Trichlorfon~Metrifonate

Anthelmintic is used for treating domestic animals for control of internal parasites and has been tested in patients with Alzheimer's disease. Metrifonate is slowly converted in the body by a nonenzymatic process to the long-acting cholinesterase inhibitor Dichlorvos

General

Type : Organophosphate, Insecticide, Anthelmintic

Chemical_Nomenclature : (2,2,2-Trichloro-1-hydroxyethyl)-phosphonic acid dimethyl ester

Canonical SMILES : COP(=O)(C(C(Cl)(Cl)Cl)O)OC

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

InChIKey : NFACJZMKEDPNKN-UHFFFAOYSA-N

Other name(s) : Trichlorphon  ||  Promem  ||  Metriphonate  ||  Metrifonate  ||  Chlorofos  ||  Dylox  ||  Dipterex  ||  Proxol  ||  Neguvon  ||  MFT


MW : 257.44

Formula : C4H8Cl3O4P

CAS_number : 52-68-6

PubChem : 5853

UniChem : NFACJZMKEDPNKN-UHFFFAOYSA-N

Wikipedia : Metrifonate

Target

Families : Trichlorfon~Metrifonate ligand of proteins in family
BCHE ACHE ACPH_Peptidase_S9

Protein :
human-APEH

References (66)

Title : Modulation of dopaminergic neurotransmission induced by sublethal Doses of the organophosphate trichlorfon in cockroaches - Daiane_2014_Ecotoxicol.Environ.Saf_109C_56
Author(s) : Daiane Stu Rmer G , de Freitas TC , de Avila Heberle M , de Assis DR , Vinade L , Batista Pereira A , Luis Franco J , Andre Dal Belo C
Ref : Ecotoxicology & Environmental Safety , 109C :56 , 2014
Abstract :
PubMedSearch : Daiane_2014_Ecotoxicol.Environ.Saf_109C_56
PubMedID: 25164203

Title : Blood acylpeptide hydrolase activity is a sensitive marker for exposure to some organophosphate toxicants - Quistad_2005_Toxicol.Sci_86_291
Author(s) : Quistad GB , Klintenberg R , Casida JE
Ref : Toxicol Sci , 86 :291 , 2005
Abstract :
PubMedSearch : Quistad_2005_Toxicol.Sci_86_291
PubMedID: 15888665
Gene_locus related to this paper: human-APEH

Title : Alzheimer's disease: seeking new ways to preserve brain function. Interview by Alice V. Luddington - Davis_1999_Geriatrics_54_42
Author(s) : Davis KL
Ref : Geriatrics , 54 :42 , 1999
Abstract :
PubMedSearch : Davis_1999_Geriatrics_54_42
PubMedID: 10024872

Title : Metrifonate benefits cognitive, behavioral, and global function in patients with Alzheimer's disease [see comments] - Morris_1998_Neurology_50_1222
Author(s) : Morris JC , Cyrus PA , Orazem J , Mas J , Bieber F , Ruzicka BB , Gulanski B
Ref : Neurology , 50 :1222 , 1998
Abstract :
PubMedSearch : Morris_1998_Neurology_50_1222
PubMedID: 9595967

Title : The clinical trial protocol of the Metrifonate in Alzheimer's Trial (MALT) - McKeith_1998_Dement.Geriatr.Cogn.Disord_2_2
Author(s) : McKeith IG
Ref : Dementia & Geriatric Cognitive Disorders , 2 :2 , 1998
Abstract :
PubMedSearch : McKeith_1998_Dement.Geriatr.Cogn.Disord_2_2
PubMedID: 9718228

Title : Invited review: Cholinesterase inhibitors for Alzheimer's disease therapy: from tacrine to future applications - Giacobini_1998_Neurochem.Int_32_413
Author(s) : Giacobini E
Ref : Neurochem Int , 32 :413 , 1998
Abstract :
PubMedSearch : Giacobini_1998_Neurochem.Int_32_413
PubMedID: 9676739

Title : Beyond the cholinergic hypothesis: the effect of metrifonate and other cholinesterase inhibitors on neuropsychiatric symptoms in Alzheimer's disease - Kaufer_1998_Dement.Geriatr.Cogn.Disord_2_8
Author(s) : Kaufer D
Ref : Dementia & Geriatric Cognitive Disorders , 2 :8 , 1998
Abstract :
PubMedSearch : Kaufer_1998_Dement.Geriatr.Cogn.Disord_2_8
PubMedID: 9718229

