Compounds > irindalone
Page last updated: 2024-11-06

irindalone

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

Cross-References

ID SourceID
PubMed CID65845
CHEMBL ID73461
SCHEMBL ID247221
MeSH IDM0158812

Synonyms (21)

Synonym
irindalone
CHEMBL73461 ,
1-[2-[4-[(1r,3s)-3-(4-fluorophenyl)-2,3-dihydro-1h-inden-1-yl]piperazin-1-yl]ethyl]imidazolidin-2-one
bdbm50020232
1-(2-{4-[(1r,3s)-3-(4-fluoro-phenyl)-indan-1-yl]-piperazin-1-yl}-ethyl)-imidazolidin-2-one
1-(2-{4-[3-(4-fluoro-phenyl)-indan-1-yl]-piperazin-1-yl}-ethyl)-imidazolidin-2-one(irindalone)
irindalonum
unii-4f39t8n10k
irindalone [inn]
(+)-(1r,3s)-1-(2-(4-(3-(p-fluorophenyl)-1-indanyl)-1-piperazinyl)ethyl)-2-imidazolidinone
irindalona
irindalonum [latin]
96478-43-2
irindalona [spanish]
4f39t8n10k ,
SCHEMBL247221
DTXSID30242274
CS-6668
HY-101632
Q27259505
AKOS040733464

Research Excerpts

Overview

Irindalone is a new antihypertensive agent with affinity to serotonin (5-HT2) receptors and at higher concentrations also to alpha 1-adrenoceptors.

ExcerptReferenceRelevance
"Irindalone is a new antihypertensive agent with affinity to serotonin (5-HT2) receptors and at higher concentrations also to alpha 1-adrenoceptors. "( Cardiovascular effects of irindalone, a new S2-serotonergic antagonist, in the rat.
Carlsson, S; Gradin, K; Hedner, T; Persson, B, 1990)		2.02

Dosage Studied

ExcerptRelevanceReference
" Subsequently a dose-response curve of pressor responses to phenylephrine was constructed in pithed rats."( Antihypertensive effects of chronic 5-hydroxytryptamine (5-HT2) receptor blockade with irindalone in the spontaneously hypertensive rat.
Gradin, K; Hedner, T; Persson, B, 1991)		0.5
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (7)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
5-hydroxytryptamine receptor 2CRattus norvegicus (Norway rat)IC50 (µMol)0.13250.00040.629810.0000AID4791; AID4826; AID4837
5-hydroxytryptamine receptor 2ARattus norvegicus (Norway rat)IC50 (µMol)0.13250.00040.908610.0000AID4791; AID4826; AID4837
Alpha-1B adrenergic receptorRattus norvegicus (Norway rat)IC50 (µMol)0.34800.00021.874210.0000AID36869
Alpha-1D adrenergic receptorRattus norvegicus (Norway rat)IC50 (µMol)0.34800.00021.270410.0000AID36869
5-hydroxytryptamine receptor 2BRattus norvegicus (Norway rat)IC50 (µMol)0.13250.00040.615610.0000AID4791; AID4826; AID4837
Alpha-1A adrenergic receptorRattus norvegicus (Norway rat)IC50 (µMol)0.34800.00001.819410.0000AID36869
D(2) dopamine receptorRattus norvegicus (Norway rat)IC50 (µMol)1.45000.00010.54948.4000AID61545; AID64449; AID64608
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (24)

