Page last updated: 2024-12-06

olsalazine

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

Description

Olsalazine is a prodrug of mesalamine, an aminosalicylate used to treat inflammatory bowel disease (IBD). It is synthesized by reacting 5-aminosalicylic acid with the diacid chloride of dicarboxylic acid. Upon oral administration, olsalazine is cleaved by intestinal bacteria into two molecules of mesalamine, which then acts as an anti-inflammatory agent. It is thought to work by suppressing the production of inflammatory mediators such as leukotrienes and prostaglandins, thereby reducing inflammation in the gut. It is studied extensively due to its efficacy in treating IBD, particularly ulcerative colitis. Olsalazine has a good safety profile, though side effects such as diarrhea, headache, and abdominal pain can occur.'

olsalazine: cpd with 2 salicylate molecules linked together by an azo bond [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

olsalazine : An azobenzene that consists of two molecules of 4-aminosalicylic acid joined by an azo linkage. A prodrug for mesalazine, an anti-inflammatory drug, it is used (as the disodium salt) in the treatment of inflammatory bowel disease. [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]

Cross-References

ID SourceID
PubMed CID22419
CHEMBL ID425
CHEMBL ID1208644
CHEBI ID7770
SCHEMBL ID29768
SCHEMBL ID25119
SCHEMBL ID25118
SCHEMBL ID2628413
MeSH IDM0101640

Synonyms (69)

Synonym
BIDD:GT0392
3,3'-(e)-diazene-1,2-diylbis(6-hydroxybenzoic acid)
3,3'-azobis(6-hydroxybenzoic acid)
5,5'-azobis(salicylic acid)
olsalazinum [latin]
benzoic acid, 3,3'-azobis(6-hydroxy-
azodisal
c.i. mordant yellow 5
olsalazine [inn:ban]
olsalazina [spanish]
salicylic acid, 5,5'-azodi-
15722-48-2
olsalazine
C07323 ,
DB01250
rasal
olsalazine (inn)
D08295
A809825
5-[(2z)-2-(3-carboxy-4-oxo-cyclohexa-2,5-dien-1-ylidene)hydrazino]-2-hydroxy-benzoic acid
olsalazina
olsalazinum
dipentium
unii-uls5i8j03o
uls5i8j03o ,
CHEMBL425
c. i. mordant yellow 5
CHEMBL1208644
CHEBI:7770 ,
3,3'-diazene-1,2-diylbis(6-hydroxybenzoic acid)
5,5'-azodisalicylic acid
olsalazine [inn]
olsalazine [mi]
olsalazine [vandf]
olsalazine [who-dd]
SCHEMBL29768
SCHEMBL25119
SCHEMBL25118
SCHEMBL2628413
QQBDLJCYGRGAKP-UHFFFAOYSA-N
Q-201512
DTXSID8023391 ,
5-[(3-carboxy-4-hydroxyphenyl)diazenyl]-2-hydroxybenzoic acid
(e)-5,5'-(diazene-1,2-diyl)bis(2-hydroxybenzoic acid)
(z)-5,5'-(diazene-1,2-diyl)bis(2-hydroxybenzoic acid)
AC-8144
5-[(e)-2-(3-carboxy-4-hydroxyphenyl)diazen-1-yl]-2-hydroxybenzoic acid
3,3'-(1,2-diazenediyl)bis(6-hydroxy-benzoic acid)
Q347621
SY107522
1004301-38-5
AS-15939
5,5'-(diazene-1,2-diyl)bis(2-hydroxybenzoic acid)
cj91b
gtpl11578
YSZC1205
AKOS037643377
salicylic aciddipentium
JBC ,
5-[(e)-(3-carboxy-4-oxidanyl-phenyl)diazenyl]-2-oxidanyl-benzoic acid
STARBLD0009635
bdbm50548283
CS-0009548
HY-B0174A
F88555
EN300-18560034
5-[2-(3-carboxy-4-hydroxyphenyl)diazen-1-yl]-2-hydroxybenzoic acid
AKOS040744639
PD055722

Research Excerpts

Overview

Olsa is a broad-spectrum anti-cancer agent acting as a DNA-methylation inhibitor. It depends on gut microbiota to liberate its anti-inflammatory moiety 5-ASA. Olsalazine appears to be a suitable therapy for the treatment of first attacks as well as acute exacerbation of acute ulcerative colitis.

