Page last updated: 2024-12-05

tiaramide

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

tiaramide: NTA-194, solantal, FK 1160 refer to mono-HCl salt; RN given refers to parent cpd; structure [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID5469
CHEMBL ID274239
CHEBI ID135504
SCHEMBL ID25172
MeSH IDM0044530

Synonyms (39)

Synonym
32527-55-2
tiaramide
5-chloro-3-{2-[4-(2-hydroxyethyl)piperazin-1-yl]-2-oxoethyl}-1,3-benzothiazol-2(3h)-one
1-piperazineethanol, 4-((5-chloro-2-oxo-3(2h)-benzothiazolyl)acetyl)-
4-((5-chloro-2-oxo-3(2h)-benzothiazolyl)acetyl)-1-piperazineethanol
tiaramidum [inn-latin]
5-chlor-2,3-dihydro-3-(4-(2-hydroxyethyl)piperazinylcarbonylmethyl)-2-benzothiazolon
tiaramide [inn:ban]
einecs 251-083-7
1-piperazineethanol, 4-((5-chloro-2-oxo-3-benzothiazolinyl)acetyl)-
tiaramida [inn-spanish]
brn 1030245
1-piperazineethanol, 4-[(5-chloro-2-oxo-3(2h)-benzothiazolyl)acetyl]-
rhc 2592a
5-chloro-3-[2-[4-(2-hydroxyethyl)piperazin-1-yl]-2-oxo-ethyl]-1,3-benzothiazol-2-one
usv 2592
OPREA1_708738
CHEBI:135504
rhc-2592a
tialamide
CHEMBL274239
D08592
tiaramide (inn)
5-chloro-3-[2-[4-(2-hydroxyethyl)piperazin-1-yl]-2-oxoethyl]-1,3-benzothiazol-2-one
unii-bb17wgm686
bb17wgm686 ,
tiaramida
tiaramidum
tiaramide [who-dd]
tiaramide [mi]
2(3h)-benzothiazolone, 5-chloro-3-(2-(4-(2-hydroxyethyl)-1-piperazinyl)-2-oxoethyl)-
1-piperazineethanol, 4-((5-chloro-2-oxo-3(2h)-benzothiazolyl)acetyl)
tiaramide [inn]
SCHEMBL25172
DTXSID0023666
5-chloro-3-{2-[4-(2-hydroxyethyl)-1-piperazinyl]-2-oxoethyl}-1,3-benzothiazol-2(3h)-one
sr-01000944979
SR-01000944979-1
Q27274575

Research Excerpts

Overview

Tiaramide hydrochloride is a new non-steroidal anti-inflammatory agent. It has been shown to inhibit allergic responses both in vitro and in vivo.

ExcerptReferenceRelevance
"Tiaramide (RHC 2592-A) is an analgesic agent with antiallergic activity in vivo. "( Antiallergic activity of tiaramide (RHC 2592-A).
Coutts, S; Khandwala, A; Weinryb, I, 1982
)
2.01
"Tiaramide hydrochloride is a new non-steroidal anti-inflammatory agent previously shown to inhibit allergic responses both in vitro and in vivo. "( A trial of tiaramide in asthma.
Harvey, JE; Jones, P; Tanser, AR, 1985
)
2.1

Actions

ExcerptReferenceRelevance
"Tiaramide did not inhibit intracellular Ca mobilization, and it did not affect the calmodulin-dependent cyclic nucleotide phosphodiesterase of rabbit brain."( Inhibition of phospholipase A2 by tiaramide in rabbit platelets.
Takano, S, 1985
)
1.27

Treatment

ExcerptReferenceRelevance
"3. Tiaramide treatment did not impair ethanol elimination from blood of rats, but pyrazole pretreatment caused a drastic decrease of the piperazineacetic acid metabolite in the liver and serum of rats treated with tiaramide."( Metabolism of tiaramide in vitro. II. Oxidation of piperazineethanol group in tiaramide by 105 000 g supernatants from monkey and rat liver.
Iwasaki, K; Noguchi, H, 1982
)
1.14

