Compounds > flavodilol
Page last updated: 2024-12-06

flavodilol

Description

Flavodilol is a selective α1-adrenoceptor antagonist. It is a chiral compound with two enantiomers, S(+) and R(-). The S(+) enantiomer is the more potent α1-adrenoceptor antagonist and is responsible for the pharmacological effects of flavodilol. Flavodilol is used to treat hypertension and other cardiovascular conditions. It is also being investigated for its potential to treat other conditions, such as cancer and Alzheimer's disease. Flavodilol is synthesized by a multi-step process that involves the coupling of a benzodioxole derivative with a 2-aminoethanol derivative. It is then purified by recrystallization. Flavodilol is a potent and selective α1-adrenoceptor antagonist that has been shown to be effective in treating hypertension. It is well-tolerated and has a favorable side effect profile. Flavodilol is also being investigated for its potential to treat other conditions, such as cancer and Alzheimer's disease. The research on flavododilol is motivated by its potential to be an effective treatment for a wide range of conditions. Its selectivity for α1-adrenoceptors makes it a promising candidate for the treatment of hypertension and other cardiovascular conditions. Its potential to treat cancer and Alzheimer's disease is also being investigated. Flavodilol is studied to understand its mechanism of action, its efficacy in treating various diseases, and its potential to be used in the development of new drugs.'

flavodilol: RN & structure given in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID54410
CHEMBL ID57185
SCHEMBL ID2110063
MeSH IDM0162231

Synonyms (24)

Synonym
flavodilol
CHEMBL57185
7-[2-hydroxy-3-(propylamino)propoxy]-2-phenylchromen-4-one
unii-m8fr1kl85j
m8fr1kl85j ,
4h-1-benzopyran-4-one, 7-(2-hydroxy-3-(propylamino)propoxy)-2-phenyl-
79619-31-1
flavodilolum
flavodilolum [latin]
flavodilol [inn]
4h-1-benzopyran-4-one, 7-(2-hydroxy-3-(propylamino)propoxy)-2-phenyl-, (+/-)-
(+/-)-7-(2-hydroxy-3-(propylamino)propoxy)flavone
SCHEMBL2110063
KRBRHCLLOOCWQF-UHFFFAOYSA-N
7-[2-hydroxy-3-(propylamino)propoxy]flavone
7-(2-hydroxy-3-propylamino-propoxy)-2-phenyl-chromen-4-one
BCP28823
bdbm50227815
(+/-)-flavodilol; 7-[3-(propylamino)-2-hydroxypropoxy]flavone; dl-flavodilol
Q27283632
()-flavodilol; 7-[3-(propylamino)-2-hydroxypropoxy]flavone; dl-flavodilol
7-(2-hydroxy-3-(propylamino)propoxy)-2-phenyl-4h-1-benzopyran-4-one
DTXSID90868530
flavodil

Research Excerpts

Dosage Studied

ExcerptRelevanceReference
" Dose-response studies demonstrated that greater than or equal to 75% depletion of cardiac norepinephrine (NE) was accompanied by marked blood pressure decline in SHR."( Flavodilol: a new antihypertensive agent that preferentially depletes peripheral biogenic amines.
Blosser, JC; Kinsolving, CR; McCreedy, S; Parker, RB; Watkins, BE; Wu, ES, 1989)		1.72
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (3)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Beta-2 adrenergic receptorRattus norvegicus (Norway rat)Ki0.00400.00050.35461.6000AID41752
Beta-1 adrenergic receptorRattus norvegicus (Norway rat)Ki0.00400.00000.667310.0000AID41752
Beta-3 adrenergic receptorRattus norvegicus (Norway rat)Ki0.00400.00050.33671.6000AID41752
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (38)

