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Details

Stereochemistry ACHIRAL
Molecular Formula C6H14FO3P
Molecular Weight 184.146
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ISOFLUROPHATE

SMILES

CC(C)OP(=O)(F)OC(C)C

InChI

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

HIDE SMILES / InChI
Isofluorophate (diisopropyl fluorophosphate) is an irreversile acetylcholinesterase inhibitor. It was used in ophthalmology as a miotic agent in treatment of chronic glaucoma.

Originator

Curator's Comment:: On Dec. 11th, 1941, Bernard Charles Saunders, University of Cambridge, UK, reported at a Ministry of Supply meeting in London the highly toxic nature of an ester of monofluorophosphoric acid, diisopropyl fluorophosphate (DFP), as a lethal inhalant.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
6 µM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
FLOROPRYL

Approved Use

Isoflurophate is used as ocular drops in the treatment of chronic glaucoma. Isoflurophate is an organophosphorus compound that acts as an irreversible cholinesterase inhibitor. As such, it displays parasympathomimetic effects. Isoflurophate is used in the eye to treat certain types of glaucoma and other eye conditions, such as accommodative esotropia. They may also be used in the diagnosis of certain eye conditions, such as accommodative esotropia. Isoflurophate damages the acetylcholinesterase enzyme and is therefore irreversible, however, pralidoxime can displace organophosphates such as isoflurophate from acetylcholinesterase, but only if administered before isoflurophate damages (alkylates) the enzyme.

