CBDP

cyclic metabolite of tri-o-cresyl phosphate; synergist for cholinesterase inhibitor, carboxylesterase inhibitor, close to phenylsaligenin cyclic phosphate. Saligenin cyclic o-tolyl phosphate (SCOTP) has been proposed as the active metabolite of tri-o-cresyl phosphate (TOCP), a neurotoxic organophosphate. TRI-O-CRESYL PHOSPHATE (TOCP) is metabolized in vitro and in vivo to form potent esterase inhibitors. CBDP and Phenyl-OBDP are potent NTE inhibitors. TRI-O-CBESYL PHOSPHATE (TOCP) is metabolized in vitro and in vivo to form potent esterase inhibitors. CBDP and Phenyl-BDPO are potent NTE inhibitors

General

Type : Organophosphate, Cyclic OP, NTE inhibitor, Not A\/B H target

Chemical_Nomenclature : 2-(2-methylphenoxy)-4H-1,3,2$l^{5}-benzodioxaphosphinine 2-oxide

Canonical SMILES : CC1=CC=CC=C1OP2(=O)OCC3=CC=CC=C3O2

InChI : InChI=1S\/C14H13O4P\/c1-11-6-2-4-8-13(11)17-19(15)16-10-12-7-3-5-9-14(12)18-19\/h2-9H,10H2,1H3

InChIKey : LKQSEFCGKYFESN-UHFFFAOYSA-N

Other name(s) : BRN 2538084  ||  2-(o-Cresyl)-4H-1,3,2-benzodioxaphoran-2-one  ||  2-(2-Cresyl)-4H-1-3-2-benzodioxaphosphorin-2-oxide  ||  4H-1,3,2-Benzodioxaphosphorin, 2-(o-tolyloxy)-, 2-oxide  ||  4H-1,3,2-Benzodioxaphosphorin, 2-(2-methylphenoxy)-, 2-oxide  ||  2-(o-cresyl)-4H-1,3,2-benzodioxaphosphoran-2-one  ||  2-(2-cresyl)-4H-1,3,2-benzodioxaphosphorin-2-oxide  ||  LS-107599  ||  2-tolylsaligenin phosphate  ||  cresylsaligenyl phosphate  ||  cresylsaligenin phosphate  ||  2-TSLPH  ||  o-TSP  ||  saligenin cyclic-3-tolylphosphate  ||  SCOTP  ||  0-tosylsaligenin phosphate  ||  2-(o-cresyl)-4H-1-3-2-benzodioxaphosphorin-2-oxide  ||  C000516  ||  2-(o-cresyl)-4H-1:3:2-benzodioxaphosphorin-2-oxide


MW : 276

Formula : C14H13O4P

CAS_number : 1222-87-3

PubChem : 104993

UniChem : LKQSEFCGKYFESN-UHFFFAOYSA-N

Target

Families : CBDP ligand of proteins in family
ACHE BCHE Carb_B_Chordata

Structure :
2Y1K 4BBZ 4BC0 4BC1

Protein :
human-BCHE mouse-ACHE

References (42)

Title : Inhibition kinetics of acetylcholinesterase and butyrylcholinesterase from various species by 2-(2-cresyl)-4H-1,3,2-benzodioxaphosphorin-2-oxide (CBDP) - Horn_2024_Toxicol.Lett_396_28
Author(s) : Horn G , Rappengluck S , Worek F
Ref : Toxicol Lett , 396 :28 , 2024
Abstract :
PubMedSearch : Horn_2024_Toxicol.Lett_396_28
PubMedID: 38642675

Title : 1-(3-Tert-Butylphenyl)-2,2,2-Trifluoroethanone as a Potent Transition-State Analogue Slow-Binding Inhibitor of Human Acetylcholinesterase: Kinetic, MD and QM\/MM Studies - Zueva_2020_Biomolecules_10_1608
Author(s) : Zueva IV , Lushchekina SV , Pottie IR , Darvesh S , Masson P
Ref : Biomolecules , 10 : , 2020
Abstract :
PubMedSearch : Zueva_2020_Biomolecules_10_1608
PubMedID: 33260981

Title : Assessment of neurotoxic effects of tri-cresyl phosphates (TCPs) and cresyl saligenin phosphate (CBDP) using a combination of in vitro techniques - Hausherr_2017_Neurotoxicol_59_210
Author(s) : Hausherr V , Schobel N , Liebing J , van Thriel C
Ref : Neurotoxicology , 59 :210 , 2017
Abstract :
PubMedSearch : Hausherr_2017_Neurotoxicol_59_210
PubMedID: 27288108