Assay IDTitleYearJournalArticle
AID36869Inhibition of [3H]prazosin binding to alpha-1 adrenergic receptor from rat cortical membranes1988Journal of medicinal chemistry, Dec, Volume: 31, Issue:12
Antihypertensive activity in a series of 1-piperazino-3-phenylindans with potent 5-HT2-antagonistic activity.
AID204369In vitro inhibition of [3H]5-HT transporter uptake in rat brain synaptosomes1988Journal of medicinal chemistry, Dec, Volume: 31, Issue:12
Antihypertensive activity in a series of 1-piperazino-3-phenylindans with potent 5-HT2-antagonistic activity.
AID64449Inhibition of [3H]spiperone binding to Dopamine receptor D2 from rat striatal membranes1988Journal of medicinal chemistry, Dec, Volume: 31, Issue:12
Antihypertensive activity in a series of 1-piperazino-3-phenylindans with potent 5-HT2-antagonistic activity.
AID32959Displacement of [3H]prazosin from alpha-1 adrenoceptors in whole rat brain membranes1993Journal of medicinal chemistry, Sep-17, Volume: 36, Issue:19
Stereospecific and selective 5-HT2 antagonism in a series of 5-substituted trans-1-piperazino-3-phenylindans.
AID177864Inhibition of 5-HT induced pressor response in pithed rats, after intravenous administration, activity is expressed as ED501988Journal of medicinal chemistry, Dec, Volume: 31, Issue:12
Antihypertensive activity in a series of 1-piperazino-3-phenylindans with potent 5-HT2-antagonistic activity.
AID230116Ratio of phenylephrine ED50/ 5-HT ED501988Journal of medicinal chemistry, Dec, Volume: 31, Issue:12
Antihypertensive activity in a series of 1-piperazino-3-phenylindans with potent 5-HT2-antagonistic activity.
AID65813In vitro inhibition of [3H]dopamine uptake in rat brain synaptosomes1988Journal of medicinal chemistry, Dec, Volume: 31, Issue:12
Antihypertensive activity in a series of 1-piperazino-3-phenylindans with potent 5-HT2-antagonistic activity.
AID64608Displacement of [3H]spiperone from dopamine D2 receptors in rat striatal membranes1993Journal of medicinal chemistry, Sep-17, Volume: 36, Issue:19
Stereospecific and selective 5-HT2 antagonism in a series of 5-substituted trans-1-piperazino-3-phenylindans.
AID64858In vitro inhibition of [3H]dopamine uptake in rat brain synaptosomes1988Journal of medicinal chemistry, Dec, Volume: 31, Issue:12
Antihypertensive activity in a series of 1-piperazino-3-phenylindans with potent 5-HT2-antagonistic activity.
AID177735Inhibition of 5-HT induced pressor response in pithed rats, after intravenous administration1988Journal of medicinal chemistry, Dec, Volume: 31, Issue:12
Antihypertensive activity in a series of 1-piperazino-3-phenylindans with potent 5-HT2-antagonistic activity.
AID177876Inhibition of L-5-HTP (L-5-hydroxytryptophan) induced head twitches in rat1988Journal of medicinal chemistry, Dec, Volume: 31, Issue:12
Antihypertensive activity in a series of 1-piperazino-3-phenylindans with potent 5-HT2-antagonistic activity.
AID172549Inhibition of phenylephrine induced pressor response in pithed rats (following i.v. administration of 0.31 mg/kg)1988Journal of medicinal chemistry, Dec, Volume: 31, Issue:12
Antihypertensive activity in a series of 1-piperazino-3-phenylindans with potent 5-HT2-antagonistic activity.
AID174033Tested for inhibition of pergolide-induced rotation in 6-OH-DA-lesioned rats after 2 hr1993Journal of medicinal chemistry, Sep-17, Volume: 36, Issue:19
