Page last updated: 2024-12-05

hexoprenaline

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

Description

Hexoprenaline is a synthetic β2-adrenergic receptor agonist. It was developed in the 1960s as a bronchodilator for the treatment of asthma. Its synthesis involves several steps, including the condensation of 3,4-dihydroxyphenylacetone with the appropriate amine. Hexoprenaline exhibits bronchodilatory effects through activation of β2-adrenergic receptors in the smooth muscle of the bronchi, leading to relaxation and opening of the airways. Its importance lies in its ability to provide relief from bronchospasm, a common symptom of asthma. However, its use has been largely superseded by other β2-adrenergic agonists, such as salbutamol, due to its longer duration of action and potential side effects. Despite its limited clinical use, hexoprenaline continues to be studied for its potential therapeutic applications in other areas, such as the treatment of premature labor and the prevention of bronchospasm in patients undergoing anesthesia.'

Hexoprenaline: Stimulant of adrenergic beta 2 receptors. It is used as a bronchodilator, antiasthmatic agent, and tocolytic agent. [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID3609
CHEMBL ID1589896
SCHEMBL ID121449
MeSH IDM0010329

Synonyms (34)

Synonym
alpha,alpha'-(hexamethylenebis(iminomethylene))bis(3,4-dihydroxybenzylalcohol)
hexoprenaline
hexoprenalinum [inn-latin]
st-1512 ,
hexoprenalino [inn-spanish]
ipradol
1,2-benzenediol, 4,4'-(1,6-hexanediylbis(imino(1-hydroxy-2,1-ethanediyl)))bis-
esoprenalina [dcit]
hexoprenaline [inn:ban]
1,12-bis(3,4-dihydroxyphenyl)-3,10-diaza-1,12-dodecandiol
ipradol (tn)
3215-70-1
hexoprenaline (inn)
D08039
4-[2-[6-[[2-(3,4-dihydroxyphenyl)-2-hydroxyethyl]amino]hexylamino]-1-hydroxyethyl]benzene-1,2-diol
st1512
hexoprenalino
hexoprenalinum
g9l6b3w684 ,
esoprenalina
unii-g9l6b3w684
CHEMBL1589896
hexoprenaline [inn]
hexoprenaline [mi]
hexoprenaline [who-dd]
SCHEMBL121449
DTXSID7048322
DB08957
hexoprenalin
J-018657
Q4134964
3215-70-1(free base)
1,2-benzenediol,4,4'-[1,6-hexanediylbis[imino(1-hydroxy-2,1-ethanediyl)]]bis-
AKOS040746895

Research Excerpts

Overview

Hexoprenaline is a betamimetic substance which increases both local blood flow and number of ureter contractions. It is a beta-adrenergic agent used for tocolysis after the 26th week of pregnancy.

ExcerptReferenceRelevance
"Hexoprenaline is a betamimetic substance which increases both local blood flow and number of ureter contractions."( Prevention of urological complications after radical operation of cervical carcinoma.
Gitsch, E; Philipp, K, 1982
)
0.99
"Hexoprenaline is a beta-adrenergic agent used for tocolysis after the 26th week of pregnancy. "( Hexoprenaline activates potassium channels of human myometrial myocytes.
Adelwoehrer, NE; Mahnert, W, 1993
)
3.17
"Hexoprenaline is a selective beta 2-mimetic drug used in tocology for the prevention of premature labor and immature birth. "( [Hexoprenaline--a new tocolytic for treatment of premature labor].
Heilmann, L; Siekmann, U, 1985
)
2.62

Pharmacokinetics

ExcerptReferenceRelevance
" However, little is known regarding the potential of this drug to undergo placental transfer or whether the pregnant state alters any of the pharmacokinetic parameters."( Hexoprenaline pharmacokinetics in pregnant and nonpregnant sheep.
Ahokas, RA; Anderson, GD; Lipshitz, J; Maduska, AL; Meyer, MC; Morrison, JC; Schneider, J; Whybrew, WD; Yau, MK, 1981
)
1.71

Dosage Studied

ExcerptRelevanceReference
"25 mg/puff) when administered as metered aerosol in a dosage of one puff followed by two puffs 30 min later produced the same maximum improvement of ventilatory function."( Hexoprenaline and terbutaline administered by inhalation. A comparison between two beta2-adrenoreceptor agonists with respect to effect on bronchial obstruction, heart rate, blood pressure and muscle tremor.
Hörnblad, Y; Leideman, T; Ripe, E, 1978
)
1.7
" The dosage varied according to the obstetrical situation and the resultant indication for tocolysis."( [Hexoprenalin as a tocolytic drug (author's transl)].
Reinold, E, 1979
)
0.26
" The dosage varied according to the obstetrical situation and the resultant indication for tocolysis."( [Hexoprenalin as a tocolytic drug (author's transl)].
Reinold, E, 1979
)
0.26
"3 microgram/min = dosage for massive tocolysis) the uterine activity decreased on average by 73."( [Intrauterine pressure and fetal and maternal heart rate on administration of the betamimetic agent, hexoprenaline during labour (author's transl)].
Bernaschek, G; Hondros, K; Schaller, A, 1981
)
0.48
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (7)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
phosphopantetheinyl transferaseBacillus subtilisPotency100.00000.141337.9142100.0000AID1490
GLS proteinHomo sapiens (human)Potency22.38720.35487.935539.8107AID624170
vitamin D3 receptor isoform VDRAHomo sapiens (human)Potency35.48130.354828.065989.1251AID504847
DNA polymerase kappa isoform 1Homo sapiens (human)Potency0.44670.031622.3146100.0000AID588579
peripheral myelin protein 22Rattus norvegicus (Norway rat)Potency0.12820.005612.367736.1254AID624032
ATP-dependent phosphofructokinaseTrypanosoma brucei brucei TREU927Potency0.70790.060110.745337.9330AID492961
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Bile salt export pumpHomo sapiens (human)IC50 (µMol)1,000.00000.11007.190310.0000AID1449628
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (22)

