Page last updated: 2024-11-10

latoconazole

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

Description

latoconazole: RN refers to cpd without isomeric designation; latoconazole is (E)-isomer; structure given in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID3002820
CHEMBL ID1555126
CHEBI ID31761
SCHEMBL ID342635
MeSH IDM0196961

Synonyms (51)

Synonym
AC-5318
(2e)-2-[4-(2-chlorophenyl)-1,3-dithiolan-2-ylidene]-2-imidazol-1-yl-acetonitrile
[4-(2-chloro-phenyl)-1,3-dithiolan-2-ylidene]-2-imidazol-1-yl-acetonitrile
101530-10-3
lanoconazole
astat
nnd-318
tjn-318
(+-)-(e)-(4-(2-chlorophenyl)-1,3-dithiolan-2-ylidene)-1-imidazolylacetonitrile
1h-imidazole-1-acetonitrile, alpha-(4-(2-chlorophenyl)-1,3-dithiolan-2-ylidene)-, (e)-(+-)-
brn 4819111
1h-imidazole-1-acetonitrile, alpha-(4-(2-chlorophenyl)-1,3-dithiolan-2-ylidene)-, (alphae)-
(e)-alpha-(4-(2-chlorophenyl)-1,3-dithiolan-2-ylidene)-1h-imidazole-1-acetonitrile
lanoconazole [inn]
(+-)-alpha-((e)-4-(o-chlorophenyl)-1,3-dithiolan-2-ylidene)imidazole-1-acetonitrile
astat (tn)
D01092
lanoconazole (jp17/inn)
latoconazole
NCGC00164544-01
(2e)-2-[4-(2-chlorophenyl)-1,3-dithiolan-2-ylidene]-2-imidazol-1-ylacetonitrile
unii-4e7858311f
4e7858311f ,
1h-imidazole-1-acetonitrile, alpha-(4-(2-chlorophenyl)-1,3-dithiolan-2-ylidene)-
(4-(2-chlorophenyl)-1,3-dithiolan-2-ylidene)-1-imidazolylacetonitrile
126509-69-1
2-[4-(2-chlorophenyl)-1,3-dithiolan-2-ylidene]-2-imidazol-1-yl-acetonitrile
AKOS015900193
lanoconazole [jan]
lanoconazole [mi]
lanoconazole [who-dd]
lanoconazole [mart.]
(+/-)-.alpha.-((e)-4-(o-chlorophenyl)-1,3-dithiolan-2-ylidene)imidazole-1-acetonitrile
CHEMBL1555126
SCHEMBL342635
J-000422
sr-01000945047
SR-01000945047-1
lanoconazole, vetranal(tm), analytical standard
CHEBI:31761
()--[(e)-4-(o-chlorophenyl)-1,3-dithiolan-2-ylidene]imidazole-1-acetonitrile;()--[(e)-4-(o-chlorophenyl)-1,3-dithiolan-2-ylidene]imidazole-1-acetonitrile
153222-93-6
bdbm50248305
AS-12927
dsstox_gsid_46428
AMY32553
Q27259479
1h-imidazole-1-acetonitrile, alpha-[4-(2-chlorophenyl)-1,3-dithiolan-2-ylidene]-, (alphae)-
lanoconazole 100 microg/ml in acetonitrile
2-(4-(2-chlorophenyl)-1,3-dithiolan-2-ylidene)-2-(1h-imidazol-1-yl)acetonitrile
AT35543

Research Excerpts

Pharmacokinetics

ExcerptReferenceRelevance
" The amount of lanoconazole in the stratum corneum after once daily repeated administration reached a steady state on day 3, and it was eliminated from the stratum corneum with a half-life of approximately 11 h after discontinuing application."( Pharmacokinetics of lanoconazole in human skin after repeated topical application.
Amagishi, H; Hashimoto, S; Imai, H; Inoue, G; Luo, J; Ninomiya, R; Otani, N; Uemura, N; Wakuda, H, 2022
)
0.72