Title : The pharmacological basis for metrifonate's favourable tolerability in the treatment of Alzheimer's disease - Schmidt_1998_Dement.Geriatr.Cogn.Disord_2_15
Author(s) : Schmidt BH , Heinig R
Ref : Dementia & Geriatric Cognitive Disorders , 2 :15 , 1998
Abstract :
PubMedSearch : Schmidt_1998_Dement.Geriatr.Cogn.Disord_2_15
PubMedID: 9718230

Title : Evaluating response to metrifonate - Tariot_1998_J.Clin.Psychiatry_9_33
Author(s) : Tariot PN
Ref : J Clin Psychiatry , 9 :33 , 1998
Abstract :
PubMedSearch : Tariot_1998_J.Clin.Psychiatry_9_33
PubMedID: 9720485

Title : Inhibition of carboxylesterases in SH-SY5Y human and NB41A3 mouse neuroblastoma cells by organophosphorus esters - Ehrich_1998_J.Toxicol.Environ.Health_53_385
Author(s) : Ehrich M , Correll L
Ref : J Toxicol Environ Health , 53 :385 , 1998
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PubMedID: 9515941

Title : Preclinical pharmacology of metrifonate - Jann_1998_Pharmacotherapy_18_55
Author(s) : Jann MW
Ref : Pharmacotherapy , 18 :55 , 1998
Abstract :
PubMedSearch : Jann_1998_Pharmacotherapy_18_55
PubMedID: 9543466

Title : Pharmacokinetics, pharmacodynamics, and safety of metrifonate in patients with Alzheimer's disease - Pettigrew_1998_J.Clin.Pharmacol_38_236
Author(s) : Pettigrew LC , Bieber F , Lettieri J , Wermeling DP , Schmitt FA , Tikhtman AJ , Ashford JW , Smith CD , Wekstein DR , Markesbery WR , Orazem J , Ruzicka BB , Mas J , Gulanski B
Ref : Journal of Clinical Pharmacology , 38 :236 , 1998
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PubMedSearch : Pettigrew_1998_J.Clin.Pharmacol_38_236
PubMedID: 98210831

Title : Effect of subchronic treatment with metrifonate and tacrine on brain cholinergic function in aged F344 rats - Giovannini_1998_Eur.J.Pharmacol_354_17
Author(s) : Giovannini MG , Scali C , Bartolini L , Schmidt B , Pepeu G
Ref : European Journal of Pharmacology , 354 :17 , 1998
Abstract :
PubMedSearch : Giovannini_1998_Eur.J.Pharmacol_354_17
PubMedID: 9726626

Title : Pharmacokinetics and neurotoxicity of dipterex in hens. A comparative study of administration methods - Xie_1998_J.Toxicol.Sci_23_25
Author(s) : Xie X , Piao FY , Tian Y , Yamauchi T
Ref : Journal of Toxicological Sciences , 23 :25 , 1998
Abstract :
PubMedSearch : Xie_1998_J.Toxicol.Sci_23_25
PubMedID: 9513919

Title : Effects of metrifonate on cognitive decline in Alzheimer disease: a double-blind, placebo-controlled, 6-month study - Becker_1998_Alzheimer.Dis.Assoc.Disord_12_54
Author(s) : Becker RE , Colliver JA , Markwell SJ , Moriearty PL , Unni LK , Vicari S
Ref : lzheimer Disease & Associated Disorders , 12 :54 , 1998
Abstract :
PubMedSearch : Becker_1998_Alzheimer.Dis.Assoc.Disord_12_54
PubMedID: 9539412

Title : Metrifonate: overview of safety and efficacy - Cummings_1998_Pharmacotherapy_18_43
Author(s) : Cummings JL
Ref : Pharmacotherapy , 18 :43 , 1998
Abstract :
PubMedSearch : Cummings_1998_Pharmacotherapy_18_43
PubMedID: 9543464

Title : Metrifonate treatment of the cognitive deficits of Alzheimer's disease. Metrifonate Study Group [see comments] [published erratum appears in Neurology 1998 Jul\;51(1):332] - Cummings_1998_Neurology_50_1214
Author(s) : Cummings JL , Cyrus PA , Bieber F , Mas J , Orazem J , Gulanski B
Ref : Neurology , 50 :1214 , 1998
Abstract :
PubMedSearch : Cummings_1998_Neurology_50_1214
PubMedID: 9595966

Title : Schistosomiasis in Saudi Arabia, Egypt, and Iraq - Youssef_1998_Urology_51_170
Author(s) : Youssef AR , Cannon JM , Al Juburi AZ , Cockett AT
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PubMedSearch : Youssef_1998_Urology_51_170
PubMedID: 9610576

