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Identification
NameEthyl biscoumacetate
Accession NumberDB08794
TypeSmall Molecule
GroupsWithdrawn
Description

Ethyl biscoumacetate is a courmarin that is used as an anticoagulant. It has actions similar to those of Warfarin. (From Martindale, The Extra Pharmacopoeia, 30th ed, p226)

Structure
Thumb
Synonyms
SynonymLanguageCode
PelentanNot AvailableNot Available
TromexanNot AvailableNot Available
Prescription ProductsNot Available
Generic Prescription ProductsNot Available
Over the Counter ProductsNot Available
International BrandsNot Available
Brand mixturesNot Available
SaltsNot Available
Categories
CAS number548-00-5
WeightAverage: 408.3576
Monoisotopic: 408.084517488
Chemical FormulaC22H16O8
InChI KeySEGSDVUVOWIWFX-UHFFFAOYSA-N
InChI
InChI=1S/C22H16O8/c1-2-28-20(25)15(16-18(23)11-7-3-5-9-13(11)29-21(16)26)17-19(24)12-8-4-6-10-14(12)30-22(17)27/h3-10,15,26-27H,2H2,1H3
IUPAC Name
ethyl 2,2-bis(2-hydroxy-4-oxo-4H-chromen-3-yl)acetate
SMILES
CCOC(=O)C(C1=C(O)OC2=CC=CC=C2C1=O)C1=C(O)OC2=CC=CC=C2C1=O
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as coumarins and derivatives. These are polycyclic aromatic compounds containing a 1-benzopyran moiety with a ketone group at the C2 carbon atom (1-benzopyran-2-one).
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassCoumarins and derivatives
Sub ClassNot Available
Direct ParentCoumarins and derivatives
Alternative Parents
Substituents
  • Coumarin
  • Chromone
  • 1-benzopyran
  • Benzopyran
  • Pyranone
  • Benzenoid
  • Pyran
  • Heteroaromatic compound
  • Vinylogous acid
  • Carboxylic acid ester
  • Oxacycle
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Pharmacology
IndicationNot Available
PharmacodynamicsNot Available
Mechanism of actionNot Available
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organismsNot Available
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.937
Blood Brain Barrier+0.5382
Caco-2 permeable+0.6023
P-glycoprotein substrateSubstrate0.6415
P-glycoprotein inhibitor INon-inhibitor0.7527
P-glycoprotein inhibitor IINon-inhibitor0.7433
Renal organic cation transporterNon-inhibitor0.8741
CYP450 2C9 substrateNon-substrate0.7999
CYP450 2D6 substrateNon-substrate0.9049
CYP450 3A4 substrateNon-substrate0.6717
CYP450 1A2 substrateNon-inhibitor0.6524
CYP450 2C9 substrateInhibitor0.8453
CYP450 2D6 substrateNon-inhibitor0.9562
CYP450 2C19 substrateInhibitor0.6966
CYP450 3A4 substrateNon-inhibitor0.9273
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.6137
Ames testNon AMES toxic0.6498
CarcinogenicityNon-carcinogens0.9167
BiodegradationNot ready biodegradable0.7564
Rat acute toxicity2.7178 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.938
hERG inhibition (predictor II)Non-inhibitor0.896
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point153-154Rosicky, J.; U.S. Patent 2,482,511; September 20,1949; assigned to Spojene Farmaceuticke Zovody (Czechoslovakia).
water solubility153 mg/L (at 20 °C)YALKOWSKY,SH & DANNENFELSER,RM (1992)
Predicted Properties
PropertyValueSource
Water Solubility0.0861 mg/mLALOGPS
logP2.18ALOGPS
logP3.22ChemAxon
logS-3.7ALOGPS
pKa (Strongest Acidic)7.13ChemAxon
pKa (Strongest Basic)-5.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area119.36 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity123.2 m3·mol-1ChemAxon
Polarizability39.96 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
References
Synthesis Reference

Rosicky, J.; U.S. Patent 2,482,511; September 20,1949; assigned to Spojene Farmaceuticke Zovody (Czechoslovakia).

