Warfarin
Katalognummer:
B611796
CAS-Nummer:
81-81-2
Molekulargewicht:
308.3 g/mol
InChI-Schlüssel:
PJVWKTKQMONHTI-UHFFFAOYSA-N
Achtung:
Nur für Forschungszwecke. Nicht für den menschlichen oder tierärztlichen Gebrauch.
Übersicht
Beschreibung
Warfarin ist ein bekanntes Antikoagulans, das zur Vorbeugung und Behandlung von Blutgerinnseln eingesetzt wird. Es wird häufig Personen verschrieben, bei denen das Risiko besteht, dass sich schädliche Blutgerinnsel bilden, wie z. B. bei Patienten mit Vorhofflimmern, tiefer Venenthrombose oder Lungenembolie . This compound wirkt, indem es die Synthese von Vitamin-K-abhängigen Gerinnungsfaktoren hemmt und so die Gerinnungsfähigkeit des Blutes reduziert .
Wirkmechanismus
Target of Action
Warfarin primarily targets the enzyme Vitamin K Epoxide Reductase (VKOR) . This enzyme plays a crucial role in the vitamin K cycle, which is essential for the synthesis of several clotting factors .
Mode of Action
This compound exerts its anticoagulant effect by antagonizing Vitamin K . It achieves this by inhibiting VKOR , thereby disrupting the vitamin K cycle . This inhibition prevents the reactivation of Vitamin K1, which is essential for the synthesis of biologically active forms of various clotting factors .
Biochemical Pathways
The inhibition of VKOR by this compound leads to a decrease in the plasma concentrations of Vitamin K-dependent clotting factors, including Factors II, VII, IX, and X , as well as the regulatory proteins C and S . This results in a reduced ability of the blood to clot, thereby exerting an anticoagulant effect .
Pharmacokinetics
This compound is essentially completely absorbed, reaching a maximum plasma concentration between 2 and 6 hours . It distributes into a small volume of distribution (10 L/70kg) and is eliminated by hepatic metabolism with a very small clearance (0.2 L/h/70kg) . The elimination half-life is about 35 hours . This compound is approximately 99% bound to the plasma protein albumin, which leads to its relatively low volume of distribution .
Result of Action
The primary result of this compound’s action is a decrease in the blood’s ability to clot . This is achieved by reducing the concentrations of active clotting factors in the blood .
Action Environment
The action of this compound can be influenced by various environmental factors. For instance, dietary intake of Vitamin K can affect the efficacy of this compound, as Vitamin K can counteract this compound’s mechanism of action . Additionally, numerous drug interactions can either increase or decrease this compound’s effectiveness . Therefore, the dose of this compound must be carefully monitored and adjusted based on periodic blood tests .
Biochemische Analyse
Biochemical Properties
Warfarin’s biotransformation is a complex process involving over nine different metabolites . It interacts with cytochrome P450 2C (Cyp2c) enzymes, which are instrumental in the biotransformation of this compound to its 7-hydroxylated metabolite .
Cellular Effects
This compound alters vitamin K metabolism, which has significant consequences as vitamin K-dependent (VKD) proteins function in numerous physiologies in many tissues . These proteins may be poorly carboxylated and dysfunctional if the second activity is not ubiquitously expressed similar to VKORC1 .
Molecular Mechanism
This compound inhibits the vitamin K oxidoreductase (VKORC1), which generates vitamin K hydroquinone (KH 2) required for the carboxylation and consequent activation of VKD proteins . This compound uncouples the 2 reactions that fully reduce KO .
Temporal Effects in Laboratory Settings
It is known that this compound’s metabolism involves a rate-limiting step in the biotransformation of this compound to its 7-hydroxylated metabolite .
Dosage Effects in Animal Models
It is known that this compound’s metabolism is a complex process involving over nine different metabolites .
Metabolic Pathways
This compound is involved in the metabolic pathway of vitamin K. It inhibits VKORC1, which generates KH 2 required for the carboxylation and consequent activation of VKD proteins .
Transport and Distribution
It is known that this compound interacts with Cyp2c enzymes during its metabolism .
Subcellular Localization
This compound and VKORC1 both reside in the endoplasmic reticulum and mediate VKD protein modification during secretion
Vorbereitungsmethoden
Synthesewege und Reaktionsbedingungen
Warfarin kann durch verschiedene Verfahren synthetisiert werden. Ein gängiger Syntheseweg beinhaltet die Kondensation von 4-Hydroxycumarin mit Benzylidenaceton unter basischen Bedingungen . Die Reaktion verwendet typischerweise Natriumhydroxid als Base und Ethanol als Lösungsmittel. Das Produkt wird dann durch Umkristallisation gereinigt.
