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186691-13-4 分子结构
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(1R,2S,4R,5S)-7-{[2-hydroxy-2,2-bis(thiophen-2-yl)acetyl]oxy}-9,9-dimethyl-3-oxa-9-azatricyclo[3.3.1.0^{2,4}]nonan-9-ium

ChemBase编号:1218
分子式:C19H22NO4S2+
平均质量:392.51228
单一同位素质量:392.09902519
SMILES和InChIs

SMILES:
s1c(C(O)(C(=O)OC2C[C@H]3[N+]([C@H]([C@H]4O[C@@H]34)C2)(C)C)c2sccc2)ccc1
Canonical SMILES:
O=C(C(c1cccs1)(c1cccs1)O)OC1C[C@@H]2[C@H]3[C@@H]([C@H](C1)[N+]2(C)C)O3
InChI:
InChI=1S/C19H22NO4S2/c1-20(2)12-9-11(10-13(20)17-16(12)24-17)23-18(21)19(22,14-5-3-7-25-14)15-6-4-8-26-15/h3-8,11-13,16-17,22H,9-10H2,1-2H3/q+1/t11?,12-,13+,16+,17-
InChIKey:
LERNTVKEWCAPOY-KYQOMENCSA-N

引用这个纪录

CBID:1218 http://www.chembase.cn/molecule-1218.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
(1R,2S,4R,5S)-7-{[2-hydroxy-2,2-bis(thiophen-2-yl)acetyl]oxy}-9,9-dimethyl-3-oxa-9-azatricyclo[3.3.1.0^{2,4}]nonan-9-ium
IUPAC传统名
(1R,2S,4R,5S)-7-{[2-hydroxy-2,2-bis(thiophen-2-yl)acetyl]oxy}-9,9-dimethyl-3-oxa-9-azatricyclo[3.3.1.0^{2,4}]nonan-9-ium
商标名
Spiriva
别名
Tiotropium bromide
Tiotropium
CAS号
186691-13-4
PubChem SID
160964678
46504448
PubChem CID
3086654
3086655

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 DB01409 external link
PubChem 3086655 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 10.351076  质子受体
质子供体 LogD (pH = 5.5) -1.7571676 
LogD (pH = 7.4) -1.7481594  Log P -1.7572837 
摩尔折射率 109.182 cm3 极化性 38.91962 Å3
极化表面积 59.06 Å2 可自由旋转的化学键
里宾斯基五规则 true 
Log P -0.55  LOG S -4.44 
溶解度 1.56e-02 g/l 

分子性质

分子性质

生物活性(PubChem)

详细说明

详细说明

DrugBank DrugBank
DrugBank -  DB01409 external link
Item Information
Drug Groups approved
Description Tiotropium is a long-acting, 24 hour, anticholinergic bronchodilator used in the management of chronic obstructive pulmonary disease (COPD). Tiotropium is a muscarinic receptor antagonist, on topical application it acts mainly on M3 muscarinic receptors located in the airways to produce smooth muscle relaxation, thus producing a bronchodilatory effect.
Indication Used in the management of chronic obstructive pulmonary disease (COPD).
Pharmacology Tiotropium is a long–acting, antimuscarinic agent, which is often referred to as an anticholinergic. It has similar affinity to the subtypes of muscarinic receptors, M1 to M5. In the airways, it exhibits pharmacological effects through inhibition of M3–receptors at the smooth muscle leading to bronchodilation. The competitive and reversible nature of antagonism was shown with human and animal origin receptors and isolated organ preparations. In preclinical in vitro as well as in vivo studies prevention of methacholine–induced bronchoconstriction effects were dose–dependent and lasted longer than 24 hours. The bronchodilation following inhalation of tiotropium is predominantly a site–specific effect.
Toxicity No mortality was observed at inhalation tiotropium doses up to 32.4 mg/kg in mice, 267.7 mg/kg in rats, and 0.6 mg/kg in dogs. These doses correspond to 7,300, 120,000, and 850 times the recommended human daily dose on a mg/m2 basis, respectively.
Affected Organisms
Humans and other mammals
Biotransformation The extent of biotransformation appears to be small. This is evident from a urinary excretion of 74% of unchanged substance after an intravenous dose to young healthy volunteers. Tiotropium, an ester, is nonenzymatically cleaved to the alcohol N–methylscopine and dithienylglycolic acid, neither of which bind to muscarinic receptors. In vitro experiments with human liver microsomes and human hepatocytes suggest that a fraction of the administered dose (74% of an intravenous dose is excreted unchanged in the urine, leaving 25% for metabolism) is metabolized by cytochrome P450–dependent oxidation and subsequent glutathione conjugation to a variety of Phase II metabolites. Via inhibition studies, it is evident that CYP450 2D6 and 3A4 are involved in the metabolic pathway that is responsible for the elimination of a small part of the administered dose.
Absorption Bioavailability is 19.5% following administration by inhalation. Oral solutions of tiotropium have an absolute bioavailability of 2-3%.
Half Life 5-6 days
Protein Binding 72% bound to plasma proteins.
Elimination Intravenously administered tiotropium was mainly excreted unchanged in urine (74%). After dry powder inhalation, urinary excretion was 14% of the dose, the remainder being mainly non-absorbed drug in the gut which was eliminated via the feces.
Distribution * 32 L/kg
Clearance * 880 mL/min [young healthy volunteers receiving IV administration]
* Renal cl=326 mL/min [COPD patients (<58 years)]
* Renal cl=163 mL/min [COPD patients (>70 years)]
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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