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
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
| Molecular Formula | C4H8Cl3O4P |
| Molecular Weight | 257.437 |
| Charge | 0 |
| Count |
|
| Stereochemistry | RACEMIC |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 1 |
| E/Z Centers | 0 |
| Optical Activity | ( + / - ) |
DescriptionCurator's Comment: Description was created based on several sources including http://pmep.cce.cornell.edu/profiles/extoxnet/pyrethrins-ziram/trichlorfon-ext.html and http://onlinelibrary.wiley.com/doi/10.1111/j.1527-3458.1999.tb00083.x/pdf
Curator's Comment: Description was created based on several sources including http://pmep.cce.cornell.edu/profiles/extoxnet/pyrethrins-ziram/trichlorfon-ext.html and http://onlinelibrary.wiley.com/doi/10.1111/j.1527-3458.1999.tb00083.x/pdf
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).
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL3199 |
1.44 µM [IC50] | ||
Target ID: CHEMBL3403 |
0.22 µM [IC50] | ||
Target ID: CHEMBL220 |
525.0 µM [Ki] | ||
Target ID: CHEMBL1914 |
36.7 µM [Ki] |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Curative | Unknown Approved UseUnknown |
|||
| Primary | Unknown Approved UseUnknown |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Activity profiles of 309 ToxCast™ chemicals evaluated across 292 biochemical targets. | 2011-03-28 |
|
| Why so few drugs for Alzheimer's disease? Are methods failing drugs? | 2010-11 |
|
| Expression characteristics of potential biomarker genes in Tra catfish, Pangasianodon hypophthalmus, exposed to trichlorfon. | 2010-09 |
|
| Acetylcholinesterase biosensor based on Prussian blue-modified electrode for detecting organophosphorous pesticides. | 2010-08-15 |
|
| Impact of hookworm infection and deworming on anaemia in non-pregnant populations: a systematic review. | 2010-07 |
|
| Concurrent helminthic infection protects schoolchildren with Plasmodium vivax from anemia. | 2010-06-21 |
|
| Efficacy study of Prunus amygdalus (almond) nuts in scopolamine-induced amnesia in rats. | 2010-06 |
|
| Luminescent Mycena: new and noteworthy species. | 2010-04-06 |
|
| Immunohistological studies on neoplasms of female and male Onchocerca volvulus: filarial origin and absence of Wolbachia from tumor cells. | 2010-04 |
|
| Impact of environmental chemicals on key transcription regulators and correlation to toxicity end points within EPA's ToxCast program. | 2010-03-15 |
|
| Mass spectrometric analyses of organophosphate insecticide oxon protein adducts. | 2010-01 |
|
| Tunga penetrans: painful lesions on the feet-the first imported case from Guinea-bissau. | 2010 |
|
| Enzyme Inhibition by Molluscicidal Components of Myristica fragrans Houtt. in the Nervous Tissue of Snail Lymnaea acuminata. | 2010 |
|
| Treatment of urinary schistosomiasis: methodological issues and research needs identified through a Cochrane systematic review. | 2009-11 |
|
| Ultrasonographic screening of urinary schistosomiasis infected patients in Agulu community, Anambra state, southeast Nigeria. | 2009-10-28 |
|
| Trichlorfon induces apoptosis in SH-SY5Y neuroblastoma cells via the endoplasmic reticulum? | 2009-09-14 |
|
| In vitro reactivation of trichlorfon-inhibited butyrylcholinesterase using HI-6, obidoxime, pralidoxime and K048. | 2009-06 |
|
| Do antenatal parasite infections devalue childhood vaccination? | 2009-05-26 |
|
| In vivo 1H-magnetic resonance spectroscopy can detect metabolic changes in APP/PS1 mice after donepezil treatment. | 2009-04-07 |
|
| Have last-observation-carried-forward analyses caused us to favour more toxic dementia therapies over less toxic alternatives? A systematic review. | 2009-03-24 |
|
| Longitudinal multimodal imaging in mild to moderate Alzheimer disease: a pilot study with memantine. | 2008-12 |
|
| Improvement of acetylcholinesterase-based assay for organophosphates in way of identification by reactivators. | 2008-10-19 |
|
| Prize sessions. | 2008-10 |
|
| The effects of rivastigmine plus selegiline on brain acetylcholinesterase, (Na, K)-, Mg-ATPase activities, antioxidant status, and learning performance of aged rats. | 2008-08 |
