U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C60H90N6O14
Molecular Weight 1119.3884
Optical Activity UNSPECIFIED
Defined Stereocenters 8 / 8
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of EMODEPSIDE

SMILES

CC(C)C[C@@H]1N(C)C(=O)[C@@H](C)OC(=O)[C@H](CC(C)C)N(C)C(=O)[C@@H](CC2=CC=C(C=C2)N3CCOCC3)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](CC4=CC=C(C=C4)N5CCOCC5)OC1=O

InChI

InChIKey=ZMQMTKVVAMWKNY-YSXLEBCMSA-N
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

HIDE SMILES / InChI
Emodepside is a semi-synthetic product (originated by Astellas and out-licensed to Bayer for animal and human use); its precursor is synthesized by a fungus living in the leaves of Camellia japonica. It is a potent antihelminthic drug used in combination with praziquantel (as Profender®) and in combination with toltrazuril (as Procox®) for the treatment of parasitic worms in cats and dogs. Emodepside, a semi-synthetic derivative of PF1022A, belongs to a new class of anthelmintic drugs, the cyclooctadepsipeptides, and shows good efficacy against macrocyclic lactone-, levamisole- or benzimidazole-resistant nematode populations. Although putative receptors for emodepside have already been discovered, its mode of action is still not fully understood. It has being suggested that GABA(A)-receptor UNC-49 is associated with the emodepside mode of action. It has also being shown that Emodepside binds to a presynaptic latrophilin receptor in nematodes. The following presynaptic signal transduction occurs via activation of Gqalpha protein and phospholipase-Cbeta, which leads to mobilization of diacylglycerol (DAG). DAG then activates UNC-13 and synaptobrevin, two proteins which play an important role in presynaptic vesicle-functioning. This finally leads to the release of a currently unidentified transmitter. The transmitter (or modulator) exerts its effects at the postsynaptic membrane and induces a flaccid paralysis of the pharynx and the somatic musculature in nematodes.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: unc-49, Caenorhabditis elegans, UniProtKB - G5ECD3
Target ID: G5EDW2
Gene ID: 174419.0
Gene Symbol: lat-1
Target Organism: Caenorhabditis elegans
4.0 nM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
PROFENDER

Approved Use

PROFENDER Topical Solution is indicated for the treatment and control of hookworm infections caused by Ancylostoma tubaeforme (adults, immature adults, and fourth stage larvae), roundworm infections caused by Toxocara cati (adults and fourth stage larvae), and tapeworm infections caused by Dipylidium caninum (adults) and Taenia taeniaeformis (adults) in cats.

Launch Date

1.18307514E12
PubMed

PubMed

TitleDatePubMed
The effect of the anthelmintic emodepside at the neuromuscular junction of the parasitic nematode Ascaris suum.
2003 Jan
Evaluation of the efficacy of emodepside plus praziquantel topical solution against ascarid infections (Toxocara cati or Toxascaris leonina) in cats.
2005 Oct
SLO, SLO, quick, quick, slow: calcium-activated potassium channels as regulators of Caenorhabditis elegans behaviour and targets for anthelmintics.
2007 Dec
The calcium-activated potassium channel, SLO-1, is required for the action of the novel cyclo-octadepsipeptide anthelmintic, emodepside, in Caenorhabditis elegans.
2007 Dec
Effects of the novel anthelmintic emodepside on the locomotion, egg-laying behaviour and development of Caenorhabditis elegans.
2007 May
Developing novel anthelmintics from plant cysteine proteinases.
2008 Sep 1
Canine and feline cardiopulmonary parasitic nematodes in Europe: emerging and underestimated.
2010 Jul 23
Patents