Launch Date

-402364800000
PubMed

PubMed

TitleDatePubMed
Granzymes: a family of lymphocyte granule serine proteases.
2001
Carboxylesterase: specificity and spontaneous reactivation of an endogenous scavenger for organophosphorus compounds.
2001 Dec
Organophosphorus compounds alter intracellular F-actin content in SH-SY5Y human neuroblastoma cells.
2001 Dec
Eptastigmine: ten years of pharmacology, toxicology, pharmacokinetic, and clinical studies.
2001 Winter
Differential alteration of glyceraldehyde-3-phosphate dehydrogenase (GAPDH) mRNA in the central nervous system of hens treated with diisopropylphosphorofluoridate (DFP).
2002 Apr
Presence of a mobilizable intracellular pool of hepatocyte growth factor in human polymorphonuclear neutrophils.
2002 Apr 15
Analysis of organophosphorus compound adducts of serine proteases by liquid chromatography-tandem mass spectrometry.
2002 Aug 25
Involvement of nitric oxide in myotoxicity produced by diisopropylphosphorofluoridate (DFP)-induced muscle hyperactivity.
2002 Dec
Deacylation of N-arylformamides and N-arylacetamides by formamidase in rat liver.
2002 Dec
A butyrylcholinesterase in the early development of the brine shrimp (Artemia salina) larvae: a target for phthalate ester embryotoxicity?
2002 Dec 13
Rapid assessment of organophosphorous/carbamate exposure in the bivalve mollusc Mytilus edulis using combined esterase activities as biomarkers.
2002 Dec 3
An antibody that binds to primary specific pocket-associated structure in the active site of bovine thrombin.
2002 Feb
Ionomycin-induced neutrophil NADPH oxidase activity is selectively inhibited by the serine protease inhibitor diisopropyl fluorophosphate.
2002 Feb
Characterization of the residues involved in the human alpha-thrombin-haemadin complex: an exosite II-binding inhibitor.
2002 Feb 26
Purification and some properties of a keratinolytic enzyme from an alkaliphilic Nocardiopsis sp. TOA-1.
2002 Jan
Effect of meconium on the rate of in vitro subtype conversion of swine pulmonary surfactant.
2002 Jan
Different expressions of organophosphate-resistant acetylcholinesterases in the bivalve mollusk Scapharca inaequivalvis living in three different habitats.
2002 Jan
Lecithin: cholesterol acyltransferase is insufficient to prevent oxidative modification of low-density lipoprotein.
2002 Jan
Protein levels of neurofilament subunits in the hen central nervous system following prevention and potentiation of diisopropyl phosphorofluoridate (DFP)-induced delayed neurotoxicity(1).
2002 Jan 1
Characterization and molecular cloning of a glutamyl endopeptidase from Staphylococcus epidermidis.
2002 Jul
Radiosynthesis and mouse brain distribution studies of [11C] CP-126,998: a PET ligand for in vivo study of acetylcholinesterase.
2002 Jul
Purification and characterization of an esterase from Acinetobacter lwoffii I6C-1.
2002 Jun
Covalent reactivity of phosphonate monophenyl esters with serine proteinases: an overlooked feature of presumed transition state analogs.
2002 Jun 15
Early differential elevation and persistence of phosphorylated cAMP-response element binding protein (p-CREB) in the central nervous system of hens treated with diisopropyl phosphorofluoridate, an OPIDN-causing compound.
2002 Mar
Functional proteomics using microchannel plate detectors.
2002 Mar
EstB from Burkholderia gladioli: a novel esterase with a beta-lactamase fold reveals steric factors to discriminate between esterolytic and beta-lactam cleaving activity.
2002 Mar
Dipeptidyl peptidase with strict substrate specificity of an anaerobic periodontopathogen Porphyromonas gingivalis.
2002 Mar 19
Purification and characterization of a collagenolytic protease from the filefish, Novoden modestrus.
2002 Mar 31
[Amylases of the fungus Aspergillus flavipes associated with Fucus evanescens].
2002 Mar-Apr
Sulfur mustard-stimulated protease: a target for antivesicant drugs.
2002 Mar-Apr
Degradation of glyceraldehyde-3-phosphate dehydrogenase induced by acetylleucine chloromethyl ketone in U937 cells.
2002 May 15
Kinetic analysis of a unique direct prothrombinase, fgl2, and identification of a serine residue critical for the prothrombinase activity.
2002 May 15
Identification and characterization of prolylcarboxypeptidase as an endothelial cell prekallikrein activator.
2002 May 17
Rat mast cell protease 4 is a beta-chymase with unusually stringent substrate recognition profile.
2002 May 24
Production of interleukin-1 activity of Kupffer cells from mice treated with the acidic mannan fraction of baker's yeast.
2002 Nov
Characterization of the receptor-destroying enzyme activity from infectious salmon anaemia virus.
2002 Nov
A mechanism-based probe for gp120-Hydrolyzing antibodies.
2002 Nov 4
Atomic resolution crystal structure of squid ganglion DFPase.
2002 Oct
Behavioral characteristics of rat lines selected for differential hypothermic responses to cholinergic or serotonergic agonists.
2002 Sep
Identification of two cysteine residues involved in the binding of UDP-GalNAc to UDP-GalNAc:polypeptide N-acetylgalactosaminyltransferase 1 (GalNAc-T1).
2002 Sep
High-activity enzyme-polyurethane coatings.
2002 Sep 30
Gulf War related exposure factors influencing topical absorption of 14C-permethrin.
2002 Sep 5
Purification and characterization of PrbA, a new esterase from Enterobacter cloacae hydrolyzing the esters of 4-hydroxybenzoic acid (parabens).
2003 Apr 11
AMPA receptor potentiation by acetylcholinesterase is age-dependently upregulated at synaptogenesis sites of the rat brain.
2003 Feb
Influence of gender on thermoregulation and cholinesterase inhibition in the long-evans rat exposed to diazinon.
2003 Feb 14
Structural and enzymatic characterization of physarolisin (formerly physaropepsin) proves that it is a unique serine-carboxyl proteinase.
2003 Feb 21
Chlorophyllase as a serine hydrolase: identification of a putative catalytic triad.
2003 Jan
Protease-activated receptor mediated RhoA signaling and cytoskeletal reorganization in LNCaP cells.
2003 Jan 28
Lesions of rat skeletal muscle after local block of acetylcholinesterase and neuromuscular stimulation.
2003 Jun
The cholinesterase inhibitor DFP facilitates the expression of paradoxical sleep (PS) propensity in rats subjected to short-term PS deprivation.
2003 Mar 7
Patents

