Page last updated: 2024-11-06

lonapalene

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

Description

RS 43179: used in treatment of psoriasis [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID56237
CHEMBL ID36648
CHEBI ID177429
SCHEMBL ID120134
MeSH IDM0133376

Synonyms (42)

Synonym
CHEBI:177429
(4-acetyloxy-6-chloro-2,3-dimethoxynaphthalen-1-yl) acetate
lonapalene
rs-43179
D04770
91431-42-4
lonapalene (usan)
CHEMBL36648 ,
acetic acid 4-acetoxy-6-chloro-2,3-dimethoxy-naphthalen-1-yl ester (ionapalene)
acetic acid 4-acetoxy-6-chloro-2,3-dimethoxy-naphthalen-1-yl ester
bdbm50004677
acetic acid 4-acetoxy-7-chloro-2,3-dimethoxy-naphthalen-1-yl ester
acetic acid 4-acetoxy-6-chloro-2,3-dimethoxy-naphthalen-1-yl ester (lonapalane)
unii-wif31q54nj
lonapalenum [latin]
rs 43179
wif31q54nj ,
1,4-naphthalenediol, 6-chloro-2,3-dimethoxy-, diacetate
lonapalene [usan:inn]
6-chloro-2,3-dimethoxy-1,4-naphthalenediol diacetate
lonapaleno [spanish]
6-chloro-2,3-dimethoxynaphthalene-1,4-diol diacetate
lonapalenum
lonapaleno
lonapalene [mi]
lonapalene [inn]
lonapalene [usan]
lonapalene [mart.]
SCHEMBL120134
IFWMVQUGSGWCRP-UHFFFAOYSA-N
6-chloro-2,3-dimethoxy-1,4-diacetyloxynaphthalene
6-chloro-1,4-diacetoxy-2,3-dimethoxynaphthalene
AC-31483
DTXSID00238563
HY-U00156
CS-7197
(4-acetyloxy-7-chloro-2,3-dimethoxynaphthalen-1-yl)acetate
rs4317
6-chloro-2,3-dimethoxynaphthalene-1,4-diyl diacetate
Q27292653
MS-25159
AKOS040742581

Research Excerpts

Actions

ExcerptReferenceRelevance
"Lonapalene was shown to inhibit platelet cyclooxygenase, with substrate diversion towards 12-HETE production."( Effect of lonapalene on metabolism of exogenous arachidonic acid in human platelets.
Gibert, C; Moragas, JM; Puig, L; Solá, J; Vila, L, 1989
)
1.4
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (2)

ClassDescription
organochlorine compoundAn organochlorine compound is a compound containing at least one carbon-chlorine bond.
naphthalenesAny benzenoid aromatic compound having a skeleton composed of two ortho-fused benzene rings.
[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]

Protein Targets (7)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Prostaglandin G/H synthase 1 Bos taurus (cattle)IC50 (µMol)750.00000.00051.41288.2000AID160710
Prostaglandin G/H synthase 2 Bos taurus (cattle)IC50 (µMol)750.00000.00050.57393.4000AID160710
3',5'-cyclic-AMP phosphodiesterase Sus scrofa (pig)IC50 (µMol)1,000.00000.00103.40026.4000AID158620
Bile salt export pumpHomo sapiens (human)IC50 (µMol)14.39000.11007.190310.0000AID1449628
Phospholipase A2, major isoenzymeSus scrofa (pig)IC50 (µMol)1,000.00000.04804.12088.0000AID158620
Polyunsaturated fatty acid 5-lipoxygenaseRattus norvegicus (Norway rat)IC50 (µMol)0.64670.00462.018210.0000AID3637; AID6790; AID7062
5-lipoxygenase Bos taurus (cattle)IC50 (µMol)17.00000.18001.75824.0000AID54297; AID6881; AID6882
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (33)

Processvia Protein(s)Taxonomy
response to oxidative stressProstaglandin G/H synthase 1 Bos taurus (cattle)
cellular oxidant detoxificationProstaglandin G/H synthase 1 Bos taurus (cattle)
meiotic spindle organizationProstaglandin G/H synthase 2 Bos taurus (cattle)
prostaglandin biosynthetic processProstaglandin G/H synthase 2 Bos taurus (cattle)
ovarian cumulus expansionProstaglandin G/H synthase 2 Bos taurus (cattle)
positive regulation of protein phosphorylationProstaglandin G/H synthase 2 Bos taurus (cattle)
response to oxidative stressProstaglandin G/H synthase 2 Bos taurus (cattle)
cyclooxygenase pathwayProstaglandin G/H synthase 2 Bos taurus (cattle)
positive regulation of embryonic developmentProstaglandin G/H synthase 2 Bos taurus (cattle)
cellular response to interleukin-1Prostaglandin G/H synthase 2 Bos taurus (cattle)
cellular oxidant detoxificationProstaglandin G/H synthase 2 Bos taurus (cattle)
regulation of neuroinflammatory responseProstaglandin G/H synthase 2 Bos taurus (cattle)
positive regulation of oocyte maturationProstaglandin G/H synthase 2 Bos taurus (cattle)
positive regulation of meiotic cell cycle process involved in oocyte maturationProstaglandin G/H synthase 2 Bos taurus (cattle)
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 (12)

