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81846-19-7 分子结构
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2-{[(1S,2S,3aR,9aR)-2-hydroxy-1-[(3R)-3-hydroxyoctyl]-1H,2H,3H,3aH,4H,9H,9aH-cyclopenta[b]naphthalen-5-yl]oxy}acetic acid

ChemBase编号:258
分子式:C23H34O5
平均质量:390.51306
单一同位素质量:390.24062419
SMILES和InChIs

SMILES:
O[C@@H]1[C@H]([C@H]2[C@@H](C1)Cc1c(C2)cccc1OCC(=O)O)CC[C@H](O)CCCCC
Canonical SMILES:
CCCCC[C@H](CC[C@@H]1[C@@H](O)C[C@@H]2[C@H]1Cc1cccc(c1C2)OCC(=O)O)O
InChI:
InChI=1S/C23H34O5/c1-2-3-4-7-17(24)9-10-18-19-11-15-6-5-8-22(28-14-23(26)27)20(15)12-16(19)13-21(18)25/h5-6,8,16-19,21,24-25H,2-4,7,9-14H2,1H3,(H,26,27)/t16-,17-,18+,19-,21+/m1/s1
InChIKey:
PAJMKGZZBBTTOY-YRIDSSQKSA-N

引用这个纪录

CBID:258 http://www.chembase.cn/molecule-258.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-{[(1S,2S,3aR,9aR)-2-hydroxy-1-[(3R)-3-hydroxyoctyl]-1H,2H,3H,3aH,4H,9H,9aH-cyclopenta[b]naphthalen-5-yl]oxy}acetic acid
IUPAC传统名
viveta
商标名
Remodulin
Viveta
别名
treprostinil
Treprostinil
CAS号
81846-19-7
PubChem SID
160963721
PubChem CID
54786

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 DB00374 external link
PubChem 54786 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 3.760436  质子受体
质子供体 LogD (pH = 5.5) 2.2637904 
LogD (pH = 7.4) 0.7241018  Log P 4.0042095 
摩尔折射率 108.0016 cm3 极化性 42.45696 Å3
极化表面积 86.99 Å2 可自由旋转的化学键 10 
里宾斯基五规则 true 
Log P 3.53  LOG S -4.73 
溶解度 7.31e-03 g/l 

分子性质

分子性质

理化性质 生物活性(PubChem)
溶解度
Insoluble at 25°C expand 查看数据来源
疏水性(logP)
4.1 expand 查看数据来源

详细说明

详细说明

DrugBank DrugBank
DrugBank -  DB00374 external link
Item Information
Drug Groups approved; investigational
Description Treprostinil is a synthetic analogue of prostacyclin, used to treat pulmonary hypertension. Treprostinil is marketed as Remodulin®. [Wikipedia]
Indication For use as a continuous subcutaneous infusion or intravenous infusion (for those not able to tolerate a subcutaneous infusion) for the treatment of pulmonary arterial hypertension in patients with NYHA Class II-IV symptoms to diminish symptoms associated with exercise.
Pharmacology Pulmonary arterial hypertension (PAH) is a disease in which blood pressure is abnormally high in the arteries between the heart and lungs. PAH is characterized by symptoms of shortness of breath during physical exertion. The condition can ultimately lead to heart failure. Treprostinil is a potent oral antiplatelet agent. The major pharmacologic actions of treprostinil are direct vasodilation of pulmonary and systemic arterial vascular beds and inhibition of platelet aggregation. In animals, the vasodilatory effects reduce right and left ventricular afterload and increase cardiac output and stroke volume. Other studies have shown that treprostinil causes a dose-related negative inotropic and lusitropic effect. No major effects on cardiac conduction have been observed.
Toxicity Symptoms of overdose are extensions of its dose-limiting pharmacologic effects and include flushing, headache, hypotension, nausea, vomiting, and diarrhea. Most events were self-limiting and resolved with reduction or withholding of treprostinil.
Affected Organisms
Humans and other mammals
Biotransformation Substantially metabolized by the liver, but the precise enzymes responsible are unknown. Five metabolites have been described (HU1 through HU5) however, the biological activity and metabolic fate of these are unknown. The chemical structure of HU1 is unknown. The metabolite HU5 is the glucuronide conjugate of treprostinil. The other metabolites are formed by oxidation of the 3-hydroxyoctyl side chain (HU2) and subsequent additional oxidation (HU3) or dehydration (HU4). Study results of in vitro human hepatic cytochrome P450 demonstrates that treprostinil does not inhibit CYP-1A2, 2C9, 2C19, 2D6, 2E1, or 3A. Whether treprostinil induces these enzymes has not been studied.
Absorption Relatively rapid and complete after subcutaneous infusion, with an absolute bioavailability approximately 100%. In patients with mild (n=4) or moderate (n=5) hepatic insufficiency and portopulmonary hypertension following a subcutaneous dose of 10 ng per kg of body weight per min for 150 mins the AUC 0-∞ was increased 3-fold and 5-fold respectively.
Half Life Terminal elimination half-life is approximately 2 to 4 hours. Plasma half-life is 34 and 85 minutes for intravenous and subcutaneous infusion of the drug, respectively.
Protein Binding Human plasma protein binding is approximately 91% in in vitro concentrations ranging from 330 to 10,000 µ/L.
Distribution * 14 L/70 kg
External Links
Wikipedia
RxList
Drugs.com

参考文献

参考文献

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专利

专利

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