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
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 |
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| Hepatotoxicity of trichlorfon and dichlorvos in isolated rat hepatocytes. | 1992 Nov 22 |
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| Inhibition-based determination of metrifonate in liquid and solid samples using the triple integration chemical hydrolysis-pervaporation-enzymic derivatisation. | 2001 Jan 26 |
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| Topical treatment of tungiasis: a randomized, controlled trial. | 2003 Oct |
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| Mapping and sequencing of acetylcholinesterase genes from the platyhelminth blood fluke Schistosoma. | 2003 Sep 18 |
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| Direct analysis of the kinetic profiles of organophosphate-acetylcholinesterase adducts by MALDI-TOF mass spectrometry. | 2003 Sep 23 |
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| Cholinesterase inhibitors modify the activity of intrinsic cardiac neurons. | 2004 Aug |
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| Systematic review of cholinergic drugs for neuroleptic-induced tardive dyskinesia: a meta-analysis of randomized controlled trials. | 2004 Nov |
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| [Relationship between acute dipterex poisoning and oxidative stress and free radical damage]. | 2004 Nov |
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| Patterns of Schistosoma haematobium infection, impact of praziquantel treatment and re-infection after treatment in a cohort of schoolchildren from rural KwaZulu-Natal/South Africa. | 2004 Oct 7 |
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| Serine hydrolase targets of organophosphorus toxicants. | 2005 Dec 15 |
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| Dissociable effects of acetylcholinesterase inhibitors and phosphodiesterase type 5 inhibitors on object recognition memory: acquisition versus consolidation. | 2005 Feb |
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| Effects of the cholinesterase inhibitors donepezil and metrifonate on scopolamine-induced impairments in the spatial cone field orientation task in rats. | 2005 Jan 6 |
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| Metrifonate for Alzheimer's disease. | 2006 Apr 19 |
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| Response from Savioli and colleagues from the Department of Neglected Tropical Diseases, World Health Organization. | 2006 Jun |
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| Neuropsychiatric symptoms as a predictor of caregiver burden in Alzheimer's disease. | 2006 Mar |
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| Pharmacological and molecular enhancement of learning in aging and Alzheimer's disease. | 2006 Mar-May |
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| Calcium-independent tacrine-induced relaxation of rat gastric corpus smooth muscles. | 2006 Nov |
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| Comparative brain cholinesterase-inhibiting activity of Glycyrrhiza glabra, Myristica fragrans, ascorbic acid, and metrifonate in mice. | 2006 Summer |
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| Effects of trichlorfon on progesterone production in cultured human granulosa-lutein cells. | 2007 Aug |
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| Noncholinesterase effects induced by organophosphate pesticides and their relationship to cognitive processes: implication for the action of acylpeptide hydrolase. | 2007 Dec |
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| Effects of trichlorfon on malondialdehyde and antioxidant system in human erythrocytes. | 2007 Dec |
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| 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 |
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| [Different therapeutic efficacy of pralidoxime chloride PAM-Cl on AChE against acute toxicity of methamidophos, dichlorvos and omethoate]. | 2007 Oct |
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| A comparative study on the relationship between various toxicological endpoints in Caenorhabditis elegans exposed to organophosphorus insecticides. | 2008 |
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| The effects of rivastigmine plus selegiline on brain acetylcholinesterase, (Na, K)-, Mg-ATPase activities, antioxidant status, and learning performance of aged rats. | 2008 Aug |
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| Longitudinal multimodal imaging in mild to moderate Alzheimer disease: a pilot study with memantine. | 2008 Dec |
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| Effect of intermittent preventive treatment of malaria on health and education in schoolchildren: a cluster-randomised, double-blind, placebo-controlled trial. | 2008 Jul 12 |
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| The synergistic effect of concomitant schistosomiasis, hookworm, and trichuris infections on children's anemia burden. | 2008 Jun 4 |
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| Pharmacodynamics of memantine: an update. | 2008 Mar |
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| Effect of glabridin from Glycyrrhiza glabra on learning and memory in mice. | 2008 Mar |
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| Incident diabetes and pesticide exposure among licensed pesticide applicators: Agricultural Health Study, 1993-2003. | 2008 May 15 |
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| Controlling schistosomiasis: significant decrease of anaemia prevalence one year after a single dose of praziquantel in Nigerian schoolchildren. | 2008 May 28 |
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| Prize sessions. | 2008 Oct |
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| 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 |
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| Treatment of urinary schistosomiasis: methodological issues and research needs identified through a Cochrane systematic review. | 2009 Nov |
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| Trichlorfon induces apoptosis in SH-SY5Y neuroblastoma cells via the endoplasmic reticulum? | 2009 Sep 14 |
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| Tunga penetrans: painful lesions on the feet-the first imported case from Guinea-bissau. | 2010 |
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| Enzyme Inhibition by Molluscicidal Components of Myristica fragrans Houtt. in the Nervous Tissue of Snail Lymnaea acuminata. | 2010 |
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| Immunohistological studies on neoplasms of female and male Onchocerca volvulus: filarial origin and absence of Wolbachia from tumor cells. | 2010 Apr |
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| Acetylcholinesterase biosensor based on Prussian blue-modified electrode for detecting organophosphorous pesticides. | 2010 Aug 15 |
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| Impact of hookworm infection and deworming on anaemia in non-pregnant populations: a systematic review. | 2010 Jul |
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| Efficacy study of Prunus amygdalus (almond) nuts in scopolamine-induced amnesia in rats. | 2010 Jun |
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| Concurrent helminthic infection protects schoolchildren with Plasmodium vivax from anemia. | 2010 Jun 21 |
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| Luminescent Mycena: new and noteworthy species. | 2010 Mar-Apr |
|
| Why so few drugs for Alzheimer's disease? Are methods failing drugs? | 2010 Nov |
|
| 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
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56042-26-3
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37VCQ9C0OG
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5853
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SUBSTANCE RECORD