Industrielle Produktionsverfahren
Die industrielle Produktion von this compound beinhaltet die großtechnische Synthese unter Verwendung ähnlicher Verfahren wie im Labormaßstab. Der Prozess wird auf Ausbeute und Reinheit optimiert und beinhaltet oft kontinuierliche Durchflussreaktoren und fortschrittliche Reinigungstechniken . Das Endprodukt wird für die medizinische Verwendung zu Tabletten oder injizierbaren Lösungen verarbeitet.
Analyse Chemischer Reaktionen
Arten von Reaktionen
Warfarin unterliegt verschiedenen chemischen Reaktionen, darunter Oxidations-, Reduktions- und Substitutionsreaktionen .
Häufige Reagenzien und Bedingungen
Oxidation: this compound kann mit Reagenzien wie Kaliumpermanganat oder Wasserstoffperoxid unter sauren Bedingungen oxidiert werden.
Reduktion: Die Reduktion von this compound kann mit Reduktionsmitteln wie Natriumborhydrid oder Lithiumaluminiumhydrid erreicht werden.
Hauptprodukte
Die Hauptprodukte, die aus diesen Reaktionen gebildet werden, hängen von den spezifischen Reagenzien und Bedingungen ab, die verwendet werden. So kann die Oxidation von this compound zur Bildung von Chinonen führen, während die Reduktion Hydroxyderivate liefern kann .
Wissenschaftliche Forschungsanwendungen
This compound hat ein breites Spektrum an wissenschaftlichen Forschungsanwendungen:
Industrie: Im Agrarsektor wird this compound als Rodentizid zur Kontrolle von Nagetierpopulationen eingesetzt.
Wirkmechanismus
This compound übt seine antikoagulatorische Wirkung aus, indem es das Enzym Vitamin-K-Epoxid-Reduktase hemmt . Dieses Enzym ist für die Umwandlung von Vitamin-K-Epoxid zurück in seine aktive Form, Vitamin-K-Hydrochinon, verantwortlich. Durch die Blockierung dieser Umwandlung reduziert this compound den Gehalt an aktivem Vitamin K, was zu einer verminderten Synthese von Vitamin-K-abhängigen Gerinnungsfaktoren (II, VII, IX und X) führt . Dies führt zu einer verminderten Blutgerinnungsfähigkeit.
Wissenschaftliche Forschungsanwendungen
Warfarin has a wide range of scientific research applications:
Vergleich Mit ähnlichen Verbindungen
Warfarin wird häufig mit anderen Antikoagulanzien verglichen, insbesondere mit direkten oralen Antikoagulanzien (DOACs) wie Apixaban, Dabigatran und Rivaroxaban . Im Gegensatz zu this compound, das Vitamin-K-abhängige Gerinnungsfaktoren hemmt, hemmen DOACs direkt bestimmte Gerinnungsfaktoren (z. B. Faktor Xa oder Thrombin) . Dieser Unterschied im Mechanismus macht DOACs schneller wirksam und weniger abhängig von Ernährungsfaktoren, aber sie können auch andere Nebenwirkungsprofile haben .
Ähnliche Verbindungen
Apixaban: Direkter Faktor-Xa-Hemmer.
Dabigatran: Direkter Thrombin-Hemmer.
Rivaroxaban: Direkter Faktor-Xa-Hemmer.
This compound bleibt aufgrund seiner langen Anwendungsgeschichte, der etablierten Überwachungsprotokolle und seiner Rolle bei Patienten mit bestimmten Erkrankungen, bei denen DOACs möglicherweise nicht geeignet sind, einzigartig .