ExcerptReferenceRelevance
"Olsalazine is a typical 5-aminosalicylic acid (5-ASA) drug that depends on gut microbiota to liberate its anti-inflammatory moiety 5-ASA in the treatment of ulcerative colitis (UC). "( Pharmacokinetic and gut microbiota analyses revealed the effect of Lactobacillus acidophilus on the metabolism of Olsalazine in ulcerative colitis rats.
Feng, Y; Li, Z; Liu, L; Ma, S; Mei, Q; Wang, J; Wang, S; Wang, X; Wang, Y; Xu, Z; Yan, R; Yang, P, 2022
)
2.37
"Olsalazine (Olsa) is a broad-spectrum anti-cancer agent acting as a DNA-methylation inhibitor. "( Furin-Mediated Self-Assembly of Olsalazine Nanoparticles for Targeted Raman Imaging of Tumors.
Barman, I; Bulte, JWM; Raj, P; Siddhanta, S; Yuan, Y; Zhang, J, 2021
)
2.35
"Olsalazine is an excellent generator of 5-ASA in the colon."( Comparative bioavailability of 5-aminosalicylic acid from a controlled release preparation and an azo-bond preparation.
Abildgaard, K; Christensen, LA; Fallingborg, J; Hansen, SH; Jacobsen, BA; Rasmussen, HH; Rasmussen, SN, 1994
)
1.01
"Olsalazine is an orally administered drug designed to deliver 5-aminosalicylate to the large bowel with minimal systemic absorption."( Olsalazine is contraindicated during pelvic radiation therapy: results of a double-blind, randomized clinical trial.
Collins, RT; Deming, RL; Frank, AR; Hyland, G; Mailliard, JA; Martenson, JA; Moertel, CG; Moore, RL; Morton, RF; O'Fallon, JR; Tewfik, HH; Urias, RE, 1996
)
2.46
"Olsalazine appears to be a suitable therapy for the treatment of first attacks as well as acute exacerbation of mild to moderate acute ulcerative colitis, and for the maintenance of remission in patients with chronic ulcerative colitis."( Olsalazine. A review of its pharmacodynamic and pharmacokinetic properties, and therapeutic potential in inflammatory bowel disease.
Fitton, A; Wadworth, AN, 1991
)
2.45
"Olsalazine is a compound consisting of two 5-amino salicylate (5-ASA) molecules linked by an azo bond, which, administered orally, is split by colonic bacteria to liberate 5-ASA. "( Double-blind placebo-controlled study of olsalazine in the treatment of ulcerative colitis.
Das, KM; Molinas, S; Zinberg, J, 1990
)
1.99
"Olsalazine is a very effective means of delivery of 5-aminosalicylic acid to the colonic mucosa in active disease."( Longterm olsalazine treatment: pharmacokinetics, tolerance and effects on local eicosanoid formation in ulcerative colitis and Crohn's colitis.
Bukhave, K; Lauritsen, K; Rask-Madsen, J; Staerk Laursen, L, 1988
)
1.41
"Olsalazine is a new drug for the treatment of ulcerative and Crohn's colitis. "( Induction of and adaptation to olsalazine induced intestinal volume load.
Berglindh, T; Bergqvist, E; Landström, E, 1988
)
2
"Olsalazine is a novel compound presently under development for the treatment of ulcerative colitis. "( Olsalazine does not increase the bile acid losses in subjects with a permanent ileostomy.
Järnerot, G; Sandberg-Gertzén, H; Tobiasson, P; Vikterlöf, KJ, 1988
)
3.16

Treatment

Olsalazine treatment significantly (P < 0.01) reduced the elevation in glutathione peroxidase activity in neoplastic tissues of rats treated with the carcinogen. Olsalazine treatment decreased all cyclooxygen enzyme and lipoxygenase products to baseline levels. Treatment with olsalazines led to significant cell growth inhibition and increased the apoptotic rate in all three cell lines.