Bioavailability

ExcerptReferenceRelevance
" KP-103 proved to be highly effective in achieving mycological cure and preventing relapse against tinea pedis presumably because of its good bioavailability in the skin based on its low keratin-affinity, along with its potent antifungal activity."( In vivo fungicidal effect of KP-103 in a guinea pig model of interdigital tinea pedis determined by using a new method for removing the antimycotic carryover effect.
Arika, T; Tatsumi, Y; Yamaguchi, H; Yokoo, M, 2002
)
0.31

Dosage Studied

ExcerptRelevanceReference
"Therapeutic efficacy of clinical dosage forms of latoconazole (NND-318, CAS 101530-10-3), related compound of ketene dithioacetals with an imidazole ring, was examined on two experimental tinea models: a recently developed tinea pedis model and a conventional tinea corporis model in guinea pigs."( Therapeutic efficacy of latoconazole in formulations of clinical use on experimental dermatophytosis in guinea pigs.
Niwano, Y; Ohmi, T; Oka, H; Tanaka, T; Uchida, M; Yamaguchi, H, 1992
)
0.84
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (2)

ClassDescription
conazole antifungal drugAny conazole antifungal agent that has been used for the treatment of fungal infections in animals or humans.
imidazole antifungal drugAny imidazole antifungal agent that has been used for the treatment of fungal infections in humans or animals.
[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 (6)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
glp-1 receptor, partialHomo sapiens (human)Potency12.58930.01846.806014.1254AID624172
peripheral myelin protein 22Rattus norvegicus (Norway rat)Potency11.42390.005612.367736.1254AID624032
lamin isoform A-delta10Homo sapiens (human)Potency10.00000.891312.067628.1838AID1487
[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)
ATP-binding cassette sub-family C member 3Homo sapiens (human)IC50 (µMol)133.00000.63154.45319.3000AID1473740
Multidrug resistance-associated protein 4Homo sapiens (human)IC50 (µMol)133.00000.20005.677410.0000AID1473741
Bile salt export pumpHomo sapiens (human)IC50 (µMol)9.65000.11007.190310.0000AID1473738
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (36)

Processvia Protein(s)Taxonomy
xenobiotic metabolic processATP-binding cassette sub-family C member 3Homo sapiens (human)
xenobiotic transmembrane transportATP-binding cassette sub-family C member 3Homo sapiens (human)
bile acid and bile salt transportATP-binding cassette sub-family C member 3Homo sapiens (human)
glucuronoside transportATP-binding cassette sub-family C member 3Homo sapiens (human)
xenobiotic transportATP-binding cassette sub-family C member 3Homo sapiens (human)
transmembrane transportATP-binding cassette sub-family C member 3Homo sapiens (human)
leukotriene transportATP-binding cassette sub-family C member 3Homo sapiens (human)
monoatomic anion transmembrane transportATP-binding cassette sub-family C member 3Homo sapiens (human)
transport across blood-brain barrierATP-binding cassette sub-family C member 3Homo sapiens (human)
prostaglandin secretionMultidrug resistance-associated protein 4Homo sapiens (human)
cilium assemblyMultidrug resistance-associated protein 4Homo sapiens (human)
platelet degranulationMultidrug resistance-associated protein 4Homo sapiens (human)
xenobiotic metabolic processMultidrug resistance-associated protein 4Homo sapiens (human)
xenobiotic transmembrane transportMultidrug resistance-associated protein 4Homo sapiens (human)
bile acid and bile salt transportMultidrug resistance-associated protein 4Homo sapiens (human)
prostaglandin transportMultidrug resistance-associated protein 4Homo sapiens (human)
urate transportMultidrug resistance-associated protein 4Homo sapiens (human)
glutathione transmembrane transportMultidrug resistance-associated protein 4Homo sapiens (human)
transmembrane transportMultidrug resistance-associated protein 4Homo sapiens (human)
cAMP transportMultidrug resistance-associated protein 4Homo sapiens (human)
leukotriene transportMultidrug resistance-associated protein 4Homo sapiens (human)
monoatomic anion transmembrane transportMultidrug resistance-associated protein 4Homo sapiens (human)
export across plasma membraneMultidrug resistance-associated protein 4Homo sapiens (human)
transport across blood-brain barrierMultidrug resistance-associated protein 4Homo sapiens (human)
guanine nucleotide transmembrane transportMultidrug resistance-associated protein 4Homo sapiens (human)
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 (22)

