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

Stem definitionDrug idCAS RN
anticoagulants, dicoumarol derivatives 48 152-72-7

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • G 23350
  • G-23350
  • sintrom
  • acenocoumarin
  • nicoumalone
  • acenocoumarol
A coumarin that is used as an anticoagulant. Its actions and uses are similar to those of WARFARIN. (From Martindale, The Extra Pharmacopoeia, 30th ed, p233)
  • Molecular weight: 353.33
  • Formula: C19H15NO6
  • CLOGP: 2.64
  • LIPINSKI: 0
  • HAC: 8
  • HDO: 2
  • TPSA: 106.74
  • ALOGS: -4.52
  • ROTB: 5

Drug dosage:

DoseUnitRoute
5 mg O

ADMET properties:

PropertyValueReference
MRTD (Maximum Recommended Therapeutic Daily Dose) 0.57 ยตM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BA (Bioavailability) 60 % Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
Vd (Volume of distribution) 0.24 L/kg Lombardo F, Berellini G, Obach RS
CL (Clearance) 1.28 mL/min/kg Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma) 0.02 % Lombardo F, Berellini G, Obach RS
t_half (Half-life) 7.22 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) 2 Bocci G, Oprea TI, Benet LZ

Approvals:

None

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
Drug interaction 631.28 21.53 366 6938 228765 63252953
Hypocoagulable state 250.53 21.53 51 7253 1156 63480562
International normalised ratio increased 225.82 21.53 109 7195 46316 63435402
Torsade de pointes 115.47 21.53 47 7257 13304 63468414
Cardiac failure 114.00 21.53 89 7215 89053 63392665
Upper gastrointestinal haemorrhage 90.73 21.53 44 7260 18808 63462910
Abdominal wall haematoma 86.29 21.53 26 7278 3029 63478689
Muscle haemorrhage 85.27 21.53 26 7278 3153 63478565
Hypomagnesaemia 83.87 21.53 48 7256 28689 63453029
Acute kidney injury 83.05 21.53 125 7179 263290 63218428
Haematoma 80.37 21.53 50 7254 34770 63446948
Erythrodermic psoriasis 72.77 21.53 18 7286 1000 63480718
Bradycardia 72.39 21.53 63 7241 73164 63408554
Atrial fibrillation 66.02 21.53 74 7230 116562 63365156
Retroperitoneal haematoma 62.14 21.53 20 7284 2893 63478825
Cardio-respiratory arrest 62.12 21.53 53 7251 59906 63421812
Anticoagulation drug level above therapeutic 61.97 21.53 17 7287 1418 63480300
Thermohypoaesthesia 61.38 21.53 11 7293 122 63481596
Sight disability 60.58 21.53 11 7293 132 63481586
Electrocardiogram QT prolonged 60.40 21.53 52 7252 59478 63422240
Vascular resistance pulmonary decreased 59.44 21.53 10 7294 74 63481644
Gingival bleeding 59.42 21.53 29 7275 12558 63469160
Hypokalaemia 55.57 21.53 64 7240 103740 63377978
Left-to-right cardiac shunt 54.62 21.53 10 7294 126 63481592