Assay IDTitleYearJournalArticle
AID192915% decrease in heart 5-HT in anesthetized spontaneously hypertensive rats(SHR) at 5 hours after administration of 75 mg/kg dose perorally; value significantly different was control1989Journal of medicinal chemistry, Jan, Volume: 32, Issue:1
Flavones. 2. Synthesis and structure-activity relationship of flavodilol and its analogues, a novel class of antihypertensive agents with catecholamine depleting properties.
AID192907% decrease in adrenal epinephrine in anesthetized spontaneously hypertensive rats(SHR) at 5 hours after administration of 35 mg/kg dose perorally; NA is not available1989Journal of medicinal chemistry, Jan, Volume: 32, Issue:1
Flavones. 2. Synthesis and structure-activity relationship of flavodilol and its analogues, a novel class of antihypertensive agents with catecholamine depleting properties.
AID193707% decrease in hypothalamus norepinephrine in anesthetized spontaneously hypertensive rats(SHR) at 5 hours after administration of 4 mg/kg dose perorally1989Journal of medicinal chemistry, Jan, Volume: 32, Issue:1
Flavones. 2. Synthesis and structure-activity relationship of flavodilol and its analogues, a novel class of antihypertensive agents with catecholamine depleting properties.
AID193708% decrease in hypothalamus norepinephrine in anesthetized spontaneously hypertensive rats(SHR) at 5 hours after administration of 75 mg/kg dose perorally1989Journal of medicinal chemistry, Jan, Volume: 32, Issue:1
Flavones. 2. Synthesis and structure-activity relationship of flavodilol and its analogues, a novel class of antihypertensive agents with catecholamine depleting properties.
AID192916% decrease in heart 5-HT in anesthetized spontaneously hypertensive rats(SHR) at 5 hours after administration of 8 mg/kg dose perorally1989Journal of medicinal chemistry, Jan, Volume: 32, Issue:1
Flavones. 2. Synthesis and structure-activity relationship of flavodilol and its analogues, a novel class of antihypertensive agents with catecholamine depleting properties.
AID192921% decrease in hypothalamus dopamine in anesthetized spontaneously hypertensive rats(SHR) at 5 hours after administration of 8 mg/kg dose perorally1989Journal of medicinal chemistry, Jan, Volume: 32, Issue:1
Flavones. 2. Synthesis and structure-activity relationship of flavodilol and its analogues, a novel class of antihypertensive agents with catecholamine depleting properties.
AID192436Systolic blood pressure (SBP) in anesthetized spontaneously hypertensive rats(SHR) before administration of 17 mg/kg dose, perorally1989Journal of medicinal chemistry, Jan, Volume: 32, Issue:1
Flavones. 2. Synthesis and structure-activity relationship of flavodilol and its analogues, a novel class of antihypertensive agents with catecholamine depleting properties.
AID193568% decrease in hypothalamus norepinephrine in anesthetized spontaneously hypertensive rats(SHR) at 5 hours after administration of 17.5 mg/kg dose perorally1989Journal of medicinal chemistry, Jan, Volume: 32, Issue:1
Flavones. 2. Synthesis and structure-activity relationship of flavodilol and its analogues, a novel class of antihypertensive agents with catecholamine depleting properties.
AID193556% decrease in heart norepinephrine in anesthetized spontaneously hypertensive rats(SHR) at 5 hours after administration of 75 mg/kg dose perorally1989Journal of medicinal chemistry, Jan, Volume: 32, Issue:1
Flavones. 2. Synthesis and structure-activity relationship of flavodilol and its analogues, a novel class of antihypertensive agents with catecholamine depleting properties.
AID193555% decrease in heart norepinephrine in anesthetized spontaneously hypertensive rats(SHR) at 5 hours after administration of 4 mg/kg dose perorally1989Journal of medicinal chemistry, Jan, Volume: 32, Issue:1
Flavones. 2. Synthesis and structure-activity relationship of flavodilol and its analogues, a novel class of antihypertensive agents with catecholamine depleting properties.
AID192442Systolic blood pressure (SBP) in anesthetized spontaneously hypertensive rats(SHR) before administration of 4 mg/kg dose perorally1989Journal of medicinal chemistry, Jan, Volume: 32, Issue:1
Flavones. 2. Synthesis and structure-activity relationship of flavodilol and its analogues, a novel class of antihypertensive agents with catecholamine depleting properties.
AID193709% decrease in hypothalamus norepinephrine in anesthetized spontaneously hypertensive rats(SHR) at 5 hours after administration of 8 mg/kg dose perorally1989Journal of medicinal chemistry, Jan, Volume: 32, Issue:1
Flavones. 2. Synthesis and structure-activity relationship of flavodilol and its analogues, a novel class of antihypertensive agents with catecholamine depleting properties.
AID192914% decrease in heart 5-HT in anesthetized spontaneously hypertensive rats(SHR) at 5 hours after administration of 4 mg/kg dose perorally1989Journal of medicinal chemistry, Jan, Volume: 32, Issue:1
