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81-81-2 分子结构
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2-hydroxy-3-(3-oxo-1-phenylbutyl)-4H-chromen-4-one

ChemBase编号:564
分子式:C19H16O4
平均质量:308.32794
单一同位素质量:308.10485899
SMILES和InChIs

SMILES:
o1c(O)c(C(CC(=O)C)c2ccccc2)c(=O)c2c1cccc2
Canonical SMILES:
CC(=O)CC(c1c(O)oc2c(c1=O)cccc2)c1ccccc1
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/h2-10,15,22H,11H2,1H3
InChIKey:
QTXVAVXCBMYBJW-UHFFFAOYSA-N

引用这个纪录

CBID:564 http://www.chembase.cn/molecule-564.html

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名称和登记号

名称和登记号

名称 登记号
IUPAC标准名
2-hydroxy-3-(3-oxo-1-phenylbutyl)-4H-chromen-4-one
IUPAC传统名
rodex
商标名
Warf 42
Warfarat
Warfarin Plus
Warfarin Q
Warfarine
Warficide
Warfilone
Zoocoumarin
Coumadin Tabs
Athrombin
Athrombin-K
Athrombine-K
Brumolin
Co-Rax
Coumadin
Coumafen
Coumafene
Coumaphen
Coumaphene
Coumarins
Coumefene
D-Con
Dethmor
Dethnel
Dicusat E
Frass-Ratron
Jantoven
Kumader
Kumadu
Kumatox
Kypfarin
Latka 42
Mar-Frin
Marevan
Maveran
Panwarfin
Place-Pax
Prothromadin
RAX
Rosex
Sofarin
Solfarin
Sorexa Plus
Temus W
Tintorane
Tox-Hid
Vampirinip II
Vampirinip III
别名
Warfarin sodium
Warfarin
CAS号
81-81-2
PubChem SID
160964027
PubChem CID
54678486

数据来源

数据来源

所有数据来源 商品来源 非商品来源
数据来源 数据ID
DrugBank DB00682 external link
PubChem 54678486 external link
数据来源 数据ID 价格

理论计算性质

理论计算性质

ALOGPS 2.1 JChem
LOG S -3.81  溶解度 4.77e-02 g/l 
Log P 2.55 
摩尔折射率 95.9858 cm3 极化性 33.25637 Å3
极化表面积 63.6 Å2 可自由旋转的化学键
里宾斯基五规则 true  Acid pKa 7.5484066 
质子受体 质子供体
LogD (pH = 5.5) 3.5164902  LogD (pH = 7.4) 3.2873127 
Log P 3.5203567 

