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152-72-7 分子结构
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2-hydroxy-3-[1-(4-nitrophenyl)-3-oxobutyl]-4H-chromen-4-one

ChemBase编号:1226
分子式:C19H15NO6
平均质量:353.3255
单一同位素质量:353.08993721
SMILES和InChIs

SMILES:
o1c(O)c(C(CC(=O)C)c2ccc([N+](=O)[O-])cc2)c(=O)c2c1cccc2
Canonical SMILES:
CC(=O)CC(c1c(O)oc2c(c1=O)cccc2)c1ccc(cc1)[N+](=O)[O-]
InChI:
InChI=1S/C19H15NO6/c1-11(21)10-15(12-6-8-13(9-7-12)20(24)25)17-18(22)14-4-2-3-5-16(14)26-19(17)23/h2-9,15,23H,10H2,1H3
InChIKey:
WWBYDEQHYAEHLT-UHFFFAOYSA-N

引用这个纪录

CBID:1226 http://www.chembase.cn/molecule-1226.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-[1-(4-nitrophenyl)-3-oxobutyl]-4H-chromen-4-one
IUPAC传统名
acenocumarol
商标名
Sintrom
Sinthrome
Syncoumar
Syncumar
Syntrom
Zotil
Sinthrom
Sinkumar
Sincoumar
Neositron
Ascumar
Mini-sintrom
别名
Nitrowarfarin
Nitrovarfarian
Nitrophenylacetylethyl-4-hydroxycoumarine
Acenocoumarolum [INN-latin]
Nicoumalone
Nicumalon
Acenocoumarin
Acenocoumarol
CAS号
152-72-7
PubChem SID
160964686
PubChem CID
54676537

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 DB01418 external link
PubChem 54676537 external link
数据来源 数据ID 价格

理论计算性质

理论计算性质

JChem ALOGPS 2.1
Acid pKa 7.019987  质子受体
质子供体 LogD (pH = 5.5) 3.4474232 
LogD (pH = 7.4) 2.9293098  Log P 3.460341 
摩尔折射率 103.3105 cm3 极化性 35.16633 Å3
极化表面积 109.42 Å2 可自由旋转的化学键
里宾斯基五规则 true 
Log P 2.55  LOG S -4.53 
溶解度 1.05e-02 g/l 

分子性质

分子性质

理化性质 生物活性(PubChem)
溶解度
practically insoluble [MSDS] expand 查看数据来源
疏水性(logP)
1.98 [SANGSTER (1994)] expand 查看数据来源