Eigenschaften
IUPAC Name |
4-hydroxy-3-(3-oxo-1-phenylbutyl)chromen-2-one |
Source
|
|---|---|---|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
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 |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
InChI Key |
PJVWKTKQMONHTI-UHFFFAOYSA-N |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
Canonical SMILES |
CC(=O)CC(C1=CC=CC=C1)C2=C(C3=CC=CC=C3OC2=O)O |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
Molecular Formula |
C19H16O4 |
Source
|
| Record name | WARFARIN | |
| Source | CAMEO Chemicals | |
| URL | https://cameochemicals.noaa.gov/chemical/5240 | |
| Description | CAMEO Chemicals is a chemical database designed for people who are involved in hazardous material incident response and planning. CAMEO Chemicals contains a library with thousands of datasheets containing response-related information and recommendations for hazardous materials that are commonly transported, used, or stored in the United States. CAMEO Chemicals was developed by the National Oceanic and Atmospheric Administration's Office of Response and Restoration in partnership with the Environmental Protection Agency's Office of Emergency Management. | |
| Explanation | CAMEO Chemicals and all other CAMEO products are available at no charge to those organizations and individuals (recipients) responsible for the safe handling of chemicals. However, some of the chemical data itself is subject to the copyright restrictions of the companies or organizations that provided the data. | |
| Record name | WARFARIN | |
| Source | ILO-WHO International Chemical Safety Cards (ICSCs) | |
| URL | https://www.ilo.org/dyn/icsc/showcard.display?p_version=2&p_card_id=0821 | |
| Description | The International Chemical Safety Cards (ICSCs) are data sheets intended to provide essential safety and health information on chemicals in a clear and concise way. The primary aim of the Cards is to promote the safe use of chemicals in the workplace. | |
| Explanation | Creative Commons CC BY 4.0 | |
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
DSSTOX Substance ID |
DTXSID5023742 |
Source
|
| Record name | Warfarin | |
| Source | EPA DSSTox | |
| URL | https://comptox.epa.gov/dashboard/DTXSID5023742 | |
| Description | DSSTox provides a high quality public chemistry resource for supporting improved predictive toxicology. | |
Molecular Weight |
308.3 g/mol |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
Physical Description |
Warfarin is an odorless and colorless solid. Used as a rodenticide for Norway rats and for house mice. (EPA, 1998), Colorless, odorless, crystalline powder. [rodenticide]; [NIOSH], Solid, COLOURLESS-TO-WHITE POWDER., Colorless, odorless, crystalline powder or solid., Colorless, odorless, crystalline powder. [Note: Rodenticide.] |
Source
|
| Record name | WARFARIN | |
| Source | CAMEO Chemicals | |
| URL | https://cameochemicals.noaa.gov/chemical/5240 | |
| Description | CAMEO Chemicals is a chemical database designed for people who are involved in hazardous material incident response and planning. CAMEO Chemicals contains a library with thousands of datasheets containing response-related information and recommendations for hazardous materials that are commonly transported, used, or stored in the United States. CAMEO Chemicals was developed by the National Oceanic and Atmospheric Administration's Office of Response and Restoration in partnership with the Environmental Protection Agency's Office of Emergency Management. | |
| Explanation | CAMEO Chemicals and all other CAMEO products are available at no charge to those organizations and individuals (recipients) responsible for the safe handling of chemicals. However, some of the chemical data itself is subject to the copyright restrictions of the companies or organizations that provided the data. | |
| Record name | Warfarin | |
| Source | Haz-Map, Information on Hazardous Chemicals and Occupational Diseases | |
| URL | https://haz-map.com/Agents/673 | |
| Description | Haz-Map® is an occupational health database designed for health and safety professionals and for consumers seeking information about the adverse effects of workplace exposures to chemical and biological agents. | |
| Explanation | Copyright (c) 2022 Haz-Map(R). All rights reserved. Unless otherwise indicated, all materials from Haz-Map are copyrighted by Haz-Map(R). No part of these materials, either text or image may be used for any purpose other than for personal use. Therefore, reproduction, modification, storage in a retrieval system or retransmission, in any form or by any means, electronic, mechanical or otherwise, for reasons other than personal use, is strictly prohibited without prior written permission. | |
| Record name | Warfarin | |
| Source | Human Metabolome Database (HMDB) | |
| URL | http://www.hmdb.ca/metabolites/HMDB0001935 | |
| Description | The Human Metabolome Database (HMDB) is a freely available electronic database containing detailed information about small molecule metabolites found in the human body. | |
| Explanation | HMDB is offered to the public as a freely available resource. Use and re-distribution of the data, in whole or in part, for commercial purposes requires explicit permission of the authors and explicit acknowledgment of the source material (HMDB) and the original publication (see the HMDB citing page). We ask that users who download significant portions of the database cite the HMDB paper in any resulting publications. | |
