Structural characterization of dimethyldithiodenafil and dimethylthiocarbodenafil, analogs of sildenafil.

Abstract:

:Two analogs of sildenafil (compounds 1 and 2) were detected in three powder products acquired from online drug markets during an LC-UV-MS analysis of psychotropic drugs. Their structures were established by high-resolution mass spectrometry and NMR spectroscopy. Compound 1 was identified as 5-(5-(3,5-dimethylpiperazine-1-carbonothioyl)-2-ethoxyphenyl)-1-methyl-3-propyl-1H-pyrazolo[4,3-d]pyrimidine-7(6H)-thione and named dimethyldithiodenafil. Compound 2 was identified as 5-(5-(3,5-dimethylpiperazine-1-carbonothioyl)-2-ethoxyphenyl)-1-methyl-3-propyl-1H-pyrazolo[4,3-d]pyrimidin-7(6H)-one and named dimethylthiocarbodenafil. Compound 1 was subjected to the phosphodiesterase assay (IC50=0.20nM). The three powder products were found to contain 12-19mg of dimethyldithiodenafil and 1.4-3.9mg of dimethylthiocarbodenafil per tube.

journal_name

J Pharm Biomed Anal

authors

Sakamoto M,Suzuki J,Saito Y,Shimizu S,Kobayashi K,Nagashima M,Moriyasu T,Fukaya H,Saito K

doi

10.1016/j.jpba.2017.09.025

subject

Has Abstract

pub_date

2018-01-30 00:00:00

pages

136-141

eissn

0731-7085

issn

1873-264X

pii

S0731-7085(17)32373-7

journal_volume

148

pub_type

杂志文章
  • Characterization of interaction and the effect of carbamazepine on the structure of human serum albumin.

    abstract::The binding of carbamazepine (CBZ) to human serum albumin (HSA) was investigated under simulative physiological conditions. In this study, intrinsic fluorescence of tryptophan-214 in HSA was monitored upon the addition of CBZ. Binding constant of CBZ-HSA was calculated by the remarkable static quenching effect of CBZ ...

    journal_title:Journal of pharmaceutical and biomedical analysis

    pub_type: 杂志文章

    doi:10.1016/j.jpba.2010.05.025

    authors: Kalanur SS,Seetharamappa J,Kalalbandi VK

    更新日期:2010-11-02 00:00:00

  • HPLC analysis of naturally occurring free D-amino acids in mammals.

    abstract::D-amino acids are currently recognized as naturally occurring physiologically active substances and biomarkers in mammals. The progress of analytical technologies, mostly high resolution chromatographic or electrodriven separation methods, has significantly contributed to the advances in D-amino acid research in real ...

    journal_title:Journal of pharmaceutical and biomedical analysis

    pub_type: 杂志文章,评审

    doi:10.1016/j.jpba.2012.01.041

    authors: Miyoshi Y,Koga R,Oyama T,Han H,Ueno K,Masuyama K,Itoh Y,Hamase K

    更新日期:2012-10-01 00:00:00

  • Study of ocular pharmacokinetics of in situ gel system for S(-)-satropane evaluated by microdialysis.

    abstract::S(-)-Satropane is currently being developed to in situ forming ophthalmic gel, a new ophthalmic delivery system, for the treatment of glaucoma. To evaluate the pharmacokinetic profiles of S(-)-satropane, the microdialysis method was employed. The concentration of S(-)-satropane in dialysates was measured by using liqu...

    journal_title:Journal of pharmaceutical and biomedical analysis

    pub_type: 杂志文章

    doi:10.1016/j.jpba.2008.06.001

    authors: Fu J,Feng X,Yuan H,Yan L,Kuang X,Xia Z,Gao X,Yu C,Lu Y,Chen HZ

    更新日期:2008-11-04 00:00:00

  • Improved sample preparation method for fast LC-MS/MS analysis of vitamin D metabolites in serum.

