Ethyl biscoumacetate
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Overview
- DrugBank ID
- DB08794
- Type
- Small Molecule
- Clinical Trials
- Phase 0
- 0
- Phase 1
- 0
- Phase 2
- 0
- Phase 3
- 0
- Phase 4
- 0
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- Withdrawn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
- 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
Pharmacology
- Indication
Not Available
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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
- Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.
- Toxicity
Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- 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.
Drug Interaction Integrate drug-drug
interactions in your softwareAbametapir The serum concentration of Ethyl biscoumacetate can be increased when it is combined with Abametapir. Abciximab The risk or severity of bleeding can be increased when Abciximab is combined with Ethyl biscoumacetate. Aceclofenac The risk or severity of bleeding and hemorrhage can be increased when Aceclofenac is combined with Ethyl biscoumacetate. Acemetacin The risk or severity of bleeding and hemorrhage can be increased when Ethyl biscoumacetate is combined with Acemetacin. Acenocoumarol The 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
- Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.
- 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
- External Links
- PubChem Compound
- 54685524
- PubChem Substance
- 99445264
- ChemSpider
- 10444159
- BindingDB
- 35538
- ChEBI
- 135659
- ChEMBL
- CHEMBL2106261
- ZINC
- ZINC000095564733
- Wikipedia
- Ethyl_biscoumacetate
Clinical Trials
- Clinical Trials
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Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 153-154 Rosicky, J.; U.S. Patent 2,482,511; September 20,1949; assigned to Spojene Farmaceuticke Zovody (Czechoslovakia). water solubility 153 mg/L (at 20 °C) YALKOWSKY,SH & DANNENFELSER,RM (1992) - Predicted Properties
Property Value Source Water Solubility 0.0677 mg/mL ALOGPS logP 2.18 ALOGPS logP 1.67 Chemaxon logS -3.8 ALOGPS pKa (Strongest Acidic) 4.82 Chemaxon pKa (Strongest Basic) -6.7 Chemaxon Physiological Charge -2 Chemaxon Hydrogen Acceptor Count 5 Chemaxon Hydrogen Donor Count 2 Chemaxon Polar Surface Area 119.36 Å2 Chemaxon Rotatable Bond Count 5 Chemaxon Refractivity 104.95 m3·mol-1 Chemaxon Polarizability 39.98 Å3 Chemaxon Number of Rings 4 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.937 Blood Brain Barrier + 0.5382 Caco-2 permeable + 0.6023 P-glycoprotein substrate Substrate 0.6415 P-glycoprotein inhibitor I Non-inhibitor 0.7527 P-glycoprotein inhibitor II Non-inhibitor 0.7433 Renal organic cation transporter Non-inhibitor 0.8741 CYP450 2C9 substrate Non-substrate 0.7999 CYP450 2D6 substrate Non-substrate 0.9049 CYP450 3A4 substrate Non-substrate 0.6717 CYP450 1A2 substrate Non-inhibitor 0.6524 CYP450 2C9 inhibitor Inhibitor 0.8453 CYP450 2D6 inhibitor Non-inhibitor 0.9562 CYP450 2C19 inhibitor Inhibitor 0.6966 CYP450 3A4 inhibitor Non-inhibitor 0.9273 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.6137 Ames test Non AMES toxic 0.6498 Carcinogenicity Non-carcinogens 0.9167 Biodegradation Not ready biodegradable 0.7564 Rat acute toxicity 2.7178 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.938 hERG inhibition (predictor II) Non-inhibitor 0.896
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-0bt9-0006900000-fa0237e147f720231657 Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-056r-0009500000-f6451e08b9d35111a01b Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-08g0-0109300000-0b683c49c066ff82668a Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-0a4i-1007900000-f133797e34b3bb7c5dd6 Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-00b9-0904100000-d487aa7fe46f91587bc7 Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-00fr-0956000000-70dc2050510448aa61af Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 204.2959385 predictedDarkChem Lite v0.1.0 [M-H]- 186.77856 predictedDeepCCS 1.0 (2019) [M+H]+ 204.4967385 predictedDarkChem Lite v0.1.0 [M+H]+ 189.13655 predictedDeepCCS 1.0 (2019) [M+Na]+ 204.1034385 predictedDarkChem Lite v0.1.0 [M+Na]+ 195.62657 predictedDeepCCS 1.0 (2019)
Enzymes
1. DetailsGlutamine synthetase
