Page last updated: 2024-12-06

2,3,4,7,8-pentachlorodibenzofuran

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

2,3,4,7,8-pentachlorodibenzofuran: structure given in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID42128
CHEMBL ID335558
CHEBI ID81508
SCHEMBL ID2281485
MeSH IDM0116813

Synonyms (27)

Synonym
2,3,4,7,8-pentachlorodibenzofuran
dibenzofuran, 2,3,4,7,8-pentachloro-
ccris 3492
hsdb 7178
4-pecdf
57117-31-4
2,3,4,7,8-pentachlorodibenzo[b,d]furan
2,3,4,7,8-pentachlorodibenzofuran (pecdf)
2,3,4,7,8-pecdf
pecdf
2,3,4,7,8-pentachloro-dibenzofuran
chebi:81508 ,
CHEMBL335558 ,
C18106
pcdf 114
bdbm50408369
unii-u4c2rv3124
u4c2rv3124 ,
2,3,4,7,8-pentachlorodibenzofuran [iarc]
2,3,4,7,8-pentachlorodibenzofuran [mi]
pentachlorodibenzofuran, 2,3,4,7,8-
2,3,4,7,8-pentachlorodibenzofuran [hsdb]
SCHEMBL2281485
OGBQILNBLMPPDP-UHFFFAOYSA-N
DTXSID7030066
Q26841329
2,3,4,7,8-penta-chlorodibenzofuran

Research Excerpts

Toxicity

2,3,4,7,8-pentachlorodibenzofuran (4PeCDF), a ubiquitous and acutely toxic environmental contaminant, was examined in three adult male Rhesus monkeys administered a single iv dose of 34 micrograms.

ExcerptReferenceRelevance
"2,3,7,8-Tetrachlorodibenzo-p-dixoin 2,3,4,7,8-pentachlorodibenzofuran (PCDF), and 1,2,3,4,7,8-hexachlorodibenzofuran (HCDF) are highly toxic members of a class of environmental contaminants, the polychlorinated aromatic hydrocarbons (PCAH), which exhibit a similar and highly characteristic spectrum of toxic effects."( Relative toxicity and tumor-promoting ability of 2,3,7,8-tetrachlorodibenzo-p-dioxin (TCDD), 2,3,4,7,8-pentachlorodibenzofuran (PCDF), and 1,2,3,4,7,8-hexachlorodibenzofuran (HCDF) in hairless mice.
Birnbaum, LS; Elwell, MR; Harris, MW; Hébert, CD, 1990
)
0.77
" In conclusion, 4-PeCDF is maternally and fetally toxic regardless of the gestation day of exposure, but induced terata only at doses where overt maternal and fetal toxicity were observed, in contrast to previously reported studies in the mice where teratogenic effects were observed at nonfetotoxic dose levels."( Developmental toxicity of 2,3,4,7,8-pentachlorodibenzofuran in the Fischer 344 rat.
Birnbaum, LS; Couture, LA; Harris, MW, 1989
)
0.58
"The hamsters have been known to be the least sensitive mammalian species to the acute toxicity of highly toxic polyhalogenated hydrocarbons such as 2,3,7,8-tetrachlorodibenzo-p-dioxin."( [Tissue distribution, inductive effect on liver enzymes and acute toxicity of 2,3,4,7,8-pentachlorodibenzofuran in Golden Syrian hamsters].
Hokama, Y; Kamimura, H; Koga, N; Nakashima, H; Yoshimura, H, 1989
)
0.51
" Since 4PeCDF and 2,3,7,8-tetrachlorodibenzo-p-dioxin (TCDD) produce a similar spectrum of toxic effects, the biochemical mechanism(s) of toxicity for these chemicals may be similar."( The acute toxicity of 2,3,4,7,8-pentachlorodibenzofuran (4PeCDF) in the male Fischer rat.
Birnbaum, LS; Brewster, DW; Uraih, LC, 1988
)
0.59
"The toxicity and disposition of 2,3,4,7,8-pentachlorodibenzofuran (4PeCDF), a ubiquitous and acutely toxic environmental contaminant, was examined in three adult male Rhesus monkeys administered a single iv dose of 34 micrograms (0."( Toxicity and disposition of 2,3,4,7,8-pentachlorodibenzofuran (4PeCDF) in the rhesus monkey (Macaca mulatta).
Birnbaum, LS; Brewster, DW; Elwell, MR, 1988
)
0.85