Toxicity

ExcerptReferenceRelevance
"The identification of a safe and reliable alternative for patients with non-steroidal anti-inflammatory drug (NSAID)-induced urticaria/angioedema is a frequent problem for dermatologists and other practitioners."( Safety of selective cyclooxygenase-2 inhibitors and a basic non-steroidal anti-inflammatory drug (NSAID) in Japanese patients with NSAID-induced urticaria and/or angioedema: Comparison of meloxicam, etodolac and tiaramide.
Chiba, Y; Ikezawa, Z; Inomata, N; Kambara, T; Onoda, M; Osuna, H; Takeshita, Y; Yamaguchi, J, 2007
)
0.53

Dosage Studied

The results of this provocative test following the single and multiple dosage administration of tiaramide were compared to baseline skin responses. The high recovery of tertiary amine N-oxides in human urine after tiaramide dosing reflects the high activity of N-Oxidation of Tiaramide by human liver microsomes.

ExcerptRelevanceReference
" This provides a simple, rapid and reproducible way of obtaining linear dose-response curves by plotting times of exposures against absolute or percent increases in sRaw."( Drug effect on bronchial response to PGF2 alpha and water inhalation.
Bianco, S; Damonte, C; Robuschi, M, 1983
)
0.27
" After oral dosing with 1-[(5-chloro-2-oxo-3(2H)-benzothiazolyl)acetyl]-piperazine (DETR), M-I was detected in the urine, and the urinary excretion by male and female rats was similar to that in mice."( Terminal N-sulphoconjugation of an alicyclic amine (piperazine), identified as a new metabolite of tiaramide in mouse and rat.
Iwasaki, K; Noda, K; Noguchi, H; Shiraga, T; Tada, K, 1983
)
0.48
" The results of this provocative test following the single and multiple dosage administration of tiaramide were compared to baseline skin responses."( Preliminary report on the effects of tiaramide on the ice cube test in patients with idiopathic cold urticaria.
Kaplan, AP; Natbony, SF; Neiss, ES; Petillo, JJ; Vukovich, RA; Zisblatt, M, 1983
)
0.76
" THC is a very weak inhibitor of 3'-5' cyclic adenosine monophosphate phosphodiesterase which is affected only at very high dosage (10(-2) M)."( New pharmacological aspects on the antiasthmatic activity of tiaramide-HCl.
Berti, F; Brunelli, G; Folco, GC; Lombroso, M; Niada, R; Nicosia, S; Omini, C; Rossoni, G; ViganĂ², T, 1982
)
0.51
" The high recovery of tertiary amine N-oxides in human urine after tiaramide dosing reflects the high activity of N-oxidation of tiaramide by human liver microsomes."( Metabolism of tiaramide in vitro. I. Oxidative metabolism of tiaramide by human and rat liver microsomes.
Iwasaki, K; Kamataki, T; Kato, R; Noguchi, H, 1982
)
0.86
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
benzothiazoles
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Bioassays (47)

