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9005-49-6 分子结构
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3-[(5-{[6-carboxy-4,5-dihydroxy-3-(sulfooxy)oxan-2-yl]oxy}-6-(hydroxymethyl)-3-(sulfoamino)-4-(sulfooxy)oxan-2-yl)oxy]-6-({5-acetamido-4,6-dihydroxy-2-[(sulfooxy)methyl]oxan-3-yl}oxy)-4-hydroxy-5-(sulfooxy)oxane-2-carboxylic acid

ChemBase编号:290
分子式:C26H42N2O37S5
平均质量:1134.92788
单一同位素质量:1134.00699529
SMILES和InChIs

SMILES:
S(=O)(=O)(O)NC1C(OS(=O)(=O)O)C(OC2OC(C(O)C(O)C2OS(=O)(=O)O)C(=O)O)C(OC1OC1C(O)C(OS(=O)(=O)O)C(OC1C(=O)O)OC1C(O)C(NC(=O)C)C(OC1COS(=O)(=O)O)O)CO
Canonical SMILES:
OCC1OC(OC2C(OC(C(C2O)OS(=O)(=O)O)OC2C(COS(=O)(=O)O)OC(C(C2O)NC(=O)C)O)C(=O)O)C(C(C1OC1OC(C(=O)O)C(C(C1OS(=O)(=O)O)O)O)OS(=O)(=O)O)NS(=O)(=O)O
InChI:
InChI=1S/C26H42N2O37S5/c1-4(30)27-7-9(31)13(6(56-23(7)39)3-55-67(43,44)45)58-26-19(65-70(52,53)54)12(34)16(20(62-26)22(37)38)60-24-8(28-66(40,41)42)15(63-68(46,47)48)14(5(2-29)57-24)59-25-18(64-69(49,50)51)11(33)10(32)17(61-25)21(35)36/h5-20,23-26,28-29,31-34,39H,2-3H2,1H3,(H,27,30)(H,35,36)(H,37,38)(H,40,41,42)(H,43,44,45)(H,46,47,48)(H,49,50,51)(H,52,53,54)
InChIKey:
HTTJABKRGRZYRN-UHFFFAOYSA-N

引用这个纪录

CBID:290 http://www.chembase.cn/molecule-290.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
3-[(5-{[6-carboxy-4,5-dihydroxy-3-(sulfooxy)oxan-2-yl]oxy}-6-(hydroxymethyl)-3-(sulfoamino)-4-(sulfooxy)oxan-2-yl)oxy]-6-({5-acetamido-4,6-dihydroxy-2-[(sulfooxy)methyl]oxan-3-yl}oxy)-4-hydroxy-5-(sulfooxy)oxane-2-carboxylic acid
IUPAC传统名
heparin
商标名
Normiflo
Lovenox
Lovenox HP
Clexane
别名
Ardeparin
LMWH
Low Molecular Weight Heparin
enoxaparin
Enoxaparin
CAS号
9005-49-6
PubChem SID
46505194
46507450
160963753
PubChem CID
772

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 价格

理论计算性质

理论计算性质

JChem ALOGPS 2.1
Acid pKa -2.791999  质子受体 33 
质子供体 15  LogD (pH = 5.5) -25.637262 
LogD (pH = 7.4) -27.264605  Log P -8.346764 
摩尔折射率 195.9082 cm3 极化性 86.5905 Å3
极化表面积 610.49 Å2 可自由旋转的化学键 20 
里宾斯基五规则 false 
Log P -1.68  LOG S -2.02 
溶解度 1.08e+01 g/l 

分子性质

分子性质

理化性质 生物活性(PubChem)
溶解度
> 200 mg/mL expand 查看数据来源
Soluble expand 查看数据来源
疏水性(logP)
-13.2 expand 查看数据来源

