acenocoumarol 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: 2.66
  • LIPINSKI: 0
  • HAC: 8
  • HDO: 2
  • TPSA: 106.74
  • ALOGS: -3.98
  • ROTB: 5

Drug dosage:

DoseUnitRoute
5 mg O

ADMET properties:

PropertyValueReference
MRTD (Maximum Recommended Therapeutic Daily Dose) 0.57 ┬ÁM/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

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 948.48 18.59 581 10067 202513 46472901
International normalised ratio increased 501.12 18.59 234 10414 46649 46628765
Hypocoagulable state 260.97 18.59 58 10590 989 46674425
Cardiac failure 178.83 18.59 147 10501 79801 46595613
Haematoma 164.59 18.59 98 10550 31774 46643640
Torsade de pointes 118.25 18.59 57 10591 12097 46663317
Abdominal wall haematoma 116.91 18.59 38 10610 2843 46672571
Atrial fibrillation 102.37 18.59 122 10526 103468 46571946
Acute kidney injury 96.88 18.59 184 10464 235671 46439743
Muscle haemorrhage 96.32 18.59 34 10614 3270 46672144
Hyperkalaemia 92.38 18.59 83 10565 50626 46624788
Upper gastrointestinal haemorrhage 87.73 18.59 52 10596 16686 46658728
Hypomagnesaemia 69.64 18.59 50 10598 22160 46653254
Bradycardia 63.64 18.59 77 10571 66221 46609193
Anaemia 60.26 18.59 160 10488 255619 46419795
Gingival bleeding 57.97 18.59 35 10613 11604 46663810
Hyponatraemia 57.05 18.59 91 10557 101241 46574173
Cerebral haemorrhage 56.76 18.59 49 10599 28322 46647092
Sight disability 54.81 18.59 11 10637 111 46675303
Thermohypoaesthesia 54.72 18.59 11 10637 112 46675302
Subdural haematoma 54.42 18.59 35 10613 12962 46662452
Erythrodermic psoriasis 54.11 18.59 16 10632 873 46674541
Vascular resistance pulmonary decreased 53.09 18.59 10 10638 70 46675344
Haematuria 52.94 18.59 46 10602 26812 46648602
Melaena 51.61 18.59 46 10602 27726 46647688
Prothrombin time prolonged 50.76 18.59 30 10618 9566 46665848
Left-to-right cardiac shunt 48.48 18.59 10 10638 117 46675297
Electrocardiogram QT prolonged 48.24 18.59 59 10589 51266 46624148
Drug hypersensitivity 43.98 18.59 3 10645 243822 46431592
Haemorrhage intracranial 43.01 18.59 30 10618 12694 46662720
Hypokalaemia 42.75 18.59 74 10574 87950 46587464
Retroperitoneal haematoma 40.40 18.59 17 10631 2623 46672791
Amaurosis 38.62 18.59 11 10637 525 46674889
Respiratory tract infection 37.56 18.59 40 10608 29932 46645482
Extensor plantar response 37.09 18.59 13 10635 1223 46674191
Optic ischaemic neuropathy 36.23 18.59 12 10636 951 46674463
Gastrointestinal sounds abnormal 35.78 18.59 17 10631 3489 46671925
Multimorbidity 35.45 18.59 11 10637 707 46674707
Right ventricular failure 34.64 18.59 29 10619 16064 46659350
Cardio-respiratory arrest 33.98 18.59 54 10594 59815 46615599
Neuromyelitis optica spectrum disorder 33.91 18.59 11 10637 817 46674597
Rash 33.44 18.59 20 10628 356492 46318922
Coagulopathy 33.10 18.59 30 10618 18469 46656945
Vessel puncture site haemorrhage 32.77 18.59 7 10641 98 46675316
Stupor 32.69 18.59 16 10632 3504 46671910
Euphoric mood 32.59 18.59 17 10631 4255 46671159
