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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
Structure of DIAMFENETIDE

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)

HIDE SMILES / InChI
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.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Preventing
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Chemoprophylaxis with diamfenetide against experimental infections of Fasciola hepatica in ruminants.
1980 Feb
Studies of the effect of diamphenethide and oxyclozanide on the metabolism of Fasciola hepatica.
1981 Apr
Fasciola hepatica in vitro: increased susceptibility to fasciolicides in a defined serum-free medium.
1987 Aug
Diamphenethide--a reassessment of its pharmacological action.
1988
Target sites of anthelmintics.
1997
Patents

Sample Use Guides

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
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.
Name Type Language
DIAMFENETIDE
INN   MART.   MI  
INN  
Official Name English
NSC-291838
Code English
DIAMPHENETHIDE
Common Name English
DIAMFENETIDE [MART.]
Common Name English
COMPOUND-68-198
Code English
COMPOUND 68-198
Code English
.BETA.,.BETA.'-OXYBIS(P-ACETOPHENETIDIDE)
Common Name English
diamfenetide [INN]
Common Name English
DIAMFENETIDE [MI]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C250
Created by admin on Sat Dec 16 16:56:31 GMT 2023 , Edited by admin on Sat Dec 16 16:56:31 GMT 2023
Code System Code Type Description
NSC
291838
Created by admin on Sat Dec 16 16:56:31 GMT 2023 , Edited by admin on Sat Dec 16 16:56:31 GMT 2023
PRIMARY
EPA CompTox
DTXSID5046229
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PUBCHEM
37384
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NCI_THESAURUS
C78090
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SMS_ID
100000082903
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MERCK INDEX
m1109
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PRIMARY Merck Index
ChEMBL
CHEMBL2104259
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INN
3235
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ECHA (EC/EINECS)
252-886-5
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EVMPD
SUB07063MIG
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FDA UNII
U4TFJ7GB6T
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CAS
36141-82-9
Created by admin on Sat Dec 16 16:56:31 GMT 2023 , Edited by admin on Sat Dec 16 16:56:31 GMT 2023
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