Page last updated: 2024-12-11

bay 44-4400

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

Description

Bay 44-4400: a semisynthetic derivative of anthelminitic cyclodepsipeptide; PF1022A [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

emodepside : A cyclooctadepsipeptide consisting of D-lactoyl, N-methyl-L-leucyl, 3-[4-(4-morpholinyl)phenyl]-D-lactoyl, N-methyl-L-leucyl, D-lactoyl, N-methyl-L-leucyl, 3-[4-(4-morpholinyl)phenyl]-D-lactoyl, and N-methyl-L-leucyl residues joined in sequence to give a 24-membered macrocycle. An anthelmintic, it is used with praziquantel for the treatment and control of hookworm, roundworm and tapeworm infections in cats. [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]

Cross-References

ID SourceID
PubMed CID6918632
CHEMBL ID2104404
CHEBI ID78739
SCHEMBL ID167580
MeSH IDM0404888

Synonyms (45)

Synonym
bay-44-4400
pf-1022-221
emodepside
(3s,6r,9s,12r,15s,18r,21s,24r)-4,6,10,16,18,22-hexamethyl-3,9,15,21-tetrakis(2-methylpropyl)-12,24-bis[(4-morpholin-4-ylphenyl)methyl]-1,7,13,19-tetraoxa-4,10,16,22-tetrazacyclotetracosane-2,5,8,11,14,17,20,23-octone
155030-63-0
C18390
cyclo((r)-lactoyl-n-methyl-l-leucyl-(r)-3-(p-morpholinophenyl)lactoyl-n-methyl-l-leucyl-(r)-lactoyl-n-methyl-l-leucyl-(r)-3-(p-morpholinophenyl)lactoyl-n-methyl-l-leucyl)
emodepside [inn]
unii-yz647y5gc9
yz647y5gc9 ,
chebi:78739 ,
pf 1022-221
CHEMBL2104404
bay 44-4400
emodepside [green book]
emodepside component of profender
emodepside component of procox
cyclo((.alpha.r)-.alpha.-hydroxy-4-(4-morpholinyl)benzenepropanoyl-n-methyl-l-leucyl-(2r)-2-hydroxypropanoyl-n-methyl-l-leucyl-(.alpha.r)-.alpha.-hydroxy-4-(4-morpholinyl)benzenepropanoyl-n-methyl-l-leucyl-(2r)-2-hydroxypropanoyl-n-methyl-l-leucyl)
emodepside [mi]
emodepside [ema epar veterinary]
procox component emodepside
profender component emodepside
SCHEMBL167580
emodepsida
emodepsidum
cyclo {d-lactoyl-n-methyl-l-leucyl-3-[4-(4-morpholinyl)phenyl]-d-lactoyl-n-methyl-l-leucyl-d-lactoyl-n-methyl-l-leucyl-3-[4-(4-morpholinyl)phenyl]-d-lactoyl-n-methyl-l-leucyl}
(3s,6r,9s,12r,15s,18r,21s,24r)-3,9,15,21-tetraisobutyl-4,6,10,16,18,22-hexamethyl-12,24-bis[4-(morpholin-4-yl)benzyl]-1,7,13,19-tetraoxa-4,10,16,22-tetraazacyclotetracosane-2,5,8,11,14,17,20,23-octone
cyclo [d-2-hydroxypropanoyl-n-methyl-l-leucyl-3-[4-(4-morpholinyl)phenyl]-d-2-hydroxypropanoyl-n-methyl-l-leucyl-d-2-hydroxypropanoyl-n-methyl-l-leucyl-3-[4-(4-morpholinyl)phenyl]-d-2-hydroxypropanoyl-n-methyl-l-leucyl]
cyclo[(r)-lactoyl-n-methyl-l-leucyl-(r)-3-(p-morpholinophenyl)lactoyl-n-methyl-l-leucyl-(r)-lactoyl-n-methyl-l-leucyl-(r)-3-(p-morpholinophenyl)lactoyl-n-methyl-l-leucyl]
AC-31930
DTXSID50165799 ,
E74446
DB11403
Q1339032
4,6,10,16,18,22-hexamethyl-3,9,15,21-tetrakis(2-methylpropyl)-12,24-bis[(4-morpholin-4-ylphenyl)methyl]-1,7,13,19-tetraoxa-4,10,16,22-tetrazacyclotetracosane-2,5,8,11,14,17,20,23-octone
NCGC00507682-01
(3s,6r,9s,12r,15s,18r,21s,24r)-3,9,15,21-tetraisobutyl-4,6,10,16,18,22-hexamethyl-12,24-bis(4-morpholinobenzyl)-1,7,13,19-tetraoxa-4,10,16,22-tetraazacyclotetracosan-2,5,8,11,14,17,20,23-octaone
A929940
(3~{s},6~{r},9~{s},12~{r},15~{s},18~{r},21~{s},24~{r})-4,6,10,16,18,22-hexamethyl-3,9,15,21-tetrakis(2-methylpropyl)-12,24-bis[(4-morpholin-4-ylphenyl)methyl]-1,7,13,19-tetraoxa-4,10,16,22-tetrazacyclotetracosane-2,5,8,11,14,17,20,23-octone
8I2 ,
emodepside (ema epar veterinary)
(3s,6r,9s,12r,15s,18r,21s,24r)-3,9,15,21-tetraisobutyl-4,6,10,16,18,22-hexamethyl-12,24-bis(4-(morpholin-4-yl)benzyl)-1,7,13,19-tetraoxa-4,10,16,22-tetraazacyclotetracosane-2,5,8,11,14,17,20,23-octone
cyclo (d-2-hydroxypropanoyl-n-methyl-l-leucyl-3-(4-(4-morpholinyl)phenyl)-d-2-hydroxypropanoyl-n-methyl-l-leucyl-d-2-hydroxypropanoyl-n-methyl-l-leucyl-3-(4-(4-morpholinyl)phenyl)-d-2-hydroxypropanoyl-n-methyl-l-leucyl)
dtxcid6088290
AKOS040759291

