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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
Pelentan
Tromexan
External Identifiers Not Available
Prescription ProductsNot Available
Generic Prescription ProductsNot Available
Over the Counter ProductsNot Available
International BrandsNot Available
Brand mixturesNot Available
SaltsNot Available
Categories
UNII08KL644731
CAS number548-00-5
WeightAverage: 408.3576
Monoisotopic: 408.084517488
Chemical FormulaC22H16O8
InChI KeyInChIKey=SEGSDVUVOWIWFX-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
Related Articles
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 inhibitorInhibitor0.8453
CYP450 2D6 inhibitorNon-inhibitor0.9562
CYP450 2C19 inhibitorInhibitor0.6966
CYP450 3A4 inhibitorNon-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
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
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 ReferencesNot Available
External Links
ATC CodesB01AA08
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug Interactions
Drug
AbciximabAbciximab may increase the anticoagulant activities of Ethyl biscoumacetate.
AcenocoumarolEthyl biscoumacetate may increase the anticoagulant activities of Acenocoumarol.
Acetylsalicylic acidAcetylsalicylic acid may increase the anticoagulant activities of Ethyl biscoumacetate.
AlteplaseAlteplase may increase the anticoagulant activities of Ethyl biscoumacetate.
Aminosalicylic AcidAminosalicylic Acid may increase the anticoagulant activities of Ethyl biscoumacetate.
AnagrelideAnagrelide may increase the anticoagulant activities of Ethyl biscoumacetate.
ApixabanApixaban may increase the anticoagulant activities of Ethyl biscoumacetate.
ArgatrobanEthyl biscoumacetate may increase the anticoagulant activities of Argatroban.
Bismuth SubsalicylateBismuth Subsalicylate may increase the anticoagulant activities of Ethyl biscoumacetate.
BivalirudinEthyl biscoumacetate may increase the anticoagulant activities of Bivalirudin.
CaffeineCaffeine may increase the anticoagulant activities of Ethyl biscoumacetate.
CangrelorCangrelor may increase the anticoagulant activities of Ethyl biscoumacetate.
CelecoxibCelecoxib may increase the anticoagulant activities of Ethyl biscoumacetate.
CilostazolCilostazol may increase the anticoagulant activities of Ethyl biscoumacetate.
CitalopramCitalopram may increase the anticoagulant activities of Ethyl biscoumacetate.
ClopidogrelClopidogrel may increase the anticoagulant activities of Ethyl biscoumacetate.
Collagenase clostridium histolyticumThe risk or severity of adverse effects can be increased when Ethyl biscoumacetate is combined with Collagenase clostridium histolyticum.
Cyproterone acetateThe therapeutic efficacy of Ethyl biscoumacetate can be decreased when used in combination with Cyproterone acetate.
Dabigatran etexilateDabigatran etexilate may increase the anticoagulant activities of Ethyl biscoumacetate.
DalteparinEthyl biscoumacetate may increase the anticoagulant activities of Dalteparin.
DanaparoidEthyl biscoumacetate may increase the anticoagulant activities of Danaparoid.
DasatinibDasatinib may increase the anticoagulant activities of Ethyl biscoumacetate.
DeferasiroxThe risk or severity of adverse effects can be increased when Ethyl biscoumacetate is combined with Deferasirox.
Deoxycholic AcidThe risk or severity of adverse effects can be increased when Ethyl biscoumacetate is combined with Deoxycholic Acid.
DesirudinEthyl biscoumacetate may increase the anticoagulant activities of Desirudin.
DesogestrelDesogestrel may decrease the anticoagulant activities of Ethyl biscoumacetate.
DesvenlafaxineDesvenlafaxine may increase the anticoagulant activities of Ethyl biscoumacetate.
DiclofenacDiclofenac may increase the anticoagulant activities of Ethyl biscoumacetate.
DienogestThe therapeutic efficacy of Ethyl biscoumacetate can be decreased when used in combination with Dienogest.
DiflunisalDiflunisal may increase the anticoagulant activities of Ethyl biscoumacetate.
DihydrocodeineDihydrocodeine may increase the anticoagulant activities of Ethyl biscoumacetate.
DipyridamoleDipyridamole may increase the anticoagulant activities of Ethyl biscoumacetate.