General ReferenceNot Available
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug Interactions
Drug
AbciximabAgents with Antiplatelet Properties may enhance the anticoagulant effect of Anticoagulants.
AcenocoumarolMay enhance the anticoagulant effect of other Anticoagulants.
Acetylsalicylic acidAgents with Antiplatelet Properties may enhance the anticoagulant effect of Anticoagulants.
AlteplaseThrombolytic Agents may enhance the anticoagulant effect of Anticoagulants.
Aminosalicylic AcidSalicylates may enhance the anticoagulant effect of Anticoagulants.
AnagrelideAgents with Antiplatelet Properties may enhance the anticoagulant effect of Anticoagulants.
ApixabanApixaban may enhance the anticoagulant effect of Anticoagulants.
ArgatrobanMay enhance the anticoagulant effect of other Anticoagulants.
Bismuth SubsalicylateSalicylates may enhance the anticoagulant effect of Anticoagulants.
BivalirudinMay enhance the anticoagulant effect of other Anticoagulants.
CelecoxibNonsteroidal Anti-Inflammatory Agents may enhance the anticoagulant effect of Anticoagulants.
CilostazolAgents with Antiplatelet Properties may enhance the anticoagulant effect of Anticoagulants.
CitalopramAgents with Antiplatelet Properties may enhance the anticoagulant effect of Anticoagulants.
ClopidogrelAgents with Antiplatelet Properties may enhance the anticoagulant effect of Anticoagulants.
Cyproterone acetateProgestins may diminish the therapeutic effect of Anticoagulants. More specifically, the potential prothrombotic effects of some progestins and progestin-estrogen combinations may counteract anticoagulant effects.
Dabigatran etexilateDabigatran Etexilate may enhance the anticoagulant effect of Anticoagulants.
DalteparinMay enhance the anticoagulant effect of other Anticoagulants.
DanaparoidMay enhance the anticoagulant effect of other Anticoagulants.
DasatinibDasatinib may enhance the anticoagulant effect of Anticoagulants.
DeferasiroxMay enhance the adverse/toxic effect of Deferasirox. Specifically, the risk for GI ulceration/irritation or GI bleeding may be increased.
DesogestrelEstrogen Derivatives may diminish the anticoagulant effect of Anticoagulants. More specifically, the potential prothrombotic effects of some estrogens and progestin-estrogen combinations may counteract anticoagulant effects.
DesvenlafaxineAgents with Antiplatelet Properties may enhance the anticoagulant effect of Anticoagulants.
DiflunisalAgents with Antiplatelet Properties may enhance the anticoagulant effect of Anticoagulants.
DipyridamoleAgents with Antiplatelet Properties may enhance the anticoagulant effect of Anticoagulants.
DrospirenoneEstrogen Derivatives may diminish the anticoagulant effect of Anticoagulants. More specifically, the potential prothrombotic effects of some estrogens and progestin-estrogen combinations may counteract anticoagulant effects.
DuloxetineAgents with Antiplatelet Properties may enhance the anticoagulant effect of Anticoagulants.
EnoxaparinMay enhance the anticoagulant effect of other Anticoagulants.
EpoprostenolProstacyclin Analogues may enhance the adverse/toxic effect of Anticoagulants. Specifically, the antiplatelet effects of these agents may lead to an increased risk of bleeding with the combination.
EptifibatideAgents with Antiplatelet Properties may enhance the anticoagulant effect of Anticoagulants.
EscitalopramAgents with Antiplatelet Properties may enhance the anticoagulant effect of Anticoagulants.
EstropipateEstrogen Derivatives may diminish the anticoagulant effect of Anticoagulants. More specifically, the potential prothrombotic effects of some estrogens and progestin-estrogen combinations may counteract anticoagulant effects.
Ethinyl EstradiolEstrogen Derivatives may diminish the anticoagulant effect of Anticoagulants. More specifically, the potential prothrombotic effects of some estrogens and progestin-estrogen combinations may counteract anticoagulant effects.
EthynodiolEstrogen Derivatives may diminish the anticoagulant effect of Anticoagulants. More specifically, the potential prothrombotic effects of some estrogens and progestin-estrogen combinations may counteract anticoagulant effects.