Euphoric mood 48.47 21.53 19 7285 4868 63476850
Gastrointestinal sounds abnormal 48.26 21.53 18 7286 4033 63477685
Subdural haematoma 47.41 21.53 26 7278 14302 63467416
Lower gastrointestinal haemorrhage 45.90 21.53 21 7283 7869 63473849
Haematuria 45.86 21.53 33 7271 29124 63452594
Multimorbidity 44.97 21.53 11 7293 583 63481135
Anaemia 44.87 21.53 102 7202 293328 63188390
Amaurosis 44.70 21.53 11 7293 598 63481120
Hyperkalaemia 44.43 21.53 42 7262 54161 63427557
Stupor 43.74 21.53 17 7287 4258 63477460
Vessel puncture site haemorrhage 42.28 21.53 8 7296 122 63481596
Respiratory tract infection 41.58 21.53 36 7268 41447 63440271
Optic ischaemic neuropathy 41.51 21.53 12 7292 1210 63480508
Hypocalcaemia 41.19 21.53 32 7272 31681 63450037
Haemorrhage intracranial 40.70 21.53 23 7281 13396 63468322
Right ventricular failure 40.44 21.53 25 7279 17163 63464555
Neuromyelitis optica spectrum disorder 38.92 21.53 11 7293 1023 63480695
Syncope 38.72 21.53 57 7247 117328 63364390
Hyponatraemia 37.87 21.53 55 7249 111845 63369873
Disorganised speech 36.73 21.53 11 7293 1254 63480464
Extensor plantar response 36.34 21.53 11 7293 1300 63480418
Pupillary reflex impaired 35.42 21.53 12 7292 2035 63479683
Wound haemorrhage 33.00 21.53 12 7292 2504 63479214
Cardiac failure chronic 32.94 21.53 14 7290 4404 63477314
Mucocutaneous haemorrhage 31.62 21.53 6 7298 93 63481625
Cerebral haemorrhage 31.47 21.53 27 7277 30702 63451016
Pain 31.06 21.53 24 7280 740604 62741114
Acute generalised exanthematous pustulosis 30.92 21.53 18 7286 11081 63470637
Platelet dysfunction 30.82 21.53 6 7298 107 63481611
Haemarthrosis 30.33 21.53 12 7292 3149 63478569
Ventricular tachycardia 30.02 21.53 22 7282 19957 63461761
Serotonin syndrome 28.96 21.53 25 7279 28657 63453061
Neurological decompensation 28.81 21.53 11 7293 2627 63479091
Tetany 27.95 21.53 10 7294 1991 63479727
Rash 26.38 21.53 16 7288 560855 62920863
Drug reaction with eosinophilia and systemic symptoms 25.42 21.53 25 7279 33811 63447907
Transaminases increased 25.11 21.53 24 7280 31343 63450375
Acute leukaemia 25.06 21.53 8 7296 1126 63480592
Dermatitis exfoliative generalised 24.90 21.53 11 7293 3796 63477922
Pyogenic granuloma 24.71 21.53 6 7298 308 63481410
Subdural haemorrhage 23.64 21.53 10 7294 3108 63478610
Ecchymosis 23.25 21.53 15 7289 11079 63470639
Hyperreflexia 23.09 21.53 12 7292 5922 63475796
Metabolic acidosis 22.77 21.53 27 7277 45042 63436676
Conjunctival haemorrhage 22.30 21.53 10 7294 3577 63478141
Disorientation 22.22 21.53 25 7279 39427 63442291
Pulmonary hypertension 21.73 21.53 24 7280 37099 63444619