Research Excerpts

Toxicity

ExcerptReferenceRelevance
" No adverse reactions were observed in the European study, and only mild ones of short duration in a few cats from both treatment groups of the North American study."( Field evaluation of the efficacy and safety of emodepside/praziquantel spot-on solution against naturally acquired nematode and cestode infections in domestic cats.
Altreuther, G; Buch, J; Charles, SD; Davis, WL; Krieger, KJ; Radeloff, I, 2005
)
0.33
" No suspected adverse drug reactions were observed in the study."( Field evaluation of the efficacy and safety of emodepside plus praziquantel tablets (Profender tablets for dogs) against naturally acquired nematode and cestode infections in dogs.
Altreuther, G; Krieger, KJ; LeSueur, C; Radeloff, I; Schimmel, A, 2009
)
0.35
" No treated animals showed adverse events."( Efficacy and safety of emodepside 2.1%/praziquantel 8.6% spot-on formulation in the treatment of feline aelurostrongylosis.
Bartolini, R; Di Cesare, A; Heine, J; Iorio, R; Lohr, B; Milillo, P; Pampurini, F; Schaper, R; Traversa, D, 2009
)
0.35
"No suspected adverse drug reactions were observed in any of the 403 dogs enrolled in the three studies including 234 dogs treated with emodepside/toltrazuril suspension."( Field evaluations of the efficacy and safety of Emodepside plus toltrazuril (Procox® oral suspension for dogs) against naturally acquired nematode and Isospora spp. infections in dogs.
Adler, K; Altreuther, G; Gasda, N; Hellmann, K; Hutchens, D; Krieger, KJ; Schimmel, A; Thurieau, H, 2011
)
0.37
" It is concluded that Seresto(®) is chemically compatible with solvents used in major spot-on formulations on the market and is dermally and systemically safe for adult dogs and cats when used concomitantly with Advocate(®) and Profender(®) spot-on formulations."( Chemical Compatibility and Safety of Imidacloprid/Flumethrin Collar (Seresto®) Concomitantly Used with Imidacloprid/Moxidectin (Advocate®, Advantage® Multi) and Emodepside/Praziquantel (Profender®) Spot-on Formulations.
Crafford, D; Deuster, K; Fourie, J; Krüdewagen, EM; Remer, C; Schunack, B; Stanneck, D; Wolken, S, 2015
)
0.42
" The aims of this study were i) to characterize the population pharmacokinetic properties of emodepside, ii) to link its exposure to adverse events in healthy volunteers, and iii) to propose an optimized dosing regimen for a planned phase II study in onchocerciasis patients."( Drug development for the treatment of onchocerciasis: Population pharmacokinetic and adverse events modeling of emodepside.
Assmus, F; Hoglund, RM; Monnot, F; Scandale, I; Specht, S; Tarning, J, 2022
)
0.72
"Plasma concentration-time profiles and adverse event data were obtained from 142 subjects enrolled in three phase I studies, including a single-dose, and a multiple-dose, dose-escalation study as well as a relative bioavailability study."( Drug development for the treatment of onchocerciasis: Population pharmacokinetic and adverse events modeling of emodepside.
Assmus, F; Hoglund, RM; Monnot, F; Scandale, I; Specht, S; Tarning, J, 2022
)
0.72