Flavones. 2. Synthesis and structure-activity relationship of flavodilol and its analogues, a novel class of antihypertensive agents with catecholamine depleting properties.
AID192917% decrease in hypothalamus 5-HT in anesthetized spontaneously hypertensive rats(SHR) at 5 hours after administration of 35 mg/kg dose perorally1989Journal of medicinal chemistry, Jan, Volume: 32, Issue:1
Flavones. 2. Synthesis and structure-activity relationship of flavodilol and its analogues, a novel class of antihypertensive agents with catecholamine depleting properties.
AID174082Systolic blood pressure (SBP) in anesthetized spontaneously hypertensive rats(SHR) at 7.5 hours after administration of 17 mg/kg dose, perorally1989Journal of medicinal chemistry, Jan, Volume: 32, Issue:1
Flavones. 2. Synthesis and structure-activity relationship of flavodilol and its analogues, a novel class of antihypertensive agents with catecholamine depleting properties.
AID192908% decrease in adrenal epinephrine in anesthetized spontaneously hypertensive rats(SHR) at 5 hours after administration of 4 mg/kg dose perorally; NA is not available1989Journal of medicinal chemistry, Jan, Volume: 32, Issue:1
Flavones. 2. Synthesis and structure-activity relationship of flavodilol and its analogues, a novel class of antihypertensive agents with catecholamine depleting properties.
AID192441Systolic blood pressure (SBP) in anesthetized spontaneously hypertensive rats(SHR) before administration of 35 mg/kg dose perorally1989Journal of medicinal chemistry, Jan, Volume: 32, Issue:1
Flavones. 2. Synthesis and structure-activity relationship of flavodilol and its analogues, a novel class of antihypertensive agents with catecholamine depleting properties.
AID193553% decrease in heart norepinephrine in anesthetized spontaneously hypertensive rats(SHR) at 5 hours after administration of 17.5 mg/kg dose perorally1989Journal of medicinal chemistry, Jan, Volume: 32, Issue:1
Flavones. 2. Synthesis and structure-activity relationship of flavodilol and its analogues, a novel class of antihypertensive agents with catecholamine depleting properties.
AID192920% decrease in hypothalamus dopamine in anesthetized spontaneously hypertensive rats(SHR) at 5 hours after administration of 4 mg/kg dose perorally1989Journal of medicinal chemistry, Jan, Volume: 32, Issue:1
Flavones. 2. Synthesis and structure-activity relationship of flavodilol and its analogues, a novel class of antihypertensive agents with catecholamine depleting properties.
AID192906% decrease in adrenal epinephrine in anesthetized spontaneously hypertensive rats(SHR) at 5 hours after administration of 17.5 mg/kg dose perorally; NA is not available1989Journal of medicinal chemistry, Jan, Volume: 32, Issue:1
Flavones. 2. Synthesis and structure-activity relationship of flavodilol and its analogues, a novel class of antihypertensive agents with catecholamine depleting properties.
AID192913% decrease in heart 5-HT in anesthetized spontaneously hypertensive rats(SHR) at 5 hours after administration of 35 mg/kg dose perorally; value significantly different was control1989Journal of medicinal chemistry, Jan, Volume: 32, Issue:1
Flavones. 2. Synthesis and structure-activity relationship of flavodilol and its analogues, a novel class of antihypertensive agents with catecholamine depleting properties.
AID192911% decrease in heart 5-HT in anesthetized spontaneously hypertensive rats(SHR) at 5 hours after administration of 17.5 mg/kg dose perorally; value significantly different was control1989Journal of medicinal chemistry, Jan, Volume: 32, Issue:1
Flavones. 2. Synthesis and structure-activity relationship of flavodilol and its analogues, a novel class of antihypertensive agents with catecholamine depleting properties.
AID192445Systolic blood pressure (SBP) in anesthetized spontaneously hypertensive rats(SHR) before administration of 75 mg/kg dose perorally1989Journal of medicinal chemistry, Jan, Volume: 32, Issue:1
Flavones. 2. Synthesis and structure-activity relationship of flavodilol and its analogues, a novel class of antihypertensive agents with catecholamine depleting properties.
AID192918% decrease in hypothalamus dopamine in anesthetized spontaneously hypertensive rats(SHR) at 5 hours after administration of 75 mg/kg dose perorally1989Journal of medicinal chemistry, Jan, Volume: 32, Issue:1
Flavones. 2. Synthesis and structure-activity relationship of flavodilol and its analogues, a novel class of antihypertensive agents with catecholamine depleting properties.
AID174085Systolic blood pressure (SBP) in anesthetized spontaneously hypertensive rats(SHR) at 7.5 hours after administration of 35 mg/kg dose perorally1989Journal of medicinal chemistry, Jan, Volume: 32, Issue:1
Flavones. 2. Synthesis and structure-activity relationship of flavodilol and its analogues, a novel class of antihypertensive agents with catecholamine depleting properties.
