Ethyl biscoumacetate

Identification

Name
Ethyl biscoumacetate
Accession Number
DB08794
Type
Small Molecule
Groups
Withdrawn
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
  • Ethyl bis(4-hydroxy-2-oxo-2h-1-benzopyran-3-yl)acetate
  • Ethyldicoumarol
International/Other Brands
Pelentan / Tromexan
Categories
UNII
08KL644731
CAS number
548-00-5
Weight
Average: 408.362
Monoisotopic: 408.084517475
Chemical Formula
C22H16O8
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

Pharmacology

Indication
Not Available
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
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
(1,2,6,7-3H)TestosteroneThe therapeutic efficacy of Ethyl biscoumacetate can be increased when used in combination with (1,2,6,7-3H)Testosterone.
(R)-warfarinThe risk or severity of bleeding can be increased when Ethyl biscoumacetate is combined with (R)-warfarin.
(S)-WarfarinThe risk or severity of bleeding can be increased when Ethyl biscoumacetate is combined with (S)-Warfarin.
1-TestosteroneThe therapeutic efficacy of Ethyl biscoumacetate can be increased when used in combination with 1-Testosterone.
18-methyl-19-nortestosteroneThe therapeutic efficacy of Ethyl biscoumacetate can be increased when used in combination with 18-methyl-19-nortestosterone.
2,5-Dimethoxy-4-ethylthioamphetamineThe risk or severity of adverse effects can be increased when 2,5-Dimethoxy-4-ethylthioamphetamine is combined with Ethyl biscoumacetate.
3,4-MethylenedioxyamphetamineThe risk or severity of adverse effects can be increased when 3,4-Methylenedioxyamphetamine is combined with Ethyl biscoumacetate.
3,5-diiodothyropropionic acid3,5-diiodothyropropionic acid may increase the anticoagulant activities of Ethyl biscoumacetate.
4-Bromo-2,5-dimethoxyamphetamineThe risk or severity of adverse effects can be increased when 4-Bromo-2,5-dimethoxyamphetamine is combined with Ethyl biscoumacetate.
4-hydroxycoumarinThe risk or severity of bleeding can be increased when Ethyl biscoumacetate is combined with 4-hydroxycoumarin.
Food Interactions
Not Available

References

Synthesis Reference

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

General References
Not Available
External Links
PubChem Compound
54685524
PubChem Substance
99445264
ChemSpider
10444159
BindingDB
35538
ChEBI
135659
ChEMBL
CHEMBL2106261
Wikipedia
Ethyl_biscoumacetate
ATC Codes
B01AA08 — Ethyl biscoumacetate

Clinical Trials

Clinical Trials
Not Available

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/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

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
4-hydroxycoumarin / Benzopyran / 1-benzopyran / Pyranone / Pyran / Benzenoid / Heteroaromatic compound / Vinylogous acid / Carboxylic acid ester / Lactone
show 10 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not 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). 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. [PubMed:7195738]
Kind
Protein
Organism
Human
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 on October 08, 2010 15:27 / Updated on October 11, 2018 22:27