详细说明

详细说明

DrugBank DrugBank
DrugBank -  DB01418 external link
Item Information
Drug Groups approved
Description Acenocoumarol is a coumarin derivative used as an anticoagulant. Coumarin derivatives inhibit the reduction of vitamin K by vitamin K reductase. This prevents carboxylation of vitamin K-dependent clotting factors, II, VII, XI and X, and interferes with coagulation. Hematocrit, hemoglobin, international normalized ratio and liver panel should be monitored. Patients on acenocoumarol are prohibited from giving blood.
Indication For the treatment and prevention of thromboembolic diseases. More specifically, it is indicated for the for the prevention of cerebral embolism, deep vein thrombosis, pulmonary embolism, thromboembolism in infarction and transient ischemic attacks. It is used for the treatment of deep vein thrombosis and myocardial infarction.
Pharmacology Acenocoumarol inhibits the reduction of vitamin K by vitamin K reductase. This prevents carboxylation of certain glutamic acid residues near the N-terminals of clotting factors II, VII, IX and X, the vitamin K-dependent clotting factors. Glutamic acid carboxylation is important for the interaction between these clotting factors and calcium. Without this interaction, clotting cannot occur. Both the extrinsic (via factors VII, X and II) and intrinsic (via factors IX, X and II) are affected by acenocoumarol.
Toxicity The onset and severity of the symptoms are dependent on the individual's sensitivity to oral anticoagulants, the severity of the overdosage, and the duration of treatment. Bleeding is the major sign of toxicity with oral anticoagulant drugs. The most frequent symptoms observed are: cutaneous bleeding (80%), haematuria (with renal colic) (52%), haematomas, gastrointestinal bleeding, haematemesis, uterine bleeding, epistaxis, gingival bleeding and bleeding into the joints. Further symptoms include tachycardia, hypotension, peripheral circulatory disorders due to loss of blood, nausea, vomiting, diarrhoea and abdominal pains.
Affected Organisms
Humans and other mammals
Biotransformation Extensively metabolized in the liver via oxidation forming two hydroxy metabolites and keto reduction producing two alcohol metabolites. Reduction of the nitro group produces an amino metabolite which is further transformed to an acetoamido metabolite. Metabolites do not appear to be pharmacologically active.
Absorption Rapidly absorbed orally with greater than 60% bioavailability. Peak plasma levels are attained 1 to 3 hours following oral administration.
Half Life 8 to 11 hours.
Protein Binding 98.7% protein bound, mainly to albumin
Elimination Mostly via the kidney as metabolites
Distribution The volume of distribution at steady-state appeared to be significantly dose dependent: 78 ml/kg for doses < or = 20 microg/kg and 88 ml/kg for doses > 20 microg/kg respectively
References
Cesar JM, Garcia-Avello A, Navarro JL, Herraez MV: Aging and oral anticoagulant therapy using acenocoumarol. Blood Coagul Fibrinolysis. 2004 Oct;15(8):673-6. [Pubmed]
Lengyel M: [Warfarin or acenocoumarol is better in the anticoagulant treatment of chronic atrial fibrillation?] Orv Hetil. 2004 Dec 26;145(52):2619-21. [Pubmed]
Ufer M: Comparative pharmacokinetics of vitamin K antagonists: warfarin, phenprocoumon and acenocoumarol. Clin Pharmacokinet. 2005;44(12):1227-46. [Pubmed]
Montes R, Ruiz de Gaona E, Martinez-Gonzalez MA, Alberca I, Hermida J: The c.-1639G > A polymorphism of the VKORC1 gene is a major determinant of the response to acenocoumarol in anticoagulated patients. Br J Haematol. 2006 Apr;133(2):183-7. [Pubmed]
Girard P, Nony P, Erhardtsen E, Delair S, Ffrench P, Dechavanne M, Boissel JP: Population pharmacokinetics of recombinant factor VIIa in volunteers anticoagulated with acenocoumarol. Thromb Haemost. 1998 Jul;80(1):109-13. [Pubmed]
External Links
Wikipedia

参考文献

参考文献

供应商提供 Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • Girard P, Nony P, Erhardtsen E, Delair S, Ffrench P, Dechavanne M, Boissel JP: Population pharmacokinetics of recombinant factor VIIa in volunteers anticoagulated with acenocoumarol. Thromb Haemost. 1998 Jul;80(1):109-13. Pubmed
  • Cesar JM, Garcia-Avello A, Navarro JL, Herraez MV: Aging and oral anticoagulant therapy using acenocoumarol. Blood Coagul Fibrinolysis. 2004 Oct;15(8):673-6. Pubmed
  • Lengyel M: [Warfarin or acenocoumarol is better in the anticoagulant treatment of chronic atrial fibrillation?] Orv Hetil. 2004 Dec 26;145(52):2619-21. Pubmed
  • Ufer M: Comparative pharmacokinetics of vitamin K antagonists: warfarin, phenprocoumon and acenocoumarol. Clin Pharmacokinet. 2005;44(12):1227-46. Pubmed
  • Montes R, Ruiz de Gaona E, Martinez-Gonzalez MA, Alberca I, Hermida J: The c.-1639G > A polymorphism of the VKORC1 gene is a major determinant of the response to acenocoumarol in anticoagulated patients. Br J Haematol. 2006 Apr;133(2):183-7. Pubmed
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