DrospirenoneDrospirenone may decrease the anticoagulant activities of Ethyl biscoumacetate.
DuloxetineDuloxetine may increase the anticoagulant activities of Ethyl biscoumacetate.
EdoxabanEdoxaban may increase the anticoagulant activities of Ethyl biscoumacetate.
EnoxaparinEthyl biscoumacetate may increase the anticoagulant activities of Enoxaparin.
EpoprostenolThe risk or severity of adverse effects can be increased when Epoprostenol is combined with Ethyl biscoumacetate.
EptifibatideEptifibatide may increase the anticoagulant activities of Ethyl biscoumacetate.
EscitalopramEscitalopram may increase the anticoagulant activities of Ethyl biscoumacetate.
EstradiolEstradiol may decrease the anticoagulant activities of Ethyl biscoumacetate.
EstropipateEstropipate may decrease the anticoagulant activities of Ethyl biscoumacetate.
Ethinyl EstradiolEthinyl Estradiol may decrease the anticoagulant activities of Ethyl biscoumacetate.
EthynodiolEthynodiol may decrease the anticoagulant activities of Ethyl biscoumacetate.
EtodolacEtodolac may increase the anticoagulant activities of Ethyl biscoumacetate.
EtonogestrelThe therapeutic efficacy of Ethyl biscoumacetate can be decreased when used in combination with Etonogestrel.
FenoprofenFenoprofen may increase the anticoagulant activities of Ethyl biscoumacetate.
FloctafenineFloctafenine may increase the anticoagulant activities of Ethyl biscoumacetate.
FluoxetineFluoxetine may increase the anticoagulant activities of Ethyl biscoumacetate.
FlurbiprofenFlurbiprofen may increase the anticoagulant activities of Ethyl biscoumacetate.
FluvoxamineFluvoxamine may increase the anticoagulant activities of Ethyl biscoumacetate.
Fondaparinux sodiumEthyl biscoumacetate may increase the anticoagulant activities of Fondaparinux sodium.
HeparinEthyl biscoumacetate may increase the anticoagulant activities of Heparin.
Hydroxyprogesterone caproateThe therapeutic efficacy of Ethyl biscoumacetate can be decreased when used in combination with Hydroxyprogesterone caproate.
IbritumomabThe risk or severity of adverse effects can be increased when Ethyl biscoumacetate is combined with Ibritumomab.
IbrutinibThe risk or severity of adverse effects can be increased when Ibrutinib is combined with Ethyl biscoumacetate.
IbuprofenIbuprofen may increase the anticoagulant activities of Ethyl biscoumacetate.
IcosapentIcosapent may increase the anticoagulant activities of Ethyl biscoumacetate.
Icosapent ethylIcosapent ethyl may increase the anticoagulant activities of Ethyl biscoumacetate.
IloprostThe risk or severity of adverse effects can be increased when Iloprost is combined with Ethyl biscoumacetate.
IndomethacinIndomethacin may increase the anticoagulant activities of Ethyl biscoumacetate.
KetoprofenKetoprofen may increase the anticoagulant activities of Ethyl biscoumacetate.
KetorolacKetorolac may increase the anticoagulant activities of Ethyl biscoumacetate.
LevomilnacipranLevomilnacipran may increase the anticoagulant activities of Ethyl biscoumacetate.
LevonorgestrelThe therapeutic efficacy of Ethyl biscoumacetate can be decreased when used in combination with Levonorgestrel.
Magnesium salicylateMagnesium salicylate may increase the anticoagulant activities of Ethyl biscoumacetate.
Medroxyprogesterone AcetateThe therapeutic efficacy of Ethyl biscoumacetate can be decreased when used in combination with Medroxyprogesterone Acetate.
Mefenamic acidMefenamic acid may increase the anticoagulant activities of Ethyl biscoumacetate.
Megestrol acetateThe therapeutic efficacy of Ethyl biscoumacetate can be decreased when used in combination with Megestrol acetate.
MeloxicamMeloxicam may increase the anticoagulant activities of Ethyl biscoumacetate.
MestranolMestranol may decrease the anticoagulant activities of Ethyl biscoumacetate.
MilnacipranMilnacipran may increase the anticoagulant activities of Ethyl biscoumacetate.
NabumetoneNabumetone may increase the anticoagulant activities of Ethyl biscoumacetate.
