Page last updated: 2024-11-04

mercaptoethanol

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

Description

Mercaptoethanol: A water-soluble thiol derived from hydrogen sulfide and ethanol. It is used as a reducing agent for disulfide bonds and to protect sulfhydryl groups from oxidation. [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID1567
CHEMBL ID254951
CHEBI ID41218
MeSH IDM0013443

Synonyms (102)

Synonym
2-mercaptoethyl alcohol
.beta.-hydroxyethylmercaptan
usaf ek-4196
2-hydroxyethyl mercaptan
nsc-3723
2-thioethanol
thiomonoglycol
thioethylene glycol
2-hydroxyethanethiol
2-hydroxy-1-ethanethiol
ethylene glycol, monothio-
.beta.-mercaptoethanol
2-mercapto-1-ethanol
monothioglycol
nsc3723
ethanol, 2-mercapto-
hydroxyethyl mercaptan
2-me
1-hydroxy-2-mercaptoethane
.beta.-hydroxyethanethiol
wln: sh2q
1-mercapto-2-hydroxyethane
1-ethanol-2-thiol
monothioethylene glycol
KBIO1_000784
DIVK1C_000784
einecs 200-464-6
un2966
brn 0773648
beta-hydroxyethanethiol
hsdb 5199
beta-hydroxyethylmercaptan
emery 5791
nsc 3723
ccris 2097
ai3-07710
mercaptoetanol
monothioethyleneglycol
2-sulfanylethan-1-ol
bdbm7971
BME ,
beta-mercaptoethanol
2-sulfanylethanol
IDI1_000784
inchi=1/c2h6os/c3-1-2-4/h3-4h,1-2h
mercaptoethanol
2-mercaptoethanol ,
60-24-2
C00928
thioglycol
2-mercaptoethanol, for electrophoresis
2-mercaptoethanol, for molecular biology, for electrophoresis, suitable for cell culture, bioreagent, 99% (gc/titration)
CHEBI:41218 ,
DB03345
NINDS_000784
b-mercaptoethanol
hydroxyethyl sulfide
2-mercaptoethanol, bioultra, for molecular biology, >=99.0% (gc)
2-mercaptoethanol, >=99.0%
M1948
CHEMBL254951
AKOS000118900
2-hydroxyethylmercaptan
HMS502H06
M0058
A832651
4-01-00-02428 (beilstein handbook reference)
ec 200-464-6
thioglycol [un2966] [poison]
unii-14r9k67urn
14r9k67urn ,
|a-mercaptoethanol
cuprate(6-), [.mu.-[[2,2'-[(1-methyl-1,2-ethanediyl)bis[imino(6-fluoro-1,3,5-triazine-4,2-diyl)imino[2-(hydroxy-.kappa.o)-5-sulfo-3,1-phenylene](2,1-diazenediyl-.kappa.n2)(phenylmethylene)-2,1-diazenediyl-.kappa.n1]]bis[4-sulfobenzoato-.kappa.o]](10-)]]di
155613-89-1
2-mercaptoethanol [mi]
fema no. 4582
BP-21398
un 2966
2-sulfanylethanol #
2-sulfanyl-ethanol
2-mercapto-ethanol
mercaptoethyl alcohol
2mercaptoethanol
2-hydroxy-ethanethiol
2-mercaptoethan-1-ol
2-mercapto ethanol
hsch2ch2oh
Q-200296
DTXSID4026343 ,
STL482546
F0001-1577
CCG-231050
2-mercaptoethanol, for hplc derivatization, >=99.0% (gc)
mfcd00004890
2-mercaptoethanol, saj special grade, >=99.0%
2-mercaptoethanol, for synthesis, 99.0%
Q411084
cuprate(6-), .mu.-2,2-(1-methyl-1,2-ethanediyl)bisimino(6-fluoro-1,3,5-triazine-4,2-diyl)imino(2-hyd
beta-sulfanylethanol
beta -mercaptoethanol
EN300-19346
Z104473584

Research Excerpts

Overview

2-Mercaptoethanol is considered to be an important "off-flavor" in dry wines. 2-chlorothioxanthone is a suitable internal standard.

ExcerptReferenceRelevance
"2-Mercaptoethanol, considered to be an important "off-flavor" in dry wines, also decreased during the experimental period (54 days) in the presence of O(2), and the respective disulfide was formed."( Influence of some technological parameters on the formation of dimethyl sulfide, 2-mercaptoethanol, methionol, and dimethyl sulfone in port wines.
Guedes De Pinho, P; Hogg, T; Rodrigues, P; Silva Ferreira, AC, 2003
)
1.1
"2-Mercaptoethanol is a useful stabilizer, and 2-chlorothioxanthone is a suitable internal standard."( High-speed liquid chromatographic determination of phenylpyruvic acid.
Hayashi, T; Kawai, S; Ohno, T; Sugiura, T; Terada, H, 1976
)
0.81

Effects

2-Mercaptoethanol (2-ME) has been shown to improve maturation and embryo development in different species. 2-ME has a beneficial effect on the mean life span of laboratory rodents.

