Acenocoumarol (CHEM002440)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (3)XML
Record Information
Version1.0
Creation Date2009-07-23 18:26:19 UTC
Update Date2026-05-14 17:00:16 UTC
Accession NumberCHEM002440
Identification
Common NameAcenocoumarol
ClassSmall Molecule
DescriptionAcenocoumarol is a coumarin derivative used as an anticoagulant. Coumarin derivatives inhibit the reduction of vitamin K by vitamin K reductase. This prevents carboxylation of vitamin K-dependent clotting factors, II, VII, XI and X, and interferes with coagulation. Hematocrit, hemoglobin, international normalized ratio and liver panel should be monitored. Patients on acenocoumarol are prohibited from giving blood.
Contaminant Sources
  • HMDB Contaminants - Urine
  • STOFF IDENT Compounds
  • T3DB toxins
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Anticoagulant
  • Aromatic Hydrocarbon
  • Drug
  • Ester
  • Human Neurotoxin
  • Metabolite
  • Organic Compound
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
3-(alpha-(4'-Nitrophenyl)-beta-acetylethyl)-4-hydroxycoumarinChEBI
3-(alpha-(p-Nitrophenol)-beta-acetylethyl)-4-hydroxycoumarinChEBI
3-(alpha-Acetonyl-4-nitrobenzyl)-4-hydroxycoumarinChEBI
3-(alpha-Acetonyl-p-nitrobenzyl)-4-hydroxycoumarinChEBI
3-(alpha-p-Nitrophenyl-beta-acetylethyl)-4-hydroxycoumarinChEBI
4-Hydroxy-3-(1-(4-nitrophenyl)-3-oxobutyl)-2H-1-benzopyran-2-oneChEBI
4-Hydroxy-3-[1-(4-nitrophenyl)-3-oxobutyl]-2H-chromen-2-oneChEBI
AcenocoumarinChEBI
AcenocoumarolumChEBI
AcenocumarolChEBI
AcenocumaroloChEBI
AcenokumarinChEBI
NicoumaloneChEBI
NicumalonChEBI
Nitrophenylacetylethyl-4-hydroxycoumarineChEBI
NitrovarfarianChEBI
NitrowarfarinChEBI
Mini-sintromKegg
3-(a-(4'-Nitrophenyl)-b-acetylethyl)-4-hydroxycoumarinGenerator
3-(Α-(4'-nitrophenyl)-β-acetylethyl)-4-hydroxycoumarinGenerator
3-(a-(p-Nitrophenol)-b-acetylethyl)-4-hydroxycoumarinGenerator
3-(Α-(p-nitrophenol)-β-acetylethyl)-4-hydroxycoumarinGenerator
3-(a-Acetonyl-4-nitrobenzyl)-4-hydroxycoumarinGenerator
3-(Α-acetonyl-4-nitrobenzyl)-4-hydroxycoumarinGenerator
3-(a-Acetonyl-p-nitrobenzyl)-4-hydroxycoumarinGenerator
3-(Α-acetonyl-p-nitrobenzyl)-4-hydroxycoumarinGenerator
3-(a-p-Nitrophenyl-b-acetylethyl)-4-hydroxycoumarinGenerator
3-(Α-p-nitrophenyl-β-acetylethyl)-4-hydroxycoumarinGenerator
Ciba-geigy brand OF acenocoumarolHMDB
Mini sintromHMDB
Novartis brand OF acenocoumarolHMDB
SinkumarHMDB
SyncoumarHMDB
SynthromHMDB
Acenocoumarol alliance brandHMDB
Acenocoumarol novartis brandHMDB
Alliance brand OF acenocoumarolHMDB
Ciba geigy brand OF acenocoumarolHMDB
MiniSintromHMDB
SyncumarHMDB
Acenocoumarol ciba-geigy brandHMDB
SinthromeHMDB
SintromHMDB
Chemical FormulaC19H15NO6
Average Molecular Mass353.326 g/mol
Monoisotopic Mass353.090 g/mol
CAS Registry Number152-72-7
IUPAC Name4-hydroxy-3-[1-(4-nitrophenyl)-3-oxobutyl]-2H-chromen-2-one
Traditional Nameacenocumarolo
SMILESCC(=O)CC(C1=CC=C(C=C1)[N+]([O-])=O)C1=C(O)C2=CC=CC=C2OC1=O
InChI IdentifierInChI=1S/C19H15NO6/c1-11(21)10-15(12-6-8-13(9-7-12)20(24)25)17-18(22)14-4-2-3-5-16(14)26-19(17)23/h2-9,15,22H,10H2,1H3
InChI KeyVABCILAOYCMVPS-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as 4-hydroxycoumarins. These are coumarins that contain one or more hydroxyl groups attached to C4-position the coumarin skeleton.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassCoumarins and derivatives
Sub ClassHydroxycoumarins
Direct Parent4-hydroxycoumarins
Alternative Parents
Substituents
  • 4-hydroxycoumarin
  • Benzopyran
  • 1-benzopyran
  • Nitrobenzene
  • Nitroaromatic compound
  • Pyranone
  • Monocyclic benzene moiety
  • Pyran
  • Benzenoid
  • Heteroaromatic compound
  • Vinylogous acid
  • Ketone
  • Lactone
  • C-nitro compound
  • Organic nitro compound
  • Oxacycle
  • Organic oxoazanium
  • Organoheterocyclic compound
  • Allyl-type 1,3-dipolar organic compound
  • Propargyl-type 1,3-dipolar organic compound
  • Organic 1,3-dipolar compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxide
  • Organic oxygen compound
  • Organic nitrogen compound
  • Carbonyl group
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Extracellular
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
Applications
Biological Roles
Chemical Roles
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point196-199°C
Boiling PointNot Available
Solubilitypractically insoluble
Predicted Properties
PropertyValueSource
Water Solubility0.011 g/LALOGPS
logP2.53ALOGPS
logP2.68ChemAxon
logS-4.5ALOGPS
pKa (Strongest Acidic)5.79ChemAxon
pKa (Strongest Basic)-6.8ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area109.42 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity94.18 m³·mol⁻¹ChemAxon
Polarizability34.35 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0005-4394000000-cee5104d5911648240f0Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0h90-9486300000-ff32bbb6638456fac0abSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0009000000-a9c658b6227fbe717786Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4r-0009000000-b7023b451fda1f0da396Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-3509000000-10dd28ff6a33134ff631Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-1009000000-bb35e9834abd3581b7c9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-2009000000-0b9b626833d64db8299cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9104000000-feadec6c8ab265c3c1b3Spectrum
Toxicity Profile
Route of ExposureIngestion (9) ; dermal (9). Rapidly absorbed orally with greater than 60% bioavailability. Peak plasma levels are attained 1 to 3 hours following oral administration.