ExcerptReferenceRelevance
"Olsalazine treatment significantly (P < 0.01) reduced the elevation in glutathione peroxidase activity in neoplastic tissues of rats treated with the carcinogen."( Endogenous antioxidant status in neoplastic and adjacent tissues in 1,2-dimethylhydrazine-induced colon cancer in rats: effects of olsalazine.
Freeman, HJ; Godin, DV; Moghadasian, MH, 1996
)
1.22
"Olsalazine treatment decreased all cyclooxygenase and lipoxygenase products to baseline levels."( Experimental colitis in mice: effects of olsalazine on eicosanoid production in colonic tissue.
Garrelds, IM; van Dijk, AP; Wilson, JH; Zijlstra, FJ, 1992
)
1.27
"Treatment with olsalazine led to significant cell growth inhibition and increased the apoptotic rate in all three cell lines."( Olsalazine inhibits cell proliferation and DNA methylation in canine lymphoid tumor cell lines.
Itoh, S; Iwahana, M; Tsukamoto, A; Yamazaki, J, 2021
)
2.4
"Treatment with olsalazine, a 5-aminosalicylic acid compound (disodium-azodisalicylate), was well tolerated without recurrence of pulmonary symptoms."( Olsalazine as an alternative therapy in a patient with sulfasalazine-induced eosinophilic pneumonia.
Nadorp, JH; Scherpenisse, J; van den Bosch, JM; van der Valk, PD; van Hees, PA, 1988
)
2.06

Toxicity

Adverse events requiring the withdrawal of therapy seem to occur less frequently with balsalazide, mesalamine, and olsalazine compared with sulfasalazine.

ExcerptReferenceRelevance
" In both treatment groups, three patients dropped out because of adverse effects."( Relapse-preventing effect and safety of sulfasalazine and olsalazine in patients with ulcerative colitis in remission: a prospective, double-blind, randomized multicenter study. The Ulcerative Colitis Multicenter Study Group.
Rijk, MC; van Lier, HJ; van Tongeren, JH, 1992
)
0.53
"To determine whether there is a difference in short-term adverse events in patients with ulcerative colitis treated with mesalazine, olsalazine or balsalazide."( Systematic review: short-term adverse effects of 5-aminosalicylic acid agents in the treatment of ulcerative colitis.
Bjorkman, D; Kane, SV; Loftus, EV, 2004
)
0.53
" Outcomes of interest were the frequencies of patients experiencing adverse events and those withdrawn due to adverse events."( Systematic review: short-term adverse effects of 5-aminosalicylic acid agents in the treatment of ulcerative colitis.
Bjorkman, D; Kane, SV; Loftus, EV, 2004
)
0.32
" sulfasalazine for active colitis showed significantly fewer patients with adverse events with mesalazine."( Systematic review: short-term adverse effects of 5-aminosalicylic acid agents in the treatment of ulcerative colitis.
Bjorkman, D; Kane, SV; Loftus, EV, 2004
)
0.32
"All three 5-aminosalicylic acid agents are safe in the short term."( Systematic review: short-term adverse effects of 5-aminosalicylic acid agents in the treatment of ulcerative colitis.
Bjorkman, D; Kane, SV; Loftus, EV, 2004
)
0.32
" Adverse events requiring the withdrawal of therapy seem to occur less frequently with balsalazide, mesalamine, and olsalazine compared with sulfasalazine."( The short- and long-term safety of 5-aminosalicylate products in the treatment of ulcerative colitis.
Baker, DE; Kane, S, 2004
)
0.53
"5 million adverse drug reaction (ADR) reports for 8620 drugs/biologics that are listed for 1191 Coding Symbols for Thesaurus of Adverse Reaction (COSTAR) terms of adverse effects."( Assessment of the health effects of chemicals in humans: II. Construction of an adverse effects database for QSAR modeling.
Benz, RD; Contrera, JF; Kruhlak, NL; Matthews, EJ; Weaver, JL, 2004
)
0.32