ExcerptReferenceRelevance
"2-Mercaptoethanol (2-ME) has a beneficial effect on the mean life span of laboratory rodents. "( Effect of 2-mercaptoethanol on posthypoxic and age-related biochemical and behavioural changes in mice and rats.
Fischer, HD; Jähkel, M; Oehler, J; Pénzes, L; Rostock, A; Rudolph, E; Siegemund, C; Wustmann, C, 1990
)
1.38
"Beta-mercaptoethanol (BME) has been shown to improve maturation and embryo development in different species."( Beta-mercaptoethanol supplementation of in vitro maturation medium does not influence nuclear and cytoplasmic maturation of equine oocytes.
Bucci, D; Galeati, G; Iacono, E; Mari, G; Merlo, B; Spinaci, M, 2016
)
1.4
"2-Mercaptoethanol (2-ME) has a beneficial effect on the mean life span of laboratory rodents. "( Effect of 2-mercaptoethanol on posthypoxic and age-related biochemical and behavioural changes in mice and rats.
Fischer, HD; Jähkel, M; Oehler, J; Pénzes, L; Rostock, A; Rudolph, E; Siegemund, C; Wustmann, C, 1990
)
1.38

Actions

Mercaptoethanol was found to lower by 3 per cent the activity of semen alkaline phosphatase. 2-MercaptoEthanol was also found to inhibit biotin transport.

ExcerptReferenceRelevance
"Mercaptoethanol was found to lower by 3 per cent the activity of semen alkaline phosphatase."( [Effect of biologically active substances on the alkaline phosphatase activity, viability and fertility of bull spermatozoa].
Al-Hanak, H; Iotova, M; Kichev, G; Marinov, MF; Zakhariev, Z, 1983
)
0.99
"2-Mercaptoethanol was found to inhibit biotin transport."( Biotin uptake by cold-shocked cells, spheroplasts, and repressed cells of Saccharomyces cerevisiae: lack of feedback control.
Cicmanec, JF; Lichstein, HC, 1974
)
0.81

Treatment

Mercaptoethanol (2ME) treatment brought the density of the material of P from old mice back to the levels of young mice. Treatment of big growth hormone (GH) obtained from human pituitary resulted in a 60% conversion to small GH.

ExcerptReferenceRelevance
"Mercaptoethanol treatment reduced the expression levels of NFE2L2, NF-κB, p65, TNF-α, IL-1β and increased the expression levels of SOD1, MMP9, and GCLC."( Mercaptoethanol Protects the Aorta from Dissection by Inhibiting Oxidative Stress, Inflammation, and Extracellular Matrix Degeneration in a Mouse Model.
Li, D; Wang, C; Xi, Z; Xu, Z; Zhang, L, 2018
)
2.64
"2-Mercaptoethanol (2ME) treatment brought the density of the material of P from old mice back to the levels of young mice."( Disulfide bonds and the structure of the chromatin complex in relation to aging.
Tam, CF; Tas, S; Walford, RL, 1980
)
0.82
"Mercaptoethanol-treated cells contain an abundance of mitochondria."( Effect of thiols on macroconidia of Fusarium sulphureum.
Barran, LR; Schneider, EF, 1979
)
0.98
"Mercaptoethanol treatment of big growth hormone (GH) obtained from human pituitary resulted in a 60% conversion to small GH. "( Big growth hormone (GH): conversion to small GH without peptide bond cleavage.
Benveniste, R; Frohman, LA; Stachura, ME; Szabo, M, 1975
)
1.7
"By treatment with mercaptoethanol, these particles were drastically damaged, and in some cases the internal substances were partially released, producing empty inner membranes of various degrees of disintegration."( Separation and structure of components of nuclear polyhedrosis virus of the silkworm.
Himeno, M; Khosaka, T; Onodera, K, 1971
)
0.57