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
Drug interaction 505.91 19.74 393 6700 225553 34724285
International normalised ratio increased 270.52 19.74 149 6944 47178 34902660
Hypocoagulable state 234.07 19.74 51 7042 895 34948943
Haemorrhage intracranial 193.25 19.74 84 7009 15862 34933976
Cardiac failure 94.52 19.74 104 6989 91144 34858694
Hepatic vein dilatation 71.52 19.74 15 7078 217 34949621
Liver palpable 67.88 19.74 15 7078 281 34949557
Subdural haematoma 61.86 19.74 43 7050 20378 34929460
Anaemia 60.84 19.74 141 6952 233194 34716644
Labelled drug-drug interaction medication error 58.69 19.74 37 7056 14902 34934936
Upper gastrointestinal haemorrhage 57.59 19.74 45 7048 25473 34924365
Haematoma 57.46 19.74 45 7048 25560 34924278
Inferior vena cava dilatation 53.83 19.74 15 7078 745 34949093
Ventricular enlargement 51.16 19.74 14 7079 650 34949188
Atrial enlargement 50.99 19.74 14 7079 658 34949180
Lower gastrointestinal haemorrhage 43.74 19.74 26 7067 9426 34940412
Retroperitoneal haematoma 42.10 19.74 17 7076 2661 34947177
Fixed eruption 41.95 19.74 15 7078 1685 34948153
Acute kidney injury 40.84 19.74 145 6948 304843 34644995
Abdominal wall haematoma 40.81 19.74 15 7078 1822 34948016
Hyperkalaemia 39.76 19.74 59 7034 69330 34880508
Melaena 37.70 19.74 41 7052 35339 34914499
Dyspnoea at rest 36.26 19.74 17 7076 3811 34946027
Epistaxis 35.49 19.74 51 7042 58200 34891638
Spontaneous haematoma 35.40 19.74 10 7083 522 34949316
Chest wall haematoma 34.00 19.74 8 7085 200 34949638
Influenza virus test positive 32.54 19.74 7 7086 115 34949723
Anticoagulation drug level above therapeutic 31.78 19.74 13 7080 2103 34947735
Ejection fraction decreased 31.22 19.74 28 7065 19126 34930712
Lividity 30.44 19.74 7 7086 158 34949680
Rales 30.35 19.74 21 7072 9862 34939976
Gastroduodenal haemorrhage 29.79 19.74 7 7086 174 34949664
Breath sounds abnormal 29.44 19.74 18 7075 6863 34942975
Renal haemorrhage 29.09 19.74 11 7082 1446 34948392
Ventricular tachycardia 28.65 19.74 31 7062 26548 34923290
Immobilisation prolonged 26.77 19.74 4 7089 5 34949833
Electrocardiogram PR prolongation 26.32 19.74 9 7084 886 34948952
Oesophageal adenocarcinoma stage 0 25.97 19.74 4 7089 7 34949831
Atrial tachycardia 25.02 19.74 13 7080 3632 34946206
Cardiac murmur 24.89 19.74 17 7076 7820 34942018
Cardiac failure chronic 24.80 19.74 17 7076 7862 34941976
Muscle haemorrhage 24.77 19.74 13 7080 3705 34946133
Coronary artery stenosis 23.96 19.74 18 7075 9598 34940240
Haematoma muscle 22.59 19.74 9 7084 1359 34948479
Lactic acidosis 21.98 19.74 31 7062 34741 34915097
Orthopnoea 20.94 19.74 13 7080 5090 34944748
Thyroid disorder 20.84 19.74 11 7082 3171 34946667
Subdural haemorrhage 20.81 19.74 11 7082 3180 34946658
Quadrantanopia 20.67 19.74 5 7088 141 34949697
Cardiac ventricular thrombosis 20.45 19.74 8 7085 1152 34948686
Cerebral haemorrhage 20.41 19.74 30 7063 34907 34914931
Blood cyanide increased 20.08 19.74 4 7089 44 34949794
Atrioventricular block 19.89 19.74 15 7078 8048 34941790
Haematuria 19.75 19.74 36 7057 50030 34899808