Title : Teratogenic effects of trichlorfon (Metrifonate) on the guinea-pig brain. Determination of the effective dose and the sensitive period - Hjelde_1998_Neurochem.Int_32_469
Author(s) : Hjelde T , Mehl A , Schanke TM , Fonnum F
Ref : Neurochem Int , 32 :469 , 1998
Abstract :
PubMedSearch : Hjelde_1998_Neurochem.Int_32_469
PubMedID: 9676746

Title : Safety and tolerability of metrifonate in patients with Alzheimer's disease: results of a maximum tolerated dose study - Cutler_1998_Life.Sci_62_1433
Author(s) : Cutler NR , Jhee SS , Cyrus P , Bieber F , TanPiengco P , Sramek JJ , Gulanski B
Ref : Life Sciences , 62 :1433 , 1998
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PubMedSearch : Cutler_1998_Life.Sci_62_1433
PubMedID: 9585171

Title : Metrifonate for Alzheimer's disease: is the next cholinesterase inhibitor better? [editorial\; comment] -
Author(s) : Knopman DS
Ref : Neurology , 50 :1203 , 1998
PubMedID: 9595961

Title : Human mortality in organophosphate poisonings - Yamashita_1997_Vet.Hum.Toxicol_39_84
Author(s) : Yamashita M , Tanaka J , Ando Y
Ref : Vet Hum Toxicol , 39 :84 , 1997
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PubMedID: 9080632

Title : [The pharmacokinetic interaction of cholinolytics and cholinesterase reactivators as a reflection of the modulation of their binding in blood plasma and in brain tissue] - Elaeva_1997_Eksp.Klin.Farmakol_60_64
Author(s) : Elaeva NL , Predtechenskii MB , Kul'bitskii GN , Babaina EV , Trefilov VV
Ref : Eksperimentalnaia i Klinicheskaia Farmakologiia , 60 :64 , 1997
Abstract :
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PubMedID: 9376763

Title : Treating Alzheimer's disease.Pharmacologic options now and in the near future - Tariot_1997_Postgrad.Med_101_73
Author(s) : Tariot PN , Schneider L , Porsteinsson AP
Ref : Postgrad Med , 101 :73 , 1997
Abstract :
PubMedSearch : Tariot_1997_Postgrad.Med_101_73
PubMedID: 9194867

Title : Effects of cholinesterase inhibitors on the secretion of beta-amyloid precursor protein in cell cultures - Lahiri_1997_Ann.N.Y.Acad.Sci_826_416
Author(s) : Lahiri DK , Farlow MR , Nurnberger JI, Jr. , Greig NH
Ref : Annals of the New York Academy of Sciences , 826 :416 , 1997
Abstract :
PubMedSearch : Lahiri_1997_Ann.N.Y.Acad.Sci_826_416
PubMedID: 9329715

Title : Effects of combined chronic nimodipine and acute metrifonate treatment on spatial and avoidance behavior - Riekkinen_1997_Eur.J.Pharmacol_322_1
Author(s) : Riekkinen M , Schmidt B , Kuitunen J , Riekkinen P
Ref : European Journal of Pharmacology , 322 :1 , 1997
Abstract :
PubMedSearch : Riekkinen_1997_Eur.J.Pharmacol_322_1
PubMedID: 9088863

Title : Effects of metrifonate on memory impairment and cholinergic dysfunction in rats - Itoh_1997_Eur.J.Pharmacol_322_11
Author(s) : Itoh A , Nitta A , Katono Y , Usui M , Naruhashi K , Iida R , Hasegawa T , Nabeshima T
Ref : European Journal of Pharmacology , 322 :11 , 1997
Abstract :
PubMedSearch : Itoh_1997_Eur.J.Pharmacol_322_11
PubMedID: 9088864

Title : Behavioral characterization of metrifonate-improved acquisition of spatial information in medial septum-lesioned rats - Riekkinen_1997_Eur.J.Pharmacol_323_11
Author(s) : Riekkinen P, Jr. , Schmidt B , Riekkinen M
Ref : European Journal of Pharmacology , 323 :11 , 1997
Abstract :
PubMedSearch : Riekkinen_1997_Eur.J.Pharmacol_323_11
PubMedID: 9105871

Title : Effect of metrifonate on extracellular brain acetylcholine and object recognition in aged rats - Scali_1997_Eur.J.Pharmacol_325_173
Author(s) : Scali C , Giovannini MG , Bartolini L , Prosperi C , Hinz V , Schmidt B , Pepeu G
Ref : European Journal of Pharmacology , 325 :173 , 1997
Abstract :
PubMedSearch : Scali_1997_Eur.J.Pharmacol_325_173
PubMedID: 9163564