Stereospecific and selective 5-HT2 antagonism in a series of 5-substituted trans-1-piperazino-3-phenylindans.
AID4837Displacement of [3H]ketanserin from 5-hydroxytryptamine 2 receptor in rat cortical membranes1993Journal of medicinal chemistry, Sep-17, Volume: 36, Issue:19
Stereospecific and selective 5-HT2 antagonism in a series of 5-substituted trans-1-piperazino-3-phenylindans.
AID172548Inhibition of 5-HT induced pressor response in pithed rats, after intravenous administration of 0.02 mg/kg1988Journal of medicinal chemistry, Dec, Volume: 31, Issue:12
Antihypertensive activity in a series of 1-piperazino-3-phenylindans with potent 5-HT2-antagonistic activity.
AID145898In vitro inhibition of [3H]norepinephrine uptake in rat brain synaptosomes1988Journal of medicinal chemistry, Dec, Volume: 31, Issue:12
Antihypertensive activity in a series of 1-piperazino-3-phenylindans with potent 5-HT2-antagonistic activity.
AID4826Inhibition of [3H]spiperone binding to 5-hydroxytryptamine 2 receptor from rat cortical membranes1988Journal of medicinal chemistry, Dec, Volume: 31, Issue:12
Antihypertensive activity in a series of 1-piperazino-3-phenylindans with potent 5-HT2-antagonistic activity.
AID145709In vitro inhibition of [3H]norepinephrine uptake in rat brain synaptosomes1988Journal of medicinal chemistry, Dec, Volume: 31, Issue:12
Antihypertensive activity in a series of 1-piperazino-3-phenylindans with potent 5-HT2-antagonistic activity.
AID130902Inhibition of methyl phenidate induced stereotyped gnawing in mice1988Journal of medicinal chemistry, Dec, Volume: 31, Issue:12
Antihypertensive activity in a series of 1-piperazino-3-phenylindans with potent 5-HT2-antagonistic activity.
AID189203Percent reduction of blood pressure in spontaneously hypertensive rat after 10 min at intraperitoneal administration of 5 mg/kg1988Journal of medicinal chemistry, Dec, Volume: 31, Issue:12
Antihypertensive activity in a series of 1-piperazino-3-phenylindans with potent 5-HT2-antagonistic activity.
AID179783Inhibition of quipazine-induced head twitches in rats after 2 hrs of pretreatment1993Journal of medicinal chemistry, Sep-17, Volume: 36, Issue:19
Stereospecific and selective 5-HT2 antagonism in a series of 5-substituted trans-1-piperazino-3-phenylindans.
AID61545Binding affinity at dopamine D2 receptor by [3H]spiperone displacement.1994Journal of medicinal chemistry, Apr-01, Volume: 37, Issue:7
Development of a receptor-interaction model for serotonin 5-HT2 receptor antagonists. Predicting selectivity with respect to dopamine D2 receptors.
AID4791Binding affinity at serotonin 5-hydroxytryptamine 2 receptor by [3H]ketanserin displacement.1994Journal of medicinal chemistry, Apr-01, Volume: 37, Issue:7
Development of a receptor-interaction model for serotonin 5-HT2 receptor antagonists. Predicting selectivity with respect to dopamine D2 receptors.
AID176857Tested for inhibition of quipazine-induced head twitches after 24 hours of pretreatment1993Journal of medicinal chemistry, Sep-17, Volume: 36, Issue:19
Stereospecific and selective 5-HT2 antagonism in a series of 5-substituted trans-1-piperazino-3-phenylindans.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (8)