Toxicity

ExcerptReferenceRelevance
"When added to Eagle's Minimum Essential Medium supplemented with 10% bovine serum (MEM-10BS), 1mM cysteine was highly toxic to cultured cells."( Cytotoxicity of cysteine in culture media.
Nakayasu, M; Nishiuch, Y; Oikawa, A; Sasaki, M, 1976
)
0.26
" We observed this acute toxic effect despite the administration of sufficient mesna to prevent hemorrhagic cystitis."( Ifosfamide-induced subclinical tubular nephrotoxicity despite mesna.
Goren, MP; Horowitz, ME; Pratt, CB; Wright, RK, 1987
)
0.27
" These negative attributes may be caused by toxic and genotoxic metabolites, respectively."( In vitro/in vivo effects of Mesna on the genotoxicity and toxicity of cyclophosphamide--a study aimed at clarifying the mechanism of Mesna's anticarcinogenic activity.
Bos, RP; Niemeyer, U; Pool, BL; Schmähl, D; Theuws, JL, 1988
)
0.27
" Serum ALT levels were measured at 24 hours after a toxic but nonlethal dose of ACP that insured 48 hour survival of the animals."( Protection against acetaminophen-induced hepatotoxicity by L-CySSME and its N-acetyl and ethyl ester derivatives.
Cohen, JF; Nagasawa, HT; Rathbun, WB; Shoeman, DW, 1996
)
0.29
"Of all the bioassays to determine acute toxicity described in the literature, those that employ bacteria as indicator organisms are usually the most rapid and the most economic, although alone they cannot predict the possible toxic effect of any type of substance."( A trial to compare the effects of pH, buffer concentration, and NaCl, on one fluorescent and two bioluminescent bacterial tests for acute toxicity.
Carnero, M; Fernández-Crehuet, J; Gómez-Aracena, J; Mariscal, A, 1997
)
0.3

Pharmacokinetics

ExcerptReferenceRelevance
" mesna administration, the mean half-life of mesna was 21."( Pharmacokinetics of intravenous and oral sodium 2-mercaptoethane sulphonate (mesna) in normal subjects.
James, CA; Mant, TG; Rogers, HJ, 1987
)
0.27
" On the other hand, pharmacokinetic parameters of AMA did not significantly change."( Simultaneous determination of amantadine and rimantadine by HPLC in rat plasma with pre-column derivatization and fluorescence detection for pharmacokinetic studies.
Fujii, Y; Higashi, Y; Uemori, I, 2005
)
0.33
"To develop and validate a novel precolumn derivatization method for the quantitative determination and pharmacokinetic application of acetylshikonin in macaque monkeys by liquid chromatography-electrospray ionization tandem mass spectrometry (LC-ESI-MS/MS)."( Quantitative determination of acetylshikonin in macaque monkey blood by LC-ESI-MS/MS after precolumn derivatization with 2-mercaptoethanol and its application in pharmacokinetic study.
Dou, GF; Du, A; Gu, RL; Meng, ZY; Sun, DX; Tian, HF; Wu, ZN; Yuan, D, 2008
)
0.55
" After the administration of acetylshikonin (80 mg/kg, po) in macaque monkeys, the pharmacokinetic parameters were obtained through the non-compartmental analysis, where the area under the concentration-time curve to the last measurable concentration, the terminal elimination halflife, and the mean residual time were 615."( Quantitative determination of acetylshikonin in macaque monkey blood by LC-ESI-MS/MS after precolumn derivatization with 2-mercaptoethanol and its application in pharmacokinetic study.
Dou, GF; Du, A; Gu, RL; Meng, ZY; Sun, DX; Tian, HF; Wu, ZN; Yuan, D, 2008
)
0.55
"The method was validated and applied to the quantitative determination and pharmacokinetic study of acetylshikonin in the blood samples of macaque monkeys."( Quantitative determination of acetylshikonin in macaque monkey blood by LC-ESI-MS/MS after precolumn derivatization with 2-mercaptoethanol and its application in pharmacokinetic study.
Dou, GF; Du, A; Gu, RL; Meng, ZY; Sun, DX; Tian, HF; Wu, ZN; Yuan, D, 2008
)
0.55