Bioavailability

ExcerptReferenceRelevance
" TCDD (2,3,7,8-tetrachlorodibenzo-p-dioxin) and 2,3,4,7,8-penta-chlorodibenzofuran (4PeCDF) were previously found to be poorly absorbed in 3 months male Fischer 344 rats within 3 days after dermal administration."( Age-related changes in dermal absorption of 2,3,7, 8-tetrachlorodibenzo-p-dioxin and 2,3,4,7,8-pentachlorodibenzofuran.
Banks, YB; Birnbaum, LS; Brewster, DW, 1990
)
0.5

Dosage Studied

ExcerptRelevanceReference
"Treatment of 25-day-old female Sprague-Dawley rats with 2,3,7,8-tetrachlorodibenzo-p-dioxin (TCDD) significantly lowered constitutive uterine peroxidase activity and decreased uterine wet weights in a dose-response fashion."( 2,3,7,8-Tetrachlorodibenzo-p-dioxin as an antiestrogen: effect on rat uterine peroxidase activity.
Astroff, B; Safe, S, 1990
)
0.28
" Female hairless mice (HRS/J hr/hr) were treated dermally with the initiator MNNG, then dosed twice weekly for 20 weeks with acetone, TCDD (2."( Relative toxicity and tumor-promoting ability of 2,3,7,8-tetrachlorodibenzo-p-dioxin (TCDD), 2,3,4,7,8-pentachlorodibenzofuran (PCDF), and 1,2,3,4,7,8-hexachlorodibenzofuran (HCDF) in hairless mice.
Birnbaum, LS; Elwell, MR; Harris, MW; Hébert, CD, 1990
)
0.5
" The data were compared with a dose-response curve for 2,3,7,8-tetrachlorodibenzo-p-dioxin (TCDD)."( Teratogenic potency of 2,3,4,7,8-pentachlorodibenzofuran and of three mixtures of polychlorinated dibenzo-p-dioxins and dibenzofurans in mice. Problems with risk assessment using TCDD toxic-equivalency factors.
Golor, G; Hagenmaier, H; Nagao, T; Neubert, D, 1993
)
0.6
" In the PHAH-group dosed 1 microgram TEQ/kg body wt/week, the volume fraction of the liver occupied by foci was significantly lower compared to the TEQ equivalent dosed TCDD group (3."( Induction of altered hepatic foci by a mixture of dioxin-like compounds with and without 2,2',4,4',5,5'-hexachlorobiphenyl in female Sprague-Dawley rats.
Brouwer, A; Haag-Grönlund, M; Koeman, JH; Scheu, G; van den Berg, M; van der Plas, SA; Wärngård, L; Wester, P, 1999
)
0.3
" 4-PeCDF RPFs were derived using estimation methods that either did or did not assume parallelism of the 4-PeCDF and TCDD dose-response curves."( Recommended relative potency factors for 2,3,4,7,8-pentachlorodibenzofuran: the impact of different dose metrics.
Budinsky, RA; Fontaine, D; Landenberger, B; Paustenbach, D; Starr, TB, 2006
)
0.6
" Pulmonary CYP1A1-associated 7-ethoxyresorufin-O-deethylase (EROD) activity was increased in all dosed groups."( Pulmonary lesions in female Harlan Sprague-Dawley rats following two-year oral treatment with dioxin-like compounds.
Brix, AE; Easterling, M; Jokinen, MP; Miller, RA; Nyska, A; Sells, DM; Walker, NJ; Wyde, ME; Yoshizawa, K, 2007
)
0.34
" By using a toxicokinetic model for 4-PeCDF, the dose-response relationship for combined liver tumors (hepatocellular adenomas and cholangiocarcinomas) in rats was assessed in terms of lifetime average liver concentration and lifetime average adipose concentration with data from both the lifetime and the stop-exposure components of the bioassay."( Estimates of cancer potency of 2,3,4,7,8-pentachlorodibenzofuran using both nonlinear and linear approaches.
Aylward, LL; Budinsky, RA; Kirman, CR; Long, TF; Rowlands, JC; Simon, T, 2008
)
0.63
" Increases in the incidence of acute and/or chronic active inflammation of the uterus were observed in all dosed groups, including the stop-exposure group (withdrawal after thirty-week exposure) of PeCDF and the 1,000 microg/kg and/or higher group dosed with PCB153."( Reproductive lesions in female Harlan Sprague-Dawley rats following two-year oral treatment with dioxin and dioxin-like compounds.
Brix, AE; Jokinen, MP; Kissling, GE; Nyska, A; Orzech, DP; Sells, DM; Walker, NJ; Wyde, M; Yoshizawa, K, 2009
)
0.35
" Body and relative organ masses of quail, pheasants, and chickens dosed in ovo with TCDD, PeCDF, or TCDF were not consistently affected."( Developmental and posthatch effects of in ovo exposure to 2,3,7,8-TCDD, 2,3,4,7,8-PECDF, and 2,3,7,8-TCDF in Japanese quail (Coturnix japonica), common pheasant (Phasianus colchicus), and white leghorn chicken (Gallus gallus domesticus) embryos.
Bursian, SJ; Cohen-Barnhouse, AM; Fitzgerald, SD; Giesy, JP; Jones, PD; Kay, D; Kennedy, SW; Link, JE; Newsted, JL; Wiseman, S; Zwiernik, MJ, 2011
)
0.37
" However, the PenCDF dose-response relationship on the wasting syndrome has been superficial."( [Effect of Cynaropicrin on 2,3,4,7,8-Pentachlorodibenzofuran-induced Wasting Syndrome and Oxidative Stress].
Furue, M; Ishii, Y; Kuroki, H; Mitoma, C; Takeda, T; Uchi, H; Yamada, H; Yamada, K, 2015
)
0.71
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
polychlorinated dibenzofuranA member of the class of benzofurans that is benzofuran in which two or more of the hydrogens have reen replaced by chlorines.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Protein Targets (2)