    abstract::Despite the fact that more than 90% of vitamin D analysis are performed using immuno-enzymatic techniques, it is liquid chromatography coupled with tandem mass spectrometry that is currently the reference method. It allows for specific and selective analysis of all relevant vitamin D metabolites from a variety of biol...

    journal_title:Journal of pharmaceutical and biomedical analysis

    pub_type: 杂志文章

    doi:10.1016/j.jpba.2020.113529

    authors: Rola R,Kowalski K,Bieńkowski T,Studzińska S

    更新日期:2020-10-25 00:00:00

  • Finding of an isoleucine derivative of a recombinant protein for pharmaceutical use.

    abstract::Protein modification generally occurs by addition to the amino acid side-chains of protein at the post-translational stage, for example, by enzymatic or chemical reactions after polypeptide synthesis. Recently, the recombinant hirudin analog CX-397, a potent thrombin inhibitor, was found to contain methylated Ile resi...

    journal_title:Journal of pharmaceutical and biomedical analysis

    pub_type: 杂志文章,评审

    doi:10.1016/s0731-7085(02)00703-3

    authors: Muramatsu R,Misawa S,Hayashi H

    更新日期:2003-04-01 00:00:00

  • Metabolic profiling of icariin in rat feces, urine, bile and plasma after oral administration using ultra-high performance liquid chromatography/quadrupole time-of-flight mass spectrometry.

    abstract::Icariin, the major flavonoid constituent of the traditional Chinese medicine Epimedii Folium, is extensively researched owing to its comprehensive beneficial effects. This study aimed at identifying the in vivo metabolites and the metabolic profiling in rats after oral administration at a dose of icariin (100 mg/kg) w...

    journal_title:Journal of pharmaceutical and biomedical analysis

    pub_type: 杂志文章

    doi:10.1016/j.jpba.2019.02.021

    authors: Wang T,Feng X,Ding L,Wang K,Qiao M,Chai L,Li Y,Qiu F

    更新日期:2019-05-10 00:00:00

  • Determination of the optical purity of indacrinone by proton nuclear magnetic resonance spectroscopy using chiral lanthanide chelates.

    abstract::A simple, specific and reliable 1H-NMR spectroscopic method for the quantitative determination of the optical purity of indacrinone is described. After conversion of the S(+)- and R(-)-enantiomers to their methyl ester derivatives, they were coordinated with chiral europium(III) or praseodymium(III) shift reagents in ...

    journal_title:Journal of pharmaceutical and biomedical analysis

    pub_type: 杂志文章

    doi:10.1016/0731-7085(89)80016-0

    authors: Hanna GM,Lau-Cam CA

    更新日期:1989-01-01 00:00:00

  • High-throughput miniaturized immunoassay for human interleukin-13 secreted from NK3.3 cells using homogenous time-resolved fluorescence.

    abstract::A miniaturized immunoassay for human interleukin-13 (IL-13) using homogeneous time-resolved fluorescence (HTRF) has been developed. In this assay, IL-13 which was secreted from NK3.3 cells stimulated with interleukin-2 (IL-2) was detected by measuring the time-resolved fluorescence after adding a mixture of three reag...

    journal_title:Journal of pharmaceutical and biomedical analysis

    pub_type: 杂志文章

    doi:10.1016/s0731-7085(01)00596-9

    authors: Enomoto K,Araki A,Nakajima T,Ohta H,Dohi K,Préaudat M,Seguin P,Mathis G,Suzuki R,Kominami G,Takemoto H

    更新日期:2002-04-01 00:00:00

  • Urtica dioica L. leaf chemical composition: A never-ending disclosure by means of HR-MS/MS techniques.

    abstract::The metabolite profiling of plant extracts always represents an exciting challenge, as the chemical diversity of natural products is still far beyond the researchers' imagination, even focusing on a plant that is thought to have already been broadly investigated. Herein UHPLC-HRMS/MS techniques were applied to an alco...