EtodolacAgents with Antiplatelet Properties may enhance the anticoagulant effect of Anticoagulants.
EtonogestrelProgestins may diminish the therapeutic effect of Anticoagulants. More specifically, the potential prothrombotic effects of some progestins and progestin-estrogen combinations may counteract anticoagulant effects.
FenoprofenAgents with Antiplatelet Properties may enhance the anticoagulant effect of Anticoagulants.
FloctafenineAgents with Antiplatelet Properties may enhance the anticoagulant effect of Anticoagulants.
FluoxetineAgents with Antiplatelet Properties may enhance the anticoagulant effect of Anticoagulants.
FluvoxamineAgents with Antiplatelet Properties may enhance the anticoagulant effect of Anticoagulants.
Fondaparinux sodiumMay enhance the anticoagulant effect of other Anticoagulants.
HeparinMay enhance the anticoagulant effect of other Anticoagulants.
HomoharringtonineMay enhance the adverse/toxic effect of Omacetaxine. Specifically, the risk for bleeding-related events may be increased.
IbritumomabMay enhance the adverse/toxic effect of Ibritumomab. Both agents may contribute to an increased risk of bleeding.
IbuprofenAgents with Antiplatelet Properties may enhance the anticoagulant effect of Anticoagulants.
IcosapentOmega-3 Fatty Acids may enhance the anticoagulant effect of Anticoagulants.
Icosapent ethylOmega-3 Fatty Acids may enhance the anticoagulant effect of Anticoagulants.
IloprostProstacyclin Analogues may enhance the adverse/toxic effect of Anticoagulants. Specifically, the antiplatelet effects of these agents may lead to an increased risk of bleeding with the combination.
IndomethacinAgents with Antiplatelet Properties may enhance the anticoagulant effect of Anticoagulants.
KetoprofenAgents with Antiplatelet Properties may enhance the anticoagulant effect of Anticoagulants.
KetorolacAgents with Antiplatelet Properties may enhance the anticoagulant effect of Anticoagulants.
LevomilnacipranAgents with Antiplatelet Properties may enhance the anticoagulant effect of Anticoagulants.
LevonorgestrelProgestins may diminish the therapeutic effect of Anticoagulants. More specifically, the potential prothrombotic effects of some progestins and progestin-estrogen combinations may counteract anticoagulant effects.
Magnesium salicylateSalicylates may enhance the anticoagulant effect of Anticoagulants.
Medroxyprogesterone AcetateProgestins may diminish the therapeutic effect of Anticoagulants. More specifically, the potential prothrombotic effects of some progestins and progestin-estrogen combinations may counteract anticoagulant effects.
Mefenamic acidAgents with Antiplatelet Properties may enhance the anticoagulant effect of Anticoagulants.
Megestrol acetateProgestins may diminish the therapeutic effect of Anticoagulants. More specifically, the potential prothrombotic effects of some progestins and progestin-estrogen combinations may counteract anticoagulant effects.
MeloxicamAgents with Antiplatelet Properties may enhance the anticoagulant effect of Anticoagulants.
MestranolEstrogen Derivatives may diminish the anticoagulant effect of Anticoagulants. More specifically, the potential prothrombotic effects of some estrogens and progestin-estrogen combinations may counteract anticoagulant effects.
MilnacipranAgents with Antiplatelet Properties may enhance the anticoagulant effect of Anticoagulants.
NabumetoneAgents with Antiplatelet Properties may enhance the anticoagulant effect of Anticoagulants.
NadroparinMay enhance the anticoagulant effect of other Anticoagulants.
NaproxenAgents with Antiplatelet Properties may enhance the anticoagulant effect of Anticoagulants.
NorelgestrominEstrogen Derivatives may diminish the anticoagulant effect of Anticoagulants. More specifically, the potential prothrombotic effects of some estrogens and progestin-estrogen combinations may counteract anticoagulant effects.