Title : Metrifonate treatment enhances acquisition of eyeblink conditioning in aging rabbits - Kronforst-Collins_1997_Pharmacol.Biochem.Behav_56_103
Author(s) : Kronforst-Collins MA , Moriearty PL , Ralph M , Becker RE , Schmidt B , Thompson LT , Disterhoft JF
Ref : Pharmacology, Biochemistry & Behavior , 56 :103 , 1997
Abstract :
PubMedSearch : Kronforst-Collins_1997_Pharmacol.Biochem.Behav_56_103
PubMedID: 8981616

Title : Metrifonate improves associative learning and retention in aging rabbits - Kronforst-Collins_1997_Behav.Neurosci_111_1031
Author(s) : Kronforst-Collins MA , Moriearty PL , Schmidt B , Disterhoft JF
Ref : Behavioral Neuroscience , 111 :1031 , 1997
Abstract :
PubMedSearch : Kronforst-Collins_1997_Behav.Neurosci_111_1031
PubMedID: 9383522

Title : Chronic nimodipine and acute metrifonate treatment decreases age- related cortical high voltage spindles in rats - Riekkinen_1997_Psychopharmacology_129_91
Author(s) : Riekkinen P, Jr. , Schmidt B , Jakala P , Koivisto E , Bjorklund M
Ref : Psychopharmacology , 129 :91 , 1997
Abstract :
PubMedSearch : Riekkinen_1997_Psychopharmacology_129_91
PubMedID: 9122369

Title : Effects of metrifonate on impairment of learning and dysfunction of cholinergic neuronal system in basal forebrain-lesioned rats - Itoh_1997_Behav.Brain.Res_83_165
Author(s) : Itoh A , Nitta A , Hirose M , Hasegawa T , Nabeshima T
Ref : Behavioural Brain Research , 83 :165 , 1997
Abstract :
PubMedSearch : Itoh_1997_Behav.Brain.Res_83_165
PubMedID: 9062677

Title : Using the Hungarian Birth Defects Registry for surveillance, research and intervention - Siffel_1997_Cent.Eur.J.Public.Health_5_79
Author(s) : Siffel C , Czeizel AE
Ref : Central European Journal of Public Health , 5 :79 , 1997
Abstract :
PubMedSearch : Siffel_1997_Cent.Eur.J.Public.Health_5_79
PubMedID: 9208163

Title : [Recent data on the treatment of bovine hypodermyiasis using metrifonate (Neguvon) and ivermectin (Ivomec) in microdoses] - Charbon_1997_Schweiz.Arch.Tierheilkd_139_550
Author(s) : Charbon JL , Pfister K
Ref : Schweiz Arch Tierheilkd , 139 :550 , 1997
Abstract :
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PubMedID: 9451918

Title : Subchronic neurotoxicity screening studies with six organophosphate insecticides: an assessment of behavior and morphology relative to cholinesterase inhibition - Sheets_1997_Fundam.Appl.Toxicol_35_101
Author(s) : Sheets LP , Hamilton BF , Sangha GK , Thyssen JH
Ref : Fundamental & Applied Toxicology , 35 :101 , 1997
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PubMedID: 9024678

Title : Effects of metrifonate on radial arm maze acquisition in middle-aged rats - Dachir_1997_Brain.Res_777_251
Author(s) : Dachir S , Schmidt B , Levy A
Ref : Brain Research , 777 :251 , 1997
Abstract :
PubMedSearch : Dachir_1997_Brain.Res_777_251
PubMedID: 9449438

Title : Subchronic treatment increases the duration of the cognitive enhancement induced by metrifonate - Riekkinen_1997_Eur.J.Pharmacol_338_105
Author(s) : Riekkinen M , Schmidt BH , Riekkinen P, Jr.
Ref : European Journal of Pharmacology , 338 :105 , 1997
Abstract :
PubMedSearch : Riekkinen_1997_Eur.J.Pharmacol_338_105
PubMedID: 9455990

Title : A study of the aneugenic activity of trichlorfon detected by centromere- specific probes in human lymphoblastoid cell lines - Doherty_1996_Mutat.Res_372_221
Author(s) : Doherty AT , Ellard S , Parry EM , Parry JM
Ref : Mutat Res , 372 :221 , 1996
Abstract :
PubMedSearch : Doherty_1996_Mutat.Res_372_221
PubMedID: 9015141

