Coumarin
Identification
- Name
- Coumarin
- Accession Number
- DB04665
- Description
- Not Available
- Type
- Small Molecule
- Groups
- Experimental
- Structure
Structure for Coumarin (DB04665)
- Weight
- Average: 146.1427
Monoisotopic: 146.036779436 - Chemical Formula
- C9H6O2
- Synonyms
- 1,2-benzopyrone
- 2H-1-benzopyran-2-one
- 2H-benzo(b)pyran-2-one
- Coumarinic lactone
- Cumarin
- External IDs
- NSC-8774
Pharmacology
Accelerate your drug discovery research with the industry’s only fully connected ADMET dataset, ideal for:Accelerate your drug discovery research with our fully connected ADMET dataset- Indication
- Not Available
- Contraindications & Blackbox Warnings
Contraindications & Blackbox WarningsWith our commercial data, access important information on dangerous risks, contraindications, and adverse effects.Our Blackbox Warnings cover Risks, Contraindications, and Adverse Effects- Pharmacodynamics
- Not Available
- Mechanism of action
Target Actions Organism UCytochrome P450 2A6 Not Available Humans - Absorption
- Not Available
- Volume of distribution
- Not Available
- Protein binding
- Not Available
- Metabolism
Hover over products below to view reaction partners
- Route of elimination
- Not Available
- Half-life
- Not Available
- Clearance
- Not Available
- Adverse Effects
Reduce medical errorsand improve treatment outcomes with our comprehensive & structured data on drug adverse effects.Reduce medical errors & improve treatment outcomes with our adverse effects data- Toxicity
- Not Available
- Affected organisms
- 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 softwareAbatacept The metabolism of Coumarin can be increased when combined with Abatacept. Abciximab The risk or severity of bleeding can be increased when Abciximab is combined with Coumarin. Abiraterone The metabolism of Coumarin can be decreased when combined with Abiraterone. Aceclofenac The risk or severity of bleeding and hemorrhage can be increased when Aceclofenac is combined with Coumarin. Acemetacin The risk or severity of bleeding and hemorrhage can be increased when Acemetacin is combined with Coumarin. Acenocoumarol The metabolism of Acenocoumarol can be decreased when combined with Coumarin. Acetaminophen Acetaminophen may increase the anticoagulant activities of Coumarin. Acetic acid The risk or severity of bleeding can be increased when Acetic acid is combined with Coumarin. Acetohexamide Acetohexamide may increase the anticoagulant activities of Coumarin. Acetyl sulfisoxazole The risk or severity of bleeding can be increased when Acetyl sulfisoxazole is combined with Coumarin. 
Improve patient outcomesBuild effective decision support tools with the industry’s most comprehensive drug-drug interaction checker.Learn more - Food Interactions
- Avoid herbs and supplements with anticoagulant/antiplatelet activity. Examples include garlic, ginger, bilberry, danshen, piracetam, and ginkgo biloba.
- Ensure consistent Vitamin K intake.
Categories
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This 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).
- Kingdom
- Organic compounds
- Super Class
- Phenylpropanoids and polyketides
- Class
- Coumarins and derivatives
- Sub Class
- Not Available
- Direct Parent
- Coumarins and derivatives
- Alternative Parents
- 1-benzopyrans / Pyranones and derivatives / Benzenoids / Heteroaromatic compounds / Lactones / Oxacyclic compounds / Organooxygen compounds / Organic oxides / Hydrocarbon derivatives
- Substituents
- 1-benzopyran / Aromatic heteropolycyclic compound / Benzenoid / Benzopyran / Coumarin / Heteroaromatic compound / Hydrocarbon derivative / Lactone / Organic oxide / Organic oxygen compound
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- coumarins (CHEBI:28794) / coumarins, Phenylpropanoids (C05851) / a coumarin (COUMARIN)
Chemical Identifiers
- UNII
- A4VZ22K1WT
- CAS number
- 91-64-5
- InChI Key
- ZYGHJZDHTFUPRJ-UHFFFAOYSA-N
- InChI
- InChI=1S/C9H6O2/c10-9-6-5-7-3-1-2-4-8(7)11-9/h1-6H
- IUPAC Name
- 2H-chromen-2-one
- SMILES
- O=C1OC2=CC=CC=C2C=C1
References
- Synthesis Reference
Ernst-Christian Witte, Peter Neubert, Androniki Roesch, "2H-1-benzopyran-2-one derivatives, processes for the preparation thereof and pharmaceutical compositions containing them." U.S. Patent US4670439, issued May, 1974.