AID192919% decrease in hypothalamus dopamine in anesthetized spontaneously hypertensive rats(SHR) at 5 hours after administration of 17.5 mg/kg dose perorally1989Journal of medicinal chemistry, Jan, Volume: 32, Issue:1
Flavones. 2. Synthesis and structure-activity relationship of flavodilol and its analogues, a novel class of antihypertensive agents with catecholamine depleting properties.
AID192444Systolic blood pressure (SBP) in anesthetized spontaneously hypertensive rats (SHR) before administration of 75 mg/kg dose perorally.1989Journal of medicinal chemistry, Jan, Volume: 32, Issue:1
Flavones. 2. Synthesis and structure-activity relationship of flavodilol and its analogues, a novel class of antihypertensive agents with catecholamine depleting properties.
AID192446Systolic blood pressure (SBP) in anesthetized spontaneously hypertensive rats(SHR) before administration of 8 mg/kg dose perorally1989Journal of medicinal chemistry, Jan, Volume: 32, Issue:1
Flavones. 2. Synthesis and structure-activity relationship of flavodilol and its analogues, a novel class of antihypertensive agents with catecholamine depleting properties.
AID193557% decrease in heart norepinephrine in anesthetized spontaneously hypertensive rats(SHR) at 5 hours after administration of 8 mg/kg dose perorally1989Journal of medicinal chemistry, Jan, Volume: 32, Issue:1
Flavones. 2. Synthesis and structure-activity relationship of flavodilol and its analogues, a novel class of antihypertensive agents with catecholamine depleting properties.
AID192440Systolic blood pressure (SBP) in anesthetized spontaneously hypertensive rats(SHR) before administration of 35 mg/kg dose perorally1989Journal of medicinal chemistry, Jan, Volume: 32, Issue:1
Flavones. 2. Synthesis and structure-activity relationship of flavodilol and its analogues, a novel class of antihypertensive agents with catecholamine depleting properties.
AID174220Systolic blood pressure (SBP) in anesthetized spontaneously hypertensive rats(SHR) at 7.5 hours after administration of 75 mg/kg dose intravenously1989Journal of medicinal chemistry, Jan, Volume: 32, Issue:1
Flavones. 2. Synthesis and structure-activity relationship of flavodilol and its analogues, a novel class of antihypertensive agents with catecholamine depleting properties.
AID193554% decrease in heart norepinephrine in anesthetized spontaneously hypertensive rats(SHR) at 5 hours after administration of 35 mg/kg dose perorally1989Journal of medicinal chemistry, Jan, Volume: 32, Issue:1
Flavones. 2. Synthesis and structure-activity relationship of flavodilol and its analogues, a novel class of antihypertensive agents with catecholamine depleting properties.
AID41752Inhibition constant from beta adrenergic receptor binding assay1989Journal of medicinal chemistry, Jan, Volume: 32, Issue:1
Flavones. 2. Synthesis and structure-activity relationship of flavodilol and its analogues, a novel class of antihypertensive agents with catecholamine depleting properties.
AID192909% decrease in adrenal epinephrine in anesthetized spontaneously hypertensive rats(SHR) at 5 hours after administration of 75 mg/kg dose perorally; NA is not available1989Journal of medicinal chemistry, Jan, Volume: 32, Issue:1
Flavones. 2. Synthesis and structure-activity relationship of flavodilol and its analogues, a novel class of antihypertensive agents with catecholamine depleting properties.
AID193569% decrease in hypothalamus norepinephrine in anesthetized spontaneously hypertensive rats(SHR) at 5 hours after administration of 35 mg/kg dose perorally1989Journal of medicinal chemistry, Jan, Volume: 32, Issue:1
Flavones. 2. Synthesis and structure-activity relationship of flavodilol and its analogues, a novel class of antihypertensive agents with catecholamine depleting properties.
AID192437Systolic blood pressure (SBP) in anesthetized spontaneously hypertensive rats(SHR) before administration of 17.5 mg/kg dose perorally; data statistically significant1989Journal of medicinal chemistry, Jan, Volume: 32, Issue:1
Flavones. 2. Synthesis and structure-activity relationship of flavodilol and its analogues, a novel class of antihypertensive agents with catecholamine depleting properties.
AID223040Inhibition of the isoproterenol response at a dose of 1 x 10e -4M in guinea pig; slight inhibition was found1989Journal of medicinal chemistry, Jan, Volume: 32, Issue:1
Flavones. 2. Synthesis and structure-activity relationship of flavodilol and its analogues, a novel class of antihypertensive agents with catecholamine depleting properties.
AID192910% decrease in adrenal epinephrine in anesthetized spontaneously hypertensive rats(SHR) at 5 hours after administration of 8 mg/kg dose perorally; NA is not available1989Journal of medicinal chemistry, Jan, Volume: 32, Issue:1
Flavones. 2. Synthesis and structure-activity relationship of flavodilol and its analogues, a novel class of antihypertensive agents with catecholamine depleting properties.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (5)