Bioavailability

ExcerptReferenceRelevance
" The bioavailability of ifosfamide after oral administration exceeds 95%."( Ifosfamide and mesna.
Dana, WJ; Schoenike, SE, 1990
)
0.28
" The bioavailability of oral MESNA is in the range of 20-50% and its unpleasant taste severely limits patient compliance."( [Urinary bioavailability of sodium-2-mercaptoethanesulfonate (Uromitexan) following intravenous, subcutaneous and continuous subcutaneous administration].
Brunner, KW; Cerny, T; Küpfer, A; Roth, B, 1989
)
0.28
"The bioavailability of orally administered sodium 2-mercaptoethane sulfonate (mesna, Uromitexan drink ampoules) was tested in 18 healthy probands and in 5 tumor patients."( Bioavailability of orally administered mesna.
Breuel, HP; Burkert, H; Lücker, PW; Wetzelsberger, N, 1984
)
0.27
" In-vitro studies have demonstrated that homocysteine decreases the production or bioavailability of vasodilator autacoids, such as prostacyclin and NO."( Homocysteine decreases endothelin-1 production by cultured human endothelial cells.
Atger, V; Benoit, MO; Borderie, D; Demuth, K; Lotersztajn, S; Moatti, N; Sauvaget, D, 1999
)
0.3
"Reduced nitric oxide bioavailability caused by endothelial dysfunction or damage is a contributory factor in the initiation and progression of a number of cardiovascular diseases."( A novel S-nitrosothiol (RIG200) causes prolonged relaxation in dorsal hand veins with damaged endothelium.
Khan, SQ; MacCallum, H; Megson, IL; Newby, DE; Sogo, N; Strachan, FE; Webb, DJ; Wilkinson, IB, 2000
)
0.31
" Bioavailability of AMA and RIM was 34."( Simultaneous determination of amantadine and rimantadine by HPLC in rat plasma with pre-column derivatization and fluorescence detection for pharmacokinetic studies.
Fujii, Y; Higashi, Y; Uemori, I, 2005
)
0.33
" The following study addressed the hypothesis that neuropeptide Y bioavailability is blunted in female rats under baseline conditions."( Neuropeptide Y bioavailability is suppressed in the hindlimb of female Sprague-Dawley rats.
Jackson, DN; Milne, KJ; Noble, EG; Shoemaker, JK, 2005
)
0.33
"Due to the poor solubility and bioavailability of 2-methoxyestradiol (2-ME), 2-ME emulsified drug delivery system (2-ME-SEDDS) was designed and characterized."( Preparation of 2-Methoxyestradiol Self-emulsified Drug Delivery System and the Effect on Combination Therapy with Doxorubicin Against MCF-7/ADM Cells.
He, S; Li, C; Li, T; Pan, H; Yu, C, 2022
)
0.72
" However, its poor bioavailability and rapid degradation hinder its development for clinical use."( PEGylated Polymeric Nanoparticles Loaded with 2-Methoxyestradiol for the Treatment of Uterine Leiomyoma in a Patient-Derived Xenograft Mouse Model.
Borahay, MA; Bujalowski, PJ; Enazy, SA; Kilic, G; Kirschen, GW; Motamedi, M; Oberhauser, AF; Rytting, E; Saada, J; Salama, SA; Shah, M; Vincent, K; Yang, J, 2023
)
0.91

Dosage Studied

Ramiprilat or mercaptoethanol induced leftward shifts in the BK dose-response curve. 2-MEt, a sulfhydryl reagent, produced a leftward displacement (potentiation) of the dose- response curves.