| Record name | WARFARIN | |
| Source | ILO-WHO International Chemical Safety Cards (ICSCs) | |
| URL | https://www.ilo.org/dyn/icsc/showcard.display?p_version=2&p_card_id=0821 | |
| Description | The International Chemical Safety Cards (ICSCs) are data sheets intended to provide essential safety and health information on chemicals in a clear and concise way. The primary aim of the Cards is to promote the safe use of chemicals in the workplace. | |
| Explanation | Creative Commons CC BY 4.0 | |
| Record name | WARFARIN | |
| Source | Occupational Safety and Health Administration (OSHA) | |
| URL | https://www.osha.gov/chemicaldata/714 | |
| Description | The OSHA Occupational Chemical Database contains over 800 entries with information such as physical properties, exposure guidelines, etc. | |
| Explanation | Materials created by the federal government are generally part of the public domain and may be used, reproduced and distributed without permission. Therefore, content on this website which is in the public domain may be used without the prior permission of the U.S. Department of Labor (DOL). Warning: Some content - including both images and text - may be the copyrighted property of others and used by the DOL under a license. | |
| Record name | Warfarin | |
| Source | The National Institute for Occupational Safety and Health (NIOSH) | |
| URL | https://www.cdc.gov/niosh/npg/npgd0665.html | |
| Description | The NIOSH Pocket Guide to Chemical Hazards is intended as a source of general industrial hygiene information on several hundred chemicals/classes for workers, employers, and occupational health professionals. Read more: https://www.cdc.gov/niosh/npg/ | |
| Explanation | The information provided using CDC Web site is only intended to be general summary information to the public. It is not intended to take the place of either the written law or regulations. | |
Boiling Point |
Decomposes (NIOSH, 2023), decomposes, Decomposes |
Source
|
| Record name | WARFARIN | |
| Source | CAMEO Chemicals | |
| URL | https://cameochemicals.noaa.gov/chemical/5240 | |
| Description | CAMEO Chemicals is a chemical database designed for people who are involved in hazardous material incident response and planning. CAMEO Chemicals contains a library with thousands of datasheets containing response-related information and recommendations for hazardous materials that are commonly transported, used, or stored in the United States. CAMEO Chemicals was developed by the National Oceanic and Atmospheric Administration's Office of Response and Restoration in partnership with the Environmental Protection Agency's Office of Emergency Management. | |
| Explanation | CAMEO Chemicals and all other CAMEO products are available at no charge to those organizations and individuals (recipients) responsible for the safe handling of chemicals. However, some of the chemical data itself is subject to the copyright restrictions of the companies or organizations that provided the data. | |
| Record name | WARFARIN | |
| Source | Occupational Safety and Health Administration (OSHA) | |
| URL | https://www.osha.gov/chemicaldata/714 | |
| Description | The OSHA Occupational Chemical Database contains over 800 entries with information such as physical properties, exposure guidelines, etc. | |
| Explanation | Materials created by the federal government are generally part of the public domain and may be used, reproduced and distributed without permission. Therefore, content on this website which is in the public domain may be used without the prior permission of the U.S. Department of Labor (DOL). Warning: Some content - including both images and text - may be the copyrighted property of others and used by the DOL under a license. | |
| Record name | Warfarin | |
| Source | The National Institute for Occupational Safety and Health (NIOSH) | |
| URL | https://www.cdc.gov/niosh/npg/npgd0665.html | |
| Description | The NIOSH Pocket Guide to Chemical Hazards is intended as a source of general industrial hygiene information on several hundred chemicals/classes for workers, employers, and occupational health professionals. Read more: https://www.cdc.gov/niosh/npg/ | |
| Explanation | The information provided using CDC Web site is only intended to be general summary information to the public. It is not intended to take the place of either the written law or regulations. | |
Solubility |
0.002 % (NIOSH, 2023), Solubility: 1 g in 1.5 mL water, 1.9 mL alcohol, >10,000 mL chloroform, >10,000 mL ether /Warfarin potassium/, In water, 17 mg/L at 20 °C, Soluble in acetone, dioxane; moderately soluble in methanol, ethanol, isopropanol, some oils; freely soluble in alkaline aqueous solution (forms a water-sol sodium salt); practically insoluble in benzene, cyclohexane, Skellysolves A and B., In acetone 65, chloroform 56, dioxane 100 (all in g/L, 20 °C), 0.017 mg/mL at 20 °C, Solubility in water, g/100ml at 20 °C: 0.0017 (very poor), 0.002% |
Source
|
| Record name | WARFARIN | |
| Source | CAMEO Chemicals | |
| URL | https://cameochemicals.noaa.gov/chemical/5240 | |
| Description | CAMEO Chemicals is a chemical database designed for people who are involved in hazardous material incident response and planning. CAMEO Chemicals contains a library with thousands of datasheets containing response-related information and recommendations for hazardous materials that are commonly transported, used, or stored in the United States. CAMEO Chemicals was developed by the National Oceanic and Atmospheric Administration's Office of Response and Restoration in partnership with the Environmental Protection Agency's Office of Emergency Management. | |