NadroparinEthyl biscoumacetate may increase the anticoagulant activities of Nadroparin.
NaproxenNaproxen may increase the anticoagulant activities of Ethyl biscoumacetate.
NintedanibThe risk or severity of adverse effects can be increased when Ethyl biscoumacetate is combined with Nintedanib.
NorethisteroneThe therapeutic efficacy of Ethyl biscoumacetate can be decreased when used in combination with Norethindrone.
NorgestimateNorgestimate may decrease the anticoagulant activities of Ethyl biscoumacetate.
ObinutuzumabThe risk or severity of adverse effects can be increased when Ethyl biscoumacetate is combined with Obinutuzumab.
Omega-3 fatty acidsOmega-3 fatty acids may increase the anticoagulant activities of Ethyl biscoumacetate.
Omega-3-acid ethyl estersOmega-3-acid ethyl esters may increase the anticoagulant activities of Ethyl biscoumacetate.
OxaprozinOxaprozin may increase the anticoagulant activities of Ethyl biscoumacetate.
ParoxetineParoxetine may increase the anticoagulant activities of Ethyl biscoumacetate.
Pentosan PolysulfatePentosan Polysulfate may increase the anticoagulant activities of Ethyl biscoumacetate.
PiroxicamPiroxicam may increase the anticoagulant activities of Ethyl biscoumacetate.
PrasugrelPrasugrel may increase the anticoagulant activities of Ethyl biscoumacetate.
ProgesteroneThe therapeutic efficacy of Ethyl biscoumacetate can be decreased when used in combination with Progesterone.
ReteplaseReteplase may increase the anticoagulant activities of Ethyl biscoumacetate.
RivaroxabanEthyl biscoumacetate may increase the anticoagulant activities of Rivaroxaban.
SalsalateSalsalate may increase the anticoagulant activities of Ethyl biscoumacetate.
SertralineSertraline may increase the anticoagulant activities of Ethyl biscoumacetate.
SulindacSulindac may increase the anticoagulant activities of Ethyl biscoumacetate.
TenecteplaseTenecteplase may increase the anticoagulant activities of Ethyl biscoumacetate.
Tiaprofenic acidTiaprofenic acid may increase the anticoagulant activities of Ethyl biscoumacetate.
TicagrelorTicagrelor may increase the anticoagulant activities of Ethyl biscoumacetate.
TiclopidineTiclopidine may increase the anticoagulant activities of Ethyl biscoumacetate.
TinzaparinEthyl biscoumacetate may increase the anticoagulant activities of Tinzaparin.
TipranavirTipranavir may increase the anticoagulant activities of Ethyl biscoumacetate.
TirofibanTirofiban may increase the anticoagulant activities of Ethyl biscoumacetate.
TolmetinTolmetin may increase the anticoagulant activities of Ethyl biscoumacetate.
TositumomabThe risk or severity of adverse effects can be increased when Ethyl biscoumacetate is combined with Tositumomab.
TreprostinilThe risk or severity of adverse effects can be increased when Treprostinil is combined with Ethyl biscoumacetate.
VenlafaxineVenlafaxine may increase the anticoagulant activities of Ethyl biscoumacetate.
VilazodoneVilazodone may increase the anticoagulant activities of Ethyl biscoumacetate.
Vitamin EVitamin E may increase the anticoagulant activities of Ethyl biscoumacetate.
VorapaxarThe risk or severity of adverse effects can be increased when Vorapaxar is combined with Ethyl biscoumacetate.
VortioxetineVortioxetine may increase the anticoagulant activities of Ethyl biscoumacetate.
WarfarinEthyl biscoumacetate may increase the anticoagulant activities of Warfarin.
Food InteractionsNot Available

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Manganese ion binding
Specific Function:
This enzyme has 2 functions: it catalyzes the production of glutamine and 4-aminobutanoate (gamma-aminobutyric acid, GABA), the latter in a pyridoxal phosphate-independent manner (By similarity). Essential for proliferation of fetal skin fibroblasts.
Gene Name:
GLUL
Uniprot ID:
P15104
Molecular Weight:
42064.15 Da
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:7195738 ]
Comments
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Drug created on October 08, 2010 15:27 / Updated on April 22, 2014 10:47