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
Drug interaction 1039.16 17.91 733 13444 414450 79315761
Hypocoagulable state 462.58 17.91 101 14076 2058 79728153
International normalised ratio increased 441.29 17.91 240 13937 84481 79645730
Haemorrhage intracranial 233.42 17.91 107 14070 26086 79704125
Cardiac failure 203.57 17.91 189 13988 154653 79575558
Upper gastrointestinal haemorrhage 130.57 17.91 85 14092 41295 79688916
Haematoma 126.28 17.91 91 14086 52104 79678107
Abdominal wall haematoma 118.06 17.91 41 14136 4832 79725379
Acute kidney injury 107.78 17.91 265 13912 519139 79211072
Anaemia 100.82 17.91 235 13942 444780 79285431
Subdural haematoma 100.20 17.91 65 14112 31369 79698842
Retroperitoneal haematoma 96.15 17.91 36 14141 5261 79724950
Lower gastrointestinal haemorrhage 87.39 17.91 47 14130 16078 79714133
Anticoagulation drug level above therapeutic 82.11 17.91 29 14148 3591 79726620
Hyperkalaemia 79.83 17.91 100 14077 114298 79615913
Torsade de pointes 79.48 17.91 47 14130 19265 79710946
Hepatic vein dilatation 72.50 17.91 15 14162 233 79729978
Hypomagnesaemia 70.82 17.91 62 14115 46849 79683362
Atrial fibrillation 67.67 17.91 124 14053 197762 79532449
Liver palpable 66.88 17.91 15 14162 346 79729865
Muscle haemorrhage 66.51 17.91 29 14148 6271 79723940
Cardiac failure chronic 64.69 17.91 34 14143 11101 79719110
Haematuria 62.69 17.91 69 14108 68767 79661444
Ventricular tachycardia 60.46 17.91 54 14123 41881 79688330
Gingival bleeding 60.23 17.91 37 14140 16239 79713972
Electrocardiogram QT prolonged 56.74 17.91 75 14102 90311 79639900
Bradycardia 55.51 17.91 92 14085 135465 79594746
Erythrodermic psoriasis 55.29 17.91 18 14159 1740 79728471
Stupor 54.75 17.91 26 14151 6846 79723365
Vascular resistance pulmonary decreased 54.74 17.91 10 14167 77 79730134
Hypokalaemia 54.01 17.91 94 14083 143946 79586265
Inferior vena cava dilatation 53.76 17.91 15 14162 856 79729355
Left-to-right cardiac shunt 52.13 17.91 10 14167 103 79730108
Ventricular enlargement 51.63 17.91 14 14163 718 79729493
Thermohypoaesthesia 51.36 17.91 10 14167 112 79730099
Pain 49.80 17.91 32 14145 703770 79026441
Sight disability 49.78 17.91 10 14167 133 79730078
Labelled drug-drug interaction medication error 48.82 17.91 40 14137 27610 79702601
Syncope 48.63 17.91 102 14075 179347 79550864
Melaena 48.59 17.91 57 14120 60833 79669378
Atrial enlargement 46.73 17.91 14 14163 1029 79729182
Spontaneous haematoma 46.51 17.91 15 14162 1407 79728804
Epistaxis 46.06 17.91 76 14101 111439 79618772
Mucocutaneous haemorrhage 46.04 17.91 10 14167 198 79730013
Ejection fraction decreased 44.90 17.91 42 14135 34535 79695676
Disorganised speech 44.38 17.91 16 14161 2101 79728110
Hypocalcaemia 43.65 17.91 49 14128 49875 79680336
Respiratory tract infection 41.23 17.91 47 14130 48642 79681569
Cerebral haemorrhage 41.13 17.91 51 14126 57622 79672589
Haemarthrosis 40.31 17.91 20 14157 5792 79724419
Joint swelling 39.88 17.91 3 14174 288643 79441568
Cardio-respiratory arrest 39.60 17.91 70 14107 108440 79621771
Immobilisation prolonged 39.51 17.91 8 14169 111 79730100
Fixed eruption 39.20 17.91 16 14161 2938 79727273
Chest wall haematoma 38.39 17.91 10 14167 439 79729772
Hyponatraemia 38.01 17.91 92 14085 177756 79552455
Dyspnoea at rest 36.01 17.91 20 14157 7282 79722929
Gastrointestinal sounds abnormal 35.62 17.91 18 14159 5417 79724794
Vessel puncture site haemorrhage 35.21 17.91 8 14169 196 79730015
Angina pectoris 34.11 17.91 44 14133 51688 79678523
Product dose omission issue 33.01 17.91 3 14174 247534 79482677
Orthopnoea 32.50 17.91 21 14156 10052 79720159
Euphoric mood 32.30 17.91 19 14158 7707 79722504
Drug intolerance 30.82 17.91 5 14172 264114 79466097
Hypotension 30.77 17.91 157 14020 440160 79290051
Arthralgia 30.58 17.91 34 14143 571769 79158442
Neuromyelitis optica spectrum disorder 30.08 17.91 10 14167 1032 79729179
Calciphylaxis 29.23 17.91 14 14163 3756 79726455
Pulmonary hypertension 28.78 17.91 39 14138 48041 79682170
Amaurosis 28.77 17.91 10 14167 1181 79729030
Rash 28.16 17.91 37 14140 578321 79151890
Extensor plantar response 28.11 17.91 11 14166 1810 79728401
