First systematic chiral syntheses of two pairs of enantiomers with 3,5-dihydroxyheptenoic acid chain, associated with a potent synthetic statin NK-104

Suzuki, Masahiro; Yanagawa, Yuki; Iwasaki, Hiroshi; Kanda, Hideaki; Yanagihara, Kota; Matsumoto, Hiromichi; Ohara, Yoshio; Yazaki, Yukari; Sakoda, Ryozo

doi:10.1016/s0960-894x(99)00519-3

Cited by 21 publications

(9 citation statements)

References 22 publications

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“…Its chemical name is: (+)-monocalcium bis(3R,5S,6E)-7-[2-cyclopropyl-4-(4-fluorophenyl)-3-quinolyl]-3,5-dihydroxy-6-heptenoate (C 50 H 46 CaF 2 N 2 O 8 ). Its molecular weight is 880.98 (63,65). Pitavastatin is classified as a lipophilic drug.…”

Section: Chemical Structure and Propertiesmentioning

confidence: 99%

Pitavastatin: Efficacy and Safety Profiles of A Novel Synthetic HMG‐CoA Reductase Inhibitor

Kajinami

Takekoshi

Saitō

2003

Cardiovascular Drug Reviews

122

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The use of 3-hydroxy-3-methylglutaryl coenzyme A (HMG-CoA) reductase inhibitors, statins, has been shown to reduce major cardiovascular events in both primary and secondary prevention, and statins became one of the most widely prescribed classes of drugs throughout the world. Previously, statins have been well tolerated and have shown favorable safety profiles. However, the voluntary withdrawal of cerivastatin from the market because of a disproportionate number of reports of rhabdomyolysis-associated deaths drew attention to the pharmacokinetic profile of statins, which may possibly have been related to serious drug-drug interactions.Pitavastatin (NK-104, previously called itavastatin or nisvastatin, Kowa Company Ltd., Tokyo) is a novel, fully synthetic statin, which has a potent cholesterol-lowering action. The short-term and long-term lipid-modifying effects of pitavastatin have already been investigated in subjects with primary hypercholesterolemia, heterozygous familial hypercholesterolemia, hypertriglyceridemia, and type-2 diabetes mellitus accompanied by hyperlipidemia. Within the range of daily doses from 1 to 4 mg, the efficacy of pitavastatin as a lipid-lowering drug seems to be similar, or potentially superior, to that of atorvastatin.According to the results of pharmacokinetic studies, pitavastatin showed favorable and promising safety profile; it was only slightly metabolized by the cytochrome P450 (CYP) system, its lactone form had no inhibitory effects on the CYP3A4-mediated metabolism of concomitantly administered drugs; P-glycoprotein-mediated transport did not play a major role in its disposition, and pitavastatin did not inhibit P-glycoprotein activity.It could be concluded that pitavastatin could provide a new and potentially better therapeutic choice for lipid-modifying therapy than do the currently available statins. The efficacy and safety of higher dose treatment, as well as its long-term effects in the prevention of coronary artery disease, should be further investigated.

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Section: Chemical Structure and Propertiesmentioning

confidence: 99%

Pitavastatin: Efficacy and Safety Profiles of A Novel Synthetic HMG‐CoA Reductase Inhibitor

Kajinami

Takekoshi

Saitō

2003

Cardiovascular Drug Reviews

122

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“…Another novel statin in early clinical development is pitavastatin, also known as NK-104 and previously named itavastatin or nisvastatin. It is also a totally synthetic compound, 108,109 and in contrast to the abovementioned substances, it carries a cyclopropyl group. 22 Due to premature clinical evaluation, complete pharmacokinetic data have not been published.…”

Section: Novel Statins (Rosuvastatin Pitavastatin)mentioning

confidence: 99%

Pharmacology of 3‐Hydroxy‐3‐Methylglutaryl‐Coenzyme A Reductase Inhibitors (Statins), Including Rosuvastatin and Pitavastatin

Igel

Sudhop

Bergmann

2002

The Journal of Clinical Pharma

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Coronary heart disease (CHD) is the leading cause of morbidity and mortality in the Western world, with hypercholesterolemia as the major risk factor. The 3-hydroxy-3-methylglutaryl-coenzyme A reductase inhibitors represent the most efficient drugsfor the treatment of hypercholesterolemia. They lower plasma cholesterol due to the inhibition of endogenous cholesterol synthesis in the liverand subsequent increased expression of low-density lipoprotein (LDL) receptors, resulting in an up-regulated catabolic rate for plasma LDL. The beneficial effect of statins on the incidence of CHD was clearly demonstrated in several large-scale clinical trials. Currently, five statins (atorvastatin, fluvastatin, lovastatin, pravastatin, and simvastatin) are available, and two novel compounds (pitavastatin, rosuvastatin) are undergoing clinical investigation. To point out potential mechanisms leading to increased toxicity and to compare the novel statins with the established ones, this article summarizes their pharmacological data since the prevalence of adverse events can be explained at least in part by their pharmacokinetic differences.

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“…Therefore, it is highly necessary to generate a highly efficient photoisomerizable azobenzene‐anchored DNA strand to satisfy the photocontrolled actuations at room temperature. Several research groups have found that azobenzene linked with ether bonds usually eliminate the low trans ‐to‐ cis conversion efficiency penalty . Recently, Liang's group successfully demonstrated the use of glycerol linker to integrate azobenzene into DNA strand with great improvements in its operation efficiency at room temperature .…”

Section: Discussionmentioning

confidence: 99%

Photoresponsive Self‐Assembled DNA Nanomaterials: Design, Working Principles, and Applications

Tam

Zhuang

Wong

et al. 2019

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Photoresponsive DNA nanomaterials represent a new class of remarkable functional materials. By adjusting the irradiation wavelength, light intensity, and exposure time, various photocontrolled DNA‐based systems can be reversibly or irreversibly regulated in respect of their size, shape, conformation, movement, and dissociation/association. This Review introduces the most updated progress in the development of photoresponsive DNA‐based system and emphasizes their advantages over other stimuli‐responsive systems. Their design and mechanisms to trigger the photoresponses are shown and discussed. The potential application of these photon‐responsive DNA nanomaterials in biology, biomedicine, materials science, nanophotonic and nanoelectronic are also covered and described. The challenges faced and further directions of the development of photocontrolled DNA‐based systems are also highlighted.

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First systematic chiral syntheses of two pairs of enantiomers with 3,5-dihydroxyheptenoic acid chain, associated with a potent synthetic statin NK-104

Cited by 21 publications

References 22 publications

Pitavastatin: Efficacy and Safety Profiles of A Novel Synthetic HMG‐CoA Reductase Inhibitor

Pitavastatin: Efficacy and Safety Profiles of A Novel Synthetic HMG‐CoA Reductase Inhibitor

Pharmacology of 3‐Hydroxy‐3‐Methylglutaryl‐Coenzyme A Reductase Inhibitors (Statins), Including Rosuvastatin and Pitavastatin

Photoresponsive Self‐Assembled DNA Nanomaterials: Design, Working Principles, and Applications

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