Activation Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Cytochrome P450 1A1Rattus norvegicus (Norway rat)EC50 (µMol)0.01510.00152.205710.0000AID39064
Aryl hydrocarbon receptorHomo sapiens (human)EC50 (µMol)0.01510.00151.976910.0000AID39064
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (22)

Processvia Protein(s)Taxonomy
blood vessel developmentAryl hydrocarbon receptorHomo sapiens (human)
regulation of adaptive immune responseAryl hydrocarbon receptorHomo sapiens (human)
negative regulation of T cell mediated immune response to tumor cellAryl hydrocarbon receptorHomo sapiens (human)
regulation of DNA-templated transcriptionAryl hydrocarbon receptorHomo sapiens (human)
regulation of transcription by RNA polymerase IIAryl hydrocarbon receptorHomo sapiens (human)
xenobiotic metabolic processAryl hydrocarbon receptorHomo sapiens (human)
apoptotic processAryl hydrocarbon receptorHomo sapiens (human)
response to xenobiotic stimulusAryl hydrocarbon receptorHomo sapiens (human)
response to toxic substanceAryl hydrocarbon receptorHomo sapiens (human)
regulation of gene expressionAryl hydrocarbon receptorHomo sapiens (human)
cAMP-mediated signalingAryl hydrocarbon receptorHomo sapiens (human)
intracellular receptor signaling pathwayAryl hydrocarbon receptorHomo sapiens (human)
regulation of B cell proliferationAryl hydrocarbon receptorHomo sapiens (human)
circadian regulation of gene expressionAryl hydrocarbon receptorHomo sapiens (human)
negative regulation of DNA-templated transcriptionAryl hydrocarbon receptorHomo sapiens (human)
positive regulation of DNA-templated transcriptionAryl hydrocarbon receptorHomo sapiens (human)
positive regulation of transcription by RNA polymerase IIAryl hydrocarbon receptorHomo sapiens (human)
negative regulation of inflammatory responseAryl hydrocarbon receptorHomo sapiens (human)
cellular response to molecule of bacterial originAryl hydrocarbon receptorHomo sapiens (human)
cellular response to cAMPAryl hydrocarbon receptorHomo sapiens (human)
cellular response to forskolinAryl hydrocarbon receptorHomo sapiens (human)
cellular response to 2,3,7,8-tetrachlorodibenzodioxineAryl hydrocarbon receptorHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (16)