| Explanation | CAMEO Chemicals and all other CAMEO products are available at no charge to those organizations and individuals (recipients) responsible for the safe handling of chemicals. However, some of the chemical data itself is subject to the copyright restrictions of the companies or organizations that provided the data. | |
| Record name | Warfarin | |
| Source | DrugBank | |
| URL | https://www.drugbank.ca/drugs/DB00682 | |
| Description | The DrugBank database is a unique bioinformatics and cheminformatics resource that combines detailed drug (i.e. chemical, pharmacological and pharmaceutical) data with comprehensive drug target (i.e. sequence, structure, and pathway) information. | |
| Explanation | Creative Common's Attribution-NonCommercial 4.0 International License (http://creativecommons.org/licenses/by-nc/4.0/legalcode) | |
| Record name | WARFARIN | |
| Source | Hazardous Substances Data Bank (HSDB) | |
| URL | https://pubchem.ncbi.nlm.nih.gov/source/hsdb/1786 | |
| Description | The Hazardous Substances Data Bank (HSDB) is a toxicology database that focuses on the toxicology of potentially hazardous chemicals. It provides information on human exposure, industrial hygiene, emergency handling procedures, environmental fate, regulatory requirements, nanomaterials, and related areas. The information in HSDB has been assessed by a Scientific Review Panel. | |
| Record name | Warfarin | |
| Source | Human Metabolome Database (HMDB) | |
| URL | http://www.hmdb.ca/metabolites/HMDB0001935 | |
| Description | The Human Metabolome Database (HMDB) is a freely available electronic database containing detailed information about small molecule metabolites found in the human body. | |
| Explanation | HMDB is offered to the public as a freely available resource. Use and re-distribution of the data, in whole or in part, for commercial purposes requires explicit permission of the authors and explicit acknowledgment of the source material (HMDB) and the original publication (see the HMDB citing page). We ask that users who download significant portions of the database cite the HMDB paper in any resulting publications. | |
| Record name | WARFARIN | |
| Source | ILO-WHO International Chemical Safety Cards (ICSCs) | |
| URL | https://www.ilo.org/dyn/icsc/showcard.display?p_version=2&p_card_id=0821 | |
| Description | The International Chemical Safety Cards (ICSCs) are data sheets intended to provide essential safety and health information on chemicals in a clear and concise way. The primary aim of the Cards is to promote the safe use of chemicals in the workplace. | |
| Explanation | Creative Commons CC BY 4.0 | |
| Record name | Warfarin | |
| Source | The National Institute for Occupational Safety and Health (NIOSH) | |
| URL | https://www.cdc.gov/niosh/npg/npgd0665.html | |
| Description | The NIOSH Pocket Guide to Chemical Hazards is intended as a source of general industrial hygiene information on several hundred chemicals/classes for workers, employers, and occupational health professionals. Read more: https://www.cdc.gov/niosh/npg/ | |
| Explanation | The information provided using CDC Web site is only intended to be general summary information to the public. It is not intended to take the place of either the written law or regulations. | |
Density |
Relative density (water = 1): 1.4 |
Source
|
| Record name | WARFARIN | |
| Source | ILO-WHO International Chemical Safety Cards (ICSCs) | |
| URL | https://www.ilo.org/dyn/icsc/showcard.display?p_version=2&p_card_id=0821 | |
| Description | The International Chemical Safety Cards (ICSCs) are data sheets intended to provide essential safety and health information on chemicals in a clear and concise way. The primary aim of the Cards is to promote the safe use of chemicals in the workplace. | |
| Explanation | Creative Commons CC BY 4.0 | |
Vapor Density |
Relative vapor density (air = 1): 10.6 |
Source
|
| Record name | WARFARIN | |
| Source | ILO-WHO International Chemical Safety Cards (ICSCs) | |
| URL | https://www.ilo.org/dyn/icsc/showcard.display?p_version=2&p_card_id=0821 | |
| Description | The International Chemical Safety Cards (ICSCs) are data sheets intended to provide essential safety and health information on chemicals in a clear and concise way. The primary aim of the Cards is to promote the safe use of chemicals in the workplace. | |
| Explanation | Creative Commons CC BY 4.0 | |
Vapor Pressure |
0.09 mmHg at 71 °F (NIOSH, 2023), 0.09 [mmHg], 1.5X10-3 mPa /1.125X10-8 mm Hg/ at 25 °C, Vapor pressure, Pa at 20 °C: (negligible), 0.09 mmHg at 71 °F, (71 °F): 0.09 mmHg |
Source
|
| Record name | WARFARIN | |
| Source | CAMEO Chemicals | |
| URL | https://cameochemicals.noaa.gov/chemical/5240 | |
| Description | CAMEO Chemicals is a chemical database designed for people who are involved in hazardous material incident response and planning. CAMEO Chemicals contains a library with thousands of datasheets containing response-related information and recommendations for hazardous materials that are commonly transported, used, or stored in the United States. CAMEO Chemicals was developed by the National Oceanic and Atmospheric Administration's Office of Response and Restoration in partnership with the Environmental Protection Agency's Office of Emergency Management. | |