ExcerptRelevanceReference
" Propranolol, a beta-adrenergic antagonist, when administered at a dosage of 20 mg/kg of body weight, enhanced both passive hemagglutinating and IgE (passive cutaneous anaphylaxis) antibody formation."( Enhancement of IgE antibody formation in the rabbit by adrenergic antagonists.
Cain, WA; Homer, JT, 1979
)
0.26
" This view is supported by the following facts: (a) mersalyl acted with a similar dose-response curve upon an intact as well as a detergent-dispersed cyclase preparation while no effect was observed upon a solubilized Mg2+-ATPase preparation; (b) a covalent p-chloromercuribenzoate-Sephadex preparation (but not its supernatant) inhibited the cyclase from intact membranes."( Adenylate cyclase from rat-liver plasma membrane: inhibition by mersalyl and other mercurial derivatives.
Hanoune, J; Mavier, P, 1975
)
0.25
" The optimal conditions for an effect of the thymus factor are quantitatively defined by kinetic and dose-response studies."( Amplification of the proliferative response to alloantigen by a factor present in an extract of syngeneic thymic lymphoid cells: demonstration of optimal conditions and target cell for factor activity.
Loop, SM; Wright, PW, 1979
)
0.26
" 2-ME evoked a proliferative response in cultures of congenitally athymic (nu/nu) spleen cells that exhibited a similar but lower dose-response profile compared with that of heterozygous (nu/+) littermates."( Nonspecific activation of murine lymphocytes. I. Proliferation and polyclonal activation induced by 2-mercaptoethanol and alpha-thioglycerol.
Goodman, MG; Weigle, WO, 1977
)
0.47
"A colony assay available for a subpopulation of acute myeloblastic leukemia blasts with proliferative potential was used to measure adriamycin (adria) and daunorubicin (dauno) dose-response curves following brief exposure to either drug and washing."( Cytotoxicity of adriamycin and daunorubicin for normal and leukemia progenitor cells of man.
Buick, RN; McCulloch, EA; Messner, HA; Till, JE, 1979
)
0.26
"The chemistry, pharmacology, pharmacokinetics, and adverse effects of ifosfamide and mesna are described separately, followed by a discussion of the adverse effects of concurrent ifosfamide and mesna, the clinical spectrum of ifosfamide, and the dosage and administration of the two drugs."( Ifosfamide and mesna.
Dana, WJ; Schoenike, SE, 1990
)
0.28
"One hundred and forty-six patients with advanced malignant disease were treated with 6 different dosage schedules of ifosfamide (IFX)."( Ifosfamide and mesna in the treatment of malignant disease mesna as urothelial protector.
Falkson, CI; Falkson, G; Falkson, HC, 1989
)
0.28
" Only dilutions giving results in the linear part of the dose-response curve should be considered for titre calculations."( Evaluation of different calculation methods for anti-HBs titration.
Vranckx, RP, 1989
)
0.28
" Following oral mesna dosing the mean peak mesna concentration was 19."( Pharmacokinetics of intravenous and oral sodium 2-mercaptoethane sulphonate (mesna) in normal subjects.
James, CA; Mant, TG; Rogers, HJ, 1987
)
0.27
"45 mmol/l) the otherwise bell-shaped dose-response curve for conditioned medium changed to a sigmoid curve."( Vitamin C and thiol reagents promote the in vitro growth of murine granulocyte/macrophage progenitor cells by neutralizing endogenous inhibitor(s).
Helgestad, J; Lie, SO; Storm-Mathisen, I, 1986
)
0.27
" In addition, the induction by low dosage of beta-ME requires de novo protein synthesis and is preceded by a drop in the rate of protein glycosylation."( Regulation of the glucose-regulated protein genes by beta-mercaptoethanol requires de novo protein synthesis and correlates with inhibition of protein glycosylation.
Kim, KS; Kim, YK; Lee, AS, 1987
)
0.52
" Addition of accessory cells caused a shift in the dose-response curve, resulting in strongly enhanced IL2 production at low concentrations."( T cell triggering by lectins. I. Requirements for interleukin 2 production; lectin concentration determines the accessory cell dependency.
Aarden, LA; Brouwer, MC; Roosnek, EE, 1985
)
0.27
" Results showed that (a) population differences appeared by day 4 PPI and persisted through day 24 PPI, (b) regardless of population, peak titers occurred at about the same time for primary and secondary immunizations, (c) dosage of antigen influenced differences among populations in antibody response to primary immunization, and (d) both selected lines had similar responses in 2-mercaptoethanol-sensitive and 2-mercaptoethanol-resistant antibodies to primary but not secondary immunization."( Divergent selection of chickens for antibody response to sheep erythrocytes: kinetics of primary and secondary immunizations.
Dunnington, EA; Gross, WB; Siegel, PB; Ubosi, CO,
)
0.3
" Cytotoxicity was assessed by a quantitative (51)Cr assay system and the relative frequency of CTL in individual cell populations was estimated from dose-response curves."( Generation of cytotoxic T lymphocytes in vitro. I. Response of normal and immune mouse spleen cells in mixed leukocyte cultures.
Brunner, T; Cerottini, JC; Engers, HD; Macdonald, HR, 1974
)
0.25
" Cytotoxicity was assayed on (51)Cr-labeled P-815 (DBA/2) target cells, and the relative frequency of CTL in individual cell populations was estimated from dose-response curves."( Generation of cytotoxic T lymphocytes in vitro. II. Effect of repeated exposure to alloantigens on the cytotoxic activity of long-term mixed leukocyte cultures.
Brunner, KT; Cerottini, JC; Engers, HD; Macdonald, HR, 1974
)
0.25
" A dose-response study of plasma concentration and megakaryocyte growth, using plasma collected 11 days postirradiation, demonstrated that patterns of megakaryocyte growth were related to plasma concentration; formation of single megakaryocytes was optimal over a range of 20%-30% plasma concentration, while cluster and colony formation were optimal at a plasma concentration of 30%."( Increases in circulating megakaryocyte growth-promoting activity in the plasma of rats following whole body irradiation.
Jackson, CW; Lyles, SA; Miura, M, 1984
)
0.27
"The addition of 1 X 10(-3) M or 1 X 10(-2) M 2-mercaptoethanol (2-MEt), a sulfhydryl reagent, produced a leftward displacement (potentiation) of the dose-response curves of mesenteric arterial strips for histamine, norepinephrine, serotonin, angiotensin II, prostaglandin F2 alpha and KCl."( Alterations in pharmacological receptor activities of rabbit arteries by sulfhydryl reagents.
Asano, M; Hidaka, H, 1983
)
0.52
" A close correlation was observed between the enhancement of the response to lipopolysaccharide (LPS) and the mitogenic activities of these thiol compounds in their magnitude and dose-response profiles."( Activation of murine lymphocytes by 2-mercaptoethanol and related thiol compounds and its mechanism. I. Relationship between mitogenic activities and augmenting effects on antibody synthesis in vitro.
Ohmori, H; Yamamoto, I, 1981
)
0.53
" The addition of 10(-5) M 2-ME to cystine shifted the dose-response curve to lower concentrations by about one order of magnitude."( A mechanism of the augmentation of antibody response in vitro by 2-mercaptoethanol: facilitation of cystine uptake in murine lymphocytes.
Ohmori, H; Yamamoto, I, 1982
)
0.5
" Dose-response relationships to both SNAP and AP (0."( Vasodilator action of the S-nitrosothiol, SNAP, in rat isolated perfused lung.
Emery, CJ, 1995
)
0.29
" Dosage of SRBC had no effect on the antibody titres in line HA; however, the higher dosage elicited greater antibody titres than the lower dosage in line LA."( Antibody transmitting ability of hens from lines of chickens differing in response to SRBC antigen.
Boa-Amponsem, K; Dunnington, EA; Siegel, PB, 1997
)
0.3
" Ramiprilat or mercaptoethanol induced leftward shifts in the BK dose-response curve (EC(50)=3."( Potentiation of the vascular response to kinins by inhibition of myocardial kininases.
Dendorfer, A; Dominiak, P; Inamura, N; Schäfer, U; Stewart, JM; Wolfrum, S, 2000
)
0.66
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (1)