Processvia Protein(s)Taxonomy
fatty acid metabolic processBile salt export pumpHomo sapiens (human)
bile acid biosynthetic processBile salt export pumpHomo sapiens (human)
xenobiotic metabolic processBile salt export pumpHomo sapiens (human)
xenobiotic transmembrane transportBile salt export pumpHomo sapiens (human)
response to oxidative stressBile salt export pumpHomo sapiens (human)
bile acid metabolic processBile salt export pumpHomo sapiens (human)
response to organic cyclic compoundBile salt export pumpHomo sapiens (human)
bile acid and bile salt transportBile salt export pumpHomo sapiens (human)
canalicular bile acid transportBile salt export pumpHomo sapiens (human)
protein ubiquitinationBile salt export pumpHomo sapiens (human)
regulation of fatty acid beta-oxidationBile salt export pumpHomo sapiens (human)
carbohydrate transmembrane transportBile salt export pumpHomo sapiens (human)
bile acid signaling pathwayBile salt export pumpHomo sapiens (human)
cholesterol homeostasisBile salt export pumpHomo sapiens (human)
response to estrogenBile salt export pumpHomo sapiens (human)
response to ethanolBile salt export pumpHomo sapiens (human)
xenobiotic export from cellBile salt export pumpHomo sapiens (human)
lipid homeostasisBile salt export pumpHomo sapiens (human)
phospholipid homeostasisBile salt export pumpHomo sapiens (human)
positive regulation of bile acid secretionBile salt export pumpHomo sapiens (human)
regulation of bile acid metabolic processBile salt export pumpHomo sapiens (human)
transmembrane transportBile salt export pumpHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (8)

Processvia Protein(s)Taxonomy
protein bindingBile salt export pumpHomo sapiens (human)
ATP bindingBile salt export pumpHomo sapiens (human)
ABC-type xenobiotic transporter activityBile salt export pumpHomo sapiens (human)
bile acid transmembrane transporter activityBile salt export pumpHomo sapiens (human)
canalicular bile acid transmembrane transporter activityBile salt export pumpHomo sapiens (human)
carbohydrate transmembrane transporter activityBile salt export pumpHomo sapiens (human)
ABC-type bile acid transporter activityBile salt export pumpHomo sapiens (human)
ATP hydrolysis activityBile salt export pumpHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (12)

Processvia Protein(s)Taxonomy
basolateral plasma membraneBile salt export pumpHomo sapiens (human)
Golgi membraneBile salt export pumpHomo sapiens (human)
endosomeBile salt export pumpHomo sapiens (human)
plasma membraneBile salt export pumpHomo sapiens (human)
cell surfaceBile salt export pumpHomo sapiens (human)
apical plasma membraneBile salt export pumpHomo sapiens (human)
intercellular canaliculusBile salt export pumpHomo sapiens (human)
intracellular canaliculusBile salt export pumpHomo sapiens (human)
recycling endosomeBile salt export pumpHomo sapiens (human)
recycling endosome membraneBile salt export pumpHomo sapiens (human)
extracellular exosomeBile salt export pumpHomo sapiens (human)
membraneBile salt export pumpHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (2)

Assay IDTitleYearJournalArticle
AID504749qHTS profiling for inhibitors of Plasmodium falciparum proliferation2011Science (New York, N.Y.), Aug-05, Volume: 333, Issue:6043
Chemical genomic profiling for antimalarial therapies, response signatures, and molecular targets.
AID1449628Inhibition of human BSEP expressed in baculovirus transfected fall armyworm Sf21 cell membranes vesicles assessed as reduction in ATP-dependent [3H]-taurocholate transport into vesicles incubated for 5 mins by Topcount based rapid filtration method2012Drug metabolism and disposition: the biological fate of chemicals, Dec, Volume: 40, Issue:12
Mitigating the inhibition of human bile salt export pump by drugs: opportunities provided by physicochemical property modulation, in silico modeling, and structural modification.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (133)

TimeframeStudies, This Drug (%)All Drugs %
pre-199096 (72.18)18.7374
1990's19 (14.29)18.2507
2000's7 (5.26)29.6817
2010's11 (8.27)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: 37.19

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

MetricThis Compound (vs All)
Research Demand Index37.19 (24.57)
Research Supply Index5.16 (2.92)
Research Growth Index4.47 (4.65)
Search Engine Demand Index52.19 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (37.19)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials30 (20.83%)5.53%
Reviews10 (6.94%)6.00%
Case Studies13 (9.03%)4.05%
Observational0 (0.00%)0.25%
Other91 (63.19%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]