Pharmacokinetics

ExcerptReferenceRelevance
" Terminal half-life was > 500 hours."( Safety, tolerability and pharmacokinetics of emodepside, a potential novel treatment for onchocerciasis (river blindness), in healthy male subjects.
Delhomme, S; Dennison, J; Dequatre Cheeseman, K; Gillon, JY; Monnot, F; Pedrique, B; Peña Rossi, C; Rodriguez, ML; Skrabs, S; Specht, S; Stass, H; Strub Wourgaft, N; van den Berg, F, 2021
)
0.62
" The aims of this study were i) to characterize the population pharmacokinetic properties of emodepside, ii) to link its exposure to adverse events in healthy volunteers, and iii) to propose an optimized dosing regimen for a planned phase II study in onchocerciasis patients."( Drug development for the treatment of onchocerciasis: Population pharmacokinetic and adverse events modeling of emodepside.
Assmus, F; Hoglund, RM; Monnot, F; Scandale, I; Specht, S; Tarning, J, 2022
)
0.72
" Nonlinear mixed-effects modeling was used to evaluate the population pharmacokinetic properties of emodepside."( Drug development for the treatment of onchocerciasis: Population pharmacokinetic and adverse events modeling of emodepside.
Assmus, F; Hoglund, RM; Monnot, F; Scandale, I; Specht, S; Tarning, J, 2022
)
0.72

Bioavailability

ExcerptReferenceRelevance
"Plasma concentration-time profiles and adverse event data were obtained from 142 subjects enrolled in three phase I studies, including a single-dose, and a multiple-dose, dose-escalation study as well as a relative bioavailability study."( Drug development for the treatment of onchocerciasis: Population pharmacokinetic and adverse events modeling of emodepside.
Assmus, F; Hoglund, RM; Monnot, F; Scandale, I; Specht, S; Tarning, J, 2022
)
0.72

Dosage Studied

ExcerptRelevanceReference
" In reptiles the dosage had to be increased, since the thick outer layer of the epidermis hinders the penetration of the compounds."( Effects of a combinations of emodepside and praziquantel on parasites of reptiles and rodents.
Frese, M; Harder, A; Krieger, K; Mehlhorn, H; Mevissen, I; Schmahl, G, 2005
)
0.33
" Treatments were performed at the minimum therapeutic dosage 5 days after the experimental infection."( Treatment of third-stage larvae of Toxocara cati with milbemycin oxime plus praziquantel tablets and emodepside plus praziquantel spot-on formulation in experimentally infected cats.
Böhm, C; Schaper, R; Schnieder, T; Wolken, S, 2012
)
0.38
" The drugs available for mass drug administration, (ivermectin, albendazole and diethylcarbamazine), are ineffective against adult filariae (macrofilariae) at the registered dosing regimen; this generates a real and urgent need to identify effective macrofilaricides."( Emodepside has sex-dependent immobilizing effects on adult Brugia malayi due to a differentially spliced binding pocket in the RCK1 region of the SLO-1 K channel.
Kashyap, SS; Kulke, D; Lustigman, S; Martin, RJ; Robertson, AP; Verma, S; Voronin, D, 2019
)
0.51
" The aims of this study were i) to characterize the population pharmacokinetic properties of emodepside, ii) to link its exposure to adverse events in healthy volunteers, and iii) to propose an optimized dosing regimen for a planned phase II study in onchocerciasis patients."( Drug development for the treatment of onchocerciasis: Population pharmacokinetic and adverse events modeling of emodepside.
Assmus, F; Hoglund, RM; Monnot, F; Scandale, I; Specht, S; Tarning, J, 2022
)
0.72
"Pharmacokinetic modeling and simulation was used to derive an optimized, body weight-based dosing regimen, which allows for achievement of extended emodepside exposures above target concentrations while maintaining acceptable tolerability margins."( Drug development for the treatment of onchocerciasis: Population pharmacokinetic and adverse events modeling of emodepside.
Assmus, F; Hoglund, RM; Monnot, F; Scandale, I; Specht, S; Tarning, J, 2022
)
0.72
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (1)

RoleDescription
antinematodal drugA substance used in the treatment or control of nematode infestations.
[role 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]

Drug Classes (2)

ClassDescription
semisynthetic derivativeAny organic molecular entity derived from a natural product by partial chemical synthesis.
cyclooctadepsipeptideA cyclodepsipeptide consisting of eight hydroxy- or amino-acids joined in sequence to give a macrocycle. They form the basis of a relatively new class of anthelmintic agents with a novel mechanism of action.
[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 (1)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Spike glycoproteinSevere acute respiratory syndrome-related coronavirusPotency0.79430.009610.525035.4813AID1479145
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Ceullar Components (1)

Processvia Protein(s)Taxonomy
virion membraneSpike glycoproteinSevere acute respiratory syndrome-related coronavirus
[Information is prepared from geneontology information from the June-17-2024 release]

Research

Studies (79)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's26 (32.91)29.6817
2010's40 (50.63)24.3611
2020's13 (16.46)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 10.07

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 Index10.07 (24.57)
Research Supply Index4.65 (2.92)
Research Growth Index4.73 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (10.07)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials24 (30.00%)5.53%
Reviews8 (10.00%)6.00%
Case Studies2 (2.50%)4.05%
Observational0 (0.00%)0.25%
Other46 (57.50%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]