Title : Effects of combined nimodipine and metrifonate on rat cognition and cortical EEG - Jakala_1996_Eur.J.Pharmacol_318_239
Author(s) : Jakala P , Riekkinen M , Bjorklund M , Koivisto E , Schmidt B , Riekkinen P, Jr.
Ref : European Journal of Pharmacology , 318 :239 , 1996
Abstract :
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PubMedID: 9016911

Title : [Twenty-years health surveillance of workers in dipterex packaging] - Sun_1996_Chung.Hua.Yu.Fang.I.Hsueh.Tsa.Chih_30_273
Author(s) : Sun D , Zhou H , Huang J
Ref : Chinese Journal of Preventive Medicine , 30 :273 , 1996
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PubMedSearch : Sun_1996_Chung.Hua.Yu.Fang.I.Hsueh.Tsa.Chih_30_273
PubMedID: 9388884

Title : Effects of metrifonate, a cholinesterase inhibitor, on local cerebral glucose utilization in young and aged rats - Bassant_1996_J.Cereb.Blood.Flow.Metab_16_1014
Author(s) : Bassant MH , Jazat-Poindessous F , Lamour Y
Ref : Journal of Cerebral Blood Flow & Metabolism , 16 :1014 , 1996
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PubMedSearch : Bassant_1996_J.Cereb.Blood.Flow.Metab_16_1014
PubMedID: 8784247

Title : An indirect cholinesterase inhibitor, metrifonate, increases neocortical EEG arousal in rats - Bjorklund_1996_Neuroreport_7_1097
Author(s) : Bjorklund M , Jakala P , Schmidt B , Riekkinen M , Koivisto E , Riekkinen P, Jr.
Ref : Neuroreport , 7 :1097 , 1996
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Title : Metrifonate improves spatial navigation and avoidance behavior in scopolamine-treated, medial septum-lesioned and aged rats - Riekkinen_1996_Eur.J.Pharmacol_309_121
Author(s) : Riekkinen P, Jr. , Schmidt B , Stefanski R , Kuitunen J , Riekkinen M
Ref : European Journal of Pharmacology , 309 :121 , 1996
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Title : Cholinesterase inhibitors proposed for treating dementia in Alzheimer's disease: selectivity toward human brain acetylcholinesterase compared with butyrylcholinesterase - Pacheco_1995_J.Pharmacol.Exp.Ther_274_767
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Title : Schistosoma: rate of glucose import is altered by acetylcholine interaction with tegumental acetylcholine receptors and acetylcholinesterase - Camacho_1995_Exp.Parasitol_81_584
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Title : The amount of acetylcholinesterase on the parasite surface reflects the differential sensitivity of schistosome species to metrifonate - Camacho_1994_Parasitology_108_153
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Title : Transdermal patch delivery of acetylcholinesterase inhibitors - Moriearty_1993_Meth.Find.Exp.Clin.Pharmacol_15_407
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Title : [A study on acute organophosphorus poisoning--changes in the activity and isoenzyme patterns of serum cholinesterase in human poisoning]. [Japanese] - Yamanaka_1993_Japanese.J.Hyg_48_955
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Title : Preferential inhibition of acetylcholinesterase molecular forms in rat brain - Ogane_1992_Neurochem.Res_17_489
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Title : The effect of the organophosphate trichlorfon on the neuromuscular blocking activity of atracurium in halothane-anesthetized horses - Hildebrand_1989_J.Vet.Pharmacol.Ther_12_277
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Title : Chemistry of metrifonate and dichlorvos -
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Title : [Effect of the organophosphorus compound neguvon on the dopamine content in the rat brain]. [Bulgarian] - Dishovski_1981_Eksp.Med.Morfol_20_62
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Title : Experimental study of the effect of a series of phosphoroorganic pesticides (Dipterex and Imidan) on embryogenesis - Martson_1976_Environ.Health.Perspect_13_121
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Title : Developmental toxicity in the rat after ingestion or gavage of organophosphate pesticides (Dipterex, Imidan) during pregnancy - Staples_1976_Environ.Health.Perspect_13_133
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Ref : Environmental Health Perspectives , 13 :133 , 1976
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PubMedSearch : Staples_1976_Environ.Health.Perspect_13_133
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Title : [Effect of insecticides on larvae of Musca domestica in swine manure], - Schneider_1976_Angew.Parasitol_17_128
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Title : Studies on Parafilaria bovicola (Tubangui 1934). 1. Clinical observations and chemotherapy - Viljoen_1976_J.S.Afr.Vet.Assoc_47_161
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Title : Problems of housefly (Musca domestica) control due to multiresistance to insesticides - Keiding_1975_J.Hyg.Epidemiol.Microbiol.Immunol_19_340
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