    journal_title:Journal of pharmaceutical and biomedical analysis

    pub_type: 杂志文章

    doi:10.1016/j.jpba.2021.113892

    authors: Brahmi-Chendouh N,Piccolella S,Nigro E,Hamri-Zeghichi S,Madani K,Daniele A,Pacifico S

    更新日期:2021-02-20 00:00:00

  • Quality consistency evaluation of Melissa officinalis L. commercial herbs by HPLC fingerprint and quantitation of selected phenolic acids.

    abstract::To evaluate the quality consistency of commercial medicinal herbs, a simple and reliable HPLC method with UV-vis detector was developed, both for fingerprint analysis and quantitation of some pharmacologically active constituents (marker compounds). Melissa officinalis L. (lemon balm) was chosen for this study because...

    journal_title:Journal of pharmaceutical and biomedical analysis

    pub_type: 杂志文章

    doi:10.1016/j.jpba.2013.05.020

    authors: Arceusz A,Wesolowski M

    更新日期:2013-09-01 00:00:00

  • The efficient use of microcolumns in chromatographic systems.

    abstract::Microcolumn techniques involving pre-column concentration and post-column derivatization make good use of micro-scale high-performance liquid chromatography. The efficient use of microcolumns is illustrated by some applications to the analysis of amino acids, bile acids and catecholamines. The potential of new detecto...

    journal_title:Journal of pharmaceutical and biomedical analysis

    pub_type: 杂志文章

    doi:10.1016/0731-7085(84)80073-4

    authors: Ishii D,Goto M,Takeuchi T

    更新日期:1984-01-01 00:00:00

  • Improved bioautographic assay on TLC layers for qualitative and quantitative estimation of xanthine oxidase inhibitors and superoxide scavengers.

    abstract::A new agar-free bioautographic assay for xanthine oxidase (XO) inhibitors and superoxide scavengers on TLC layers was developed and validated. Compared to the first version of TLC bioautographic agar overlay method, our bioautographic assay greatly improved the sensitivity and quantification ability. The limit of dete...

    journal_title:Journal of pharmaceutical and biomedical analysis

    pub_type: 杂志文章

    doi:10.1016/j.jpba.2017.11.077

    authors: Kong Y,Li X,Zhang N,Miao Y,Feng H,Wu T,Cheng Z

    更新日期:2018-02-20 00:00:00

  • Identification of the metabolites in normal and AA rat plasma, urine and feces after oral administration of Daphne genkwa flavonoids by LC-Q-TOF-MS spectrometry.

    abstract::Daphne genkwa Sieb. et Zucc., as a traditional oriental herb, has been widely distributed and employed in China. The major bioactive components in D. genkwa are flavonoid compounds, which showed pharmacological activities such as anti-inflammatory, analgesic, anti-tumor and immunomodulatory activities. In this study, ...

    journal_title:Journal of pharmaceutical and biomedical analysis

    pub_type: 杂志文章

    doi:10.1016/j.jpba.2019.112856

    authors: Gan L,Ji J,Wang L,Li QY,Zhang CF,Wang CZ,Yuan CS

    更新日期:2020-01-05 00:00:00

  • Quantitative analysis of fosinopril sodium by capillary zone electrophoresis and liquid chromatography.

    abstract::A capillary zone electrophoresis (CZE) method was developed for the quantitative analysis of fosinopril sodium. Validation parameters of the CZE method were evaluated and compared to an existing LC method. In terms of precision and sensitivity. LC performance was superior to that of the CZE method for this application...

    journal_title:Journal of pharmaceutical and biomedical analysis

    pub_type: 杂志文章

    doi:10.1016/0731-7085(94)00136-p

    authors: Lozano R,Warren FV Jr,Perlman S,Joseph JM

    更新日期:1995-02-01 00:00:00

  • Utilizing capillary gas chromatography mass spectrometry to determine 4-benzotrifluoride t-butyl ether as a reaction by-product in fluoxetine synthesized using potassium t-butoxide as base.

