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M1845000

Metrifonate

European Pharmacopoeia (EP) Reference Standard

Synonym(s):

Trichlorfon, (2,2,2-Trichloro-1-hydroxyethyl)phosphonic acid dimethyl ester, Metrifonate

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About This Item

Empirical Formula (Hill Notation):
C4H8Cl3O4P
CAS Number:
52-68-6
Molecular Weight:
257.44
Beilstein:
1709434
MDL number:
MFCD00055272
UNSPSC Code:
41116107
PubChem Substance ID:
329817896
NACRES:
NA.24

grade

pharmaceutical primary standard

API family

trichlorfon, metrifonate

manufacturer/tradename

EDQM

application(s)

pharmaceutical (small molecule)

format

neat

storage temp.

2-8°C

SMILES string

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

InChI

1S/C4H8Cl3O4P/c1-10-12(9,11-2)3(8)4(5,6)7/h3,8H,1-2H3

InChI key

NFACJZMKEDPNKN-UHFFFAOYSA-N

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General description

This product is provided as delivered and specified by the issuing Pharmacopoeia. All information provided in support of this product, including SDS and any product information leaflets have been developed and issued under the Authority of the issuing Pharmacopoeia.For further information and support please go to the website of the issuing Pharmacopoeia.

Application

Metrifonate EP Reference standard, intended for use in laboratory tests only as specifically prescribed in the European Pharmacopoeia.

Packaging

The product is delivered as supplied by the issuing Pharmacopoeia. For the current unit quantity, please visit the EDQM reference substance catalogue.

Other Notes

Sales restrictions may apply.

Signal Word

Danger

Hazard Classifications

Acute Tox. 4 Dermal - Acute Tox. 4 Oral - Aquatic Acute 1 - Aquatic Chronic 1 - Resp. Sens. 1 - Skin Sens. 1

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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P N Tariot
The Journal of clinical psychiatry, 59 Suppl 9, 33-37 (1998-08-28)
Metrifonate, administered orally to patients with probable Alzheimer's disease in a once-daily dose, readily enters the brain and inhibits brain acetylcholinesterase (AChE) activity in a dose-dependent fashion. Metrifonate is a prodrug, converted non-enzymatically to 2,2-dichlorovinyl dimethyl phosphate, a long-acting inhibitor
H Feldmeier et al.
Acta tropica, 44(3), 357-368 (1987-09-01)
Metrifonate is an excellent drug for the treatment of urinary schistosomiasis in areas with S. haematobium monoinfection. Toxicity apparently is negligible. Side effects due to the inhibition of acetylcholinesterase are usually scarce, light and transient in nature. At the recommended
B R Williams
American journal of health-system pharmacy : AJHP : official journal of the American Society of Health-System Pharmacists, 56(5), 427-432 (1999-03-30)
The pharmacology, pharmacokinetics, clinical efficacy, and adverse effects of metrifonate, a long-acting cholinesterase inhibitor, are discussed. Attempts to correct the central cholinergic deficits associated with Alzheimer's disease have included administration of cholinergic precursors, cholinergic agonists, and cholinesterase inhibitors. To date
J L Cummings
Pharmacotherapy, 18(2 Pt 2), 43-46 (1998-04-16)
Metrifonate is a cholinesterase inhibitor with a long-lasting inhibition that raises brain acetylcholine levels. It is well-absorbed and has limited binding to serum proteins. In preliminary studies of its utility in the treatment of Alzheimer disease's (AD), it led to
J M López-Arrieta et al.
The Cochrane database of systematic reviews, (2)(2), CD003155-CD003155 (2006-04-21)
Metrifonate is a long-acting irreversible cholinesterase inhibitor, originally used to treat schistosomiasis. Its potential to enhance central nervous system cholinergic neurotransmission led to clinical trials for the treatment of people with Alzheimer's disease (AD). Although low incidence of serious side
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