Title : Saligenin cyclic-o-tolyl phosphate (SCOTP) induces autophagy of rat spermatogonial stem cells - Xu_2016_Reprod.Toxicol_60_62
Author(s) : Xu LL , Liu ML , Wang JL , Yu M , Chen JX
Ref : Reprod Toxicol , 60 :62 , 2016
Abstract :
PubMedSearch : Xu_2016_Reprod.Toxicol_60_62
PubMedID: 26815770

Title : The effects of 8-OH-DPAT on neuroinflammation after sarin exposure in mice - Garrett_2013_Toxicology_310_22
Author(s) : Garrett TL , Joshi K , Rapp CM , Chapleau M , Cool DR , Schlager JJ , Lucot JB
Ref : Toxicology , 310 :22 , 2013
Abstract :
PubMedSearch : Garrett_2013_Toxicology_310_22
PubMedID: 23692952

Title : Inhibition pathways of the potent organophosphate CBDP with cholinesterases revealed by X-ray crystallographic snapshots and mass spectrometry - Carletti_2013_Chem.Res.Toxicol_26_280
Author(s) : Carletti E , Colletier JP , Schopfer LM , Santoni G , Masson P , Lockridge O , Nachon F , Weik M
Ref : Chemical Research in Toxicology , 26 :280 , 2013
Abstract :
PubMedSearch : Carletti_2013_Chem.Res.Toxicol_26_280
PubMedID: 23339663
Gene_locus related to this paper: human-BCHE , mouse-ACHE

Title : Cresyl saligenin phosphate makes multiple adducts on free histidine, but does not form an adduct on histidine 438 of human butyrylcholinesterase - Liyasova_2013_Chem.Biol.Interact_203_103
Author(s) : Liyasova MS , Schopfer LM , Lockridge O
Ref : Chemico-Biological Interactions , 203 :103 , 2013
Abstract :
PubMedSearch : Liyasova_2013_Chem.Biol.Interact_203_103
PubMedID: 22898212

Title : Effects of viscosity and osmotic stress on the reaction of human butyrylcholinesterase with cresyl saligenin phosphate, a toxicant related to aerotoxic syndrome: kinetic and molecular dynamics studies - Masson_2013_Biochem.J_454_387
Author(s) : Masson P , Lushchekina SV , Schopfer LM , Lockridge O
Ref : Biochemical Journal , 454 :387 , 2013
Abstract :
PubMedSearch : Masson_2013_Biochem.J_454_387
PubMedID: 23782236

Title : Identifying safer anti-wear triaryl phosphate additives for jet engine lubricants - Baker_2013_Chem.Biol.Interact_203_257
Author(s) : Baker PE , Cole TB , Cartwright M , Suzuki SM , Thummel KE , Lin YS , Co AL , Rettie AE , Kim JH , Furlong CE
Ref : Chemico-Biological Interactions , 203 :257 , 2013
Abstract :
PubMedSearch : Baker_2013_Chem.Biol.Interact_203_257
PubMedID: 23085349

Title : Cresyl saligenin phosphate, an organophosphorus toxicant, makes covalent adducts with histidine, lysine, and tyrosine residues of human serum albumin - Liyasova_2012_Chem.Res.Toxicol_25_1752
Author(s) : Liyasova MS , Schopfer LM , Lockridge O
Ref : Chemical Research in Toxicology , 25 :1752 , 2012
Abstract :
PubMedSearch : Liyasova_2012_Chem.Res.Toxicol_25_1752
PubMedID: 22793878

Title : Reaction of cresyl saligenin phosphate, the organophosphorus agent implicated in aerotoxic syndrome, with human cholinesterases: mechanistic studies employing kinetics, mass spectrometry, and X-ray structure analysis - Carletti_2011_Chem.Res.Toxicol_24_797
Author(s) : Carletti E , Schopfer LM , Colletier JP , Froment MT , Nachon F , Weik M , Lockridge O , Masson P
Ref : Chemical Research in Toxicology , 24 :797 , 2011
Abstract :
PubMedSearch : Carletti_2011_Chem.Res.Toxicol_24_797
PubMedID: 21438623
Gene_locus related to this paper: human-BCHE

Title : A murine model for sarin exposure using the carboxylesterase inhibitor CBDP - Garrett_2010_Neurotoxicol_31_502
Author(s) : Garrett TL , Rapp CM , Grubbs RD , Schlager JJ , Lucot JB
Ref : Neurotoxicology , 31 :502 , 2010
Abstract :
PubMedSearch : Garrett_2010_Neurotoxicol_31_502
PubMedID: 20510297