US4670439- General References
- Not Available
- External Links
- Human Metabolome Database
- HMDB0001218
- KEGG Compound
- C05851
- PubChem Compound
- 323
- PubChem Substance
- 46509134
- ChemSpider
- 13848793
- BindingDB
- 12342
- 2898
- ChEBI
- 28794
- ChEMBL
- CHEMBL6466
- ZINC
- ZINC000000074709
- PharmGKB
- PA134521193
- PDBe Ligand
- COU
- Wikipedia
- Coumarin
- PDB Entries
- 1z10 / 2h90 / 2pmj / 2pwb / 3crb / 3l5m / 3l66 / 3l68 / 4uti / 4utl
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 4 Completed Treatment Chronic Venous Insufficiency (CVI) 1 4 Completed Treatment Deep Vein Thrombosis / Pulmonary Embolism 1 1 Completed Treatment Hypertriglyceridemias 1 Not Available Completed Not Available Stroke, Ischemic 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 1.0 mg/mL ALOGPS logP 1.72 ALOGPS logP 1.78 ChemAxon logS -2.2 ALOGPS pKa (Strongest Basic) -6.9 ChemAxon Physiological Charge 0 ChemAxon Hydrogen Acceptor Count 1 ChemAxon Hydrogen Donor Count 0 ChemAxon Polar Surface Area 26.3 Å2 ChemAxon Rotatable Bond Count 0 ChemAxon Refractivity 41.55 m3·mol-1 ChemAxon Polarizability 14.36 Å3 ChemAxon Number of Rings 2 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter No ChemAxon Veber's Rule Yes ChemAxon MDDR-like Rule No ChemAxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9912 Blood Brain Barrier + 0.9565 Caco-2 permeable + 0.9155 P-glycoprotein substrate Non-substrate 0.6697 P-glycoprotein inhibitor I Non-inhibitor 0.854 P-glycoprotein inhibitor II Non-inhibitor 0.8663 Renal organic cation transporter Non-inhibitor 0.8301 CYP450 2C9 substrate Non-substrate 0.7966 CYP450 2D6 substrate Non-substrate 0.9117 CYP450 3A4 substrate Non-substrate 0.7139 CYP450 1A2 substrate Inhibitor 0.9117 CYP450 2C9 inhibitor Non-inhibitor 0.6943 CYP450 2D6 inhibitor Non-inhibitor 0.9105 CYP450 2C19 inhibitor Non-inhibitor 0.5 CYP450 3A4 inhibitor Non-inhibitor 0.831 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.8115 Ames test Non AMES toxic 0.887 Carcinogenicity Non-carcinogens 0.9412 Biodegradation Ready biodegradable 0.5884 Rat acute toxicity 2.4622 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.8702 hERG inhibition (predictor II) Non-inhibitor 0.9474
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Targets
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Steroid hydroxylase activity
- Specific Function
- Exhibits a high coumarin 7-hydroxylase activity. Can act in the hydroxylation of the anti-cancer drugs cyclophosphamide and ifosphamide. Competent in the metabolic activation of aflatoxin B1. Const...
- Gene Name
- CYP2A6
- Uniprot ID
- P11509
- Uniprot Name
- Cytochrome P450 2A6
- Molecular Weight
- 56501.005 Da
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- Substrate
- General Function
- Steroid 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 oxidizes a variety of structurally un...
- Gene Name
- CYP2C9
- Uniprot ID
- P11712
- Uniprot Name
- Cytochrome P450 2C9
- Molecular Weight
- 55627.365 Da
References
- Daly AK, Rettie AE, Fowler DM, Miners JO: Pharmacogenomics of CYP2C9: Functional and Clinical Considerations. J Pers Med. 2017 Dec 28;8(1). pii: jpm8010001. doi: 10.3390/jpm8010001. [PubMed:29283396]
- Flockhart Table of Drug Interactions [Link]
Drug created on September 11, 2007 17:49 / Updated on July 14, 2020 10:58