Metabolism of budralazine, a new antihypertensive agent. II. Metabolic pathways of budralazine in rats.

Moroi, Reimei; Ono, Kenji; Saito, Tadashi; Akimoto, Takeshi; Sano, Mitsuji

doi:10.1248/cpb.25.830

Cited by 20 publications

(8 citation statements)

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“…Acetylation proceeds via an uncyclized intermediate (20) which has not been isolated and which results in 3-methyl-s-triazolo[3,4-a]phthalazine (21). [60][61][62] This compound undergoes further metabolism to 9-hydroxy-3-methyl-s-triazolophthalazine and 3-hydroxymethyl-~-triazolo[~,~-a]phthalazines6~~7 (13) which are both excreted as conjugates in the urine.…”

Section: Metabolismmentioning

confidence: 99%

“…The metabolic pathways identified in man are shown in Figure 15 although the relative importance of each pathway in an individual depends heavily on acetylator status and other factors. Acetylation proceeds via an uncyclized intermediate (20) which has not been isolated and which results in 3-methyl-s-triazolo[3,4-a]phthalazine (21). [60][61][62] This compound undergoes further metabolism to 9-hydroxy-3-methyl-s-triazolophthalazine and 3-hydroxymethyl-~-triazolo[~,~-a]phthalazines6~~7 (13) which are both excreted as conjugates in the urine.…”

Section: Metabolismmentioning

confidence: 99%

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Hydralazine and related compounds: Chemistry, metabolism, and mode of action

Reece

1981

Medicinal Research Reviews

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Section: Metabolismmentioning

confidence: 99%

Section: Metabolismmentioning

confidence: 99%

Hydralazine and related compounds: Chemistry, metabolism, and mode of action

Reece

1981

Medicinal Research Reviews

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“…Metabolite V is formed in a three step process by decarbethoxylation to the free hydrazine metabolite III, which is further acetylated to IV and cyclized analogously to other hydrazine containing drugs (11)(12)(13)(14).…”

Section: Discussionmentioning

confidence: 99%

Studies on the metabolism of cadralazine in rat

Simonotti¹,

Zanol²,

Parravicini³

et al. 1982

European Journal of Drug Metabolism and Pharmacokinetics

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metabolism in rat; TLC-MS analysis; GC-MS quantitation; synthesis of 3-pyrazolylpyridazine derivatives as standards. SUMMARYThe metabolism of cadralazine I was studied after oral administration to rat. Besides consistent amount of unchanged drug, three metabolites were separated in urine by TLC and GC and their structures elucidated by mass spectrometry in comparison with synthetie samples. A specific and sensitive method was developed to detect the decarbethoxylated metabolite III at nanogram levels.

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“…Phthalazin-1(2H)-one derivatives are of considerable interest due to their antidiabetic, 10 antiallergic, 11 vasorelaxant, 12 PDE4 inhibitor, 13 VEGF (vascular endothelial growth factor) receptor tyrosine kinase (for the treatment of cancer), 14 antiasthmatic, 15 and herbicidal 16 activities. A number of established drug molecules like Hydralazine, 17,18 Budralazine, 19,20 Azelastine, 21,22 Ponalrestat, 23 and Zopolrestat, 24 were prepared from the corresponding phthalazinones.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, antimicrobial and cytotoxicity studies of some novel modified Strobilurin derivatives

Sridhara¹,

Reddy²,

Keshavayya³

et al. 2011

J. Braz. Chem. Soc.

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Uma série de novas 3-isoxazolinas substituídas, derivadas do metil-3-metóxi-2-(4-oxo-3,4-diidroftalazin-1-il)prop-2-enoato foram estudadas e sintetizadas a partir do metil-(4-oxo-3,4-diidroftalazin-1-il)acetato, o qual foi preparado a partir do anidrido ftálico. As estruturas dos novos compostos sintetizados foram caracterizadas por dados espectrais e suas atividades antimicrobianas e citotóxicas estudadas. Vários desses compostos mostraram boa atividade antimicrobiana.A series of some new 3-isoxazoline substituted methyl-3-methoxy-2-(4-oxo-3,4-dihydrophthalazin-1-yl)prop-2-enoate derivatives were designed and synthesized from methyl-(4-oxo-3,4-dihydrophthalazin-1-yl)acetate, which in turn was prepared from phthalic anhydride. The structures of synthesized new compounds were characterized by spectral data and studied for their antimicrobial activities and cytotoxicity. Several of these compounds showed good antimicrobial activity.Keywords: phthalazin-1(2H)-one, β-methoxyacrylate, strobilurins, isoxazoline IntroductionNitrogen-containing heterocyclic molecules constitute the largest portion of chemical entities, which are part of many natural products, fine chemicals, and biologically active pharmaceuticals. Strobilurins and their analogues constitute a large group of compounds that represent a new class of plant-protecting agents 1 that meet all the demands that are made nowadays for pesticides. They exhibit efficacy against a broad-spectrum of fungal diseases, possess significant post-infective activity, and have a unique mode of action. 2 Intensive studies aimed at a search for novel biologically active methoxyacrylate fungicides are currently under way by different manufacturers. 3 Studies on the structure of natural methoxyacrylates have made possible to create a novel class of synthetic fungicides with enhanced stability, high activity, and a broad spectrum of action. β-Methoxyacrylate which is a critical and common structural element of strobilurins, fund use in agrochemical agents, 4 antivirals, 5 antimalarials, 6 and fungicides. 7 There has been extensive industrial development of these compounds and their analogues. 8,9 In finding new β-methoxyacrylate derivatives, we observed that, phthalazines attached to these pharmacophore were not studied. Phthalazin-1(2H)-one derivatives are of considerable interest due to their antidiabetic, 10 antiallergic, 11 vasorelaxant, 12 PDE4 inhibitor, 13 VEGF (vascular endothelial growth factor) receptor tyrosine kinase (for the treatment of cancer), 14 The diverse biological activities of β-methoxyacrylate, phthalazin-1(2H)-one, and isoxazoline pharmacophores envisaged us to plan a new lead compounds that may exhibit wide pharmacological activities. By combining these pharmacophore components in a molecule to give a compact system, we designed and synthesized a series of phthalazin-1(2H)-one derivatives containing β-methoxyacrylate and isoxazoline moieties. Figure 1 reveals a framework of these three important biological active pharmacophore component systems.The synth...

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Metabolism of budralazine, a new antihypertensive agent. II. Metabolic pathways of budralazine in rats.

Cited by 20 publications

References 0 publications

Hydralazine and related compounds: Chemistry, metabolism, and mode of action

Hydralazine and related compounds: Chemistry, metabolism, and mode of action

Studies on the metabolism of cadralazine in rat

Synthesis, antimicrobial and cytotoxicity studies of some novel modified Strobilurin derivatives

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