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Glutamine synthetase that catalyzes the ATP-dependent conversion of glutamate and ammonia to glutamine (PubMed:16267323, PubMed:30158707, PubMed:36289327). Its role depends on tissue localization: in the brain, it regulates the levels of toxic ammonia and converts neurotoxic glutamate to harmless glutamine, whereas in the liver, it is one of the enzymes responsible for the removal of ammonia (By similarity). Essential for proliferation of fetal skin fibroblasts (PubMed:18662667). Independently of its glutamine synthetase activity, required for endothelial cell migration during vascular development: acts by regulating membrane localization and activation of the GTPase RHOJ, possibly by promoting RHOJ palmitoylation (PubMed:30158707). May act as a palmitoyltransferase for RHOJ: able to autopalmitoylate and then transfer the palmitoyl group to RHOJ (PubMed:30158707). Plays a role in ribosomal 40S subunit biogenesis (PubMed:26711351). Through the interaction with BEST2, inhibits BEST2 channel activity by affecting the gating at the aperture in the absence of intracellular L-glutamate, but sensitizes BEST2 to intracellular L-glutamate, which promotes the opening of BEST2 and thus relieves its inhibitory effect on BEST2 (PubMed:36289327)
- Specific Function
- ATP binding
- Gene Name
- GLUL
- Uniprot ID
- P15104
- Uniprot Name
- Glutamine synthetase
- Molecular Weight
- 42064.15 Da
References
- 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]
2. DetailsCytochrome P450 3A4
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- A cytochrome P450 monooxygenase involved in the metabolism of sterols, steroid hormones, retinoids and fatty acids (PubMed:10681376, PubMed:11093772, PubMed:11555828, PubMed:12865317, PubMed:14559847, PubMed:15373842, PubMed:15764715, PubMed:19965576, PubMed:20702771, PubMed:21490593, PubMed:21576599). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase). Catalyzes the hydroxylation of carbon-hydrogen bonds (PubMed:12865317, PubMed:14559847, PubMed:15373842, PubMed:15764715, PubMed:21490593, PubMed:21576599, PubMed:2732228). Exhibits high catalytic activity for the formation of hydroxyestrogens from estrone (E1) and 17beta-estradiol (E2), namely 2-hydroxy E1 and E2, as well as D-ring hydroxylated E1 and E2 at the C-16 position (PubMed:11555828, PubMed:12865317, PubMed:14559847). Plays a role in the metabolism of androgens, particularly in oxidative deactivation of testosterone (PubMed:15373842, PubMed:15764715, PubMed:22773874, PubMed:2732228). Metabolizes testosterone to less biologically active 2beta- and 6beta-hydroxytestosterones (PubMed:15373842, PubMed:15764715, PubMed:2732228). Contributes to the formation of hydroxycholesterols (oxysterols), particularly A-ring hydroxylated cholesterol at the C-4beta position, and side chain hydroxylated cholesterol at the C-25 position, likely contributing to cholesterol degradation and bile acid biosynthesis (PubMed:21576599). Catalyzes bisallylic hydroxylation of polyunsaturated fatty acids (PUFA) (PubMed:9435160). Catalyzes the epoxidation of double bonds of PUFA with a preference for the last double bond (PubMed:19965576). Metabolizes endocannabinoid arachidonoylethanolamide (anandamide) to 8,9-, 11,12-, and 14,15-epoxyeicosatrienoic acid ethanolamides (EpETrE-EAs), potentially modulating endocannabinoid system signaling (PubMed:20702771). Plays a role in the metabolism of retinoids. Displays high catalytic activity for oxidation of all-trans-retinol to all-trans-retinal, a rate-limiting step for the biosynthesis of all-trans-retinoic acid (atRA) (PubMed:10681376). Further metabolizes atRA toward 4-hydroxyretinoate and may play a role in hepatic atRA clearance (PubMed:11093772). Responsible for oxidative metabolism of xenobiotics. Acts as a 2-exo-monooxygenase for plant lipid 1,8-cineole (eucalyptol) (PubMed:11159812). Metabolizes the majority of the administered drugs. Catalyzes sulfoxidation of the anthelmintics albendazole and fenbendazole (PubMed:10759686). Hydroxylates antimalarial drug quinine (PubMed:8968357). Acts as a 1,4-cineole 2-exo-monooxygenase (PubMed:11695850). Also involved in vitamin D catabolism and calcium homeostasis. Catalyzes the inactivation of the active hormone calcitriol (1-alpha,25-dihydroxyvitamin D(3)) (PubMed:29461981)
- Specific Function
- 1,8-cineole 2-exo-monooxygenase activity
- Gene Name
- CYP3A4
- Uniprot ID
- P08684
- Uniprot Name
- Cytochrome P450 3A4
- Molecular Weight
- 57342.67 Da
References
- Online Health [Link]
Drug created at October 08, 2010 21:27 / Updated at February 21, 2021 18:52