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 : 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 : Repeated exposure to diisopropylfluorophosphate (DFP) produces increased sensitivity to cholinergic antagonists in discrimination retention and reversal - Raffaele_1990_Psychopharmacology_100_267
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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 : Kinetic investigations into the interactions of aprophen with cholinesterases and a carboxylesterase - Rush_1986_Biochem.Pharmacol_35_4167
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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 : 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 : Brain cholinesterases. Differentiation of target enzymes for toxic organophosphorus compounds - Chemnitius_1983_Biochem.Pharmacol_32_1693
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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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