分子性质

分子性质

理化性质 生物活性(PubChem)
溶解度
17 mg/L expand 查看数据来源
疏水性(logP)
3 expand 查看数据来源

详细说明

详细说明

DrugBank DrugBank
DrugBank -  DB00682 external link
Item Information
Drug Groups approved
Description An anticoagulant that acts by inhibiting the synthesis of vitamin K-dependent coagulation factors. Warfarin is indicated for the prophylaxis and/or treatment of venous thrombosis and its extension, pulmonary embolism, and atrial fibrillation with embolization. It is also used as an adjunct in the prophylaxis of systemic embolism after myocardial infarction. Warfarin is also used as a rodenticide. [PubChem]
Indication For the treatment of retinal vascular occlusion, pulmonary embolism, cardiomyopathy, atrial fibrillation and flutter, cerebral embolism, transient cerebral ischaemia, arterial embolism and thrombosis.
Pharmacology Warfarin, a coumarin anticoagulant, is a racemic mixture of two active isomers. It is used in the prevention and treatment of thromboembolic disease including venous thrombosis, thromboembolism, and pulmonary embolism as well as for the prevention of ischemic stroke in patients with atrial fibrillation (AF).
Toxicity LD50=374 (orally in mice)
Affected Organisms
Humans and other mammals
Biotransformation Metabolized stereo- and regio-selectively by hepatic microsomal enzymes. S-warfarin is predominantly metabolized by cytochrome P450 (CYP) 2C9 to yield the 6- and 7-hydroxylated metabolites. R-warfarin is metabolized by CYP1A1, 1A2, and 3A4 to yield 6-, 8-, and 10-hydroxylated metabolites. Hydroxylated metabolites may be further conjugated prior to excretion into bile and urine. UGT1A1 appears to be responsible for producing the 6-O-glucuronide of warfarin, with a possibly contribution from UGT1A10. Five UGT1As may be involved in the formation of 7-O-glucuronide warfarin. S-warfarin has higher potency than R-warfarin and genetic polymorphisms in CYP2C9 may dramatically decrease clearance of and increase toxicity of the medication.
Absorption Rapidly absorbed following oral administration with considerable interindividual variations. Also absorbed percutaneously.
Half Life R-warfarin t1/2=37-89 hours; S-warfarin t1/2=21-43 hours.
Protein Binding 99% bound primarily to albumin
Elimination The elimination of warfarin is almost entirely by metabolism. Very little warfarin is excreted unchanged in urine. The metabolites are principally excreted into the urine; and to a lesser extent into the bile.
Distribution * 0.14 L/kg
Clearance * 0.065 +/- 0.025 mL/min/kg [CYP2C9 Genotype *1/*1]
* 0.041 +/- 0.021 [CYP2C9 Genotype *1/*2 or *1/*3]
* 0.020 +/- 0.011 [CYP2C9 Genotype *2/*2, *2/*3, or *3/*3]
References
Ansell J, Hirsh J, Poller L, Bussey H, Jacobson A, Hylek E: The pharmacology and management of the vitamin K antagonists: the Seventh ACCP Conference on Antithrombotic and Thrombolytic Therapy. Chest. 2004 Sep;126(3 Suppl):204S-233S. [Pubmed]
Whitlon DS, Sadowski JA, Suttie JW: Mechanism of coumarin action: significance of vitamin K epoxide reductase inhibition. Biochemistry. 1978 Apr 18;17(8):1371-7. [Pubmed]
Li T, Chang CY, Jin DY, Lin PJ, Khvorova A, Stafford DW: Identification of the gene for vitamin K epoxide reductase. Nature. 2004 Feb 5;427(6974):541-4. [Pubmed]
Rost S, Fregin A, Ivaskevicius V, Conzelmann E, Hortnagel K, Pelz HJ, Lappegard K, Seifried E, Scharrer I, Tuddenham EG, Muller CR, Strom TM, Oldenburg J: Mutations in VKORC1 cause warfarin resistance and multiple coagulation factor deficiency type 2. Nature. 2004 Feb 5;427(6974):537-41. [Pubmed]
Hirsh J, Fuster V, Ansell J, Halperin JL: American Heart Association/American College of Cardiology Foundation guide to warfarin therapy. J Am Coll Cardiol. 2003 May 7;41(9):1633-52. [Pubmed]
External Links
Wikipedia
RxList
Drugs.com

参考文献

参考文献

供应商提供 Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • Ansell J, Hirsh J, Poller L, Bussey H, Jacobson A, Hylek E: The pharmacology and management of the vitamin K antagonists: the Seventh ACCP Conference on Antithrombotic and Thrombolytic Therapy. Chest. 2004 Sep;126(3 Suppl):204S-233S. Pubmed
  • Whitlon DS, Sadowski JA, Suttie JW: Mechanism of coumarin action: significance of vitamin K epoxide reductase inhibition. Biochemistry. 1978 Apr 18;17(8):1371-7. Pubmed
  • Li T, Chang CY, Jin DY, Lin PJ, Khvorova A, Stafford DW: Identification of the gene for vitamin K epoxide reductase. Nature. 2004 Feb 5;427(6974):541-4. Pubmed
  • Rost S, Fregin A, Ivaskevicius V, Conzelmann E, Hortnagel K, Pelz HJ, Lappegard K, Seifried E, Scharrer I, Tuddenham EG, Muller CR, Strom TM, Oldenburg J: Mutations in VKORC1 cause warfarin resistance and multiple coagulation factor deficiency type 2. Nature. 2004 Feb 5;427(6974):537-41. Pubmed
  • Hirsh J, Fuster V, Ansell J, Halperin JL: American Heart Association/American College of Cardiology Foundation guide to warfarin therapy. J Am Coll Cardiol. 2003 May 7;41(9):1633-52. Pubmed
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专利

专利

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