Page last updated: 2024-11-05

diepoxybutane

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

Description

diepoxybutane: difunctional alkylating agent; RN given refers to cpd with unspecified isomeric designation; structure [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID11254
CHEMBL ID1964283
CHEBI ID23704
MeSH IDM0050523

Synonyms (72)

Synonym
2,2'-bioxirane, (r*,r*)-(.+/-.)-
butane, 1,2:3,4-diepoxy-, (.+/-.)-
564-00-1
NCI60_009412
298-18-0
d,l-diepoxybutane
einecs 215-979-1
brn 0079833
threitol, 1,2:3,4-dianhydro-
1,2:3,4-diepoxybutane
1,2:3,4-butadiene diepoxide
ent-26592
1,3-butadiene diepoxide
ccris 234
butadiendioxyd [german]
nsc 629
d,l-1,2:3,4-diepoxybutane
rcra waste number u085
1,2,3,4-diepoxybutane
1,1'-bi(ethylene oxide)
rcra waste no. u085
ai3-26592
hsdb 4046
butane, 1,2:3,4-diepoxy-
CHEBI:23704 ,
butadiendioxyd
1,2:3,4-dianhydrothreitol
nsc629
dioxybutadiene
wln: t3otj b- bt3otj
m 8838
1,1'-bi[ethylene oxide]
2,4-diepoxybutane
diepoxybutane
r 181
cb 1181
butadiene diepoxide ,
1,4-diepoxybutane
threitol,2:3,4-dianhydro-
butane diepoxide
2,2'-bioxirane
1464-53-5
bioxiran
butadiene dioxide
nsc-629
butane,2:3,4-diepoxy-
1,3,4-diepoxybutane
erythrithol anhydride (old name); 1,3-butadiene diepoxide
bioxirane
1,3-butadiene diepoxide, 97%
1,2,3,4-diepoxybutane dl
D3410
zfivkaoqexoyfy-uhfffaoysa-
inchi=1/c4h6o2/c1-3(5-1)4-2-6-4/h3-4h,1-2h2
2-(oxiran-2-yl)oxirane
5-19-01-00185 (beilstein handbook reference)
60ob65ynab ,
unii-60ob65ynab
B0234
FT-0606590
AKOS017342854
J-503880
J-640017
CHEMBL1964283
DTXSID0041307
J-800012
5-(dimetnmet)furfuryl alcohol hcl
1,3-butadiene diepoxide, analytical standard
Q5274970
(a+/-)-1,2;3,4-diepoxy-butane
2,2 inverted exclamation marka-bioxirane
CS-0377906

Research Excerpts

Overview

Diepoxybutane is a bifunctional alkylating agent and reacts with DNA to form monoadducts and cross-links. It is an important metabolite of 1,3-butadiene (BD), a high-volume industrial chemical classified as a probable human carcinogen.

ExcerptReferenceRelevance
"Diepoxybutane (DEB) is an alkylating agent that can be used to assess chromosome instability in repair-deficient subjects. "( Role of haemoglobin in the protection of cultured lymphocytes against diepoxybutane (DEB), assessed by in vitro induced chromosome breakage.
Chiecchio, L; Faber, A; Gaspar, J; Malheiro, I; Pinho, L; Porto, B; Rueff, J, 2003
)
2
"Diepoxybutane (DEB) is an established mutagen that induces chromosome damage following in vitro treatment of peripheral blood lymphocytes. "( The role of foetal red blood cells in protecting cultured lymphocytes against diepoxybutane-induced chromosome breaks.
Carvalho, F; Gaspar, J; Malheiro, I; Oliveira, RJ; Porto, B; Rueff, J; Sousa, C, 2006
)
2
"Diepoxybutane is a bifunctional alkylating agent and reacts with DNA to form monoadducts and cross-links."( Biomonitoring of exposure to 1,3-butadiene: detection by high-performance liquid chromatography and 32P-postlabelling of an adenine adduct formed by diepoxybutane.
Jones, NJ; Kostiainen, R; Leuratti, C; Marafante, E; Peltonen, K; Waters, R, 1993
)
1.21
"Diepoxybutane (DEB) is an important metabolite of 1,3-butadiene (BD), a high-volume industrial chemical classified as a probable human carcinogen. "( Synthesis, characterization, and in vitro quantitation of N-7-guanine adducts of diepoxybutane.
Sangaiah, R; Swenberg, JA; Yen, TY, 1997
)
1.97

Effects

ExcerptReferenceRelevance
"Diepoxybutane (DEB) has been used to assess chromosome instability both in repair-deficient and normal subjects."( Effect of red cells and plasma blood in determining individual lymphocytes sensitivity to diepoxybutane assessed by in vitro induced sister chromatid exchanges.
Barale, R; Landi, S; Ponzanelli, I, 1995
)
1.23

Actions

ExcerptReferenceRelevance
"Diepoxybutane does not cause any significant increase in the frequency of apoptosis in rat testis."( Apoptotic response of spermatogenic cells to the germ cell mutagens etoposide, adriamycin, and diepoxybutane.
Lähdetie, J; Sjöblom, T; West, A, 1998
)
1.24