详细说明

详细说明

DrugBank DrugBank
DrugBank -  DB00407 external link
Item Information
Drug Groups approved; withdrawn
Description Ardeparin, marketed under the US trade name Normiflo, is a low molecular weight heparin (LMWH) anticoagulant used for the prevention of postoperative venous thrombosis. Ardeparin is derived via peroxide degradation of heparin extracted from porcine intestinal mucosa. Its molecular weight ranges from 2000 to 15,000 with an average molecular weight of 5500 to 6500. Normiflo was withdrawn from the US market in March 2000.
Indication For prevention of deep vein thrombosis, which may result in pulmonary embolism, following knee surgery.
Pharmacology Ardeparin, an anticoagulant, is a fractionated heparin. It acts at multiple sites in the normal coagulation system to inhibit reactions that lead to the clotting of blood and the formation of fibrin clots both in vitro and in vivo.
Toxicity Symptoms of overdose may include excessive bleeding and bruising.
Affected Organisms
Humans and other mammals
Biotransformation Liver and the reticulo-endothelial system are the sites of biotransformation.
Absorption Well absorbed following subcutaneous administration, with a mean bioavailability of 92% (based on anti-factor Xa activity).
Half Life Elimination half-life for anti-factor Xa activity averages 3.3 hours following a single intravenous dose, while elimination half-life for anti-factor IIa activity averages 1.2 hours following a single intravenous dose.
External Links
Wikipedia
Drugs.com
DrugBank -  DB01225 external link
Item Information
Drug Groups approved; investigational
Description Enoxaparin is a low molecular weight heparin. Enoxaparin is used to prevent and treat deep vein thrombosis or pulmonary embolism, and is given as a subcutaneous injection. Enoxaparin binds to and accelerates the activity of antithrombin III. By activating antithrombin III, enoxaparin preferentially potentiates the inhibition of coagulation factors Xa and IIa. Factor Xa catalyzes the conversion of prothrombin to thrombin, so enoxaparin's inhibition of this process results in decreased thrombin and ultimately the prevention of fibrin clot formation. Low molecular weight heparins are less effective at inactivating factor IIa due to their shorter length compared to unfractionated heparin.
Indication For the prophylaxis of deep vein thrombosis, which may lead to pulmonary embolism, and also for the prophylaxis of ischemic complications of unstable angina and non-Q-wave myocardial infarction, when concurrently administered with aspirin.
Pharmacology Enoxaparin is a highly acidic mucopolysaccharide formed of equal parts of sulfated D-glucosamine and D-glucuronic acid with sulfaminic bridges. The molecular weight ranges from 3800 to 5000 daltons. Enoxaparin occurs in and is obtained from liver, lung, mast cells, etc., of vertebrates. Enoxaparin is a well known and commonly used anticoagulant which has antithrombotic properties. Enoxaparin inhibits reactions that lead to the clotting of blood and the formation of fibrin clots both in vitro and in vivo. Enoxaparin acts at multiple sites in the normal coagulation system. Small amounts of enoxaparin in combination with antithrombin III (enoxaparin cofactor) can inhibit thrombosis by inactivating activated Factor X and inhibiting the conversion of prothrombin to thrombin. Once active thrombosis has developed, larger amounts of enoxaparin can inhibit further coagulation by inactivating thrombin and preventing the conversion of fibrinogen to fibrin. Enoxaparin also prevents the formation of a stable fibrin clot by inhibiting the activation of the fibrin stabilizing factor. Its use should be avoided in patients with a creatinine clearance less than 20mL/min. In these patients, unfractionated heparin should only be used. As for monitoring, active partial thromboplastin time (aPTT) will only increase at high doses of low molecular weight heparins (LMWH). Therefore, monitoring aPTT is not recommended. However, anti-Xa activity can be measured to monitor the efficacy of the LMWH.
Toxicity Mouse, median lethal dose greater than 5000 mg/kg. Another side effect is heparin induced thrombocytopenia (HIT syndrome). HIT is caused by an immunological reaction that makes platelets form clots within the blood vessels, thereby using up coagulation factors.
Affected Organisms
Humans and other mammals
Biotransformation Undergoes desulfation and polymerization via the liver
Absorption Mean absolute bioavailability of enoxaparin, after 1.5 mg/kg given subcutaneously, based on anti-Factor Xa activity is approximately 100% in healthy volunteers.
Half Life 4.5 hours
Protein Binding 80% bound-albumin
Elimination Enoxaparin sodium is primarily metabolized in the liver by desulfation and/or depolymerization to lower molecular weight species with much reduced biological potency. Renal clearance of active fragments represents about 10% of the administered dose and total renal excretion of active and non-active fragments 40% of the dose.
Distribution * 4.3 L
External Links
Wikipedia
RxList
Drugs.com

参考文献

参考文献

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