Title : Development of diagnostics in the search for an explanation of aerotoxic syndrome - Schopfer_2010_Anal.Biochem_404_64
Author(s) : Schopfer LM , Furlong CE , Lockridge O
Ref : Analytical Biochemistry , 404 :64 , 2010
Abstract :
PubMedSearch : Schopfer_2010_Anal.Biochem_404_64
PubMedID: 20447373

Title : Comparison of polyethylene glycol-conjugated recombinant human acetylcholinesterase and serum human butyrylcholinesterase as bioscavengers of organophosphate compounds - Cohen_2006_Mol.Pharmacol_70_1121
Author(s) : Cohen O , Kronman C , Raveh L , Mazor O , Ordentlich A , Shafferman A
Ref : Molecular Pharmacology , 70 :1121 , 2006
Abstract :
PubMedSearch : Cohen_2006_Mol.Pharmacol_70_1121
PubMedID: 16801396

Title : Mechanism of differential inhibition of hepatic and pancreatic fatty acid ethyl ester synthase by inhibitors of serine-esterases: in vitro and cell culture studies - Kaphalia_2004_Toxicol.Appl.Pharmacol_200_7
Author(s) : Kaphalia BS , Mericle KA , Ansari GA
Ref : Toxicol Appl Pharmacol , 200 :7 , 2004
Abstract :
PubMedSearch : Kaphalia_2004_Toxicol.Appl.Pharmacol_200_7
PubMedID: 15451303

Title : Different role of carboxylesterases in toxicity and tolerance to paraoxon and DFP - Dettbarn_1999_Chem.Biol.Interact_119-120_445
Author(s) : Dettbarn WD , Yang ZP , Milatovic D
Ref : Chemico-Biological Interactions , 119-120 :445 , 1999
Abstract :
PubMedSearch : Dettbarn_1999_Chem.Biol.Interact_119-120_445
PubMedID: 10421482

Title : Prevention of tolerance to the organophosphorus anticholinesterase paraoxon with carboxylesterase inhibitors - Yang_1998_Biochem.Pharmacol_55_1419
Author(s) : Yang ZP , Dettbarn WD
Ref : Biochemical Pharmacology , 55 :1419 , 1998
Abstract :
PubMedSearch : Yang_1998_Biochem.Pharmacol_55_1419
PubMedID: 10076534

Title : The in vitro degradation of cisatracurium, the R, cis-R'-isomer of atracurium, in human and rat plasma - Welch_1995_Clin.Pharmacol.Ther_58_132
Author(s) : Welch RM , Brown A , Ravitch J , Dahl R
Ref : Clinical Pharmacology & Therapeutics , 58 :132 , 1995
Abstract :
PubMedSearch : Welch_1995_Clin.Pharmacol.Ther_58_132
PubMedID: 7648763

Title : Neuropathy target esterase inhibitors: enantiomeric separation and stereospecificity of 2-substituted-4H-1,3,2-benzodioxaphosphorin 2-oxides - Wu_1994_Chem.Res.Toxicol_7_77
Author(s) : Wu SY , Casida JE
Ref : Chemical Research in Toxicology , 7 :77 , 1994
Abstract :
PubMedSearch : Wu_1994_Chem.Res.Toxicol_7_77
PubMedID: 8155829

Title : A purified recombinant organophosphorus acid anhydrase protects mice against soman - Broomfield_1993_Chem.Biol.Interact_87_279
Author(s) : Broomfield CA
Ref : Chemico-Biological Interactions , 87 :279 , 1993
Abstract :
PubMedSearch : Broomfield_1993_Chem.Biol.Interact_87_279
PubMedID: 8393744

Title : Effect of pretreatment with CBDP on the toxicokinetics of soman stereoisomers in rats and guinea pigs - Due_1993_Arch.Toxicol_67_706
Author(s) : Due AH , Trap HC , van der Wiel HJ , Benschop HP
Ref : Archives of Toxicology , 67 :706 , 1993
Abstract :
PubMedSearch : Due_1993_Arch.Toxicol_67_706
PubMedID: 8135661

Title : Toxicokinetics of [14C]-saligenin cyclic-o-tolyl phosphate in anesthetized male F-344 rats - Burka_1993_Reprod.Toxicol_7_81
Author(s) : Burka LT , Chapin RE
Ref : Reprod Toxicol , 7 :81 , 1993
Abstract :
PubMedSearch : Burka_1993_Reprod.Toxicol_7_81
PubMedID: 8448420