Processvia Protein(s)Taxonomy
ATP bindingATP-binding cassette sub-family C member 3Homo sapiens (human)
ABC-type xenobiotic transporter activityATP-binding cassette sub-family C member 3Homo sapiens (human)
glucuronoside transmembrane transporter activityATP-binding cassette sub-family C member 3Homo sapiens (human)
ABC-type glutathione S-conjugate transporter activityATP-binding cassette sub-family C member 3Homo sapiens (human)
ABC-type bile acid transporter activityATP-binding cassette sub-family C member 3Homo sapiens (human)
ATP hydrolysis activityATP-binding cassette sub-family C member 3Homo sapiens (human)
ATPase-coupled transmembrane transporter activityATP-binding cassette sub-family C member 3Homo sapiens (human)
xenobiotic transmembrane transporter activityATP-binding cassette sub-family C member 3Homo sapiens (human)
ATPase-coupled inorganic anion transmembrane transporter activityATP-binding cassette sub-family C member 3Homo sapiens (human)
icosanoid transmembrane transporter activityATP-binding cassette sub-family C member 3Homo sapiens (human)
ABC-type transporter activityATP-binding cassette sub-family C member 3Homo sapiens (human)
guanine nucleotide transmembrane transporter activityMultidrug resistance-associated protein 4Homo sapiens (human)
protein bindingMultidrug resistance-associated protein 4Homo sapiens (human)
ATP bindingMultidrug resistance-associated protein 4Homo sapiens (human)
ABC-type xenobiotic transporter activityMultidrug resistance-associated protein 4Homo sapiens (human)
prostaglandin transmembrane transporter activityMultidrug resistance-associated protein 4Homo sapiens (human)
urate transmembrane transporter activityMultidrug resistance-associated protein 4Homo sapiens (human)
purine nucleotide transmembrane transporter activityMultidrug resistance-associated protein 4Homo sapiens (human)
ABC-type glutathione S-conjugate transporter activityMultidrug resistance-associated protein 4Homo sapiens (human)
ABC-type bile acid transporter activityMultidrug resistance-associated protein 4Homo sapiens (human)
efflux transmembrane transporter activityMultidrug resistance-associated protein 4Homo sapiens (human)
15-hydroxyprostaglandin dehydrogenase (NAD+) activityMultidrug resistance-associated protein 4Homo sapiens (human)
ATP hydrolysis activityMultidrug resistance-associated protein 4Homo sapiens (human)
glutathione transmembrane transporter activityMultidrug resistance-associated protein 4Homo sapiens (human)
ATPase-coupled transmembrane transporter activityMultidrug resistance-associated protein 4Homo sapiens (human)
xenobiotic transmembrane transporter activityMultidrug resistance-associated protein 4Homo sapiens (human)
ATPase-coupled inorganic anion transmembrane transporter activityMultidrug resistance-associated protein 4Homo sapiens (human)
ABC-type transporter activityMultidrug resistance-associated protein 4Homo sapiens (human)
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 (17)