Assay IDTitleYearJournalArticle
AID177051Compound was evaluated for antiinflammatory activity in rats by carrageenan edema test1986Journal of medicinal chemistry, Nov, Volume: 29, Issue:11
Structure-activity studies of 4,6-disubstituted 2-(morpholinocarbonyl)furo[3,2-b]indole derivatives with analgesic and antiinflammatory activities.
AID182708Compound was tested for the inhibition of rat reversed passive Arthus pleurisy after peroral administration of 10 mg/kg dose at 0.44 mL of exudate volume with 0.68 mL of control (injected intrapleurally)1992Journal of medicinal chemistry, Mar-20, Volume: 35, Issue:6
A novel synthesis and potent antiinflammatory activity of 4-hydroxy-2(1H)-oxo-1-phenyl-1,8-naphthyridine-3-carboxamides.
AID182710Compound was tested for the inhibition of rat reversed passive Arthus pleurisy after peroral administration of 10 mg/kg dose at 3.18*10e6 no of cells with 3.24*10e6 cells of control1992Journal of medicinal chemistry, Mar-20, Volume: 35, Issue:6
A novel synthesis and potent antiinflammatory activity of 4-hydroxy-2(1H)-oxo-1-phenyl-1,8-naphthyridine-3-carboxamides.
AID183040Compound was tested for the inhibition of rat reversed passive Arthus pleurisy after peroral administration of 30 mg/kg dose at 2.79*10e6 no of cells with 3.24*10e6 cells of control1992Journal of medicinal chemistry, Mar-20, Volume: 35, Issue:6
A novel synthesis and potent antiinflammatory activity of 4-hydroxy-2(1H)-oxo-1-phenyl-1,8-naphthyridine-3-carboxamides.
AID192271Antiinflammatory activity on Zymosan-induced rat's paw edema(ZPE) after peroral administration of 30 mg/kg dose with control swelling of 66.9%1992Journal of medicinal chemistry, Mar-20, Volume: 35, Issue:6
A novel synthesis and potent antiinflammatory activity of 4-hydroxy-2(1H)-oxo-1-phenyl-1,8-naphthyridine-3-carboxamides.
AID182717Compound was tested for the inhibition of rat reversed passive Arthus pleurisy after peroral administration of 100 mg/kg dose at 0.12 mL of exudate volume with 0.68 mL of control (injected intrapleurally)1992Journal of medicinal chemistry, Mar-20, Volume: 35, Issue:6
A novel synthesis and potent antiinflammatory activity of 4-hydroxy-2(1H)-oxo-1-phenyl-1,8-naphthyridine-3-carboxamides.
AID182554Compound was tested for the inhibition of Carrageenan rat's paw edema(CPE) after peroral administration of 30 mg/kg dose1992Journal of medicinal chemistry, Mar-20, Volume: 35, Issue:6
A novel synthesis and potent antiinflammatory activity of 4-hydroxy-2(1H)-oxo-1-phenyl-1,8-naphthyridine-3-carboxamides.
AID176684Compound was evaluated for analgesic activity in Adjuvant-induced arthritic pain test in rats1986Journal of medicinal chemistry, Nov, Volume: 29, Issue:11
Structure-activity studies of 4,6-disubstituted 2-(morpholinocarbonyl)furo[3,2-b]indole derivatives with analgesic and antiinflammatory activities.
AID1079939Cirrhosis, proven histopathologically. Value is number of references indexed. [column 'CIRRH' in source]
AID182561Compound was tested for the inhibition of Zymosan-induced rat's paw edema(ZPE) after peroral administration of 30 mg/kg dose1992Journal of medicinal chemistry, Mar-20, Volume: 35, Issue:6
A novel synthesis and potent antiinflammatory activity of 4-hydroxy-2(1H)-oxo-1-phenyl-1,8-naphthyridine-3-carboxamides.
AID182563Compound was tested for the inhibition of arachidonic acid-induced rat's paw edema(APE) after peroral administration of 100 mg/kg dose1992Journal of medicinal chemistry, Mar-20, Volume: 35, Issue:6
A novel synthesis and potent antiinflammatory activity of 4-hydroxy-2(1H)-oxo-1-phenyl-1,8-naphthyridine-3-carboxamides.
AID176686Compound was evaluated for analgesic activity in Randall-Selitto test in normal foot rats1986Journal of medicinal chemistry, Nov, Volume: 29, Issue:11
Structure-activity studies of 4,6-disubstituted 2-(morpholinocarbonyl)furo[3,2-b]indole derivatives with analgesic and antiinflammatory activities.
AID1079934Highest frequency of acute liver toxicity observed during clinical trials, expressed as a percentage. [column '% AIGUE' in source]
AID1079941Liver damage due to vascular disease: peliosis hepatitis, hepatic veno-occlusive disease, Budd-Chiari syndrome. Value is number of references indexed. [column 'VASC' in source]