Sample Use Guides

Each mL of Profender contains 21.4 mg emodepside and 85.7 mg praziquantel. Recommended minimum dosage is 1.36 mg/lb (3 mg/kg) emodepside and 5.45 mg/lb (12 mg/kg) praziquantel. Administer the entire contents of a unit applicator tube of PROFENDER Topical Solution topically one time.
Route of Administration: Topical
Emodepside was evaluated in a concentration range between 0.01 and 100 ug/ml against third-stage larvae (L3) and adult worms of Nippostrongylus brasiliensis and first-stage larvae (L1) of Trichinella spiralis. Emodepside had EC(50) value in the T. spiralis 0.02788 ug/ml and the N. brasiliensis 0.06188 ug/ml) motility assays.
Name Type Language
EMODEPSIDE
GREEN BOOK   INN   MI  
INN  
Official Name English
EMODEPSIDE [MI]
Common Name English
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)
Common Name English
BAY-44-4400
Code English
EMODEPSIDE [GREEN BOOK]
Common Name English
PF 1022-221
Code English
PROCOX COMPONENT EMODEPSIDE
Brand Name English
BAY 44-4400
Code English
PF-1022-221
Code English
EMODEPSIDE COMPONENT OF PROCOX
Common Name English
PROFENDER COMPONENT EMODEPSIDE
Brand Name English
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)
Common Name English
emodepside [INN]
Common Name English
EMODEPSIDE COMPONENT OF PROFENDER
Brand Name English
EMODEPSIDE [EMA EPAR VETERINARY]
Common Name English
Classification Tree Code System Code
CFR 21 CFR 524.775
Created by admin on Sat Dec 16 17:11:25 UTC 2023 , Edited by admin on Sat Dec 16 17:11:25 UTC 2023
EMA VETERINARY ASSESSMENT REPORTS PROCOX [AUTHORIZED]
Created by admin on Sat Dec 16 17:11:25 UTC 2023 , Edited by admin on Sat Dec 16 17:11:25 UTC 2023
EMA VETERINARY ASSESSMENT REPORTS PROFENDER [AUTHORIZED]
Created by admin on Sat Dec 16 17:11:25 UTC 2023 , Edited by admin on Sat Dec 16 17:11:25 UTC 2023
WHO-VATC QP52AX60
Created by admin on Sat Dec 16 17:11:25 UTC 2023 , Edited by admin on Sat Dec 16 17:11:25 UTC 2023
FDA ORPHAN DRUG 535416
Created by admin on Sat Dec 16 17:11:25 UTC 2023 , Edited by admin on Sat Dec 16 17:11:25 UTC 2023
NCI_THESAURUS C250
Created by admin on Sat Dec 16 17:11:25 UTC 2023 , Edited by admin on Sat Dec 16 17:11:25 UTC 2023
EMA VETERINARY ASSESSMENT REPORTS PROFENDER [AUTHORIZED]
Created by admin on Sat Dec 16 17:11:25 UTC 2023 , Edited by admin on Sat Dec 16 17:11:25 UTC 2023
Code System Code Type Description
EPA CompTox
DTXSID50165799
Created by admin on Sat Dec 16 17:11:25 UTC 2023 , Edited by admin on Sat Dec 16 17:11:25 UTC 2023
PRIMARY
WIKIPEDIA
EMODEPSIDE
Created by admin on Sat Dec 16 17:11:25 UTC 2023 , Edited by admin on Sat Dec 16 17:11:25 UTC 2023
PRIMARY
DAILYMED
YZ647Y5GC9
Created by admin on Sat Dec 16 17:11:25 UTC 2023 , Edited by admin on Sat Dec 16 17:11:25 UTC 2023
PRIMARY
CHEBI
78739
Created by admin on Sat Dec 16 17:11:25 UTC 2023 , Edited by admin on Sat Dec 16 17:11:25 UTC 2023
PRIMARY
ChEMBL
CHEMBL2104404
Created by admin on Sat Dec 16 17:11:25 UTC 2023 , Edited by admin on Sat Dec 16 17:11:25 UTC 2023
PRIMARY
DRUG BANK
DB11403
Created by admin on Sat Dec 16 17:11:25 UTC 2023 , Edited by admin on Sat Dec 16 17:11:25 UTC 2023
PRIMARY
INN
7893
Created by admin on Sat Dec 16 17:11:25 UTC 2023 , Edited by admin on Sat Dec 16 17:11:25 UTC 2023
PRIMARY
CAS
155030-63-0
Created by admin on Sat Dec 16 17:11:25 UTC 2023 , Edited by admin on Sat Dec 16 17:11:25 UTC 2023
PRIMARY
MESH
C468987
Created by admin on Sat Dec 16 17:11:25 UTC 2023 , Edited by admin on Sat Dec 16 17:11:25 UTC 2023
PRIMARY
FDA UNII
YZ647Y5GC9
Created by admin on Sat Dec 16 17:11:25 UTC 2023 , Edited by admin on Sat Dec 16 17:11:25 UTC 2023
PRIMARY
MERCK INDEX
m4887
Created by admin on Sat Dec 16 17:11:25 UTC 2023 , Edited by admin on Sat Dec 16 17:11:25 UTC 2023
PRIMARY Merck Index
NCI_THESAURUS
C90726
Created by admin on Sat Dec 16 17:11:25 UTC 2023 , Edited by admin on Sat Dec 16 17:11:25 UTC 2023
PRIMARY
RXCUI
354606
Created by admin on Sat Dec 16 17:11:25 UTC 2023 , Edited by admin on Sat Dec 16 17:11:25 UTC 2023
PRIMARY RxNorm
PUBCHEM
6918632
Created by admin on Sat Dec 16 17:11:25 UTC 2023 , Edited by admin on Sat Dec 16 17:11:25 UTC 2023
PRIMARY
SMS_ID
300000027871
Created by admin on Sat Dec 16 17:11:25 UTC 2023 , Edited by admin on Sat Dec 16 17:11:25 UTC 2023
PRIMARY