Title : Local application of neuropathic organophosphorus compounds to hen sciatic nerve: inhibition of neuropathy target esterase and peripheral neurological impairments - Carrera_1992_Toxicol.Appl.Pharmacol_117_218
Author(s) : Carrera V , Barril J , Mauricio M , Pellin M , Vilanova E
Ref : Toxicol Appl Pharmacol , 117 :218 , 1992
Abstract :
PubMedSearch : Carrera_1992_Toxicol.Appl.Pharmacol_117_218
PubMedID: 1471154

Title : Murine susceptibility to organophosphorus-induced delayed neuropathy (OPIDN) - Veronesi_1991_Toxicol.Appl.Pharmacol_107_311
Author(s) : Veronesi B , Padilla S , Blackmon K , Pope C
Ref : Toxicol Appl Pharmacol , 107 :311 , 1991
Abstract :
PubMedSearch : Veronesi_1991_Toxicol.Appl.Pharmacol_107_311
PubMedID: 1994513

Title : The effects of tri-o-cresyl phosphate and metabolites on rat Sertoli cell function in primary culture - Chapin_1991_Toxicol.Appl.Pharmacol_108_194
Author(s) : Chapin RE , Phelps JL , Burka LT , Abou-Donia MB , Heindel JJ
Ref : Toxicol Appl Pharmacol , 108 :194 , 1991
Abstract :
PubMedSearch : Chapin_1991_Toxicol.Appl.Pharmacol_108_194
PubMedID: 1902005

Title : Serum carboxylesterase activity in various strains of rats: sensitivity to inhibition by CBDP (2-\/o-cresyl\/4H:1:3:2-benzodioxaphosphorin-2-oxide) - Clement_1990_Arch.Toxicol_64_414
Author(s) : Clement JG , Erhardt N
Ref : Archives of Toxicology , 64 :414 , 1990
Abstract :
PubMedSearch : Clement_1990_Arch.Toxicol_64_414
PubMedID: 2403290

Title : Effects of CBDP and MEPQ on the toxicity and distribution of [3H]-soman in mice - Shapira_1990_Arch.Toxicol_64_663
Author(s) : Shapira S , Kadar T , Cohen G , Chapman S , Raveh L
Ref : Archives of Toxicology , 64 :663 , 1990
Abstract :
PubMedSearch : Shapira_1990_Arch.Toxicol_64_663
PubMedID: 2090035

Title : The interaction of Sertoli and Leydig cells in the testicular toxicity of tri-o-cresyl phosphate - Chapin_1990_Toxicol.Appl.Pharmacol_104_483
Author(s) : Chapin RE , Phelps JL , Somkuti SG , Heindel JJ , Burka LT
Ref : Toxicol Appl Pharmacol , 104 :483 , 1990
Abstract :
PubMedSearch : Chapin_1990_Toxicol.Appl.Pharmacol_104_483
PubMedID: 2385838

Title : Hepatic subcellular localization of cresylbenzodioxaphosphorin oxide (CBDP)-sensitive soman binding sites - Little_1990_Biochem.Pharmacol_40_1733
Author(s) : Little JS , Maxwell DM , Fox-Talbot MK , Brecht K , Lenz DE
Ref : Biochemical Pharmacology , 40 :1733 , 1990
Abstract :
PubMedSearch : Little_1990_Biochem.Pharmacol_40_1733
PubMedID: 2242010

Title : The effect of 2-(o-cresyl)-4H-1:3:2-benzodioxaphosphorin-2-oxide on tissue cholinesterase and carboxylesterase activities of the rat - Jimmerson_1989_Fundam.Appl.Toxicol_13_568
Author(s) : Jimmerson VR , Shih TM , Maxwell DM , Kaminskis A , Mailman RB
Ref : Fundamental & Applied Toxicology , 13 :568 , 1989
Abstract :
PubMedSearch : Jimmerson_1989_Fundam.Appl.Toxicol_13_568
PubMedID: 2612789

Title : Cresylbenzodioxaphosphorin oxide pretreatment alters soman-induced toxicity and inhibition of tissue cholinesterase activity of the rat - Jimmerson_1989_Toxicol.Lett_48_93
Author(s) : Jimmerson VR , Shih TM , Maxwell DM , Mailman RB
Ref : Toxicol Lett , 48 :93 , 1989
Abstract :
PubMedSearch : Jimmerson_1989_Toxicol.Lett_48_93
PubMedID: 2749782