| Explanation | CAMEO Chemicals and all other CAMEO products are available at no charge to those organizations and individuals (recipients) responsible for the safe handling of chemicals. However, some of the chemical data itself is subject to the copyright restrictions of the companies or organizations that provided the data. | |
| Record name | Warfarin | |
| Source | Haz-Map, Information on Hazardous Chemicals and Occupational Diseases | |
| URL | https://haz-map.com/Agents/673 | |
| Description | Haz-Map® is an occupational health database designed for health and safety professionals and for consumers seeking information about the adverse effects of workplace exposures to chemical and biological agents. | |
| Explanation | Copyright (c) 2022 Haz-Map(R). All rights reserved. Unless otherwise indicated, all materials from Haz-Map are copyrighted by Haz-Map(R). No part of these materials, either text or image may be used for any purpose other than for personal use. Therefore, reproduction, modification, storage in a retrieval system or retransmission, in any form or by any means, electronic, mechanical or otherwise, for reasons other than personal use, is strictly prohibited without prior written permission. | |
| Record name | WARFARIN | |
| Source | Hazardous Substances Data Bank (HSDB) | |
| URL | https://pubchem.ncbi.nlm.nih.gov/source/hsdb/1786 | |
| Description | The Hazardous Substances Data Bank (HSDB) is a toxicology database that focuses on the toxicology of potentially hazardous chemicals. It provides information on human exposure, industrial hygiene, emergency handling procedures, environmental fate, regulatory requirements, nanomaterials, and related areas. The information in HSDB has been assessed by a Scientific Review Panel. | |
| Record name | WARFARIN | |
| Source | ILO-WHO International Chemical Safety Cards (ICSCs) | |
| URL | https://www.ilo.org/dyn/icsc/showcard.display?p_version=2&p_card_id=0821 | |
| Description | The International Chemical Safety Cards (ICSCs) are data sheets intended to provide essential safety and health information on chemicals in a clear and concise way. The primary aim of the Cards is to promote the safe use of chemicals in the workplace. | |
| Explanation | Creative Commons CC BY 4.0 | |
| Record name | WARFARIN | |
| Source | Occupational Safety and Health Administration (OSHA) | |
| URL | https://www.osha.gov/chemicaldata/714 | |
| Description | The OSHA Occupational Chemical Database contains over 800 entries with information such as physical properties, exposure guidelines, etc. | |
| Explanation | Materials created by the federal government are generally part of the public domain and may be used, reproduced and distributed without permission. Therefore, content on this website which is in the public domain may be used without the prior permission of the U.S. Department of Labor (DOL). Warning: Some content - including both images and text - may be the copyrighted property of others and used by the DOL under a license. | |
| Record name | Warfarin | |
| Source | The National Institute for Occupational Safety and Health (NIOSH) | |
| URL | https://www.cdc.gov/niosh/npg/npgd0665.html | |
| Description | The NIOSH Pocket Guide to Chemical Hazards is intended as a source of general industrial hygiene information on several hundred chemicals/classes for workers, employers, and occupational health professionals. Read more: https://www.cdc.gov/niosh/npg/ | |
| Explanation | The information provided using CDC Web site is only intended to be general summary information to the public. It is not intended to take the place of either the written law or regulations. | |
Mechanism of Action |
Warfarin is a [vitamin K] antagonist which acts to inhibit the production of vitamin K by vitamin K epoxide reductase. The reduced form of vitamin K, vitamin KH2 is a cofactor used in the γ-carboxylation of coagulation factors VII, IX, X, and thrombin. Carboxylation induces a conformational change allowing the factors to bind Ca2+ and to phospholipid surfaces. Uncarboxylated factors VII, IX, X, and thrombin are biologically inactive and therefore serve to interrupt the coagulation cascade. The endogenous anticoagulation proteins C and S also require γ-carboxylation to function. This is particularly true in the case of thrombin which must be activated in order to form a thrombus. vitamin KH2 is converted to vitamin K epoxide as part of the γ-carboxylation reaction catalyzed by γ-glutamyl carboxylase. Vitamin K epoxide is then converted to vitamin K1 by vitamin K epoxide reductase then back to vitamin KH2 by vitamin K reductase. Warfarin binds to vitamin K epoxide reductase complex subunit 1 and irreversibly inhibits the enzyme thereby stopping the recycling of vitamin K by preventing the conversion of vitamin K epoxide to vitamin K1. This process creates a hypercoagulable state for a short time as proteins C and S degrade first with half lives of 8 and 24 hours, with the exception of factor VII which has a half life of 6 hours. Factors IX, X, and finally thrombin degrade later with half lives of 24, 36, and 50 hours resulting in a dominant anticoagulation effect. In order to reverse this anticoagulation vitamin K must be supplied, either exogenously or by removal of the vitamin K epoxide reductase inhibition, and time allowed for new coagulation factors to be synthesized. It takes approximately 2 days for new coagulation factors to be synthesized in the liver. Vitamin K2, functionally identical to vitamin K1, is synthesized by gut bacteria leading to interactions with antibiotics as elimination of these bacteria can reduce vitamin K2 |