Sample Use Guides

Topical, to the conjunctiva, a thin strip (approximately 0.5 cm) of a 0.025% ointment once every three days to three times a day.
Route of Administration: Topical
Recombinant AChE was quantitated using the extinction coefficient 119, 650 M-1 cm-1 calculated from its amino acid sequence. AChE (34 nM) was assayed using Ellman’s reagent using 160 uM acetylthiocholine and 300 uM 5,50-dithiobis-2-ntirobenzoic acid (DTNB). Thiocholine released by the enzyme reacts with excess DTNB, resulting in the formation of the thionitrobenzoate anion, which absorbs at 412 nm. To assess IC50, the inhibitors were solubilized in isopropanol and used in volumes of less than 5% of the total reaction volume. AChE (34 nM) was incubated for 30 min with each compound at an array of concentrations. The residual activity of the enzyme was assayed using 500 uM acetylthiocholine, a saturating concentration 10-fold higher than the Km of 46 uM for this substrate.
Name Type Language
ISOFLUROPHATE
HSDB   MI   ORANGE BOOK   USP   VANDF   WHO-DD  
Common Name English
DYFLOS
MART.  
Common Name English
DYFLOS [MART.]
Common Name English
ISOFLUROPHATE [WHO-DD]
Common Name English
PHOSPHOROFLUORIDIC ACID, BIS(1-METHYLETHYL) ESTER
Common Name English
ISOFLUROPHATE [HSDB]
Common Name English
NSC-727370
Code English
FLOROPRYL
Brand Name English
ISOFLUROPHATE [VANDF]
Common Name English
DI-ISOPROPYL FLUOROPHOSPHATE
Systematic Name English
ISOFLUROPHATE [ORANGE BOOK]
Common Name English
DIISOPROPYL PHOSPHOROFLUORIDATE
Systematic Name English
ISOFLUROPHATE [USP]
Common Name English
ISOFLUROPHATE [MI]
Common Name English
FLUOSTIGMINE
Common Name English
DIISOPROPYL FLUOROPHOSPHATE
Systematic Name English
Classification Tree Code System Code
NCI_THESAURUS C47792
Created by admin on Fri Jun 25 21:53:45 UTC 2021 , Edited by admin on Fri Jun 25 21:53:45 UTC 2021
EPA PESTICIDE CODE 356100
Created by admin on Fri Jun 25 21:53:45 UTC 2021 , Edited by admin on Fri Jun 25 21:53:45 UTC 2021
WHO-ATC S01EB07
Created by admin on Fri Jun 25 21:53:45 UTC 2021 , Edited by admin on Fri Jun 25 21:53:45 UTC 2021
Code System Code Type Description
EPA CompTox
55-91-4
Created by admin on Fri Jun 25 21:53:45 UTC 2021 , Edited by admin on Fri Jun 25 21:53:45 UTC 2021
PRIMARY
CAS
55-91-4
Created by admin on Fri Jun 25 21:53:45 UTC 2021 , Edited by admin on Fri Jun 25 21:53:45 UTC 2021
PRIMARY
ChEMBL
CHEMBL1025
Created by admin on Fri Jun 25 21:53:45 UTC 2021 , Edited by admin on Fri Jun 25 21:53:45 UTC 2021
PRIMARY
WIKIPEDIA
DIISOPROPYL FLUOROPHOSPHATE
Created by admin on Fri Jun 25 21:53:45 UTC 2021 , Edited by admin on Fri Jun 25 21:53:45 UTC 2021
PRIMARY
DRUG CENTRAL
1494
Created by admin on Fri Jun 25 21:53:45 UTC 2021 , Edited by admin on Fri Jun 25 21:53:45 UTC 2021
PRIMARY
FDA UNII
12UHW9R67N
Created by admin on Fri Jun 25 21:53:45 UTC 2021 , Edited by admin on Fri Jun 25 21:53:45 UTC 2021
PRIMARY
RXCUI
6027
Created by admin on Fri Jun 25 21:53:45 UTC 2021 , Edited by admin on Fri Jun 25 21:53:45 UTC 2021
PRIMARY RxNorm
DRUG BANK
DB00677
Created by admin on Fri Jun 25 21:53:45 UTC 2021 , Edited by admin on Fri Jun 25 21:53:45 UTC 2021
PRIMARY
ECHA (EC/EINECS)
200-247-6
Created by admin on Fri Jun 25 21:53:45 UTC 2021 , Edited by admin on Fri Jun 25 21:53:45 UTC 2021
PRIMARY
MERCK INDEX
M6492
Created by admin on Fri Jun 25 21:53:45 UTC 2021 , Edited by admin on Fri Jun 25 21:53:45 UTC 2021
PRIMARY Merck Index
MESH
D007531
Created by admin on Fri Jun 25 21:53:45 UTC 2021 , Edited by admin on Fri Jun 25 21:53:45 UTC 2021
PRIMARY
EVMPD
SUB14274MIG
Created by admin on Fri Jun 25 21:53:45 UTC 2021 , Edited by admin on Fri Jun 25 21:53:45 UTC 2021
PRIMARY
HSDB
2133
Created by admin on Fri Jun 25 21:53:45 UTC 2021 , Edited by admin on Fri Jun 25 21:53:45 UTC 2021
PRIMARY
PUBCHEM
5936
Created by admin on Fri Jun 25 21:53:45 UTC 2021 , Edited by admin on Fri Jun 25 21:53:45 UTC 2021
PRIMARY
NCI_THESAURUS
C65979
Created by admin on Fri Jun 25 21:53:45 UTC 2021 , Edited by admin on Fri Jun 25 21:53:45 UTC 2021
PRIMARY