Pulmonary hypertension 31.60 18.59 40 10608 35953 46639461
Drug ineffective 31.11 18.59 68 10580 677770 45997644
Syncope 30.30 18.59 71 10577 104732 46570682
Atrioventricular block 30.14 18.59 19 10629 6792 46668622
Pain 30.01 18.59 39 10609 476909 46198505
Cardiac failure chronic 29.71 18.59 15 10633 3509 46671905
Renal failure 29.68 18.59 74 10574 113520 46561894
Disorganised speech 29.39 18.59 10 10638 861 46674553
Ventricular tachycardia 29.35 18.59 27 10621 16940 46658474
Coagulation time prolonged 28.94 18.59 11 10637 1303 46674111
International normalised ratio decreased 28.92 18.59 16 10632 4504 46670910
Product dose omission issue 27.84 18.59 3 10645 168517 46506897
Ischaemic stroke 27.74 18.59 26 10622 16696 46658718
Cerebral haematoma 27.53 18.59 14 10634 3325 46672089
Activated partial thromboplastin time prolonged 27.48 18.59 18 10630 6871 46668543
Pupillary reflex impaired 27.32 18.59 12 10636 2056 46673358
Hypocalcaemia 27.13 18.59 32 10616 26753 46648661
Fatigue 27.13 18.59 62 10586 608635 46066779
Vertigo CNS origin 26.93 18.59 5 10643 32 46675382
Eosinophilia 26.50 18.59 27 10621 19190 46656224
Lower gastrointestinal haemorrhage 26.48 18.59 18 10630 7302 46668112
Gastrointestinal haemorrhage 26.38 18.59 56 10592 77317 46598097
Disorientation 26.23 18.59 37 10611 36881 46638533
Neurological decompensation 25.31 18.59 11 10637 1837 46673577
Drug reaction with eosinophilia and systemic symptoms 24.62 18.59 32 10616 29516 46645898
Mucocutaneous haemorrhage 24.52 18.59 5 10643 55 46675359
Hypercreatininaemia 23.41 18.59 7 10641 397 46675017
Ventricular fibrillation 23.27 18.59 20 10628 11476 46663938
Acute leukaemia 23.18 18.59 9 10639 1129 46674285
Off label use 22.90 18.59 32 10616 379809 46295605
International normalised ratio abnormal 22.84 18.59 12 10636 3047 46672367
Arthralgia 22.71 18.59 30 10618 364573 46310841
Tetany 22.50 18.59 10 10638 1761 46673653
Anticoagulation drug level above therapeutic 22.38 18.59 9 10639 1238 46674176
Chromatopsia 21.98 18.59 7 10641 490 46674924
Platelet dysfunction 21.97 18.59 5 10643 95 46675319
Atrioventricular block complete 21.25 18.59 16 10632 7611 46667803
Traumatic haematoma 21.13 18.59 9 10639 1431 46673983
Haemodynamic instability 21.07 18.59 16 10632 7709 46667705
Pyogenic granuloma 20.87 18.59 6 10642 296 46675118
Subdural haemorrhage 20.55 18.59 11 10637 2901 46672513
Acute generalised exanthematous pustulosis 20.35 18.59 17 10631 9388 46666026
Conjunctival haemorrhage 20.31 18.59 11 10637 2970 46672444
Haemarthrosis 20.26 18.59 11 10637 2982 46672432
Dermatitis exfoliative generalised 20.20 18.59 11 10637 3002 46672412
Toxic skin eruption 20.05 18.59 19 10629 12368 46663046
Pulmonary arterial hypertension 19.94 18.59 27 10621 25901 46649513
Rectal haemorrhage 19.65 18.59 33 10615 38222 46637192
Hyperreflexia 19.20 18.59 13 10635 5241 46670173
Arrhythmia 19.17 18.59 31 10617 34810 46640604
Epistaxis 19.05 18.59 44 10604 64261 46611153
Weight increased 18.81 18.59 7 10641 164466 46510948

