Emodepside

This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.

Identification

Generic Name
Emodepside
DrugBank Accession Number
DB11403
Background

Emodepside is an anthelmintic drug that is effective against a number of gastrointestinal nematodes, is licensed for use in cats and belongs to the class of drugs known as the octadepsipeptides, a relatively new class of anthelmintic.

Type
Small Molecule
Groups
Investigational, Vet approved
Structure
Weight
Average: 1119.408
Monoisotopic: 1118.651501602
Chemical Formula
C60H90N6O14
Synonyms
  • Emodepsida
  • émodepside
  • Emodepside
  • Emodepsidum
External IDs
  • BAY 44-4400
  • BAY-44-4400
  • PF 1022-221
  • PF-1022-221

Pharmacology

Indication

Not Available

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Pharmacodynamics

Not Available

Mechanism of action
Not Available
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Not Available
Food Interactions
Not Available

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as cyclic depsipeptides. These are natural or synthetic compounds having sequences of amino and hydroxy carboxylic acid residues (usually α-amino and α-hydroxy acids) connected in a ring. The residues are commonly but not necessarily regularly alternating.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Peptidomimetics
Sub Class
Depsipeptides
Direct Parent
Cyclic depsipeptides
Alternative Parents
Macrolide lactams / Tetracarboxylic acids and derivatives / Alpha amino acid esters / Macrolides and analogues / Macrolactams / Phenylmorpholines / Aniline and substituted anilines / Dialkylarylamines / Tertiary carboxylic acid amides / Carboxylic acid esters
show 9 more
Substituents
Alpha-amino acid ester / Alpha-amino acid or derivatives / Amine / Amino acid or derivatives / Aniline or substituted anilines / Aromatic heteromonocyclic compound / Azacycle / Benzenoid / Carbonyl group / Carboxamide group
show 28 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
semisynthetic derivative, cyclooctadepsipeptide (CHEBI:78739)
Affected organisms
Not Available

Chemical Identifiers

UNII
YZ647Y5GC9
CAS number
155030-63-0
InChI Key
ZMQMTKVVAMWKNY-YSXLEBCMSA-N
InChI
InChI=1S/C60H90N6O14/c1-37(2)31-47-57(71)77-41(9)53(67)61(11)50(34-40(7)8)60(74)80-52(36-44-17-21-46(22-18-44)66-25-29-76-30-26-66)56(70)64(14)48(32-38(3)4)58(72)78-42(10)54(68)62(12)49(33-39(5)6)59(73)79-51(55(69)63(47)13)35-43-15-19-45(20-16-43)65-23-27-75-28-24-65/h15-22,37-42,47-52H,23-36H2,1-14H3/t41-,42-,47+,48+,49+,50+,51-,52-/m1/s1
IUPAC Name
(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-yl)phenyl]methyl})-1,7,13,19-tetraoxa-4,10,16,22-tetraazacyclotetracosan-2,5,8,11,14,17,20,23-octone
SMILES
[H][C@]1(C)OC(=O)[C@]([H])(CC(C)C)N(C)C(=O)[C@@]([H])(CC2=CC=C(C=C2)N2CCOCC2)OC(=O)[C@]([H])(CC(C)C)N(C)C(=O)[C@@]([H])(C)OC(=O)[C@]([H])(CC(C)C)N(C)C(=O)[C@@]([H])(CC2=CC=C(C=C2)N2CCOCC2)OC(=O)[C@]([H])(CC(C)C)N(C)C1=O