AID192279Compound was tested for the inhibition of arachidonic acid-induced rat's paw edema(APE) after peroral administration of 100 mg/kg dose with control swelling of 51.6%1992Journal of medicinal chemistry, Mar-20, Volume: 35, Issue:6
A novel synthesis and potent antiinflammatory activity of 4-hydroxy-2(1H)-oxo-1-phenyl-1,8-naphthyridine-3-carboxamides.
AID1079935Cytolytic liver toxicity, either proven histopathologically or where the ratio of maximal ALT or AST activity above normal to that of Alkaline Phosphatase is > 5 (see ACUTE). Value is number of references indexed. [column 'CYTOL' in source]
AID192117Antiinflammatory activity on Carrageenan rat's paw edema(CPE) after peroral administration of 30 mg/kg dose1992Journal of medicinal chemistry, Mar-20, Volume: 35, Issue:6
A novel synthesis and potent antiinflammatory activity of 4-hydroxy-2(1H)-oxo-1-phenyl-1,8-naphthyridine-3-carboxamides.
AID182552Inhibition of carrageenan-induced rat's paw edema (CPE) after peroral administration of 100 mg/kg dose.1992Journal of medicinal chemistry, Mar-20, Volume: 35, Issue:6
A novel synthesis and potent antiinflammatory activity of 4-hydroxy-2(1H)-oxo-1-phenyl-1,8-naphthyridine-3-carboxamides.
AID176685Compound was evaluated for analgesic activity in Randall-Selitto test in inflamed foot rats1986Journal of medicinal chemistry, Nov, Volume: 29, Issue:11
Structure-activity studies of 4,6-disubstituted 2-(morpholinocarbonyl)furo[3,2-b]indole derivatives with analgesic and antiinflammatory activities.
AID183038Compound was tested for the inhibition of rat reversed passive Arthus pleurisy after peroral administration of 30 mg/kg dose at 0.33 mL of exudate volume with 0.68 mL of control (injected intrapleurally)1992Journal of medicinal chemistry, Mar-20, Volume: 35, Issue:6
A novel synthesis and potent antiinflammatory activity of 4-hydroxy-2(1H)-oxo-1-phenyl-1,8-naphthyridine-3-carboxamides.
AID1079944Benign tumor, proven histopathologically. Value is number of references indexed. [column 'T.BEN' in source]
AID183035Compound was tested for the inhibition of rat reversed passive Arthus pleurisy after peroral administration of 3 mg/kg dose at 0.6 mL of exudate volume with 0.68 mL of control (injected intrapleurally)1992Journal of medicinal chemistry, Mar-20, Volume: 35, Issue:6
A novel synthesis and potent antiinflammatory activity of 4-hydroxy-2(1H)-oxo-1-phenyl-1,8-naphthyridine-3-carboxamides.
AID1079943Malignant tumor, proven histopathologically. Value is number of references indexed. [column 'T.MAL' in source]
AID182698Compound was tested for the inhibition of arachidonic acid-induced rat's paw edema(APE) after peroral administration of 30 mg/kg dose1992Journal of medicinal chemistry, Mar-20, Volume: 35, Issue:6
A novel synthesis and potent antiinflammatory activity of 4-hydroxy-2(1H)-oxo-1-phenyl-1,8-naphthyridine-3-carboxamides.
AID177052Compound was evaluated for antipyretic activity in rats by yeast induced fever test1986Journal of medicinal chemistry, Nov, Volume: 29, Issue:11
Structure-activity studies of 4,6-disubstituted 2-(morpholinocarbonyl)furo[3,2-b]indole derivatives with analgesic and antiinflammatory activities.
AID1079940Granulomatous liver disease, proven histopathologically. Value is number of references indexed. [column 'GRAN' in source]
AID1079945Animal toxicity known. [column 'TOXIC' in source]
AID1079949Proposed mechanism(s) of liver damage. [column 'MEC' in source]
AID1079947Comments (NB not yet translated). [column 'COMMENTAIRES' in source]
AID1079942Steatosis, proven histopathologically. Value is number of references indexed. [column 'STEAT' in source]
AID1079936Choleostatic liver toxicity, either proven histopathologically or where the ratio of maximal ALT or AST activity above normal to that of Alkaline Phosphatase is < 2 (see ACUTE). Value is number of references indexed. [column 'CHOLE' in source]
AID183036Compound was tested for the inhibition of rat reversed passive Arthus pleurisy after peroral administration of 3 mg/kg dose at 3.17*10e6 no of cells with 3.24*10e6 cells of control1992Journal of medicinal chemistry, Mar-20, Volume: 35, Issue:6
A novel synthesis and potent antiinflammatory activity of 4-hydroxy-2(1H)-oxo-1-phenyl-1,8-naphthyridine-3-carboxamides.
AID1079933Acute liver toxicity defined via clinical observations and clear clinical-chemistry results: serum ALT or AST activity > 6 N or serum alkaline phosphatases activity > 1.7 N. This category includes cytolytic, choleostatic and mixed liver toxicity. Value is