Source
|
| Record name | Warfarin | |
| Source | DrugBank | |
| URL | https://www.drugbank.ca/drugs/DB00682 | |
| Description | The DrugBank database is a unique bioinformatics and cheminformatics resource that combines detailed drug (i.e. chemical, pharmacological and pharmaceutical) data with comprehensive drug target (i.e. sequence, structure, and pathway) information. | |
| Explanation | Creative Common's Attribution-NonCommercial 4.0 International License (http://creativecommons.org/licenses/by-nc/4.0/legalcode) | |
| Record name | WARFARIN | |
| Source | Hazardous Substances Data Bank (HSDB) | |
| URL | https://pubchem.ncbi.nlm.nih.gov/source/hsdb/1786 | |
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Color/Form |
Crystals from alcohol, White powder, The racemate forms colorless crystals | |
CAS No. |
81-81-2 |
Source
|
| Record name | WARFARIN | |
| Source | CAMEO Chemicals | |
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| Record name | (±)-Warfarin | |
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| Record name | Warfarin [INN:BAN] | |
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| Record name | Warfarin | |
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| Record name | warfarin | |
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| Record name | warfarin | |
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| Record name | 2H-1-Benzopyran-2-one, 4-hydroxy-3-(3-oxo-1-phenylbutyl)- | |
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| Record name | Warfarin | |
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| Record name | Warfarin | |
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| Record name | WARFARIN | |
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| Record name | WARFARIN | |
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| URL | https://pubchem.ncbi.nlm.nih.gov/source/hsdb/1786 | |
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| Record name | Warfarin | |
| Source | Human Metabolome Database (HMDB) | |
| URL | http://www.hmdb.ca/metabolites/HMDB0001935 | |
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| Record name | WARFARIN | |
| Source | ILO-WHO International Chemical Safety Cards (ICSCs) | |
| URL | https://www.ilo.org/dyn/icsc/showcard.display?p_version=2&p_card_id=0821 | |
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| Record name | WARFARIN | |
| Source | Occupational Safety and Health Administration (OSHA) | |
| URL | https://www.osha.gov/chemicaldata/714 | |
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| Record name | Coumarin, 3-(alpha-acetonylbenzyl)-4-hydroxy- | |
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| URL | https://www.cdc.gov/niosh-rtecs/GN456D70.html | |
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Melting Point |
322 °F (EPA, 1998), 161 °C, 322 °F |
Source
|
| Record name | WARFARIN | |
| Source | CAMEO Chemicals | |
| URL | https://cameochemicals.noaa.gov/chemical/5240 | |
| Description | CAMEO Chemicals is a chemical database designed for people who are involved in hazardous material incident response and planning. CAMEO Chemicals contains a library with thousands of datasheets containing response-related information and recommendations for hazardous materials that are commonly transported, used, or stored in the United States. CAMEO Chemicals was developed by the National Oceanic and Atmospheric Administration's Office of Response and Restoration in partnership with the Environmental Protection Agency's Office of Emergency Management. | |
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| Record name | Warfarin | |
| Source | DrugBank | |
| URL | https://www.drugbank.ca/drugs/DB00682 | |
| Description | The DrugBank database is a unique bioinformatics and cheminformatics resource that combines detailed drug (i.e. chemical, pharmacological and pharmaceutical) data with comprehensive drug target (i.e. sequence, structure, and pathway) information. | |
| Explanation | Creative Common's Attribution-NonCommercial 4.0 International License (http://creativecommons.org/licenses/by-nc/4.0/legalcode) | |
| Record name | WARFARIN | |
| Source | Hazardous Substances Data Bank (HSDB) | |
| URL | https://pubchem.ncbi.nlm.nih.gov/source/hsdb/1786 | |
| Description | The Hazardous Substances Data Bank (HSDB) is a toxicology database that focuses on the toxicology of potentially hazardous chemicals. It provides information on human exposure, industrial hygiene, emergency handling procedures, environmental fate, regulatory requirements, nanomaterials, and related areas. The information in HSDB has been assessed by a Scientific Review Panel. | |
| Record name | Warfarin | |
| Source | Human Metabolome Database (HMDB) | |
| URL | http://www.hmdb.ca/metabolites/HMDB0001935 | |
| Description | The Human Metabolome Database (HMDB) is a freely available electronic database containing detailed information about small molecule metabolites found in the human body. | |
| Explanation | HMDB is offered to the public as a freely available resource. Use and re-distribution of the data, in whole or in part, for commercial purposes requires explicit permission of the authors and explicit acknowledgment of the source material (HMDB) and the original publication (see the HMDB citing page). We ask that users who download significant portions of the database cite the HMDB paper in any resulting publications. | |
