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 |
|---|---|---|
| Pharmacokinetics of metrifonate and its rearrangement product dichlorvos in whole blood. | 1991 Feb |
|
| Inhibition-based determination of metrifonate in liquid and solid samples using the triple integration chemical hydrolysis-pervaporation-enzymic derivatisation. | 2001 Jan 26 |
|
| Metrifonate for Alzheimer's disease. | 2006 Apr 19 |
|
| Response from Savioli and colleagues from the Department of Neglected Tropical Diseases, World Health Organization. | 2006 Jun |
|
| Neuropsychiatric symptoms as a predictor of caregiver burden in Alzheimer's disease. | 2006 Mar |
|
| Calcium-independent tacrine-induced relaxation of rat gastric corpus smooth muscles. | 2006 Nov |
|
| Comparative brain cholinesterase-inhibiting activity of Glycyrrhiza glabra, Myristica fragrans, ascorbic acid, and metrifonate in mice. | 2006 Summer |
|
| Effects of trichlorfon on progesterone production in cultured human granulosa-lutein cells. | 2007 Aug |
|
| Noncholinesterase effects induced by organophosphate pesticides and their relationship to cognitive processes: implication for the action of acylpeptide hydrolase. | 2007 Dec |
|
| Effects of trichlorfon on malondialdehyde and antioxidant system in human erythrocytes. | 2007 Dec |
|
| Schistosomiasis mansoni: novel chemotherapy using a cysteine protease inhibitor. | 2007 Jan |
|
| Donepezil in Alzheimer's disease: From conventional trials to pharmacogenetics. | 2007 Jun |
|
| The PDE4 inhibitor rolipram reverses object memory impairment induced by acute tryptophan depletion in the rat. | 2007 Jun |
|
| Study on the mechanism of trichlorfon-induced inhibition of progesterone synthesis in mouse leydig tumor cells (MLTC-1). | 2007 May 5 |
|
| [Different therapeutic efficacy of pralidoxime chloride PAM-Cl on AChE against acute toxicity of methamidophos, dichlorvos and omethoate]. | 2007 Oct |
|
| The effect of trichlorfon on acetylcholinesterase activity and histopathology of cultivated fish Oreochromis niloticus. | 2007 Sep |
|
| 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 |
|
| The effects of rivastigmine plus selegiline on brain acetylcholinesterase, (Na, K)-, Mg-ATPase activities, antioxidant status, and learning performance of aged rats. | 2008 Aug |
|
| Longitudinal multimodal imaging in mild to moderate Alzheimer disease: a pilot study with memantine. | 2008 Dec |
|
| Effect of intermittent preventive treatment of malaria on health and education in schoolchildren: a cluster-randomised, double-blind, placebo-controlled trial. | 2008 Jul 12 |
|
| Drugs for treating urinary schistosomiasis. | 2008 Jul 16 |
|
| The synergistic effect of concomitant schistosomiasis, hookworm, and trichuris infections on children's anemia burden. | 2008 Jun 4 |
|
| Pharmacodynamics of memantine: an update. | 2008 Mar |
|
| Effect of glabridin from Glycyrrhiza glabra on learning and memory in mice. | 2008 Mar |
|
| Lysophospholipase from the human blood fluke, Schistosoma japonicum. | 2008 Mar |
|
| Incident diabetes and pesticide exposure among licensed pesticide applicators: Agricultural Health Study, 1993-2003. | 2008 May 15 |
|
| Controlling schistosomiasis: significant decrease of anaemia prevalence one year after a single dose of praziquantel in Nigerian schoolchildren. | 2008 May 28 |
|
| Prize sessions. | 2008 Oct |
|
| Improvement of acetylcholinesterase-based assay for organophosphates in way of identification by reactivators. | 2008 Oct 19 |
|
| In vivo 1H-magnetic resonance spectroscopy can detect metabolic changes in APP/PS1 mice after donepezil treatment. | 2009 Apr 7 |
|
| In vitro reactivation of trichlorfon-inhibited butyrylcholinesterase using HI-6, obidoxime, pralidoxime and K048. | 2009 Jun |
|
| Have last-observation-carried-forward analyses caused us to favour more toxic dementia therapies over less toxic alternatives? A systematic review. | 2009 Mar 24 |
|
| Do antenatal parasite infections devalue childhood vaccination? | 2009 May 26 |
|
| Treatment of urinary schistosomiasis: methodological issues and research needs identified through a Cochrane systematic review. | 2009 Nov |
|
| Ultrasonographic screening of urinary schistosomiasis infected patients in Agulu community, Anambra state, southeast Nigeria. | 2009 Oct 28 |
|
| Trichlorfon induces apoptosis in SH-SY5Y neuroblastoma cells via the endoplasmic reticulum? | 2009 Sep 14 |
|
| 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 |
|
| Immunohistological studies on neoplasms of female and male Onchocerca volvulus: filarial origin and absence of Wolbachia from tumor cells. | 2010 Apr |
|
| Acetylcholinesterase biosensor based on Prussian blue-modified electrode for detecting organophosphorous pesticides. | 2010 Aug 15 |
|
| Mass spectrometric analyses of organophosphate insecticide oxon protein adducts. | 2010 Jan |
|
| Impact of hookworm infection and deworming on anaemia in non-pregnant populations: a systematic review. | 2010 Jul |
|
| Efficacy study of Prunus amygdalus (almond) nuts in scopolamine-induced amnesia in rats. | 2010 Jun |
|
| Concurrent helminthic infection protects schoolchildren with Plasmodium vivax from anemia. | 2010 Jun 21 |
|
| Impact of environmental chemicals on key transcription regulators and correlation to toxicity end points within EPA's ToxCast program. | 2010 Mar 15 |
|
| Luminescent Mycena: new and noteworthy species. | 2010 Mar-Apr |
|
| Why so few drugs for Alzheimer's disease? Are methods failing drugs? | 2010 Nov |
|
| Expression characteristics of potential biomarker genes in Tra catfish, Pangasianodon hypophthalmus, exposed to trichlorfon. | 2010 Sep |
|
| Activity profiles of 309 ToxCast™ chemicals evaluated across 292 biochemical targets. | 2011 Mar 28 |
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
Sat Dec 16 10:37:03 GMT 2023
by
admin
on
Sat Dec 16 10:37:03 GMT 2023
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| Record UNII |
37VCQ9C0OG
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| Record Status |
Validated (UNII)
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| Record Version |
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37VCQ9C0OG
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RACEMATE -> ENANTIOMER |