AID192263Antiinflammatory activity on Zymosan-induced rat's paw edema(ZPE) after peroral administration of 100 mg/kg dose with control swelling of 66.9%1992Journal of medicinal chemistry, Mar-20, Volume: 35, Issue:6
A novel synthesis and potent antiinflammatory activity of 4-hydroxy-2(1H)-oxo-1-phenyl-1,8-naphthyridine-3-carboxamides.
AID182559Inhibition of Zymosan-induced rat's paw edema(ZPE) after peroral administration of 100 mg/kg dose.1992Journal of medicinal chemistry, Mar-20, Volume: 35, Issue:6
A novel synthesis and potent antiinflammatory activity of 4-hydroxy-2(1H)-oxo-1-phenyl-1,8-naphthyridine-3-carboxamides.
AID1079938Chronic liver disease either proven histopathologically, or through a chonic elevation of serum amino-transferase activity after 6 months. Value is number of references indexed. [column 'CHRON' in source]
AID192282Compound was tested for the inhibition of arachidonic acid-induced rat's paw edema(APE) after peroral administration of 30 mg/kg dose with control swelling of 33.8%1992Journal of medicinal chemistry, Mar-20, Volume: 35, Issue:6
A novel synthesis and potent antiinflammatory activity of 4-hydroxy-2(1H)-oxo-1-phenyl-1,8-naphthyridine-3-carboxamides.
AID114625Inhibition of acetic acid induced writhing in mice.1986Journal of medicinal chemistry, Nov, Volume: 29, Issue:11
Structure-activity studies of 4,6-disubstituted 2-(morpholinocarbonyl)furo[3,2-b]indole derivatives with analgesic and antiinflammatory activities.
AID114627Compound was evaluated for analgesic activity in Pressure test in mice1986Journal of medicinal chemistry, Nov, Volume: 29, Issue:11
Structure-activity studies of 4,6-disubstituted 2-(morpholinocarbonyl)furo[3,2-b]indole derivatives with analgesic and antiinflammatory activities.
AID1079937Severe hepatitis, defined as possibly life-threatening liver failure or through clinical observations. Value is number of references indexed. [column 'MASS' in source]
AID182873Compound was tested for the inhibition of rat reversed passive Arthus pleurisy after peroral administration of 100 mg/kg dose at 1.52*10e6 no of cells with 3.24*10e6 cells of control1992Journal of medicinal chemistry, Mar-20, Volume: 35, Issue:6
A novel synthesis and potent antiinflammatory activity of 4-hydroxy-2(1H)-oxo-1-phenyl-1,8-naphthyridine-3-carboxamides.
AID588220Literature-mined public compounds from Kruhlak et al phospholipidosis modelling dataset2008Toxicology mechanisms and methods, , Volume: 18, Issue:2-3
Development of a phospholipidosis database and predictive quantitative structure-activity relationship (QSAR) models.
AID1079948Times to onset, minimal and maximal, observed in the indexed observations. [column 'DELAI' in source]
AID1079946Presence of at least one case with successful reintroduction. [column 'REINT' in source]
AID1079932Highest frequency of moderate liver toxicity observed during clinical trials, expressed as a percentage. [column '% BIOL' in source]
AID192109Antiinflammatory activity on Carrageenan rat's paw edema(CPE) after peroral administration of 100 mg/kg dose with control swelling of 69.9%1992Journal of medicinal chemistry, Mar-20, Volume: 35, Issue:6
A novel synthesis and potent antiinflammatory activity of 4-hydroxy-2(1H)-oxo-1-phenyl-1,8-naphthyridine-3-carboxamides.
AID1079931Moderate liver toxicity, defined via clinical-chemistry results: ALT or AST serum activity 6 times the normal upper limit (N) or alkaline phosphatase serum activity of 1.7 N. Value is number of references indexed. [column 'BIOL' in source]
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (57)

TimeframeStudies, This Drug (%)All Drugs %
pre-199045 (78.95)18.7374
1990's6 (10.53)18.2507
2000's5 (8.77)29.6817
2010's1 (1.75)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 26.48

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be moderate demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index26.48 (24.57)
Research Supply Index4.17 (2.92)
Research Growth Index3.97 (4.65)
Search Engine Demand Index28.85 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (26.48)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials5 (8.47%)5.53%
Reviews0 (0.00%)6.00%
Case Studies5 (8.47%)4.05%
Observational0 (0.00%)0.25%
Other49 (83.05%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]