RoleDescription
geroprotectorAny compound that supports healthy aging, slows the biological aging process, or extends lifespan.
[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 (2)

ClassDescription
primary alcoholA primary alcohol is a compound in which a hydroxy group, -OH, is attached to a saturated carbon atom which has either three hydrogen atoms attached to it or only one other carbon atom and two hydrogen atoms attached to it.
alkanethiolAn alkanethiol is a compound in which a sulfanyl group, -SH, is attached to an alkyl group.
[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]

Pathways (65)

PathwayProteinsCompounds
Metabolism14961108
Biological oxidations150276
Phase II - Conjugation of compounds73122
Methylation1338
superpathway of hydrolyzable tannin biosynthesis023
chelerythrine biosynthesis1024
UDP-D-apiose biosynthesis (from UDP-D-glucuronate)110
sinapate ester biosynthesis221
raspberry ketone biosynthesis012
glucosinolate activation115
cornusiin E biosynthesis013
saponin biosynthesis II013
cichoriin interconversion013
hordatine biosynthesis113
sanguinarine and macarpine biosynthesis639
esculetin modification219
pentagalloylglucose biosynthesis012
superpathway of scopolin and esculin biosynthesis127
u03B1-tomatine biosynthesis417
solasodine glycosylation312
urea cycle633
chelerythrine biosynthesis823
sanguinarine and macarpine biosynthesis839
CMP-N-acetylneuraminate biosynthesis I (eukaryotes)738
esculetin modification221
superpathway of scopolin and esculin biosynthesis131
pyrimidine deoxyribonucleotides de novo biosynthesis II1030
pyrimidine deoxyribonucleotides de novo biosynthesis I3034
superpathway of methylglyoxal degradation1330
D-galactarate degradation I530
superpathway of L-lysine degradation33112
superpathway of microbial D-galacturonate and D-glucuronate degradation3592
geodin biosynthesis020
L-lysine fermentation to acetate and butanoate857
methylglyoxal degradation IV221
UDP-sugars interconversion1234
superpathway of demethylmenaquinol-8 biosynthesis I1133
N10-formyl-tetrahydrofolate biosynthesis1256
hordatine biosynthesis114
folate transformations I2241
superpathway of penicillin, cephalosporin and cephamycin biosynthesis1169
deacetylcephalosporin C biosynthesis444
thiosulfate disproportionation IV (rhodanese)510
ribitol degradation114
L-histidine biosynthesis1833
D-galactose degradation I (Leloir pathway)1046
L-threonine degradation II331
L-threonine degradation III (to methylglyoxal)328
u03B2-D-glucuronide and D-glucuronate degradation312
superpathway of u03B2-D-glucuronosides degradation1136
superpathway of L-citrulline metabolism1852
L-citrulline biosynthesis736
superpathway of CMP-sialic acids biosynthesis1460
alkylnitronates degradation350
raspberry ketone biosynthesis212
2-carboxy-1,4-naphthoquinol biosynthesis2129
superpathway of menaquinol-8 biosynthesis I1036
superpathway of chorismate metabolism56186
superpathway of D-glucarate and D-galactarate degradation637
cornusiin E biosynthesis014
superpathway of hydrolyzable tannin biosynthesis030
UDP-D-apiose biosynthesis (from UDP-D-glucuronate)116
L-ascorbate biosynthesis IV522
glycerol degradation II318
superpathway of glycerol degradation to 1,3-propanediol826
aminopropanol phosphate biosynthesis II328
D-galacturonate degradation I527
superpathway of hexuronide and hexuronate degradation838
saponin biosynthesis II017
superpathway of L-threonine metabolism2172
melibiose degradation114
superpathway of pyrimidine deoxyribonucleotides de novo biosynthesis4662
superpathway of pentose and pentitol degradation4661
lactose degradation III123
galactose degradation I (Leloir pathway)526

Protein Targets (1)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Glutaminyl-peptide cyclotransferaseMus musculus (house mouse)Ki2,580.00006.40006.40006.4000AID1796111
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (22)