References

General References
  1. Harder A, Holden-Dye L, Walker R, Wunderlich F: Mechanisms of action of emodepside. Parasitol Res. 2005 Oct;97 Suppl 1:S1-10. [Article]
  2. Baronsky J, Bongaerts S, Traeubel M, Weiss HC, Urbanetz N: The study of different solid forms of Emodepside. Eur J Pharm Biopharm. 2009 Jan;71(1):88-99. doi: 10.1016/j.ejpb.2008.06.003. Epub 2008 Jun 17. [Article]
  3. Martin RJ, Buxton SK, Neveu C, Charvet CL, Robertson AP: Emodepside and SL0-1 potassium channels: a review. Exp Parasitol. 2012 Sep;132(1):40-6. doi: 10.1016/j.exppara.2011.08.012. Epub 2011 Sep 3. [Article]
  4. Mehlhorn H, Schmahl G, Frese M, Mevissen I, Harder A, Krieger K: Effects of a combinations of emodepside and praziquantel on parasites of reptiles and rodents. Parasitol Res. 2005 Oct;97 Suppl 1:S65-9. [Article]
  5. Crisford A, Murray C, O'Connor V, Edwards RJ, Kruger N, Welz C, von Samson-Himmelstjerna G, Harder A, Walker RJ, Holden-Dye L: Selective toxicity of the anthelmintic emodepside revealed by heterologous expression of human KCNMA1 in Caenorhabditis elegans. Mol Pharmacol. 2011 Jun;79(6):1031-43. doi: 10.1124/mol.111.071043. Epub 2011 Mar 17. [Article]
  6. Willson J, Amliwala K, Harder A, Holden-Dye L, Walker RJ: The effect of the anthelmintic emodepside at the neuromuscular junction of the parasitic nematode Ascaris suum. Parasitology. 2003 Jan;126(Pt 1):79-86. [Article]
  7. Miltsch SM, Krucken J, Demeler J, Janssen IJ, Kruger N, Harder A, von Samson-Himmelstjerna G: Decreased emodepside sensitivity in unc-49 gamma-aminobutyric acid (GABA)-receptor-deficient Caenorhabditis elegans. Int J Parasitol. 2012 Jul;42(8):761-70. doi: 10.1016/j.ijpara.2012.05.009. Epub 2012 Jun 19. [Article]
  8. von Samson-Himmelstjerna G, Harder A, Sangster NC, Coles GC: Efficacy of two cyclooctadepsipeptides, PF1022A and emodepside, against anthelmintic-resistant nematodes in sheep and cattle. Parasitology. 2005 Mar;130(Pt 3):343-7. [Article]
  9. Holden-Dye L, Crisford A, Welz C, von Samson-Himmelstjerna G, Walker RJ, O'Connor V: Worms take to the slo lane: a perspective on the mode of action of emodepside. Invert Neurosci. 2012 Jun;12(1):29-36. doi: 10.1007/s10158-012-0133-x. Epub 2012 Apr 27. [Article]
  10. Harder A, Schmitt-Wrede HP, Krucken J, Marinovski P, Wunderlich F, Willson J, Amliwala K, Holden-Dye L, Walker R: Cyclooctadepsipeptides--an anthelmintically active class of compounds exhibiting a novel mode of action. Int J Antimicrob Agents. 2003 Sep;22(3):318-31. [Article]
  11. Jeschke R, Iinuma K, Harder A, Schindler M, Murakami T: Influence of the cyclooctadepsipeptides PF1022A and PF1022E as natural products on the design of semi-synthetic anthelmintics such as emodepside. Parasitol Res. 2005 Oct;97 Suppl 1:S11-6. [Article]
  12. Schimmel A, Schroeder I, Altreuther G, Settje T, Charles S, Wolken S, Kok DJ, Ketzis J, Young D, Hutchens D, Krieger KJ: Efficacy of emodepside plus toltrazuril (Procox((R)) oral suspension for dogs) against Toxocara canis, Uncinaria stenocephala and Ancylostoma caninum in dogs. Parasitol Res. 2011 Aug;109 Suppl 1:S1-8. doi: 10.1007/s00436-011-2397-1. [Article]
  13. Petry G, Altreuther G, Wolken S, Swart P, Kok DJ: Efficacy of emodepside plus toltrazuril oral suspension for dogs (Procox(R), Bayer) against Trichuris vulpis in naturally infected dogs. Parasitol Res. 2013 Aug;112 Suppl 1:133-8. doi: 10.1007/s00436-013-3287-5. [Article]
  14. Di Cesare A, Iorio R, Crisi P, Paoletti B, Di Costanzo R, Dimitri CF, Traversa D: Treatment of Troglostrongylus brevior (Metastrongyloidea, Crenosomatidae) in mixed lungworm infections using spot-on emodepside. J Feline Med Surg. 2015 Feb;17(2):181-5. doi: 10.1177/1098612X14533552. Epub 2014 May 2. [Article]
KEGG Compound
C18390
ChemSpider
5293825
RxNav
354606
ChEBI
78739
ChEMBL
CHEMBL2104404
PDBe Ligand
8I2
Wikipedia
Emodepside
PDB Entries
7pxh

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
2CompletedTreatmentHookworm Infections1
2CompletedTreatmentHookworm Infections / Trichuris Trichiura; Infection1
2RecruitingTreatmentOnchocerciasis1
1CompletedBasic ScienceHealthy Volunteers (HV)1
1CompletedTreatmentFilariasis1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Not Available
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.00277 mg/mLALOGPS
logP5.03ALOGPS
logP7.63Chemaxon
logS-5.6ALOGPS
pKa (Strongest Acidic)18.28Chemaxon
pKa (Strongest Basic)1.63Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count12Chemaxon
Hydrogen Donor Count0Chemaxon
Polar Surface Area211.38 Å2Chemaxon
Rotatable Bond Count14Chemaxon
Refractivity301.11 m3·mol-1Chemaxon
Polarizability123.41 Å3Chemaxon
Number of Rings5Chemaxon
Bioavailability0Chemaxon
Rule of FiveNoChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-014i-1900000000-383b512af1a081300d94
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-014i-3900000002-81231e2b94e7c4c86bf0
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-004i-1900000000-4f607ab0ed126d012c4a
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-002f-3400000009-fb924fae0fbc3d2906af
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-004i-9200000000-3f71906044dad8dd2619
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0k9i-9500000027-a471abadbaa03b2238b6
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-324.17676
predicted
DeepCCS 1.0 (2019)
[M+H]+325.82996
predicted
DeepCCS 1.0 (2019)
[M+Na]+331.9868
predicted
DeepCCS 1.0 (2019)

Drug created at February 25, 2016 18:26 / Updated at February 21, 2021 18:53