TimeframeStudies, This Drug (%)All Drugs %
pre-19902 (25.00)18.7374
1990's6 (75.00)18.2507
2000's0 (0.00)29.6817
2010's0 (0.00)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other8 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
bay-k-8644
3-Pyridinecarboxylic acid, 1,4-dihydro-2,6-dimethyl-5-nitro-4-(2-(trifluoromethyl)phenyl)-, Methyl ester: A dihydropyridine derivative, which, in contrast to NIFEDIPINE, functions as a calcium channel agonist. The compound facilitates Ca2+ influx through partially activated voltage-dependent Ca2+ channels, thereby causing vasoconstrictor and positive inotropic effects. It is used primarily as a research tool.. Bay-K-8644 : A racemate comprising equimolar amounts of (R)- and (S)-Bay-K-8644. methyl 2,6-dimethyl-5-nitro-4-[2-(trifluoromethyl)phenyl]-1,4-dihydropyridine-3-carboxylate : A pentasubstituted dihydropyridine carrying methoxycarbonyl, 2-(trifluoromethyl)phenyl and nitro substituents at positions 3, 4 and 5 respectively as well as two methyl substituents at positions 2 and 6.		1.9710(trifluoromethyl)benzenes;
C-nitro compound;
dihydropyridine;
methyl ester
cyproheptadine
Cyproheptadine: A serotonin antagonist and a histamine H1 blocker used as antipruritic, appetite stimulant, antiallergic, and for the post-gastrectomy dumping syndrome, etc.. cyproheptadine : The product resulting from the formal oxidative coupling of position 5 of 5H-dibenzo[a,d]cycloheptene with position 4 of 1-methylpiperidine resulting in the formation of a double bond between the two fragments. It is a sedating antihistamine with antimuscarinic and calcium-channel blocking actions. It is used (particularly as the hydrochloride sesquihydrate) for the relief of allergic conditions including rhinitis, conjunctivitis due to inhalant allergens and foods, urticaria and angioedema, and in pruritic skin disorders. Unlike other antihistamines, it is also a seratonin receptor antagonist, making it useful in conditions such as vascular headache and anorexia.		1.9810piperidines;
tertiary amine		anti-allergic agent;
antipruritic drug;
gastrointestinal drug;
H1-receptor antagonist;
serotonergic antagonist
ketanserin
Ketanserin: A selective serotonin receptor antagonist with weak adrenergic receptor blocking properties. The drug is effective in lowering blood pressure in essential hypertension. It also inhibits platelet aggregation. It is well tolerated and is particularly effective in older patients.. ketanserin : A member of the class of quinazolines that is quinazoline-2,4(1H,3H)-dione which is substituted at position 3 by a 2-[4-(p-fluorobenzoyl)piperidin-1-yl]ethyl group.		7.6730aromatic ketone;
organofluorine compound;
piperidines;
quinazolines		alpha-adrenergic antagonist;
antihypertensive agent;
cardiovascular drug;
EC 3.4.21.26 (prolyl oligopeptidase) inhibitor;
serotonergic antagonist
prazosin
Prazosin: A selective adrenergic alpha-1 antagonist used in the treatment of HEART FAILURE; HYPERTENSION; PHEOCHROMOCYTOMA; RAYNAUD DISEASE; PROSTATIC HYPERTROPHY; and URINARY RETENTION.. prazosin : A member of the class of piperazines that is piperazine substituted by a furan-2-ylcarbonyl group and a 4-amino-6,7-dimethoxyquinazolin-2-yl group at positions 1 and 4 respectively.		1.9710aromatic ether;
furans;
monocarboxylic acid amide;
piperazines;
quinazolines		alpha-adrenergic antagonist;
antihypertensive agent;
EC 3.4.21.26 (prolyl oligopeptidase) inhibitor
ritanserin
Ritanserin: A selective and potent serotonin-2 antagonist that is effective in the treatment of a variety of syndromes related to anxiety and depression. The drug also improves the subjective quality of sleep and decreases portal pressure.. ritanserin : A thiazolopyrimidine that is 5H-[1,3]thiazolo[3,2-a]pyrimidin-5-one which is substituted at position 7 by a methyl group and at position 6 by a 2-{4-[bis(4-fluorophenyl)methylidene]piperidin-1-yl}ethyl group. A potent and long-acting seratonin (5-hydroxytryptamine, 5-HT) antagonist of the subtype 5-HT2 (Ki = 0.39 nM), it is used in the treatment of a variety of disorders including anxiety, depression and schizophrenia. It has little sedative action.		2.6730organofluorine compound;
piperidines;
thiazolopyrimidine		antidepressant;
antipsychotic agent;
anxiolytic drug;
dopaminergic antagonist;
EC 3.4.21.26 (prolyl oligopeptidase) inhibitor;
serotonergic antagonist
phenylephrine
Phenylephrine: An alpha-1 adrenergic agonist used as a mydriatic, nasal decongestant, and cardiotonic agent.. phenylephrine : A member of the class of the class of phenylethanolamines that is (1R)-2-(methylamino)-1-phenylethan-1-ol carrying an additional hydroxy substituent at position 3 on the phenyl ring.		2.3820phenols;
phenylethanolamines;
secondary amino compound		alpha-adrenergic agonist;
cardiotonic drug;
mydriatic agent;
nasal decongestant;
protective agent;
sympathomimetic agent;
vasoconstrictor agent
w-a 335
danitracen: was MH 1980-92 (see under PIPERIDINES 1980-90); WA 335 was see DANITRACEN 1980-92; use PIPERIDINES to search DANITRACEN 1980-92; antagonists or inhibitor of serotonin, probably due to receptor blockade; it has been proposed as an antidepressant and is used in the study of serotonergic mechanisms		1.9810
sertindole
sertindole : A phenylindole that is 1H-indole which is substituted on the nitrogen by a p-chlorophenyl group, at position 5 by chlorine, and at position 3 by a piperidin-4-yl group, which is itself substituted on the nitrogen by a 2-(2-oxoimidazolidin-1-yl)ethyl group.		1.9810heteroarylpiperidine;
imidazolidinone;
organochlorine compound;
organofluorine compound;
phenylindole		alpha-adrenergic antagonist;
H1-receptor antagonist;
second generation antipsychotic;
serotonergic antagonist
tefludazine
tefludazine: RN given refers to (trans-(+-)-isomer); RN for cpd without isomeric designation not available 3/88		2.3820
octoclothepine, (s)-isomer
[no description available]		1.9810
ConditionIndicatedRelationship StrengthStudiesTrials
Blood Pressure, High
[description not available]		01.9710
Hypertension
Persistently high systemic arterial BLOOD PRESSURE. Based on multiple readings (BLOOD PRESSURE DETERMINATION), hypertension is currently defined as when SYSTOLIC PRESSURE is consistently greater than 140 mm Hg or when DIASTOLIC PRESSURE is consistently 90 mm Hg or more.		01.9710
Muscle Contraction
A process leading to shortening and/or development of tension in muscle tissue. Muscle contraction occurs by a sliding filament mechanism whereby actin filaments slide inward among the myosin filaments.		02.3820