Assay IDTitleYearJournalArticle
AID1128913Inhibition of metallo-beta-lactamase IMP-1 (unknown origin)2014European journal of medicinal chemistry, Apr-09, Volume: 76The applications of binuclear metallohydrolases in medicine: recent advances in the design and development of novel drug leads for purple acid phosphatases, metallo-β-lactamases and arginases.
AID314755Inhibition of carbonic anhydrase 9 assessed as residual activity at 2.5 mM2008Bioorganic & medicinal chemistry letters, Mar-15, Volume: 18, Issue:6
Carbonic anhydrase inhibitors: the very weak inhibitors dithiothreitol, beta-mercaptoethanol, tris(carboxyethyl)phosphine and threitol interfere with the binding of sulfonamides to isozymes II and IX.
AID314749Inhibition of carbonic anhydrase 9 assessed as residual activity at 0.1 mM2008Bioorganic & medicinal chemistry letters, Mar-15, Volume: 18, Issue:6
Carbonic anhydrase inhibitors: the very weak inhibitors dithiothreitol, beta-mercaptoethanol, tris(carboxyethyl)phosphine and threitol interfere with the binding of sulfonamides to isozymes II and IX.
AID314751Inhibition of carbonic anhydrase 9 catalytic domain assessed as residual activity at 1.0 mM2008Bioorganic & medicinal chemistry letters, Mar-15, Volume: 18, Issue:6
Carbonic anhydrase inhibitors: the very weak inhibitors dithiothreitol, beta-mercaptoethanol, tris(carboxyethyl)phosphine and threitol interfere with the binding of sulfonamides to isozymes II and IX.
AID314756Inhibition of carbonic anhydrase 2 assessed as residual activity at 10 mM2008Bioorganic & medicinal chemistry letters, Mar-15, Volume: 18, Issue:6
Carbonic anhydrase inhibitors: the very weak inhibitors dithiothreitol, beta-mercaptoethanol, tris(carboxyethyl)phosphine and threitol interfere with the binding of sulfonamides to isozymes II and IX.
AID314748Inhibition of carbonic anhydrase 9 catalytic domain assessed as residual activity at 0.1 mM2008Bioorganic & medicinal chemistry letters, Mar-15, Volume: 18, Issue:6
Carbonic anhydrase inhibitors: the very weak inhibitors dithiothreitol, beta-mercaptoethanol, tris(carboxyethyl)phosphine and threitol interfere with the binding of sulfonamides to isozymes II and IX.
AID637281Dissociation constant, pKa of the compound2012Bioorganic & medicinal chemistry, Jan-15, Volume: 20, Issue:2
Oxidative folding of lysozyme with aromatic dithiols, and aliphatic and aromatic monothiols.
AID314744Inhibition of carbonic anhydrase 2 assessed as residual activity at 0.01 mM2008Bioorganic & medicinal chemistry letters, Mar-15, Volume: 18, Issue:6
Carbonic anhydrase inhibitors: the very weak inhibitors dithiothreitol, beta-mercaptoethanol, tris(carboxyethyl)phosphine and threitol interfere with the binding of sulfonamides to isozymes II and IX.
AID314757Inhibition of carbonic anhydrase 9 catalytic domain assessed as residual activity at 10 mM2008Bioorganic & medicinal chemistry letters, Mar-15, Volume: 18, Issue:6
Carbonic anhydrase inhibitors: the very weak inhibitors dithiothreitol, beta-mercaptoethanol, tris(carboxyethyl)phosphine and threitol interfere with the binding of sulfonamides to isozymes II and IX.
AID314741Inhibition of carbonic anhydrase 2 assessed as residual activity at 0.001 mM2008Bioorganic & medicinal chemistry letters, Mar-15, Volume: 18, Issue:6
Carbonic anhydrase inhibitors: the very weak inhibitors dithiothreitol, beta-mercaptoethanol, tris(carboxyethyl)phosphine and threitol interfere with the binding of sulfonamides to isozymes II and IX.
AID314742Inhibition of carbonic anhydrase 9 catalytic domain assessed as residual activity at 0.001 mM2008Bioorganic & medicinal chemistry letters, Mar-15, Volume: 18, Issue:6
Carbonic anhydrase inhibitors: the very weak inhibitors dithiothreitol, beta-mercaptoethanol, tris(carboxyethyl)phosphine and threitol interfere with the binding of sulfonamides to isozymes II and IX.
AID314750Inhibition of carbonic anhydrase 2 assessed as residual activity at 1.0 mM2008Bioorganic & medicinal chemistry letters, Mar-15, Volume: 18, Issue:6
Carbonic anhydrase inhibitors: the very weak inhibitors dithiothreitol, beta-mercaptoethanol, tris(carboxyethyl)phosphine and threitol interfere with the binding of sulfonamides to isozymes II and IX.
AID314746Inhibition of carbonic anhydrase 9 assessed as residual activity at 0.01 mM2008Bioorganic & medicinal chemistry letters, Mar-15, Volume: 18, Issue:6