    abstract::Fluoxetine hydrochloride has been prepared using two similar synthetic routes, both of which rely upon an ether formation reaction mediated by a base. The base used can affect the impurity profile of this reaction. It was proposed that the synthesis of fluoxetine carried out using potassium t-butoxide as base and 4-ch...

    journal_title:Journal of pharmaceutical and biomedical analysis

    pub_type: 杂志文章

    doi:10.1016/s0731-7085(02)00605-2

    authors: Robbins DK,Dodson PN,Buccilli LA,Mitchell D

    更新日期:2003-02-05 00:00:00

  • Stabilization of an anthrapyrazole antitumour agent, DuP 937, on complexation with heptakis(2,6-di-O-methyl)-beta-cyclodextrin in aqueous solution.

    abstract::DuP 937, an anthrapyrazole antitumour agent that is chemically unstable in aqueous solution, was shown, by absorption spectroscopy, to form an inclusion complex with heptakis(2,6-di-O-methyl)-beta-cyclodextrin (DM beta CD) in aqueous solution. Proton nuclear magnetic resonance spectroscopy was used to determine the st...

    journal_title:Journal of pharmaceutical and biomedical analysis

    pub_type: 杂志文章

    doi:10.1016/0731-7085(94)00063-8

    authors: Raghavan K,Nemeth G,Gray D,Hussain MA

    更新日期:1994-10-01 00:00:00

  • A tandem solid phase extraction, reversed-phase HPLC method for determining SDZ WAG 994 in dog, monkey and rat blood.

    abstract::The development and validation of a sensitive and specific HPLC method for SDZ WAG 994 (I) in dog, monkey and rat blood is described. Sample preparation entailed double solid phase extraction (SPE) of I and the internal standard from 0.5 ml of animal blood using a phenyl and propyl sulfonic acid cation exchange column...

    journal_title:Journal of pharmaceutical and biomedical analysis

    pub_type: 杂志文章

    doi:10.1016/s0731-7085(96)01899-7

    authors: Cramer JA,Pasternak SJ,Athill LV

    更新日期:1997-03-01 00:00:00

  • Drug-protein binding mechanism of juglone for early pharmacokinetic profiling: Insights from ultrafiltration, multi-spectroscopic and molecular docking methods.

    abstract::Juglone (JL), as one of the major bioactive components present in the bark of Juglans mandshruica Maxim, exhibits versatile bioactivities, especially anti-cancer activity. To better understand the pharmacokinetic properties of juglone, the protein binding rate of juglone was determined by ultrafiltration method, and t...

    journal_title:Journal of pharmaceutical and biomedical analysis

    pub_type: 杂志文章

    doi:10.1016/j.jpba.2017.03.036

    authors: Zhao P,Gao G,Zhang L,Cai Q,Lu N,Cheng L,Li S,Hou X

    更新日期:2017-07-15 00:00:00

  • Biotransformation and in vitro assessment of metabolism-associated drug-drug interaction for CRx-102, a novel combination drug candidate.

    abstract::CRx-102 is an oral synergistic combination drug which contains the cardiovascular agent, dipyridamole (DP) and a very low dose of the glucocorticoid, prednisolone (PRED). CRx-102 works through a novel mechanism of action in which DP selectively amplifies the anti-inflammatory activity of PRED without replicating its s...

    journal_title:Journal of pharmaceutical and biomedical analysis

    pub_type: 杂志文章

    doi:10.1016/j.jpba.2009.04.013

    authors: Zhang ZY,Chen M,Chen J,Padval MV,Kansra VV

    更新日期:2009-09-08 00:00:00

  • Electrochemical DNA nano-biosensor for the study of spermidine-DNA interaction.

