DFP

Inhibitor of cholinesterases and many serine hydrolases (not only alpha/beta hydrolases but also trypsin chymotrypsin etc.). DFP is a parasympathomimetic drug used in ophthalmology as a miotic agent in treatment of chronic glaucoma, as a miotic in veterinary medicine, and as an experimental agent in neuroscience because of its acetylcholinesterase inhibitory properties and ability to induce delayed peripheral neuropathy. DFP can phosphorylate other residues than active serine (tyrosine, lysine) see pdb 1TRN and Grigoryan et al. BChE appears to be about 100-200 times as sensitive as AChE to DFP and DFP was used to distinguish AChE and BChE before BW284C51 and Iso-OMPA were discovered. DFP is the oxygen analogue of Mipafox.(Structures of not alpha/beta hydrolases inhibited by DFP include: 4V08, 4H1D, 3VTA, 3TT7, 3TXT, 3MH5, 3MH6, 1RS0, 1CI9, 1DUI, 1AT3, 1SUE, 1DFP, 2TGD, 4PKA, 3LH3, 3GCN, 3GCO, 3GDS, 3GDU, 3GDV, 2RCE, 2Z2X, 1PPZ, 1GNV, 1A2Q, 5PTP)

General

Type : Organophosphate

Chemical_Nomenclature : Diisopropylphosphorofluoridate

Canonical SMILES : CC(C)OP(=O)(OC(C)C)F

InChI : InChI=1S\/C6H14FO3P\/c1-5(2)9-11(7,8)10-6(3)4\/h5-6H,1-4H3

InChIKey : MUCZHBLJLSDCSD-UHFFFAOYSA-N

Other name(s) : Diisopropylphosphorofluoridate  ||  Dyflos  ||  Diflupyl  ||  Floropyl  ||  isofluorophate  ||  Fluostigmine  ||  Isoflurophate  ||  Difluorophate  ||  Diflurphate  ||  Dyphlos  ||  isofluorphate  ||  Neoglaucit  ||  PF-3  ||  PF3  ||  T-1703  ||  TL 466


MW : 184.1

Formula : C6H14FO3P

CAS_number : 55-91-4

PubChem : 5936

UniChem : MUCZHBLJLSDCSD-UHFFFAOYSA-N

Wikipedia : Diisopropyl_fluorophosphate

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Title : The timing of channel opening during miniature endplate currents at the frog and mouse neuromuscular junctions: effects of fasciculin-2, other anti-cholinesterases and vesamicol - Van der Kloot_1994_Pflugers.Arch_428_114
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Ref : Pharmazie , 47 :68 , 1992
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Title : In vitro protection of acetylcholinesterase and butyrylcholinesterase by tetrahydroaminoacridine. Comparison with physostigmine - Galli_1992_Biochem.Pharmacol_43_2427
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Title : Hypothermia: limited tolerance to repeated soman administration and cross-tolerance to oxotremorine - Clement_1991_Pharmacol.Biochem.Behav_39_305
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Title : Inhibition of cholinesterases by DFP and induction of organophosphate-detoxicating enzymes in rats - Kaliste-Korhonen_1990_Gen.Pharmacol_21_527
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Title : Toxicity of an acute dose of agent VX and other organophosphorus esters in the chicken - Wilson_1988_J.Toxicol.Environ.Health_23_103
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Title : A peptidase activity exhibited by human serum pseudocholinesterase - Boopathy_1987_Eur.J.Biochem_162_191
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Title : Effects of the organophosphate cholinesterase inhibitor (DFP) on hypothalamic acetylcholinesterase and pituitary-adrenal activity -
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Title : Kinetic investigations into the interactions of aprophen with cholinesterases and a carboxylesterase - Rush_1986_Biochem.Pharmacol_35_4167
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Title : In-vitro and in-vivo protection of acetylcholinesterase by eseroline against inactivation by diisopropyl fluorophosphate and carbamates - Galli_1985_J.Pharm.Pharmacol_37_42
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Title : Polymorphism of pseudocholinesterase in Torpedo marmorata tissues: comparative study of the catalytic and molecular properties of this enzyme with acetylcholinesterase - Toutant_1985_J.Neurochem_44_580
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Title : Mechanisms involved in the development of tolerance to DFP toxicity - Gupta_1985_Fundam.Appl.Toxicol_5_S17
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Title : Differential effects of di-isopropylfluorophosphate poisoning and its treatment on opioid antinociception in the mouse - Kitchen_1983_Life.Sci_1_669
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Title : A radiometric study of cholinesterase and its inhibition -
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