Emodepside
Star0
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
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Contraindications & Blackbox Warnings
- Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API
- 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
- Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.
- 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
- Harder A, Holden-Dye L, Walker R, Wunderlich F: Mechanisms of action of emodepside. Parasitol Res. 2005 Oct;97 Suppl 1:S1-10. [Article]
- 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]
- 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]
- 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]
- 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]
- 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]
- 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]
- 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]
- 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]
- 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]
- 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]
- 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]
- 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]
- 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]
- External Links
- KEGG Compound
- C18390
- ChemSpider
- 5293825
- 354606
- ChEBI
- 78739
- ChEMBL
- CHEMBL2104404
- PDBe Ligand
- 8I2
- Wikipedia
- Emodepside
- PDB Entries
- 7pxh
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 2 Active Not Recruiting Treatment Onchocerciasis 1 2 Completed Treatment Hookworm Infections 1 2 Completed Treatment Hookworm Infections / Trichuris Trichiura; Infection 1 1 Completed Basic Science Healthy Volunteers (HV) 1 1 Completed Treatment Filariasis 1
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
Property Value Source Water Solubility 0.00277 mg/mL ALOGPS logP 5.03 ALOGPS logP 7.63 Chemaxon logS -5.6 ALOGPS pKa (Strongest Acidic) 18.28 Chemaxon pKa (Strongest Basic) 1.63 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 12 Chemaxon Hydrogen Donor Count 0 Chemaxon Polar Surface Area 211.38 Å2 Chemaxon Rotatable Bond Count 14 Chemaxon Refractivity 301.11 m3·mol-1 Chemaxon Polarizability 123.41 Å3 Chemaxon Number of Rings 5 Chemaxon Bioavailability 0 Chemaxon Rule of Five No Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule Yes Chemaxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 324.17676 predictedDeepCCS 1.0 (2019) [M+H]+ 325.82996 predictedDeepCCS 1.0 (2019) [M+Na]+ 331.9868 predictedDeepCCS 1.0 (2019)
Drug created at February 25, 2016 18:26 / Updated at February 21, 2021 18:53