Possible Mechanisms of Action of the Antispasmodic Agent Tiropramide in the Isolated Detrusor from Rats

Uruno, Tsutomu; Shirane, Masatoshi; Koh-ichi, Wada; Tsunematsu, Rieko; Nagahamaya, Kouji; Matsuoka, Yoshikazu; Sunagane, Nobuyoshi; Kubota, Keiichi

doi:10.1016/s0021-5198(19)32419-9

Cited by 2 publications

(3 citation statements)

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“…DMSO-d6 was used as a solvent. 1 H and 13 C chemical shift values were reported on the δ scale in ppm relative to that of TMS (δ = 0.00 ppm) as an internal standard. The data acquisition and processing of NMR spectra were performed using Topspin software (3.2 version).…”

Section: Apparatus and Equipmentmentioning

confidence: 99%

“…It is used as a synthetic antispasmodic drug derived from tyrosine amino acid, which is devoid of atropine like actions and acts on smooth muscular bro cells, however avoiding, atony since it does not bind itself to calmodulin. This drug shows its therapeutic activity by predominantly increasing Ca 2+ in ux and cAMP concentration in smooth muscle possibly because of inhibition of cAMP catabolism to a lesser extent [1].Some analytical methods were reported in the literature for the determination of tiropramide in plasma [2,3] and its metabolite pro ling [4]. No information is available on stress studies of this drug substance.…”

Section: Introductionmentioning

confidence: 99%

“…Tiropramide ( N ‐[3‐[4‐(2‐Diethylaminoethoxy) phenyl]‐‐1‐(dipropyl amino)‐1‐oxopropan‐2yl] benzamide) is used as a synthetic antispasmodic drug derived from tyrosine amino acid and is devoid of atropine‐like actions and acts on smooth muscular fibro cells. This drug exhibits its therapeutic activity by predominantly increasing Ca 2+ influx and cyclic adenosine monophosphate (cAMP) concentration in smooth muscles possibly because of the inhibition of cAMP catabolism to a lesser extent (Tsutomu et al, 1992). Some analytical methods were reported in the literature for the determination of tiropramide in plasma (Imran et al, 2007; Lee et al, 2003) and its metabolite profiling (Arigoni et al, 1988).…”

Section: Introductionmentioning

confidence: 99%

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Chromatographic separation of tiropramide hydrochloride and its degradation products along with their structural characterization using liquid chromatography quadrupole time‐of‐flight tandem mass spectrometry and nuclear magnetic resonance

Tidke

Golla

Kushwah

et al. 2023

Biomedical Chromatography

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Tiropramide HCl, an antispasmodic drug is subjected to various stress conditions (hydrolytic, oxidative, photolytic and thermal) as per ICH guidelines. The drug is widely used as an antispasmodic agent but there were no comprehensive degradation studies reported on it. Hence, forced degradation studies of tiropramide HCl were carried out to establish the degradation pro le and the storage conditions to maintain its quality attributes during the shelf life and usage. A selective HPLC method was developed to separate the drug as well as all of its degradation products using Agilent C18 (250×4.6 mm; 5 µm) column. The mobile phase of 10mM ammonium formate at pH 3.6 (solvent A) and methanol (solvent B) with gradient elution at a ow rate of 1.00 mL/min was used. Tiropramide was susceptible to acidic, basic hydrolytic exposure and oxidative stress conditions in the solution. This drug was found to be stable in neutral, thermal and photolytic conditions in both solution and solid-state. Five degradation products were detected under different stress conditions. The mass spectrometric fragmentation pattern of tiropramide and its degradation products was extensively studied using LC-Q-TOF-MS/MS for their structural characterization. The position of the oxygen atom in the N-oxide degradation product was con rmed by NMR studies. The knowledge gained by these studies was used to predict drug degradation pro les which is helpful in the development of the dosage form.

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Section: Apparatus and Equipmentmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Chromatographic separation of tiropramide hydrochloride and its degradation products along with their structural characterization using liquid chromatography quadrupole time‐of‐flight tandem mass spectrometry and nuclear magnetic resonance

Tidke

Golla

Kushwah

et al. 2023

Biomedical Chromatography

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Chromatographic separation of tiropramide hydrochloride and its degradation products along with their structural characterization using LC-QTOF-MS/MS and NMR

Tidke¹,

Golla²,

Kushwah³

et al. 2022

Preprint

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Tiropramide HCl, an antispasmodic drug is subjected to various stress conditions (hydrolytic, oxidative, photolytic and thermal) as per ICH guidelines. The drug is widely used as an antispasmodic agent but there were no comprehensive degradation studies reported on it. Hence, forced degradation studies of tiropramide HCl were carried out to establish the degradation profile and the storage conditions to maintain its quality attributes during the shelf life and usage. A selective HPLC method was developed to separate the drug as well as all of its degradation products using Agilent C18 (250×4.6 mm; 5 µm) column. The mobile phase of 10mM ammonium formate at pH 3.6 (solvent A) and methanol (solvent B) with gradient elution at a flow rate of 1.00 mL/min was used. Tiropramide was susceptible to acidic, basic hydrolytic exposure and oxidative stress conditions in the solution. This drug was found to be stable in neutral, thermal and photolytic conditions in both solution and solid-state. Five degradation products were detected under different stress conditions. The mass spectrometric fragmentation pattern of tiropramide and its degradation products was extensively studied using LC-Q-TOF-MS/MS for their structural characterization. The position of the oxygen atom in the N-oxide degradation product was confirmed by NMR studies. The knowledge gained by these studies was used to predict drug degradation profiles which is helpful in the development of the dosage form.

show abstract

Possible Mechanisms of Action of the Antispasmodic Agent Tiropramide in the Isolated Detrusor from Rats

Cited by 2 publications

References 12 publications

Chromatographic separation of tiropramide hydrochloride and its degradation products along with their structural characterization using liquid chromatography quadrupole time‐of‐flight tandem mass spectrometry and nuclear magnetic resonance

Chromatographic separation of tiropramide hydrochloride and its degradation products along with their structural characterization using liquid chromatography quadrupole time‐of‐flight tandem mass spectrometry and nuclear magnetic resonance

Chromatographic separation of tiropramide hydrochloride and its degradation products along with their structural characterization using LC-QTOF-MS/MS and NMR

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