Last update 21 Nov 2024

Pibutidine Hydrochloride

Last update 21 Nov 2024

Overview

R&D Status

Clinical Result

Translational Medicine

Overview

Basic Info

Drug Type

Small molecule drug

Synonyms

3-amino-4-[4- [4- (1-piperidinomethyl)-2-pyridyloxy]-cis-2-butenylamino]-3-cyclobutene-1, 2- dione hydrochloride, Pibutidine, Pibutidine hydrochloride (JAN)

+ [3]

Target

H2 receptor

Mechanism

H2 receptor antagonists(Histamine H2 receptor antagonists)

Therapeutic Areas

Digestive System Disorders

Active Indication

Peptic Ulcer

Inactive Indication

Duodenal Ulcer

Originator Organization

Taisho Pharmaceutical Co., Ltd.

Ikeda Mohando Ltd.

Active Organization

Taisho Pharmaceutical Co., Ltd.

Inactive Organization

Taisho Pharmaceutical Holdings Co., Ltd.

Ikeda Mohando Ltd.

Drug Highest PhasePreclinical

First Approval Date-

Regulation-

Structure

Molecular FormulaC19H25ClN4O3

InChIKeyODBOENMSSFCACZ-PVOKDAACSA-N

CAS Registry126463-66-9

100 Clinical Results associated with Pibutidine Hydrochloride

100 Translational Medicine associated with Pibutidine Hydrochloride

100 Patents (Medical) associated with Pibutidine Hydrochloride

Literatures (Medical) associated with Pibutidine Hydrochloride

01 Sep 2007·Molecular Endocrinology

The Zinc Finger Protein Ras-Responsive Element Binding Protein-1 Is a Coregulator of the Androgen Receptor: Implications for the Role of the Ras Pathway in Enhancing Androgenic Signaling in Prostate Cancer

Article

Author: Cinar, Bekir ; Leiter, Andrew B. ; Ferdinand, Angeline S. ; Adam, Rosalyn M. ; Kim, Jayoung ; Chung, Leland W. K. ; Mukhopadhyay, Lipi ; Richie, Jerome P. ; Lutchman, Mohini ; Mukhopadhyay, Nishit K. ; Liu, Brian C.-S. ; Freeman, Michael R. ; Ray, Subir K.

Androgen receptor (AR) plays an important role in normal prostate function as well as in the etiology of prostate cancer. Activation of AR is dictated by hormone binding and by interactions with coregulators. Several of these coregulators are known targets of Ras-related signals. Recent evidence suggests that Ras activation may play a causal role in the progression of prostate cancer toward a more malignant and hormone-insensitive phenotype. In the present study, we used a transcription factor-transcription factor interaction array method to identify the zinc finger protein Ras-responsive element binding protein (RREB-1) as a partner and coregulator of AR. In LNCaP prostate cancer cells, RREB-1 was found to be present in a complex with endogenous AR as determined by coimmunoprecipitation, glutathione S-transferase pull down, and immunofluorescence analyses. RREB-1 bound to the prostate-specific antigen (PSA) promoter as assessed by chromatin immunoprecipitation. Transient expression of RREB-1 down-regulated AR-mediated promoter activity and suppressed expression of PSA protein. The repressor activity of RREB-1 was significantly attenuated by cotransfection of activated Ras. Moreover, expression of the dominant-negative N-17-Ras or, alternatively, use of the MAPK kinase inhibitor PD98059 [2-(2-amino-3-methyoxyphenyl)-4H-1-benzopyran-4-one] abolished the effect of Ras in attenuating RREB-1-mediated repression. Furthermore, inhibition of RREB-1 expression by RNA interference enhanced the effect of Ras on PSA promoter activity and PSA expression. In addition, activation of the Ras pathway depleted AR from the RREB-1/AR complex. Collectively, our data for the first time identify RREB-1 as a repressor of AR and further implicate the Ras/MAPK kinase pathway as a likely antagonist of the inhibitory effects of RREB-1 on androgenic signaling.

