drug intolerance 24.06 19.80 4 12656 187988 64298084
Cardiorenal syndrome 23.67 19.80 9 12651 1241 64484831
Implant site inflammation 23.52 19.80 6 12654 219 64485853
Product dose omission issue 23.10 19.80 5 12655 194742 64291330
Off label use 22.99 19.80 57 12603 632749 63853323
Benign prostatic hyperplasia 22.99 19.80 17 12643 9148 64476924
Dyspnoea exertional 22.88 19.80 47 12613 73683 64412389
Melaena 22.68 19.80 39 12621 53509 64432563
Headache 22.25 19.80 44 12616 529423 63956649
Small intestine polyp 22.23 19.80 4 12656 25 64486047
Febrile neutropenia 21.89 19.80 5 12655 187652 64298420
Coagulopathy 21.72 19.80 29 12631 31891 64454181
Delayed graft function 21.67 19.80 11 12649 3025 64483047
Disturbance in attention 21.60 19.80 33 12627 41041 64445031
Cerebral haemorrhage 21.36 19.80 37 12623 51053 64435019
International normalised ratio decreased 21.34 19.80 15 12645 7463 64478609
Accidental underdose 21.04 19.80 7 12653 655 64485417
Abdominal discomfort 20.98 19.80 5 12655 182317 64303755
Soft tissue haemorrhage 20.87 19.80 6 12654 345 64485727
Urogenital haemorrhage 20.85 19.80 7 12653 673 64485399
Hemiparesis 20.15 19.80 27 12633 29800 64456272
Traumatic haemothorax 20.10 19.80 6 12654 394 64485678
Nocturia 20.03 19.80 17 12643 11148 64474924
Product use in unapproved indication 20.02 19.80 5 12655 176613 64309459
Peripheral arterial occlusive disease 19.90 19.80 14 12646 6973 64479099
Haemoptysis 19.83 19.80 35 12625 49013 64437059

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