    abstract::An electrochemical DNA nano-biosensor is prepared by immobilization of double stranded DNA (dsDNA) onto a mixed self-assembled monolayer (SAM) composed of azide- and hydroxyl-terminated thiols. The SAMs- and dsDNA-modified gold electrodes were characterized by cyclic voltammetry (CV) and electrochemical impedance spec...

    journal_title:Journal of pharmaceutical and biomedical analysis

    pub_type: 杂志文章

    doi:10.1016/j.jpba.2008.12.035

    authors: Mehdinia A,Kazemi SH,Bathaie SZ,Alizadeh A,Shamsipur M,Mousavi MF

    更新日期:2009-04-05 00:00:00

  • Studies and analytical application of reaction of imipramine with chrome azurol S.

    abstract::Chrome azurol S (CAS) was tested as a spectrophotometric reagent for the determination of imipramine (IMP). It reacts in aqueous media with IMP forming pink-red, sparingly soluble in water ion association compound. This compound was quantitatively extracted with chloroform and the absorbance of organic phase was measu...

    journal_title:Journal of pharmaceutical and biomedical analysis

    pub_type: 杂志文章

    doi:10.1016/s0731-7085(02)00314-x

    authors: Starczewska B,Hałaburda P,Kojło A

    更新日期:2002-10-15 00:00:00

  • High-performance liquid chromatographic assay and erythrocyte partitioning of fleroxacin, a new fluoroquinolone antibiotic.

    abstract::A rapid technique for sample preparation and HPLC was developed to study in vitro the erythrocyte binding and plasma protein binding of fleroxacin in the concentration range 0.2-15 micrograms ml-1. The red blood cell partition coefficient of fleroxacin was 1.45 +/- 0.18 at 25 degrees C and was independent of concentra...

    journal_title:Journal of pharmaceutical and biomedical analysis

    pub_type: 杂志文章

    doi:10.1016/0731-7085(90)80008-d

    authors: Brunt E,Limberg J,Derendorf H

    更新日期:1990-01-01 00:00:00

  • Evaluation of different injection techniques in the gas chromatographic determination of thermolabile trace impurities in a drug substance.

    abstract::Thermodegradation of labile compounds in the hot injection port of a gas chromatograph causes many problems and can lead to ambiguous, poorly reproducible results. Splitless injection used in trace analysis in order to achieve a lower detection limit may even enhance the difficulties due to the longer residence time o...

    journal_title:Journal of pharmaceutical and biomedical analysis

    pub_type: 杂志文章

    doi:10.1016/0731-7085(95)01307-7

    authors: Klick S

    更新日期:1995-04-01 00:00:00

  • Flow extraction spectrophotometric method for the determination of diclofenac sodium in pharmaceutical preparations.

    abstract::The spectrophotometric determination of trace amounts of diclofenac was carried out by liquid-liquid extraction using acridine yellow with a flow system. The determination of diclofenac sodium in the range of 3-80 micrograms ml-1 was possible with a sampling frequency of 40 samples h-1. The method was satisfactorily a...

    journal_title:Journal of pharmaceutical and biomedical analysis

    pub_type: 杂志文章

    doi:10.1016/s0731-7085(97)00028-9

    authors: Pérez-Ruiz T,Martínez-Lozano C,Sanz A,San Miguel MT

    更新日期:1997-10-01 00:00:00

  • Metabonomic identification of the effects of the Zhimu-Baihe saponins on a chronic unpredictable mild stress-induced rat model of depression.

    abstract::The herbal pair Zhimu-Baihe (Zhimu: Anemarrhena asphodeloides; Baihe: Lilium brownii var. viridulum) is a traditional Chinese medicament used for the treatment of depression. However, the relevant mechanisms of action has not been clarified. This study investigated the anti-depressant activity of the total saponins fr...