| Record name | WARFARIN | |
| Source | ILO-WHO International Chemical Safety Cards (ICSCs) | |
| URL | https://www.ilo.org/dyn/icsc/showcard.display?p_version=2&p_card_id=0821 | |
| Description | The International Chemical Safety Cards (ICSCs) are data sheets intended to provide essential safety and health information on chemicals in a clear and concise way. The primary aim of the Cards is to promote the safe use of chemicals in the workplace. | |
| Explanation | Creative Commons CC BY 4.0 | |
| Record name | WARFARIN | |
| Source | Occupational Safety and Health Administration (OSHA) | |
| URL | https://www.osha.gov/chemicaldata/714 | |
| Description | The OSHA Occupational Chemical Database contains over 800 entries with information such as physical properties, exposure guidelines, etc. | |
| Explanation | Materials created by the federal government are generally part of the public domain and may be used, reproduced and distributed without permission. Therefore, content on this website which is in the public domain may be used without the prior permission of the U.S. Department of Labor (DOL). Warning: Some content - including both images and text - may be the copyrighted property of others and used by the DOL under a license. | |
| Record name | Warfarin | |
| Source | The National Institute for Occupational Safety and Health (NIOSH) | |
| URL | https://www.cdc.gov/niosh/npg/npgd0665.html | |
| Description | The NIOSH Pocket Guide to Chemical Hazards is intended as a source of general industrial hygiene information on several hundred chemicals/classes for workers, employers, and occupational health professionals. Read more: https://www.cdc.gov/niosh/npg/ | |
| Explanation | The information provided using CDC Web site is only intended to be general summary information to the public. It is not intended to take the place of either the written law or regulations. | |
Synthesis routes and methods I
Procedure details
Control, blank, and experimental reaction mixtures were made for each experiment. Control and blank reaction mixtures were made up with vitamin K and without vitamin K, respectively. Experimental reaction mixtures contained both vitamin K and a vitamin K antagonist. The control reaction mixture contained 3.00 ml of microsomal suspension, 0.81 ml of buffer II, 1.20 ml of an ATP-generating system (final concentrations: 1 mM ATP, 10 mM phosphocreatine, 2.5 mM Mg[acetate]2 ·4H2O, 20 μg/ml creatine phosphokinase [52 U/ml]), 0.60 ml of NADH (final concentration 2 mM), 0.30 ml of dithiothreitol (final concentration 7 mM) dissolved in buffer II, 0.060 ml of NaH14CO3 (1.0 μCi/μl; added 0.5 min prior to reaction initiation), and at the time of reaction initiation 0.030 ml of vitamin K1 (final concentration 20 μg/ml) diluted in 0.85% sodium chloride solution. This vitamin K concentration is associated with maximal in vitro incorporation of added H14CO3 into vitamin K-dependent substrate proteins (J. Biol. Chem. 251, 2770-2776). The blank reaction mixture consisted of the same components except that vitamin K was replaced by an equal volume of isotonic saline. The experimental reaction mixtures were made up in the same way as the control reaction mixtures with the exceptions that: (1) a volume of buffer II was replaced by a volume of buffer II containing an inhibitor of vitamin K-dependent carboxylation, and (2) all individual volumes were two-thirds of those in the control reaction mixtures. The sodium salts of TCP, phenindione, and warfarin were formed in aqueous sodium hydroxide solution (J. Am. Chem. Soc. 83, 2676-2679) and were freely soluble in buffer II at all concentrations used in these studies. Chloro-K1 was formulated as an oil-in-water emulsion with Tween 80 (5% v/v final concentration), while chloro-K3 was formulated as a suspension in Tween 80 (5% v/v final concentration) (Molecular Pharmacology 10, 373-380).
[Compound]
Name
vitamin K
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Three
[Compound]
Name
( 1 )
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Four
[Compound]
Name
II
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Five
[Compound]
Name
II
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Six
[Compound]
Name
vitamin K
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Seven
[Compound]
Name
( 2 )
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Seven
[Compound]
Name
vitamin K
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Nine
[Compound]
Name
vitamin K
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Ten
[Compound]
Name
vitamin K
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Eleven
[Compound]
Name
vitamin K
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Twelve
[Compound]
Name
microsomal suspension
Quantity
3 mL
Type
reactant
Reaction Step Thirteen
[Compound]
Name
II
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Fourteen
Name
Name
Name
Synthesis routes and methods II
Procedure details
To show that non-binding compounds do not significantly influence the FT-IR spectrum of a biological macromolecule when mixed with the biological macromolecule, 3 μg of NMT was mixed with 10 μg each of Bacitracin (trace 1), Erythromycin (2), Fusidic Acid (3) and a fungal extract (4) and a differential FT-IR spectrum of each sample was obtained (FIG. 3). The non-binding compounds did not alter the spectrum of NMT. However, a nonspecific binding compound, Warfarin (60 μg), did produce a detectable peak shift for NMT.
Name
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