Carbonic anhydrase inhibitors: the very weak inhibitors dithiothreitol, beta-mercaptoethanol, tris(carboxyethyl)phosphine and threitol interfere with the binding of sulfonamides to isozymes II and IX.
AID314745Inhibition of carbonic anhydrase 9 catalytic domain assessed as residual activity at 0.01 mM2008Bioorganic & medicinal chemistry letters, Mar-15, Volume: 18, Issue:6
Carbonic anhydrase inhibitors: the very weak inhibitors dithiothreitol, beta-mercaptoethanol, tris(carboxyethyl)phosphine and threitol interfere with the binding of sulfonamides to isozymes II and IX.
AID314758Inhibition of carbonic anhydrase 9 assessed as residual activity at 10 mM2008Bioorganic & medicinal chemistry letters, Mar-15, Volume: 18, Issue:6
Carbonic anhydrase inhibitors: the very weak inhibitors dithiothreitol, beta-mercaptoethanol, tris(carboxyethyl)phosphine and threitol interfere with the binding of sulfonamides to isozymes II and IX.
AID314753Inhibition of carbonic anhydrase 2 assessed as residual activity at 2.5 mM2008Bioorganic & medicinal chemistry letters, Mar-15, Volume: 18, Issue:6
Carbonic anhydrase inhibitors: the very weak inhibitors dithiothreitol, beta-mercaptoethanol, tris(carboxyethyl)phosphine and threitol interfere with the binding of sulfonamides to isozymes II and IX.
AID728442Binding affinity to Enterobacteria phage T4 lysozyme L99A/M102H double mutant expressed in Escherichia coli BL21(DE3) assessed as change in melting temperature at 2 mM at pH 5.4 by circular dichroism analysis2013Journal of medicinal chemistry, Apr-11, Volume: 56, Issue:7
The impact of introducing a histidine into an apolar cavity site on docking and ligand recognition.
AID314754Inhibition of carbonic anhydrase 9 catalytic domain assessed as residual activity at 2.5 mM2008Bioorganic & medicinal chemistry letters, Mar-15, Volume: 18, Issue:6
Carbonic anhydrase inhibitors: the very weak inhibitors dithiothreitol, beta-mercaptoethanol, tris(carboxyethyl)phosphine and threitol interfere with the binding of sulfonamides to isozymes II and IX.
AID314743Inhibition of carbonic anhydrase 9 assessed as residual activity at 0.001 mM2008Bioorganic & medicinal chemistry letters, Mar-15, Volume: 18, Issue:6
Carbonic anhydrase inhibitors: the very weak inhibitors dithiothreitol, beta-mercaptoethanol, tris(carboxyethyl)phosphine and threitol interfere with the binding of sulfonamides to isozymes II and IX.
AID314752Inhibition of carbonic anhydrase 9 assessed as residual activity at 1.0 mM2008Bioorganic & medicinal chemistry letters, Mar-15, Volume: 18, Issue:6
Carbonic anhydrase inhibitors: the very weak inhibitors dithiothreitol, beta-mercaptoethanol, tris(carboxyethyl)phosphine and threitol interfere with the binding of sulfonamides to isozymes II and IX.
AID314747Inhibition of carbonic anhydrase 2 assessed as residual activity at 0.1 mM2008Bioorganic & medicinal chemistry letters, Mar-15, Volume: 18, Issue:6
Carbonic anhydrase inhibitors: the very weak inhibitors dithiothreitol, beta-mercaptoethanol, tris(carboxyethyl)phosphine and threitol interfere with the binding of sulfonamides to isozymes II and IX.
AID1796111QC Inhibition Testing from Article 10.1021/bi051142e: \\Isolation, catalytic properties, and competitive inhibitors of the zinc-dependent murine glutaminyl cyclase.\\2005Biochemistry, Oct-11, Volume: 44, Issue:40
Isolation, catalytic properties, and competitive inhibitors of the zinc-dependent murine glutaminyl cyclase.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (5,932)

TimeframeStudies, This Drug (%)All Drugs %
pre-19904450 (75.02)18.7374
1990's712 (12.00)18.2507
2000's454 (7.65)29.6817
2010's267 (4.50)24.3611
2020's49 (0.83)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 82.21

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 very strong demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index82.21 (24.57)
Research Supply Index8.73 (2.92)
Research Growth Index4.19 (4.65)
Search Engine Demand Index151.97 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (82.21)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials29 (0.47%)5.53%
Reviews55 (0.90%)6.00%
Case Studies42 (0.68%)4.05%
Observational0 (0.00%)0.25%
Other6,011 (97.95%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]