|
| Drugs for treating urinary schistosomiasis. | 2008-07-16 |
|
| Effect of intermittent preventive treatment of malaria on health and education in schoolchildren: a cluster-randomised, double-blind, placebo-controlled trial. | 2008-07-12 |
|
| The synergistic effect of concomitant schistosomiasis, hookworm, and trichuris infections on children's anemia burden. | 2008-06-04 |
|
| Controlling schistosomiasis: significant decrease of anaemia prevalence one year after a single dose of praziquantel in Nigerian schoolchildren. | 2008-05-28 |
|
| Incident diabetes and pesticide exposure among licensed pesticide applicators: Agricultural Health Study, 1993-2003. | 2008-05-15 |
|
| Pharmacodynamics of memantine: an update. | 2008-03 |
|
| Effect of glabridin from Glycyrrhiza glabra on learning and memory in mice. | 2008-03 |
|
| Lysophospholipase from the human blood fluke, Schistosoma japonicum. | 2008-03 |
|
| Impact of cholinesterase inhibitors on behavioral and psychological symptoms of Alzheimer's disease: a meta-analysis. | 2008 |
|
| A comparative study on the relationship between various toxicological endpoints in Caenorhabditis elegans exposed to organophosphorus insecticides. | 2008 |
|
| Noncholinesterase effects induced by organophosphate pesticides and their relationship to cognitive processes: implication for the action of acylpeptide hydrolase. | 2007-12 |
|
| Effects of trichlorfon on malondialdehyde and antioxidant system in human erythrocytes. | 2007-12 |
|
| [Different therapeutic efficacy of pralidoxime chloride PAM-Cl on AChE against acute toxicity of methamidophos, dichlorvos and omethoate]. | 2007-10 |
|
| The effect of trichlorfon on acetylcholinesterase activity and histopathology of cultivated fish Oreochromis niloticus. | 2007-09 |
|
| Effects of trichlorfon on progesterone production in cultured human granulosa-lutein cells. | 2007-08 |
|
| Donepezil in Alzheimer's disease: From conventional trials to pharmacogenetics. | 2007-06 |
|
| The PDE4 inhibitor rolipram reverses object memory impairment induced by acute tryptophan depletion in the rat. | 2007-06 |
|
| Study on the mechanism of trichlorfon-induced inhibition of progesterone synthesis in mouse leydig tumor cells (MLTC-1). | 2007-05-05 |
|
| Schistosomiasis mansoni: novel chemotherapy using a cysteine protease inhibitor. | 2007-01 |
|
| Calcium-independent tacrine-induced relaxation of rat gastric corpus smooth muscles. | 2006-11 |
|
| Response from Savioli and colleagues from the Department of Neglected Tropical Diseases, World Health Organization. | 2006-06 |
|
| Metrifonate for Alzheimer's disease. | 2006-04-19 |
|
| Neuropsychiatric symptoms as a predictor of caregiver burden in Alzheimer's disease. | 2006-03 |
|
| Comparative brain cholinesterase-inhibiting activity of Glycyrrhiza glabra, Myristica fragrans, ascorbic acid, and metrifonate in mice. | 2006 |
|
| Inhibition-based determination of metrifonate in liquid and solid samples using the triple integration chemical hydrolysis-pervaporation-enzymic derivatisation. | 2001-01-26 |
|
| Pharmacokinetics of metrifonate and its rearrangement product dichlorvos in whole blood. | 1991-02 |
Sample Use Guides
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
| Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 23:21:25 GMT 2025
by
admin
on
Mon Mar 31 23:21:25 GMT 2025
|
| Record UNII |
37VCQ9C0OG
|
| Record Status |
Validated (UNII)
|
| Record Version |
|
-
Download
| Name | Type | Language | ||
|---|---|---|---|---|
|
Common Name | English | ||
|
Preferred Name | English | ||
|
Systematic Name | English | ||
|
Systematic Name | English |
| Code System | Code | Type | Description | ||
|---|---|---|---|---|---|
|
56042-26-3
Created by
admin on Mon Mar 31 23:21:25 GMT 2025 , Edited by admin on Mon Mar 31 23:21:25 GMT 2025
|
PRIMARY | |||
|
37VCQ9C0OG
Created by
admin on Mon Mar 31 23:21:25 GMT 2025 , Edited by admin on Mon Mar 31 23:21:25 GMT 2025
|
PRIMARY |
| Related Record | Type | Details | ||
|---|---|---|---|---|
|
|
RACEMATE -> ENANTIOMER |