Toxicity

ExcerptReferenceRelevance
" All three compounds showed signs of toxicity, with DEB being substantially more toxic than either CEO or EB."( In vitro genotoxicity testing of (1-chloroethenyl)oxirane, a metabolite of beta-chloroprene.
Donner, EM; Gladnick, NL; Himmelstein, MW; Snyder, RD; Valentine, R, 2001
)
0.31

Pharmacokinetics

ExcerptReferenceRelevance
"In vitro and in vivo butadiene (BD) metabolism data from laboratory animals were integrated into a rodent physiologically based pharmacokinetic (PBPK) model with flow- and diffusion-limited compartments."( Physiologically based pharmacokinetic modeling of blood and tissue epoxide measurements for butadiene.
Himmelstein, MW; Medinsky, MA; Schlosser, PM; Sweeney, LM, 1996
)
0.29
" To achieve this objective, known pathways of 1,2-epoxy-3-butene (butadiene monoepoxide; BMO) and BDE metabolism were incorporated into a physiologically based pharmacokinetic model by scaling rates determined in vitro."( Physiologically based pharmacokinetic modeling of 1,3-butadiene, 1,2-epoxy-3-butene, and 1,2:3,4-diepoxybutane toxicokinetics in mice and rats.
Bond, JA; Medinsky, MA; Schlosser, PM; Sweeney, LM, 1997
)
0.51

Dosage Studied

ExcerptRelevanceReference
" The dose-response for BMO followed a second order curve at this time interval, with maximum MN induction at the dose of 186 mumol/kg and lower induction of higher doses."( Germ cell mutagenicity of three metabolites of 1,3-butadiene in the rat: induction of spermatid micronuclei by butadiene mono-, di-, and diolepoxides in vivo.
Lähdetie, J; Peltonen, K; Sjöblom, T, 1997
)
0.3
" For the BMO studies, rats were dosed with 71, 143, or 286 mumol/kg BMO (n = 3 for each dose group)."( Disposition of butadiene epoxides in Sprague-Dawley rats.
Bond, JA; Boogaard, PJ; Medinsky, MA; Sweeney, LM; Turner, MJ; Valentine, JL, 1997
)
0.3
" The methods developed in this work provide the means to study accumulation, repair and dose-response relationships of BD-DNA adducts in vivo."( Quantitative analysis of 1,3-butadiene-induced DNA adducts in vivo and in vitro using liquid chromatography electrospray ionization tandem mass spectrometry.
Chiang, SY; Swenberg, JA; Walker, VE, 1998
)
0.3
"The time-dependent dose-response relationships for the induction of DNA double-strand breaks (DSB) assessed by pulsed-field gel electrophoresis (PFGE) and for viability (evaluated by the MTT cytotoxicity test) were investigated in order to discriminate between genotoxic and cytotoxic mechanisms of DNA fragmentation."( Discrimination between genotoxicity and cytotoxicity for the induction of DNA double-strand breaks in cells treated with aldehydes and diepoxides.
Ilinskaya, O; Lutz, WK; Vamvakas, S; Vock, EH, 1999
)
0.3
" The dose-response for mutations induced at the cII locus was essentially equal after DEB exposure of BBM1 and BBR1 fibroblasts."( Micronuclei and gene mutations in transgenic big Blue((R)) mouse and rat fibroblasts after exposure to the epoxide metabolites of 1, 3-butadiene.
Erexson, GL; Tindall, KR, 2000
)
0.31
" Finally, the dose-response study in sperm indicated a linear response for both single and repeated exposures."( DNA repair decline during mouse spermiogenesis results in the accumulation of heritable DNA damage.
Marchetti, F; Wyrobek, AJ, 2008
)
0.35
" In HL60 cells exposed for 3 h to 0-10 μM DEB, overlapping dose-response curves suggested a direct relationship between 1,4-bis-(guan-7-yl)-2,3-butanediol crosslink adduct formation (R = 0."( 1,3-Butadiene metabolite 1,2,3,4 diepoxybutane induces DNA adducts and micronuclei but not t(9;22) translocations in human cells.
Albertini, RJ; Carter, EW; Degner, A; Nicklas, JA; Tretyakova, N; Walker, DM; Walker, VE, 2019
)
0.8
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (1)

RoleDescription
mutagenAn agent that increases the frequency of mutations above the normal background level, usually by interacting directly with DNA and causing it damage, including base substitution.
[role 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]

Drug Classes (1)

ClassDescription
epoxideAny cyclic ether in which the oxygen atom forms part of a 3-membered ring.
[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 (375)

TimeframeStudies, This Drug (%)All Drugs %
pre-199088 (23.47)18.7374
1990's131 (34.93)18.2507
2000's107 (28.53)29.6817
2010's44 (11.73)24.3611
2020's5 (1.33)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 29.57

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 Index29.57 (24.57)
Research Supply Index5.96 (2.92)
Research Growth Index4.44 (4.65)
Search Engine Demand Index38.40 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (29.57)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials3 (0.79%)5.53%
Reviews9 (2.36%)6.00%
Case Studies11 (2.88%)4.05%
Observational0 (0.00%)0.25%
Other359 (93.98%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]