01 Feb 2002·Biomedical ChromatographyQ4 · MEDICINE

Differentiation between isomeric oxidative metabolites of a piperidine‐containing drug by liquid chromatography–tandem mass spectrometry with stable‐isotope tracer technique

Q4 · MEDICINE

Article

Author: Shigeji Jingu ; Naoyoshi Ogawa ; Koji Kato ; Shohei Higuchi

AbstractThis report describes the application of a liquid chromatography–tandem mass spectrometry (LC‐MS/MS) method to differentiation of hydroxylations and N‐oxidations and of two different aliphatic hydroxylations in the investigation of the metabolism of pibutidine hydrochloride, a novel H2 antagonist, the structure of which includes a piperidine ring. Pibutidine metabolites in urine samples from adult male volunteers after oral administration of pibutidine hydrochloride were separated by reversed‐phase LC and ionized using an electrospray ionization (ESI) interface. A hydroxylated form of pibutidine was distinguished from the N‐oxide by comparison of their product ion spectra, although their mass‐to‐charge ratios of protonated molecules were identical. Further, two hydroxylated compounds were present in rat microsomal incubation mixtures with pibutidine. The distinction between their positions of hydroxylation (β‐ and γ‐carbon hydroxylation) on the piperidine ring was studied using [piperidine‐2H10] pibutidine as incubation substrate. The production of the β‐hydroxylated form was accompanied by the elimination of three 2H, resulting from a mechanism including the formation of iminium/enamine. The participation of the iminium ion intermediate in the β‐hydroxylation was confirmed by the observation that a cyanide adduct of pibutidine was formed instead of the β‐hydroxylated form when another incubation was performed in the presence of cyanide. Copyright © 2001 John Wiley & Sons, Ltd.

01 Dec 2000·Journal of Pharmaceutical and Biomedical AnalysisQ3 · MEDICINE

Determination of pibutidine metabolites in human plasma by LC-MS/MS

Q3 · MEDICINE

Article

Author: Shigeji Jingu ; Naoyoshi Ogawa ; Koji Kato ; Shohei Higuchi

A novel metabolite-screening procedure for pibutidine. an H2-receptor antagonist, which uses high-performance liquid chromatography/tandem mass spectrometry (LC-MS/MS), demonstrated the presence of pibutidine and its four metabolites in plasma from volunteers who received a single dose of pibutidine hydrochloride. In order to quantitatively examine the metabolism of pibutidine, an assay based on LC-MS/MS was subsequently developed for the simultaneous determination of its metabolites in human plasma. Target analytes consisted of M-5, M-7 and M-8, which were prominently detected by the screening procedure, and M-9, which has pharmacological activity as an H2-receptor antagonist. Metabolites and their deuterated internal standards were extracted from human plasma using an Oasis HLB extraction cartridge, and chromatographed on a Monitor C18M column. No isotope effects on chromatographic retention time were observed for any deuterated compounds, which were ionized using an electrospray ionization (ESI)- interface and detected by MS/MS in the selected reaction-monitoring (SRM) mode simultaneously with the corresponding metabolites. The assay was validated over the concentration range of 0.1 to 25.6 ng ml(-1) and used to determine the plasma levels of metabolites in volunteers following oral administration of a 20-mg dose of pibutidine hydrochloride.

100 Deals associated with Pibutidine Hydrochloride

External Link

KEGG	Wiki	ATC	Drug Bank
D01861	-	-	-

R&D Status

10 top R&D records.

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Indication	Highest Phase	Country/Location	Organization	Date
Peptic Ulcer	Preclinical	JP	Taisho Pharmaceutical Co., Ltd.	01 Jan 1990
Duodenal Ulcer	Preclinical	-	Taisho Pharmaceutical Holdings Co., Ltd.	-
Duodenal Ulcer	Preclinical	-	Ikeda Mohando Ltd.	-
Duodenal Ulcer	Preclinical	JP	-	-

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