Page last updated: 2024-11-05

benzo(a)pyrene 7,8-dihydrodiol

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

Description

benzo(a)pyrene 7,8-dihydrodiol: RN given refers to cpd without isomeric designation [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID25892
CHEBI ID34562
SCHEMBL ID6735412
MeSH IDM0067839

Synonyms (16)

Synonym
benzo(a)pyrene-7,8-dihydrodiol
7,8-diol-benzo(a)pyrene
ccris 789
benzo(a)pyrene 7,8-dihydrodiol
benzo(a)pyrene, 7,8-dihydro-7,8-dihydroxy-
benzo(a)pyrene 7,8-diol
bp-7,8-dihydrodiol
benzo[a]pyrene-7,8-dihydrodiol
13345-25-0
7,8-dihydroxy-7,8-dihydrobenzo(a)pyrene
7,8-dihydrobenzo[a]pyrene-7,8-diol
SCHEMBL6735412
CHEBI:34562
7,8-dihydrobenzo[pqr]tetraphene-7,8-diol
DTXSID70928121
Q26840851

Research Excerpts

Toxicity

ExcerptReferenceRelevance
" GSH inhibited the mutagenicity at low (essentially non-lethal) concentrations of BP-diol, but did not do so at toxic concentrations."( Modulation of the cytotoxicity and mutagenicity of benzo[a]pyrene and benzo[a]pyrene 7,8-diol by glutathione and glutathione S-transferases in mammalian cells (CHO/HGPRT assay).
Hsie, AW; Recio, L, 1987
)
0.27
" (±)-anti-BPDE and B[a]P-7,8-trans-dihydrodiol, an intermediate in (±)-anti-BPDE metabolism, are toxic to A549 cells at concentrations with an IC(50) of ∼2 μM."( Aldo-keto reductases protect lung adenocarcinoma cells from the acute toxicity of B[a]P-7,8-trans-dihydrodiol.
Abedin, Z; Field, J; Sen, S, 2012
)
0.38

Bioavailability

ExcerptReferenceRelevance
"Intestinal metabolism plays a significant role in the bioavailability of ingested environmental toxicants."( Sulfation and glucuronidation of benzo[a]pyrene-7,8-dihydrodiol in intestinal mucosa of channel catfish (Ictalurus punctatus).
James, MO; van den Hurk, P,
)
0.13
"Biotransformation in the intestine may influence the bioavailability and toxicity of ingested xenobiotics."( Properties and regional expression of a CYP3A-like protein in channel catfish intestine.
Celander, MC; James, MO; Lou, Z; Rowland-Faux, L, 2005
)
0.33

Dosage Studied

ExcerptRelevanceReference
" The retention in tissues, extent of DNA adduct formation in liver and intestine, and metabolite composition of bile was investigated in southern flounder following gavage with pure [3H]- or [14C]benzo[a]pyrene (BaP), pure [14C]benzo[a]pyrene-7,8-dihydrodiol (BaP-7,8D), or hepatopancreas from spiny lobsters previously dosed with [3H]- or [14C]BaP (Metab."( Southern flounder hepatic and intestinal metabolism and DNA binding of benzo[a]pyrene (BaP) metabolites following dietary administration of low doses of BaP, BaP-7,8-dihydrodiol or a BaP metabolite mixture.
Altman, AH; Boyle, SM; Cromer, EA; James, MO; Schell, JD, 1991
)
0.28
" Similarly, sum total of free (+)-anti-benzo[a]pyrene-7,8-dihydrodiol-9,10-epoxide, glutathione conjugates and DNA-bound metabolites formed from precursor (-)-7R-trans-benzo[a]pyrene-7,8-dihydrodiol showed marked reduction in both the male and female ferrets after ETS exposure in a dose-response manner."( Depression of hepatic cytochrome P450 monooxygenases after chronic environmental tobacco smoke exposure of young ferrets.
Fujita, I; Kikkawa, Y; Rasmussen, RE; Sindhu, RK; Yamamoto, R, 1995
)
0.29
" Dose-response studies demonstrated that curcumin concentrations of >or=25 micro M were cytotoxic for oral SCC cells."( Curcumin activates the aryl hydrocarbon receptor yet significantly inhibits (-)-benzo(a)pyrene-7R-trans-7,8-dihydrodiol bioactivation in oral squamous cell carcinoma cells and oral mucosa.
Fields, HW; Mallery, SR; Morse, MA; Pei, P; Renner, RJ; Rinaldi, AL; Rodrigo, KA; Rothas, DA, 2002
)
0.31
" Inhibition of genotoxicity by spinach and peaches was not caused by any delay in maturation of micronucleated erythrocytes as shown by experiments with sampling times of 24, 48, and 72 h after dosing of BaP."( Inhibition of clastogenicity of benzo[a]pyrene and of its trans-7,8-dihydrodiol in mice in vivo by fruits, vegetables, and flavonoids.
Edenharder, R; Köttgen, V; Krieg, H; Platt, KL, 2003
)
0.32
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
pyrenes
[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]

Research

Studies (196)

TimeframeStudies, This Drug (%)All Drugs %
pre-1990108 (55.10)18.7374
1990's56 (28.57)18.2507
2000's27 (13.78)29.6817
2010's5 (2.55)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: 17.74

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 Index17.74 (24.57)
Research Supply Index5.37 (2.92)
Research Growth Index4.03 (4.65)
Search Engine Demand Index15.26 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (17.74)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews4 (1.87%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other210 (98.13%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]