    journal_title:Journal of pharmaceutical and biomedical analysis

    pub_type: 杂志文章

    doi:10.1016/j.jpba.2016.06.019

    authors: Du H,Wang K,Su L,Zhao H,Gao S,Lin Q,Ma X,Zhu B,Dong X,Lou Z

    更新日期:2016-09-05 00:00:00

  • Determination of vitamin B6 in pharmaceutical formulations by flow injection-solid phase spectrophotometry.

    abstract::In this work, a new solid phase spectrophotometric method in association with flow injection analysis for Vitamin B6 (pyridoxine) determination has been developed with direct measurement of light-absorption in C18 material. In the developed method, successive passage of the complex, previously formed in the flowing st...

    journal_title:Journal of pharmaceutical and biomedical analysis

    pub_type: 杂志文章

    doi:10.1016/s0731-7085(03)00589-2

    authors: Portela JG,Costa AC,Teixeira LS

    更新日期:2004-02-18 00:00:00

  • Determination of the species status of Fallopia multiflora, Fallopia multiflora var. angulata and Fallopia multiflora var. ciliinervis based on morphology, molecular phylogeny, and chemical analysis.

    abstract::Relationships among Fallopia multiflora (Thunb.) Haraldson., F. multiflora var. angulata (S. Y. Liu) H. J. Yan, Z. J. Fang & Shi Xiao Yu., and F. multiflora var. ciliinervis (Nakai) Yonekura & H. Ohashi. were determined based on macroscopic and microscopic morphology, molecular phylogeny, and chemical analysis. The ma...

    journal_title:Journal of pharmaceutical and biomedical analysis

    pub_type: 杂志文章

    doi:10.1016/j.jpba.2019.01.040

    authors: Xie HQ,Chu SS,Zha LP,Cheng ME,Jiang L,Ren DD,Yu Y,Peng HS,Peng DY

    更新日期:2019-03-20 00:00:00

  • Use of thermal and non thermal techniques for assessing compatibility between mirtazapine and solid lipids.

    abstract::The present investigation was aimed at the evaluation of possible interactions between mirtazapine and selected solid lipids that are commonly used to develop solid lipid nanoparticles (SLNs) and nanostructured lipidic carriers (NLCs). The solids lipids explored were palmitic acid, stearic acid, glycerylmonostearate, ...

    journal_title:Journal of pharmaceutical and biomedical analysis

    pub_type: 杂志文章

    doi:10.1016/j.jpba.2018.08.041

    authors: Kaur R,Sinha VR

    更新日期:2018-11-30 00:00:00

  • Rapid, reliable, and sensitive detection of adenosine deaminase activity by UHPLC-Q-Orbitrap HRMS and its application to inhibitory activity evaluation of traditional Chinese medicines.

    abstract::Adenosine deaminase (ADA), which is a key enzyme in the metabolism of purine nucleosides, plays important roles in diverse disorders, such as tuberculosis, diabetes, liver disorders, and cancer. Determination of the activities of ADA and its isoenzymes in body fluids has received considerable attention in the diagnosi...

    journal_title:Journal of pharmaceutical and biomedical analysis

    pub_type: 杂志文章

    doi:10.1016/j.jpba.2018.02.045

    authors: Qi S,Guan H,Deng G,Yang T,Cheng X,Liu W,Liu P,Wang C

    更新日期:2018-05-10 00:00:00

  • A fluorescence optosensor for analyzing naphazoline in pharmaceutical preparations. Comparison with other sensors.

    abstract::We have developed an optical sensor for determining and quantifying naphazoline (NPZ) based on its inherent fluorescence property. We have placed a non-ionic-exchanger solid support (Amberlite XAD-7) in a flow cell in the light path of the excitation beam and the fluorescence signal for NPZ is continuously monitored a...

    journal_title:Journal of pharmaceutical and biomedical analysis

    pub_type: 杂志文章

    doi:10.1016/j.jpba.2005.02.018

    authors: Casado-Terrones S,Fernández-Sánchez JF,Díaz BC,Carretero AS,Fernández-Gutiérrez A

    更新日期:2005-07-15 00:00:00