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 805.79 17.78 595 9097 198973 29743813
International normalised ratio increased 419.92 17.78 234 9458 47505 29895281
Hypocoagulable state 253.48 17.78 59 9633 862 29941924
Cardiac failure 174.62 17.78 172 9520 83246 29859540
Haemorrhage intracranial 138.04 17.78 76 9616 14956 29927830
Anaemia 96.18 17.78 209 9483 207783 29735003
Hyperkalaemia 74.50 17.78 99 9593 65911 29876875
Subdural haematoma 56.94 17.78 48 9644 18924 29923862
Upper gastrointestinal haemorrhage 56.59 17.78 51 9641 21977 29920809
Melaena 55.22 17.78 60 9632 32377 29910409
Acute kidney injury 53.74 17.78 202 9490 273640 29669146
Labelled drug-drug interaction medication error 49.97 17.78 35 9657 10503 29932283
Haematoma 49.20 17.78 49 9643 23904 29918882
Retroperitoneal haematoma 47.96 17.78 21 9671 2511 29940275
Epistaxis 47.19 17.78 71 9621 52910 29889876
Lower gastrointestinal haemorrhage 46.46 17.78 30 9662 7874 29934912
Fixed eruption 40.41 17.78 15 9677 1169 29941617
Muscle haemorrhage 37.51 17.78 20 9672 3683 29939103
Cardiogenic shock 35.55 17.78 35 9657 16826 29925960
Abdominal wall haematoma 35.48 17.78 15 9677 1646 29941140
Spontaneous haematoma 34.95 17.78 11 9681 519 29942267
Blood loss anaemia 33.08 17.78 24 9668 7603 29935183
Cerebral haemorrhage 32.04 17.78 46 9646 32841 29909945
Petechiae 31.37 17.78 25 9667 9106 29933680
Influenza virus test positive 29.88 17.78 7 9685 105 29942681
Haematuria 28.96 17.78 52 9640 44782 29898004
Prothrombin time prolonged 28.86 17.78 24 9668 9279 29933507
Lividity 28.74 17.78 7 9685 125 29942661
Renal haemorrhage 28.51 17.78 12 9680 1303 29941483
Bradycardia 28.00 17.78 64 9628 65462 29877324
Gastroduodenal haemorrhage 26.51 17.78 7 9685 175 29942611
Atrial fibrillation 26.47 17.78 86 9606 108038 29834748
Rectal haemorrhage 25.80 17.78 43 9649 34896 29907890
Immobilisation prolonged 24.90 17.78 4 9688 5 29942781
Hypotension 24.73 17.78 129 9563 200436 29742350
Oesophageal adenocarcinoma stage 0 24.10 17.78 4 9688 7 29942779
Therapeutic response increased 24.06 17.78 7 9685 252 29942534
Atrial tachycardia 22.83 17.78 12 9680 2147 29940639
Hyponatraemia 22.72 17.78 60 9632 67142 29875644
Completed suicide 22.12 17.78 3 9689 99489 29843297
Ventricular arrhythmia 22.11 17.78 15 9677 4273 29938513
Arrhythmia 22.09 17.78 39 9653 33130 29909656
Haematoma muscle 22.05 17.78 8 9684 584 29942202
Enterocolitis haemorrhagic 21.46 17.78 9 9683 968 29941818
Lactic acidosis 21.18 17.78 37 9655 31176 29911610
Renal failure 21.02 17.78 90 9602 128876 29813910
Hypovolaemic shock 20.64 17.78 17 9675 6483 29936303
Calciphylaxis 20.45 17.78 9 9683 1089 29941697
Electrocardiogram PR prolongation 20.20 17.78 8 9684 743 29942043
Cholestatic liver injury 20.13 17.78 10 9682 1591 29941195
Hepatitis cholestatic 19.76 17.78 18 9674 7854 29934932
Subdural haemorrhage 19.63 17.78 12 9680 2860 29939926
Arthralgia 19.20 17.78 10 9682 135781 29807005
Gastrointestinal haemorrhage 19.18 17.78 65 9627 83381 29859405
Cerebral haematoma 19.11 17.78 14 9678 4500 29938286
Atrioventricular block 18.96 17.78 17 9675 7265 29935521
Angina pectoris 18.75 17.78 34 9658 29484 29913302
Atrioventricular block complete 18.62 17.78 18 9674 8459 29934327
Drug ineffective 18.54 17.78 53 9639 340334 29602452
Mycobacterium chelonae infection 18.24 17.78 7 9685 598 29942188
Tongue haematoma 18.19 17.78 5 9687 146 29942640
Quadrantanopia 18.16 17.78 5 9687 147 29942639
Hepatic cyst ruptured 17.82 17.78 3 9689 6 29942780

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 anticoagulante
CHEBI has role CHEBI:50390 vitamin k reductase inhibitor

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Pulmonary embolism indication 59282003 DOID:9477
Venous thrombosis indication 111293003

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

External reference:

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

Pharmaceutical products:

None