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Details

Stereochemistry UNKNOWN
Molecular Formula C4H8Cl3O4P
Molecular Weight 257.437
Optical Activity ( + )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of METRIFONATE, (+)-

SMILES

COP(=O)(OC)C(O)C(Cl)(Cl)Cl

InChI

InChIKey=NFACJZMKEDPNKN-UHFFFAOYSA-N
InChI=1S/C4H8Cl3O4P/c1-10-12(9,11-2)3(8)4(5,6)7/h3,8H,1-2H3

HIDE SMILES / InChI

Molecular Formula C4H8Cl3O4P
Molecular Weight 257.437
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

Description

Trichlorfon (Metrifonate), the organophosphorous cholinesterase inhibitor, O,O-dimethylhydroxy-2,2,2-trichlorethyl-phosphonate, has been used sporadically in the treatment of human schistosomiasis for a decade. It has selective and variable schistosomicidal activity against S. haematobium that results from its partial metabolism to a highly active anti-cholinesterase, dichlorvos. Schistosomal cholinesterase is more susceptible to this metabolite than that of the human host, but transient reductions in both plasma and erythrocyte cholinesterase activity are demonstrable at therapeutic dosage. However, despite early concerns about its potential toxicity, metrifonate is well tolerated and has been used effectively and extensively in large-scale control programmes. Its potential to enhance central nervous system cholinergic neurotransmission led to clinical trials for the treatment of people with Alzheimer's disease (AD).

CNS Activity

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
1.44 µM [IC50]
0.22 µM [IC50]
525.0 µM [Ki]
36.7 µM [Ki]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
Unknown
Primary
Unknown

PubMed

Sample Use Guides

In Vivo Use Guide
Treatment of urinary schistosomiasis: Adults and children: a dose of 7.5-10 mg/kg on three occasions at intervals of 2 weeks will cure 40-80% of cases. Even when viable worms remain, egg counts after one year are reduced to less than 20% of pre-treatment levels.
Route of Administration: Oral
In Vitro Use Guide
100 ug/ml trichlorfon added at the time of hormonally stimulated resumption of meiosis of follicle cell-enclosed mouse oocytes, 16 h before in vitro ovulation, induced significant rises in first meiotic nondisjunction in oocytes from preantral follicle culture.
Substance Class Chemical
Record UNII
1MVY4KU98F
Record Status Validated (UNII)
Record Version