Details
Stereochemistry | ACHIRAL |
Molecular Formula | C20H24N2O5 |
Molecular Weight | 372.415 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CC(=O)NC1=CC=C(OCCOCCOC2=CC=C(NC(C)=O)C=C2)C=C1
InChI
InChIKey=JNEZCZPNQCQCFK-UHFFFAOYSA-N
InChI=1S/C20H24N2O5/c1-15(23)21-17-3-7-19(8-4-17)26-13-11-25-12-14-27-20-9-5-18(6-10-20)22-16(2)24/h3-10H,11-14H2,1-2H3,(H,21,23)(H,22,24)
Diamfenetide (aka diamphenethide) is a fasiolicide used in sheep. It is effective against immature flukes but with diminishing activity as the fluke ages. It has proven an effective compound for use in prophylactic programs against Fasciola hepatica. Diamphenethide is deacetylated in the host liver to an active monoamine and diamine. The amine of diamfenetide has an action
which produces an elevation of malate concentration
in Fasciola. Malate is an intermediary product of glucose in this parasite. It is known that dopamine, a putative
neurotransmitter in Fasciola has a protective effect
against diamfenetide but the mode of action of a
diamfenetide has yet to be defined in greater detail.
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: GO:0006006 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9309773 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Preventing | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
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Chemoprophylaxis with diamfenetide against experimental infections of Fasciola hepatica in ruminants. | 1980 Feb |
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Studies of the effect of diamphenethide and oxyclozanide on the metabolism of Fasciola hepatica. | 1981 Apr |
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Fasciola hepatica in vitro: increased susceptibility to fasciolicides in a defined serum-free medium. | 1987 Aug |
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Diamphenethide--a reassessment of its pharmacological action. | 1988 |
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Target sites of anthelmintics. | 1997 |
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/7369590
When given at a dosage of 10 mg/kg of body weight, diamfenetide was 87% effective in preventing the establishment of F hepatica infections in sheep that were given the drug daily for 14 days and it was 96% effective in sheep that were given the drug for 21 days. Infective cysts (4 doses of 150 each) were given by capsule at 2-day intervals during the first week of medication.
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/7242570
Adult liver flukes were collected from the common bile duct of freshly slaughtered rats 11 - 12 weeks after infection and transferred to Hedon-Fleig media at 37 deg-C. Immature liver flukes were harvested from the liver of rats 4-week post infection; the lier was finely chopped and incubated in Hedon-Fleig media at 37 deg-C. Two antibiotics, 0.006% w/v benzylpenicillin and 0.01% w/v streptomycin sulfate, were also added to the fluke cultures. Exposure of flukes to drug compounds was conducted aerobically at 37 deg-C. The active metabolite of diamphenethide is diamphenathide-amine which was determined to a have a minimum lethal dose of 2 micro-g/mL for 20 hours at 37 deg-C. However, newly excised flukes were more susceptible, disintegrating within 20 hours in 0.5 micro-g/mL. A dose and time-dependent relationship was established wherein adult flukes exposed to 25 micro-g/mL for less than 1 hour, 10 micro-g/ml for 2 h or 5 micro-g/ml for 3 h died after transfer to drug-free medium for a further 20 h. Immature flukes exposed to 2 micro-g/mL for 5 hours showed visible signs of deterioration but survived after transfer to drug-free medium.
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NCI_THESAURUS |
C250
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ACTIVE MOIETY