Ischaemic stroke 28.07 17.91 32 14145 33099 79697112
Right ventricular failure 27.58 17.91 27 14150 23470 79706741
Disorientation 27.56 17.91 44 14133 62732 79667479
Gastroduodenal haemorrhage 27.34 17.91 7 14170 287 79729924
Multimorbidity 26.92 17.91 10 14167 1429 79728782
Mitral valve incompetence 26.63 17.91 29 14148 28536 79701675
Oesophageal adenocarcinoma stage 0 26.50 17.91 4 14173 7 79730204
Procedural haemorrhage 26.29 17.91 14 14163 4692 79725519
Serotonin syndrome 26.16 17.91 36 14141 44991 79685220
Azotaemia 26.08 17.91 17 14160 8259 79721952
Fatigue 26.06 17.91 82 14095 929645 78800566
Electrocardiogram PR prolongation 25.99 17.91 10 14167 1573 79728638
Influenza virus test positive 25.78 17.91 7 14170 361 79729850
Shock haemorrhagic 25.34 17.91 24 14153 20036 79710175
Mixed liver injury 24.95 17.91 16 14161 7562 79722649
Blood bilirubin increased 24.51 17.91 43 14134 66189 79664022
Lividity 24.34 17.91 7 14170 446 79729765
Atrioventricular block 24.13 17.91 20 14157 14021 79716190
Rectal haemorrhage 23.78 17.91 46 14131 76254 79653957
Swelling 23.36 17.91 5 14172 216706 79513505
Optic ischaemic neuropathy 22.97 17.91 11 14166 2950 79727261
Posthaemorrhagic hydrocephalus 22.91 17.91 4 14173 23 79730188
Ecchymosis 22.74 17.91 20 14157 15186 79715025
Blood loss anaemia 22.41 17.91 20 14157 15478 79714733
Wound haemorrhage 22.18 17.91 12 14165 4149 79726062
Coronary artery stenosis 21.91 17.91 18 14159 12466 79717745
Nasopharyngitis 21.67 17.91 9 14168 253872 79476339
Pupillary reflex impaired 21.67 17.91 11 14166 3342 79726869
International normalised ratio fluctuation 21.36 17.91 11 14166 3443 79726768
Metabolic acidosis 21.27 17.91 46 14131 82483 79647728
Nausea 21.19 17.91 93 14084 957103 78773108
Haematoma muscle 21.15 17.91 10 14167 2605 79727606
Tetany 20.75 17.91 10 14167 2718 79727493
Congestive cardiomyopathy 20.70 17.91 17 14160 11763 79718448
Blood cyanide increased 20.61 17.91 4 14173 44 79730167
Urticaria 20.52 17.91 4 14173 185197 79545014
Platelet dysfunction 20.09 17.91 6 14171 436 79729775
Breath sounds abnormal 19.95 17.91 19 14158 15965 79714246
Infusion related reaction 19.91 17.91 8 14169 230229 79499982
Rales 19.86 17.91 21 14156 19980 79710231
Hepatic cyst ruptured 19.61 17.91 3 14174 6 79730205
Quadrantanopia 19.43 17.91 5 14172 209 79730002
Renal haemorrhage 19.40 17.91 9 14168 2247 79727964
Anxiety 19.37 17.91 10 14167 248502 79481709
Pyogenic granuloma 19.19 17.91 6 14171 509 79729702
Anuria 19.05 17.91 21 14156 20942 79709269
Musculoskeletal stiffness 18.93 17.91 4 14173 175004 79555207
Headache 18.74 17.91 57 14120 653715 79076496
Acute generalised exanthematous pustulosis 18.73 17.91 19 14158 17235 79712976
Atrial tachycardia 18.53 17.91 13 14164 7120 79723091
Acute leukaemia 18.40 17.91 8 14169 1718 79728493
Hypersensitivity 18.38 17.91 12 14165 262227 79467984
Inappropriate antidiuretic hormone secretion 18.32 17.91 23 14154 26290 79703921
Subdural haemorrhage 18.21 17.91 12 14165 5936 79724275
Cardiac ventricular thrombosis 18.19 17.91 8 14169 1765 79728446
Arrhythmia 17.95 17.91 36 14141 61236 79668975

FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

SourceCodeDescription
ATC B01AA07 BLOOD AND BLOOD FORMING ORGANS
ANTITHROMBOTIC AGENTS
ANTITHROMBOTIC AGENTS
Vitamin K antagonists
MeSH PA D000925 Anticoagulants
MeSH PA D006401 Hematologic Agents
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
Pulmonary embolism indication 59282003 DOID:9477
Venous thrombosis indication 111293003




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 4.96 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 6.11 SCIENTIFIC LITERATURE SCIENTIFIC LITERATURE
Vitamin K epoxide reductase complex subunit 1 Unclassified INHIBITOR IC50 6.11 IUPHAR

External reference:

IDSource
N0000167009 NUI
D07064 KEGG_DRUG
154 RXNORM
C0000956 UMLSCUI
CHEBI:53766 CHEBI
CHEMBL397420 ChEMBL_ID
DB01418 DRUGBANK_ID
D000074 MESH_DESCRIPTOR_UI
54676537 PUBCHEM_CID
9015 IUPHAR_LIGAND_ID
503 INN_ID
I6WP63U32H UNII
387457003 SNOMEDCT_US
79356008 SNOMEDCT_US
002087 NDDF

Pharmaceutical products:

None