Mechanism of ToxicityAcenocoumarol inhibits vitamin K reductase, resulting in depletion of the reduced form of vitamin K (vitamin KH2). As vitamin K is a cofactor for the carboxylation of glutamate residues on the N-terminal regions of vitamin K-dependent proteins, this limits the gamma-carboxylation and subsequent activation of the vitamin K-dependent coagulant proteins. The synthesis of vitamin K-dependent coagulation factors II, VII, IX, and X and anticoagulant proteins C and S is inhibited. Depression of three of the four vitamin K-dependent coagulation factors (factors II, VII, and X) results in decresed prothrombin levels and a decrease in the amount of thrombin generated and bound to fibrin. This reduces the thrombogenicity of clots. (1)
MetabolismExtensively metabolized in the liver via oxidation forming two hydroxy metabolites and keto reduction producing two alcohol metabolites. Reduction of the nitro group produces an amino metabolite which is further transformed to an acetoamido metabolite. Metabolites do not appear to be pharmacologically active. Route of Elimination: Mostly via the kidney as metabolites Half Life: 8 to 11 hours.
Toxicity ValuesLD50: 1470 mg/kg (Oral, Mouse) (10) LD50: 115 mg/kg (Intraperitoneal, Mouse) (10)
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesAcenocoumarol is an anticoagulant drug derived from coumarin. (8) For the treatment and prevention of thromboembolic diseases. More specifically, it is indicated for the for the prevention of cerebral embolism, deep vein thrombosis, pulmonary embolism, thromboembolism in infarction and transient ischemic attacks. It is used for the treatment of deep vein thrombosis and myocardial infarction.
Minimum Risk LevelNot Available
Health EffectsAcenocoumarol is an anticoagulant and may cause internal bleeding, leading to shock, loss of consciousness, and eventually death. (7)
SymptomsThe onset and severity of the symptoms are dependent on the individual's sensitivity to oral anticoagulants, the severity of the overdosage, and the duration of treatment. Bleeding is the major sign of toxicity with oral anticoagulant drugs. The most frequent symptoms observed are: cutaneous bleeding (80%), haematuria (with renal colic) (52%), haematomas, gastrointestinal bleeding, haematemesis, uterine bleeding, epistaxis, gingival bleeding and bleeding into the joints. Further symptoms include tachycardia, hypotension, peripheral circulatory disorders due to loss of blood, nausea, vomiting, diarrhoea and abdominal pains.
TreatmentThe primary antidote to acenocoumarol poisoning is immediate administration of vitamin K1 (initially slow intravenous injections of 10-25 mg repeated all 3-6 hours until normalisation of the prothrombin time; then 10 mg orally four times daily as a "maintenance dose"). It is an extremely effective antidote, provided the poisoning is caught before too much damage has been done to the victim's circulatory system. At high doses acenocoumarol can affect the body for many months, and the antidote must be administered regularly for a long period of time. (7)
Concentrations
Not Available
DrugBank IDDB01418
HMDB IDHMDB0015487
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkAcenocoumarol
Chemspider ID10443441
ChEBI ID53766
PubChem Compound ID54676537
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis Reference

Stoll, W. and Litvan, F.; U.S. Patent 2,648,682; August 11,1953; assigned to J.R. Geigy A.G.,
Switzerland.

MSDSLink
General References
1. Girard P, Nony P, Erhardtsen E, Delair S, Ffrench P, Dechavanne M, Boissel JP: Population pharmacokinetics of recombinant factor VIIa in volunteers anticoagulated with acenocoumarol. Thromb Haemost. 1998 Jul;80(1):109-13.
2. Cesar JM, Garcia-Avello A, Navarro JL, Herraez MV: Aging and oral anticoagulant therapy using acenocoumarol. Blood Coagul Fibrinolysis. 2004 Oct;15(8):673-6.
3. Lengyel M: [Warfarin or acenocoumarol is better in the anticoagulant treatment of chronic atrial fibrillation?]. Orv Hetil. 2004 Dec 26;145(52):2619-21.
4. Ufer M: Comparative pharmacokinetics of vitamin K antagonists: warfarin, phenprocoumon and acenocoumarol. Clin Pharmacokinet. 2005;44(12):1227-46.
5. Montes R, Ruiz de Gaona E, Martinez-Gonzalez MA, Alberca I, Hermida J: The c.-1639G > A polymorphism of the VKORC1 gene is a major determinant of the response to acenocoumarol in anticoagulated patients. Br J Haematol. 2006 Apr;133(2):183-7.
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=17275317