Processvia Protein(s)Taxonomy
peroxidase activityProstaglandin G/H synthase 1 Bos taurus (cattle)
heme bindingProstaglandin G/H synthase 1 Bos taurus (cattle)
metal ion bindingProstaglandin G/H synthase 1 Bos taurus (cattle)
peroxidase activityProstaglandin G/H synthase 2 Bos taurus (cattle)
prostaglandin-endoperoxide synthase activityProstaglandin G/H synthase 2 Bos taurus (cattle)
heme bindingProstaglandin G/H synthase 2 Bos taurus (cattle)
metal ion bindingProstaglandin G/H synthase 2 Bos taurus (cattle)
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 (15)

Processvia Protein(s)Taxonomy
endoplasmic reticulum membraneProstaglandin G/H synthase 1 Bos taurus (cattle)
nuclear inner membraneProstaglandin G/H synthase 2 Bos taurus (cattle)
nuclear outer membraneProstaglandin G/H synthase 2 Bos taurus (cattle)
endoplasmic reticulum membraneProstaglandin G/H synthase 2 Bos taurus (cattle)
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 (24)

Assay IDTitleYearJournalArticle
AID138456In vivo inhibitory activity in a phorbol myristyl acetate (PMA) ear edema model at a dose of 100 ug/ear1992Journal of medicinal chemistry, Aug-21, Volume: 35, Issue:17
Novel 1-(pyridylphenyl)-1-phenyl-2-imidazolylethanols with topical antiinflammatory activity.
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.
AID7062Inhibitory activity against 5-lipoxygenase of RBL-1 cell line1992Journal of medicinal chemistry, Aug-21, Volume: 35, Issue:17
Novel 1-(pyridylphenyl)-1-phenyl-2-imidazolylethanols with topical antiinflammatory activity.
AID130719In vivo inhibitory activity against arachidonic acid(AA) ear edema at a dose of 100 ug/ear1992Journal of medicinal chemistry, Aug-21, Volume: 35, Issue:17
Novel 1-(pyridylphenyl)-1-phenyl-2-imidazolylethanols with topical antiinflammatory activity.
AID132250Effective dose to inhibit 50% of mouse arachidonic acid induced ear edema assay1990Journal of medicinal chemistry, Jan, Volume: 33, Issue:1
2-substituted-1-naphthols as potent 5-lipoxygenase inhibitors with topical antiinflammatory activity.
AID20695Statistical significance, p values as compared to positive control by students t-test1986Journal of medicinal chemistry, Aug, Volume: 29, Issue:8
Topical nonsteroidal antipsoriatic agents. 1. 1,2,3,4-Tetraoxygenated naphthalene derivatives.
AID6881Inhibition of 5-lipoxygenase in bovine polymorphonuclear leukocytes1994Journal of medicinal chemistry, May-27, Volume: 37, Issue:11
Antipsoriatic anthrones with modulated redox properties. 2. Novel derivatives of chrysarobin and isochrysarobin--antiproliferative activity and 5-lipoxygenase inhibition.
AID24230Partition coefficient (logP)1986Journal of medicinal chemistry, Aug, Volume: 29, Issue:8
Topical nonsteroidal antipsoriatic agents. 1. 1,2,3,4-Tetraoxygenated naphthalene derivatives.
AID130718In vivo inhibitory activity against A-23187 ear edema at a dose of 100 ug/ear1992Journal of medicinal chemistry, Aug-21, Volume: 35, Issue:17
Novel 1-(pyridylphenyl)-1-phenyl-2-imidazolylethanols with topical antiinflammatory activity.
AID134346Compound was tested for inhibition of arachidonic acid induced mouse ear edema at 2 mg of dose1986Journal of medicinal chemistry, Aug, Volume: 29, Issue:8
Topical nonsteroidal antipsoriatic agents. 1. 1,2,3,4-Tetraoxygenated naphthalene derivatives.
AID158620Inhibitory activity against phospholipase A2 of Croatalus adamanteus1992Journal of medicinal chemistry, Aug-21, Volume: 35, Issue:17
Novel 1-(pyridylphenyl)-1-phenyl-2-imidazolylethanols with topical antiinflammatory activity.
AID54297Tested for the inhibition of lipid peroxidation in bovine brain phospholipid liposomes1993Journal of medicinal chemistry, Dec-10, Volume: 36, Issue:25
Antipsoriatic anthrones with modulated redox properties. 1. Novel 10-substituted 1,8-dihydroxy-9(10H)-anthracenones as inhibitors of 5-lipoxygenase.
AID228514Deoxyribose degradation assay as hydroxy radical formation1994Journal of medicinal chemistry, May-27, Volume: 37, Issue:11