Processvia Protein(s)Taxonomy
plasma membraneATP-binding cassette sub-family C member 3Homo sapiens (human)
basal plasma membraneATP-binding cassette sub-family C member 3Homo sapiens (human)
basolateral plasma membraneATP-binding cassette sub-family C member 3Homo sapiens (human)
membraneATP-binding cassette sub-family C member 3Homo sapiens (human)
nucleolusMultidrug resistance-associated protein 4Homo sapiens (human)
Golgi apparatusMultidrug resistance-associated protein 4Homo sapiens (human)
plasma membraneMultidrug resistance-associated protein 4Homo sapiens (human)
membraneMultidrug resistance-associated protein 4Homo sapiens (human)
basolateral plasma membraneMultidrug resistance-associated protein 4Homo sapiens (human)
apical plasma membraneMultidrug resistance-associated protein 4Homo sapiens (human)
platelet dense granule membraneMultidrug resistance-associated protein 4Homo sapiens (human)
external side of apical plasma membraneMultidrug resistance-associated protein 4Homo sapiens (human)
plasma membraneMultidrug resistance-associated protein 4Homo sapiens (human)
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 (8)

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.
AID1473835Stimulation of human MRP2 overexpressed in Sf9 cell membrane vesicles assessed as uptake of [3H]-estradiol-17beta-D-glucuronide in presence of ATP and GSH measured after 20 mins by membrane vesicle transport assay2013Toxicological sciences : an official journal of the Society of Toxicology, Nov, Volume: 136, Issue:1
A multifactorial approach to hepatobiliary transporter assessment enables improved therapeutic compound development.
AID774657Antitrypanosomal activity against amastigote stage of Trypanosoma cruzi infected in mouse NIH/3T3 cells after 48 hrs by Hoechst staining assay2013Journal of medicinal chemistry, Oct-24, Volume: 56, Issue:20
Approaches to protozoan drug discovery: phenotypic screening.
AID1495982Inhibition of fungal keratinase activity at 0.1 to 10 mg/ml relative to control2018Bioorganic & medicinal chemistry, 07-23, Volume: 26, Issue:12
Efficiency of newly prepared thiazole derivatives against some cutaneous fungi.
AID1473741Inhibition of human MRP4 overexpressed in Sf9 cell membrane vesicles assessed as uptake of [3H]-estradiol-17beta-D-glucuronide in presence of ATP and GSH measured after 20 mins by membrane vesicle transport assay2013Toxicological sciences : an official journal of the Society of Toxicology, Nov, Volume: 136, Issue:1
A multifactorial approach to hepatobiliary transporter assessment enables improved therapeutic compound development.
AID774655Selectivity ratio of cytotoxic activity against mouse NIH/3T3 cells to antitrypanosomal activity against amastigote stage of Trypanosoma cruzi2013Journal of medicinal chemistry, Oct-24, Volume: 56, Issue:20
Approaches to protozoan drug discovery: phenotypic screening.
AID1473738Inhibition of human BSEP overexpressed in Sf9 cell membrane vesicles assessed as uptake of [3H]-taurocholate in presence of ATP measured after 15 to 20 mins by membrane vesicle transport assay2013Toxicological sciences : an official journal of the Society of Toxicology, Nov, Volume: 136, Issue:1
A multifactorial approach to hepatobiliary transporter assessment enables improved therapeutic compound development.
AID1473740Inhibition of human MRP3 overexpressed in Sf9 insect cell membrane vesicles assessed as uptake of [3H]-estradiol-17beta-D-glucuronide in presence of ATP and GSH measured after 10 mins by membrane vesicle transport assay2013Toxicological sciences : an official journal of the Society of Toxicology, Nov, Volume: 136, Issue:1
A multifactorial approach to hepatobiliary transporter assessment enables improved therapeutic compound development.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (48)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's14 (29.17)18.2507
2000's14 (29.17)29.6817
2010's14 (29.17)24.3611
2020's6 (12.50)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 10.63

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 Index10.63 (24.57)
Research Supply Index3.91 (2.92)
Research Growth Index4.54 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (10.63)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials1 (2.08%)5.53%
Reviews1 (2.08%)6.00%
Case Studies7 (14.58%)4.05%
Observational0 (0.00%)0.25%
Other39 (81.25%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]