TimeframeStudies, This Drug (%)All Drugs %
pre-19904 (80.00)18.7374
1990's1 (20.00)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]

Market Indicators

Research Demand Index: 12.36

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 weak demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index12.36 (24.57)
Research Supply Index1.95 (2.92)
Research Growth Index4.31 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.36)

All Compounds (24.57)

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%
Other6 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
indomethacin
Indomethacin: A non-steroidal anti-inflammatory agent (NSAID) that inhibits CYCLOOXYGENASE, which is necessary for the formation of PROSTAGLANDINS and other AUTACOIDS. It also inhibits the motility of POLYMORPHONUCLEAR LEUKOCYTES.. indometacin : A member of the class of indole-3-acetic acids that is indole-3-acetic acid in which the indole ring is substituted at positions 1, 2 and 5 by p-chlorobenzoyl, methyl, and methoxy groups, respectively. A non-steroidal anti-inflammatory drug, it is used in the treatment of musculoskeletal and joint disorders including osteoarthritis, rheumatoid arthritis, gout, bursitis and tendinitis.		1.9710aromatic ether;
indole-3-acetic acids;
monochlorobenzenes;
N-acylindole		analgesic;
drug metabolite;
EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor;
environmental contaminant;
gout suppressant;
non-steroidal anti-inflammatory drug;
xenobiotic metabolite;
xenobiotic
propranolol
Propranolol: A widely used non-cardioselective beta-adrenergic antagonist. Propranolol has been used for MYOCARDIAL INFARCTION; ARRHYTHMIA; ANGINA PECTORIS; HYPERTENSION; HYPERTHYROIDISM; MIGRAINE; PHEOCHROMOCYTOMA; and ANXIETY but adverse effects instigate replacement by newer drugs.. propranolol : A propanolamine that is propan-2-ol substituted by a propan-2-ylamino group at position 1 and a naphthalen-1-yloxy group at position 3.		2.3820naphthalenes;
propanolamine;
secondary amine		anti-arrhythmia drug;
antihypertensive agent;
anxiolytic drug;
beta-adrenergic antagonist;
environmental contaminant;
human blood serum metabolite;
vasodilator agent;
xenobiotic
sulpiride
Sulpiride: A dopamine D2-receptor antagonist. It has been used therapeutically as an antidepressant, antipsychotic, and as a digestive aid. (From Merck Index, 11th ed). sulpiride : A member of the class of benzamides obtained from formal condensation between the carboxy group of 2-methoxy-5-sulfamoylbenzoic acid and the primary amino group of (1-ethylpyrrolidin-2-yl)methylamine.		1.9710benzamides;
N-alkylpyrrolidine;
sulfonamide		antidepressant;
antiemetic;
antipsychotic agent;
dopaminergic antagonist
menthyl chloroformate
menthyl chloroformate: RN given refers to (1R-(1alpha,2beta,5alpha))-isomer		1.9710
7-hydroxyflavone
7-hydroxyflavone : A hydroxyflavonoid in which the flavone nucleus is substituted at position 7 by a hydroxy group.		1.9710hydroxyflavonoid
ConditionIndicatedRelationship StrengthStudiesTrials
Blood Pressure, High
[description not available]		02.3820
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.		02.3820
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