Antipsoriatic anthrones with modulated redox properties. 2. Novel derivatives of chrysarobin and isochrysarobin--antiproliferative activity and 5-lipoxygenase inhibition.
AID160712Ability to inhibit Prostaglandin G/H synthase by using the bovine seminal vesicle enzyme assay on BSV cell line at a concentration of 75 uM1990Journal of medicinal chemistry, Jan, Volume: 33, Issue:1
2-substituted-1-naphthols as potent 5-lipoxygenase inhibitors with topical antiinflammatory activity.
AID104137Inhibition of 2,2'-azobis(2-aminopropane)hydrochloride (AAPH) induced lipid peroxidation in bovine brain phospholipid liposomes1994Journal of medicinal chemistry, May-27, Volume: 37, Issue:11
Antipsoriatic anthrones with modulated redox properties. 2. Novel derivatives of chrysarobin and isochrysarobin--antiproliferative activity and 5-lipoxygenase inhibition.
AID3637The compound was tested for inhibitory activity against 5-Lipoxygenase in rat RBL-11992Journal of medicinal chemistry, Jul-10, Volume: 35, Issue:14
5-lipoxygenase: properties, pharmacology, and the quinolinyl(bridged)aryl class of inhibitors.
AID228686Deoxyribose-damaging property as a measure of hydroxyl-radical formation (uM of malondialdehyde/mmol of deoxyribose released by 75 uM test compound)1993Journal of medicinal chemistry, Dec-10, Volume: 36, Issue:25
Antipsoriatic anthrones with modulated redox properties. 1. Novel 10-substituted 1,8-dihydroxy-9(10H)-anthracenones as inhibitors of 5-lipoxygenase.
AID6882Inhibitory activity against 5-lipoxygenase (inhibition of 5-HETE and LTB4 biosynthesis) in bovine polymorphonuclear leukocytes (PMNL).1993Journal of medicinal chemistry, Dec-10, Volume: 36, Issue:25
Antipsoriatic anthrones with modulated redox properties. 1. Novel 10-substituted 1,8-dihydroxy-9(10H)-anthracenones as inhibitors of 5-lipoxygenase.
AID6790Ability to inhibit 5-lipoxygenase by using a crude preparation of the cytosolic enzyme from the rat basophilic leukemia (RBL-1) cell line1990Journal of medicinal chemistry, Jan, Volume: 33, Issue:1
2-substituted-1-naphthols as potent 5-lipoxygenase inhibitors with topical antiinflammatory activity.
AID133223Percentage inhibition of the mouse arachidonic acid induced ear edema assay (AA) at a dose of 100 ug/ear1990Journal of medicinal chemistry, Jan, Volume: 33, Issue:1
2-substituted-1-naphthols as potent 5-lipoxygenase inhibitors with topical antiinflammatory activity.
AID25771Reducing activity against 2,2-diphenyl-1-picrylhydrazyl with an equimolar amount of the test compound; c = Not reactive1993Journal of medicinal chemistry, Dec-10, Volume: 36, Issue:25
Antipsoriatic anthrones with modulated redox properties. 1. Novel 10-substituted 1,8-dihydroxy-9(10H)-anthracenones as inhibitors of 5-lipoxygenase.
AID160710Inhibitory activity against Prostaglandin G/H synthase (bovine seminal vesicles)1992Journal of medicinal chemistry, Aug-21, Volume: 35, Issue:17
Novel 1-(pyridylphenyl)-1-phenyl-2-imidazolylethanols with topical antiinflammatory activity.
AID85487Antiproliferative activity against HaCaT cells1994Journal of medicinal chemistry, May-27, Volume: 37, Issue:11
Antipsoriatic anthrones with modulated redox properties. 2. Novel derivatives of chrysarobin and isochrysarobin--antiproliferative activity and 5-lipoxygenase inhibition.
AID133049Percent inhibition of arachidonic acid induced mouse ear edema at 2 mg of total dose1988Journal of medicinal chemistry, Nov, Volume: 31, Issue:11
Topical nonsteroidal antipsoriatic agents. 2. 2,3-(Alkylidenedioxy)naphthalene analogues of lonapalene.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (18)

TimeframeStudies, This Drug (%)All Drugs %
pre-19908 (44.44)18.7374
1990's9 (50.00)18.2507
2000's0 (0.00)29.6817
2010's1 (5.56)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 (%)
Trials2 (11.11%)5.53%
Reviews1 (5.56%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other15 (83.33%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]