Title : Effect of beta-naphthoflavone on o-tolyl saligenin phosphate-induced delayed neuropathy in two lines of chickens - Bursian_1989_J.Toxicol.Environ.Health_28_461
Author(s) : Bursian SJ , Lehning EJ , Correll L , Ehrich M
Ref : J Toxicol Environ Health , 28 :461 , 1989
Abstract :
PubMedSearch : Bursian_1989_J.Toxicol.Environ.Health_28_461
PubMedID: 2593176

Title : Effect of carboxylesterase inhibition on carbamate protection against soman toxicity - Maxwell_1988_J.Pharmacol.Exp.Ther_246_986
Author(s) : Maxwell DM , Brecht KM , Lenz DE , O'Neill BL
Ref : Journal of Pharmacology & Experimental Therapeutics , 246 :986 , 1988
Abstract :
PubMedSearch : Maxwell_1988_J.Pharmacol.Exp.Ther_246_986
PubMedID: 3418520

Title : Effect of route of administration on the development of organophosphate-induced delayed neurotoxicity in 4-week-old chicks - Olson_1988_J.Toxicol.Environ.Health_23_499
Author(s) : Olson BA , Bursian SJ
Ref : J Toxicol Environ Health , 23 :499 , 1988
Abstract :
PubMedSearch : Olson_1988_J.Toxicol.Environ.Health_23_499
PubMedID: 3361617

Title : Stereoisomers of soman (pinacolyl methylphosphonofluoridate): inhibition of serum carboxylic ester hydrolase and potentiation of their toxicity by CBDP (2-(2-methylphenoxy)-4H-1,3,2-benzodioxaphosphorin-2-oxide) in mice - Clement_1987_Toxicol.Appl.Pharmacol_89_141
Author(s) : Clement JG , Benschop HP , DeJong LP , Wolthuis OL
Ref : Toxicol Appl Pharmacol , 89 :141 , 1987
Abstract :
PubMedSearch : Clement_1987_Toxicol.Appl.Pharmacol_89_141
PubMedID: 3590185

Title : The effect of carboxylesterase inhibition on interspecies differences in soman toxicity - Maxwell_1987_Toxicol.Lett_39_35
Author(s) : Maxwell DM , Brecht KM , O'Neill BL
Ref : Toxicol Lett , 39 :35 , 1987
Abstract :
PubMedSearch : Maxwell_1987_Toxicol.Lett_39_35
PubMedID: 3672554

Title : Role of aliesterase in organophosphate poisoning - Clement_1984_Fundam.Appl.Toxicol_4_S96
Author(s) : Clement JG
Ref : Fundamental & Applied Toxicology , 4 :S96 , 1984
Abstract :
PubMedSearch : Clement_1984_Fundam.Appl.Toxicol_4_S96
PubMedID: 6724216

Title : Importance of aliesterase as a detoxification mechanism for soman (Pinacolyl methylphosphonofluoridate) in mice - Clement_1984_Biochem.Pharmacol_33_3807
Author(s) : Clement JG
Ref : Biochemical Pharmacology , 33 :3807 , 1984
Abstract :
PubMedSearch : Clement_1984_Biochem.Pharmacol_33_3807
PubMedID: 6508835

Title : Antidote effect of sodium fluoride against organophosphate poisoning in mice - Clement_1983_Life.Sci_32_1803
Author(s) : Clement JG , Filbert M , Filbert MG
Ref : Life Sciences , 32 :1803 , 1983
Abstract :
PubMedSearch : Clement_1983_Life.Sci_32_1803
PubMedID: 6835011

Title : Carboxylesterase inhibition and potentiation of soman toxicity -
Author(s) : Cohen SD
Ref : Archives of Toxicology , 49 :105 , 1981
PubMedID: 7053071

Title : The influence of 2-\/o-cresyl\/-4 H-1 : 3 : 2-benzodioxa-phosphorin-2-oxide (CBDP) on organophosphate poisoning and its therapy - Boskovic_1979_Arch.Toxicol_42_207
Author(s) : Boskovic B
Ref : Archives of Toxicology , 42 :207 , 1979
Abstract :
PubMedSearch : Boskovic_1979_Arch.Toxicol_42_207
PubMedID: 475595

Title : Biological activity of a tri-o-cresyl phosphate metabolite - Casida_1961_Nature_191_1396
Author(s) : Casida JE , Eto M , Baron RL
Ref : Nature , 191 :1396 , 1961
Abstract :
PubMedSearch : Casida_1961_Nature_191_1396
PubMedID: