(S)-Warfarin
This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.
Identification
- Generic Name
- (S)-Warfarin
- DrugBank Accession Number
- DB14055
- Background
Warfarin consists of a racemic mixture of two active enantiomers—R- and S- forms—each of which is cleared by different pathways. S-warfarin is 2-5 times more potent than the R-isomer in producing an anticoagulant response.1
- Type
- Small Molecule
- Groups
- Experimental, Investigational
- Structure
Structure for (S)-Warfarin (DB14055)
- Weight
- Average: 308.3279
Monoisotopic: 308.104859 - Chemical Formula
- C19H16O4
- Synonyms
- (-)-Warfarin
- (S)-4-Hydroxy-3-(3-oxo-1-phenylbutyl)-2-benzopyrone
- 4-hydroxy-3-[(1S)-3-oxo-1-phenylbutyl]-2H-chromen-2-one
- Levrowarfarin
- S-Warfarin
Pharmacology
- Indication
Not Available
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Avoid life-threatening adverse drug eventsImprove clinical decision support with information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events & improve clinical decision support.- 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.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 (S)-Warfarin can be increased when it is combined with Abametapir. Abatacept The metabolism of (S)-Warfarin can be increased when combined with Abatacept. Abciximab The risk or severity of bleeding can be increased when Abciximab is combined with (S)-Warfarin. Abiraterone The serum concentration of (S)-Warfarin can be increased when it is combined with Abiraterone. Acalabrutinib The serum concentration of (S)-Warfarin can be increased when it is combined with Acalabrutinib. Aceclofenac The risk or severity of bleeding and hemorrhage can be increased when Aceclofenac is combined with (S)-Warfarin. Acemetacin The risk or severity of bleeding and hemorrhage can be increased when (S)-Warfarin is combined with Acemetacin. Acenocoumarol The metabolism of Acenocoumarol can be decreased when combined with (S)-Warfarin. Acetaminophen The serum concentration of (S)-Warfarin can be increased when it is combined with Acetaminophen. Acetazolamide The serum concentration of (S)-Warfarin can be increased when it is combined with Acetazolamide. 
Identify potential medication risksEasily compare up to 40 drugs with our drug interaction checker.Get severity rating, description, and management advice.Learn more - Food Interactions
- Avoid drastic dietary changes.
- 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 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 / Benzene and substituted derivatives / Vinylogous acids / Heteroaromatic compounds / Lactones / Ketones / Oxacyclic compounds / Organic oxides / Hydrocarbon derivatives
- Substituents
- 1-benzopyran / 4-hydroxycoumarin / Aromatic heteropolycyclic compound / Benzenoid / Benzopyran / Carbonyl group / Heteroaromatic compound / Hydrocarbon derivative / Ketone / Lactone
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- 4-hydroxy-3-(3-oxo-1-phenylbutyl)-1-benzopyran-2-one (CHEBI:87738)
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- HP31W7FNP4
- CAS number
- 5543-57-7
- InChI Key
- PJVWKTKQMONHTI-HNNXBMFYSA-N
- InChI
- InChI=1S/C19H16O4/c1-12(20)11-15(13-7-3-2-4-8-13)17-18(21)14-9-5-6-10-16(14)23-19(17)22/h2-10,15,21H,11H2,1H3/t15-/m0/s1
- IUPAC Name
- 4-hydroxy-3-[(1S)-3-oxo-1-phenylbutyl]-2H-chromen-2-one
- SMILES
- CC(=O)C[C@@H](C1=CC=CC=C1)C1=C(O)C2=C(OC1=O)C=CC=C2
References
- General References
- Lane S, Al-Zubiedi S, Hatch E, Matthews I, Jorgensen AL, Deloukas P, Daly AK, Park BK, Aarons L, Ogungbenro K, Kamali F, Hughes D, Pirmohamed M: The population pharmacokinetics of R- and S-warfarin: effect of genetic and clinical factors. Br J Clin Pharmacol. 2012 Jan;73(1):66-76. doi: 10.1111/j.1365-2125.2011.04051.x. [Article]
- External Links
- ChemSpider
- 10533327
- ChEBI
- 87738
- ChEMBL
- CHEMBL251074
- ZINC
- ZINC000100006264
- PDBe Ligand
- SWF
- PDB Entries
- 1ha2 / 1og5 / 6wv3 / 6wv4 / 6wvb
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 3 Completed Other Relapsing Remitting Multiple Sclerosis (RRMS) 1 1 Completed Other Tumors, Solid 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 0.0472 mg/mL ALOGPS logP 2.41 ALOGPS logP 2.74 ChemAxon logS -3.8 ALOGPS pKa (Strongest Acidic) 5.56 ChemAxon pKa (Strongest Basic) -6.9 ChemAxon Physiological Charge -1 ChemAxon Hydrogen Acceptor Count 3 ChemAxon Hydrogen Donor Count 1 ChemAxon Polar Surface Area 63.6 Å2 ChemAxon Rotatable Bond Count 4 ChemAxon Refractivity 86.86 m3·mol-1 ChemAxon Polarizability 32.03 Å3 ChemAxon Number of Rings 3 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
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS Not Available Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- 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
- Jones DR, Kim SY, Boysen G, Yun CH, Miller GP: Contribution of three CYP3A isoforms to metabolism of R- and S-warfarin. Drug Metab Lett. 2010 Dec;4(4):213-9. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- 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
- CYP2C8
- Uniprot ID
- P10632
- Uniprot Name
- Cytochrome P450 2C8
- Molecular Weight
- 55824.275 Da
References
- Kaminsky LS, Zhang ZY: Human P450 metabolism of warfarin. Pharmacol Ther. 1997;73(1):67-74. doi: 10.1016/s0163-7258(96)00140-4. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- 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
- Kaminsky LS, Zhang ZY: Human P450 metabolism of warfarin. Pharmacol Ther. 1997;73(1):67-74. doi: 10.1016/s0163-7258(96)00140-4. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- 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
- CYP2C18
- Uniprot ID
- P33260
- Uniprot Name
- Cytochrome P450 2C18
- Molecular Weight
- 55710.075 Da
References
- Kaminsky LS, Zhang ZY: Human P450 metabolism of warfarin. Pharmacol Ther. 1997;73(1):67-74. doi: 10.1016/s0163-7258(96)00140-4. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Steroid hydroxylase activity
- Specific Function
- Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and im...
- Gene Name
- CYP2C19
- Uniprot ID
- P33261
- Uniprot Name
- Cytochrome P450 2C19
- Molecular Weight
- 55930.545 Da
References
- Kim SY, Kang JY, Hartman JH, Park SH, Jones DR, Yun CH, Boysen G, Miller GP: Metabolism of R- and S-warfarin by CYP2C19 into four hydroxywarfarins. Drug Metab Lett. 2012 Sep 1;6(3):157-64. [Article]
Drug created on June 12, 2018 19:35 / Updated on November 06, 2020 02:39