NorethindroneProgestins may diminish the therapeutic effect of Anticoagulants. More specifically, the potential prothrombotic effects of some progestins and progestin-estrogen combinations may counteract anticoagulant effects.
NorgestimateEstrogen Derivatives may diminish the anticoagulant effect of Anticoagulants. More specifically, the potential prothrombotic effects of some estrogens and progestin-estrogen combinations may counteract anticoagulant effects.
ObinutuzumabMay enhance the adverse/toxic effect of Obinutuzumab. Specifically, the risk of serious bleeding-related events may be increased.
OxaprozinAgents with Antiplatelet Properties may enhance the anticoagulant effect of Anticoagulants.
ParoxetineAgents with Antiplatelet Properties may enhance the anticoagulant effect of Anticoagulants.
Pentosan PolysulfatePentosan Polysulfate Sodium may enhance the anticoagulant effect of Anticoagulants.
PiperazineEstrogen Derivatives may diminish the anticoagulant effect of Anticoagulants. More specifically, the potential prothrombotic effects of some estrogens and progestin-estrogen combinations may counteract anticoagulant effects.
PiroxicamAgents with Antiplatelet Properties may enhance the anticoagulant effect of Anticoagulants.
PrasugrelAgents with Antiplatelet Properties may enhance the anticoagulant effect of Anticoagulants.
ProgesteroneProgestins may diminish the therapeutic effect of Anticoagulants. More specifically, the potential prothrombotic effects of some progestins and progestin-estrogen combinations may counteract anticoagulant effects.
ReteplaseThrombolytic Agents may enhance the anticoagulant effect of Anticoagulants.
RivaroxabanMay enhance the anticoagulant effect of Rivaroxaban.
SalsalateSalicylates may enhance the anticoagulant effect of Anticoagulants.
SertralineAgents with Antiplatelet Properties may enhance the anticoagulant effect of Anticoagulants.
SulindacAgents with Antiplatelet Properties may enhance the anticoagulant effect of Anticoagulants.
TenecteplaseThrombolytic Agents may enhance the anticoagulant effect of Anticoagulants.
Tiaprofenic acidAgents with Antiplatelet Properties may enhance the anticoagulant effect of Anticoagulants.
TicagrelorAgents with Antiplatelet Properties may enhance the anticoagulant effect of Anticoagulants.
TiclopidineAgents with Antiplatelet Properties may enhance the anticoagulant effect of Anticoagulants.
TinzaparinMay enhance the anticoagulant effect of other Anticoagulants.
TipranavirTipranavir may enhance the anticoagulant effect of Anticoagulants.
TirofibanAgents with Antiplatelet Properties may enhance the anticoagulant effect of Anticoagulants.
TolmetinAgents with Antiplatelet Properties may enhance the anticoagulant effect of Anticoagulants.
TositumomabMay enhance the adverse/toxic effect of Tositumomab and Iodine I 131 Tositumomab. Specifically, the risk of bleeding-related adverse effects may be increased.
TreprostinilProstacyclin Analogues may enhance the adverse/toxic effect of Anticoagulants. Specifically, the antiplatelet effects of these agents may lead to an increased risk of bleeding with the combination.
VenlafaxineAgents with Antiplatelet Properties may enhance the anticoagulant effect of Anticoagulants.
VilazodoneAgents with Antiplatelet Properties may enhance the anticoagulant effect of Anticoagulants.
Vitamin EVitamin E may enhance the anticoagulant effect of Anticoagulants. Vitamin E may also increase the overall risk for bleeding.
VorapaxarVorapaxar may enhance the adverse/toxic effect of Anticoagulants. More specifically, this combination is expected to increase the risk of bleeding.
Food InteractionsNot Available

Enzymes

1. Glutamine synthetase

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Glutamine synthetase P15104 Details

References:

  1. Sharaev PN, Bogdanov NG, Sarycheva IK, Zhukova EE: [Allosteric regulation of glucosamine synthetase activity by naphthoquinone derivatives and ethyl ester of di-(4-oxycumarinyl-3)-acetic acid]. Biokhimiia. 1981 Feb;46(2):342-6. Pubmed

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Drug created on October 08, 2010 15:27 / Updated on April 22, 2014 10:47