Processvia Protein(s)Taxonomy
nuclear receptor activityAryl hydrocarbon receptorHomo sapiens (human)
transcription cis-regulatory region bindingAryl hydrocarbon receptorHomo sapiens (human)
DNA-binding transcription factor activity, RNA polymerase II-specificAryl hydrocarbon receptorHomo sapiens (human)
cis-regulatory region sequence-specific DNA bindingAryl hydrocarbon receptorHomo sapiens (human)
TFIID-class transcription factor complex bindingAryl hydrocarbon receptorHomo sapiens (human)
transcription coactivator bindingAryl hydrocarbon receptorHomo sapiens (human)
DNA bindingAryl hydrocarbon receptorHomo sapiens (human)
DNA-binding transcription factor activityAryl hydrocarbon receptorHomo sapiens (human)
nuclear receptor activityAryl hydrocarbon receptorHomo sapiens (human)
protein bindingAryl hydrocarbon receptorHomo sapiens (human)
TBP-class protein bindingAryl hydrocarbon receptorHomo sapiens (human)
protein homodimerization activityAryl hydrocarbon receptorHomo sapiens (human)
protein heterodimerization activityAryl hydrocarbon receptorHomo sapiens (human)
Hsp90 protein bindingAryl hydrocarbon receptorHomo sapiens (human)
RNA polymerase II-specific DNA-binding transcription factor bindingAryl hydrocarbon receptorHomo sapiens (human)
E-box bindingAryl hydrocarbon receptorHomo sapiens (human)
sequence-specific double-stranded DNA bindingAryl hydrocarbon receptorHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (10)

Processvia Protein(s)Taxonomy
nucleusAryl hydrocarbon receptorHomo sapiens (human)
nuclear aryl hydrocarbon receptor complexAryl hydrocarbon receptorHomo sapiens (human)
nucleusAryl hydrocarbon receptorHomo sapiens (human)
nucleoplasmAryl hydrocarbon receptorHomo sapiens (human)
cytoplasmAryl hydrocarbon receptorHomo sapiens (human)
cytosolAryl hydrocarbon receptorHomo sapiens (human)
chromatinAryl hydrocarbon receptorHomo sapiens (human)
transcription regulator complexAryl hydrocarbon receptorHomo sapiens (human)
protein-containing complexAryl hydrocarbon receptorHomo sapiens (human)
cytosolic aryl hydrocarbon receptor complexAryl hydrocarbon receptorHomo sapiens (human)
aryl hydrocarbon receptor complexAryl hydrocarbon receptorHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (1)

Assay IDTitleYearJournalArticle
AID39064Affinity on cytosolic Aromatic hydrocarbon receptor (Ah)1997Journal of medicinal chemistry, Dec-19, Volume: 40, Issue:26
Three-dimensional quantitative structure-activity relationships from molecular similarity matrices and genetic neural networks. 2. Applications.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (97)

TimeframeStudies, This Drug (%)All Drugs %
pre-199022 (22.68)18.7374
1990's20 (20.62)18.2507
2000's32 (32.99)29.6817
2010's23 (23.71)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 19.18

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be moderate demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index19.18 (24.57)
Research Supply Index4.61 (2.92)
Research Growth Index4.48 (4.65)
Search Engine Demand Index18.60 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (19.18)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials1 (1.02%)5.53%
Reviews4 (4.08%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other93 (94.90%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]