NAV

Ethyl biscoumacetate

Identification

Generic Name
Ethyl biscoumacetate
DrugBank Accession Number
DB08794
Background

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)

Type
Small Molecule
Groups
Withdrawn
Structure
3D
Similar Structures
Weight
Average: 408.362
Monoisotopic: 408.084517475
Chemical Formula
C22H16O8
Synonyms
  • Ethyl bis(4-hydroxy-2-oxo-2h-1-benzopyran-3-yl)acetate
  • Ethyl biscoumacetate
  • Ethyldicoumarol
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Pharmacology

Indication

Not Available

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action
Not Available
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
Not Available

Interactions

Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
Integrate drug-drug
interactions in your software
AbametapirThe serum concentration of Ethyl biscoumacetate can be increased when it is combined with Abametapir.
AbciximabThe risk or severity of bleeding can be increased when Abciximab is combined with Ethyl biscoumacetate.
AceclofenacThe risk or severity of bleeding and hemorrhage can be increased when Aceclofenac is combined with Ethyl biscoumacetate.
AcemetacinThe risk or severity of bleeding and hemorrhage can be increased when Ethyl biscoumacetate is combined with Acemetacin.
AcenocoumarolThe risk or severity of bleeding can be increased when Acenocoumarol is combined with Ethyl biscoumacetate.
Food Interactions
  • Avoid herbs and supplements with anticoagulant/antiplatelet activity. Examples include garlic, ginger, bilberry, danshen, piracetam, and ginkgo biloba.

Products

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International/Other Brands
Pelentan / Tromexan

Categories

ATC Codes
B01AA08 — Ethyl biscoumacetate
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound 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.
Kingdom
Organic compounds
Super Class
Phenylpropanoids and polyketides
Class
Coumarins and derivatives
Sub Class
Hydroxycoumarins
Direct Parent
4-hydroxycoumarins
Alternative Parents
1-benzopyrans / Pyranones and derivatives / Benzenoids / Vinylogous acids / Heteroaromatic compounds / Lactones / Carboxylic acid esters / Oxacyclic compounds / Monocarboxylic acids and derivatives / Organic oxides
show 2 more
Substituents
1-benzopyran / 4-hydroxycoumarin / Aromatic heteropolycyclic compound / Benzenoid / Benzopyran / Carbonyl group / Carboxylic acid derivative / Carboxylic acid ester / Heteroaromatic compound / Hydrocarbon derivative
show 10 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
08KL644731
CAS number
548-00-5
InChI Key
JCLHQFUTFHUXNN-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/h3-10,15,23-24H,2H2,1H3
IUPAC Name
ethyl 2,2-bis(4-hydroxy-2-oxo-2H-chromen-3-yl)acetate
SMILES
CCOC(=O)C(C1=C(O)C2=CC=CC=C2OC1=O)C1=C(O)C2=CC=CC=C2OC1=O

References

Synthesis Reference

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

General References
Not Available
PubChem Compound
54685524
PubChem Substance
99445264
ChemSpider
10444159
BindingDB
35538
ChEBI
135659
ChEMBL
CHEMBL2106261
ZINC
ZINC000095564733
Wikipedia
Ethyl_biscoumacetate

Clinical Trials

Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)153-154Rosicky, 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 Solubility0.0677 mg/mLALOGPS
logP2.18ALOGPS
logP1.67Chemaxon
logS-3.8ALOGPS
pKa (Strongest Acidic)4.82Chemaxon
pKa (Strongest Basic)-6.7Chemaxon
Physiological Charge-2Chemaxon
Hydrogen Acceptor Count5Chemaxon
Hydrogen Donor Count2Chemaxon
Polar Surface Area119.36 Å2Chemaxon
Rotatable Bond Count5Chemaxon
Refractivity104.95 m3·mol-1Chemaxon
Polarizability39.98 Å3Chemaxon
Number of Rings4Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
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)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0bt9-0006900000-fa0237e147f720231657
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-056r-0009500000-f6451e08b9d35111a01b
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-08g0-0109300000-0b683c49c066ff82668a
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4i-1007900000-f133797e34b3bb7c5dd6
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-00b9-0904100000-d487aa7fe46f91587bc7
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-00fr-0956000000-70dc2050510448aa61af
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-204.2959385
predicted
DarkChem Lite v0.1.0
[M-H]-186.77856
predicted
DeepCCS 1.0 (2019)
[M+H]+204.4967385
predicted
DarkChem Lite v0.1.0
[M+H]+189.13655
predicted
DeepCCS 1.0 (2019)
[M+Na]+204.1034385
predicted
DarkChem Lite v0.1.0
[M+Na]+195.62657
predicted
DeepCCS 1.0 (2019)

Enzymes

Details1. Glutamine synthetase
Kind
Protein
Organism
Humans
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). E...
Gene Name
GLUL
Uniprot ID
P15104
Uniprot Name
Glutamine synthetase
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. [Article]
Details2. Cytochrome P450 3A4
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Vitamin d3 25-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. Online Health [Link]

Drug created at October 08, 2010 21:27 / Updated at February 21, 2021 18:52