Pharmacokinetics

ExcerptReferenceRelevance
" Sulphasalazine itself is poorly absorbed (3 to 12%) and its elimination half-life of about 5 to 10 hours is probably affected by the absorption process."( Clinical pharmacokinetics of sulphasalazine, its metabolites and other prodrugs of 5-aminosalicylic acid.
Klotz, U,
)
0.13
" dose the serum half-life of the O-sulphate was estimated to be 7 days."( The pharmacokinetics of olsalazine sodium in healthy volunteers after a single i.v. dose and after oral doses with and without food.
Ahnfelt, NO; Ryde, EM, 1988
)
0.58
" The toxicological, pharmacological and pharmacokinetic profiles of olsalazine are excellent; the only side-effect noted from clinical trials with olsalazine is an increased incidence of loose stools and occasional diarrhoea."( Induction of and adaptation to olsalazine induced intestinal volume load.
Berglindh, T; Bergqvist, E; Landström, E, 1988
)
0.8
" pharmacokinetic data on 670 drugs representing, to our knowledge, the largest publicly available set of human clinical pharmacokinetic data."( Trend analysis of a database of intravenous pharmacokinetic parameters in humans for 670 drug compounds.
Lombardo, F; Obach, RS; Waters, NJ, 2008
)
0.35
" Mechanisms of combination therapy have been widely discussed from a pharmacodynamic perspective."( Pharmacokinetic and gut microbiota analyses revealed the effect of Lactobacillus acidophilus on the metabolism of Olsalazine in ulcerative colitis rats.
Feng, Y; Li, Z; Liu, L; Ma, S; Mei, Q; Wang, J; Wang, S; Wang, X; Wang, Y; Xu, Z; Yan, R; Yang, P, 2022
)
0.93

Bioavailability

The aim of this investigation was to compare two formulations of the prodrug olsalazine (OLZ) with regard to local bioavailability of 5-aminosalicylic acid (5-ASA) in the colon.

ExcerptReferenceRelevance
"The aim of this investigation was to compare two formulations of the prodrug olsalazine (OLZ) with regard to local bioavailability of 5-aminosalicylic acid (5-ASA) in the colon."( Relative bioavailability of olsalazine from tablets and capsules: a drug targeted for local effect in the colon.
Huitfeldt, B; Pettersson, R; Ryde, M, 1991
)
0.8
" Sulphasalazine itself is poorly absorbed (3 to 12%) and its elimination half-life of about 5 to 10 hours is probably affected by the absorption process."( Clinical pharmacokinetics of sulphasalazine, its metabolites and other prodrugs of 5-aminosalicylic acid.
Klotz, U,
)
0.13
"Knowledge of the bioavailability of 5-aminosalicylic acid (5-ASA, mesalazine) from the different 5-ASA-containing drugs is important for rational therapy of inflammatory bowel diseases."( Comparative bioavailability of 5-aminosalicylic acid from a controlled release preparation and an azo-bond preparation.
Abildgaard, K; Christensen, LA; Fallingborg, J; Hansen, SH; Jacobsen, BA; Rasmussen, HH; Rasmussen, SN, 1994
)
0.29
"The local and systemic bioavailability of 5-ASA from a controlled release 5-ASA preparation (Pentasa--2, 4 or 6 g/day) was investigated and compared with the azo-bond 5-ASA preparation olsalazine (Dipentum--2 g/day) in 13 healthy volunteers during steady state conditions."( Comparative bioavailability of 5-aminosalicylic acid from a controlled release preparation and an azo-bond preparation.
Abildgaard, K; Christensen, LA; Fallingborg, J; Hansen, SH; Jacobsen, BA; Rasmussen, HH; Rasmussen, SN, 1994
)
0.48
" The new methodology may, therefore, be used for fast bioavailability screening of virtual libraries having millions of molecules."( Fast calculation of molecular polar surface area as a sum of fragment-based contributions and its application to the prediction of drug transport properties.
Ertl, P; Rohde, B; Selzer, P, 2000
)
0.31
"Oral bioavailability (F) is a product of fraction absorbed (Fa), fraction escaping gut-wall elimination (Fg), and fraction escaping hepatic elimination (Fh)."( Physicochemical space for optimum oral bioavailability: contribution of human intestinal absorption and first-pass elimination.
Chang, G; El-Kattan, A; Miller, HR; Obach, RS; Rotter, C; Steyn, SJ; Troutman, MD; Varma, MV, 2010
)
0.36

Dosage Studied

Olsalazine (OLZ) after single oral administration to six horses at a dosage of 30 mg/kg was investigated. The history, pharmacology, pharmacokinetics, clinical uses and efficacy, adverse effects, drug interactions, and dosage and administration of rectal mesalamine and oral olsalazines are reviewed.

ExcerptRelevanceReference
" Incubation with higher concentrations of the drugs revealed a dose-response effect on binding with complete inhibition by 100 mM 4ASA and 10 mM olsalazine, and lesser degrees of inhibition by 100 mM 5ASA, N-acetyl-5ASA, and N-acetyl-4ASA."( Inhibition of binding of interferon-gamma to its receptor by salicylates used in inflammatory bowel disease.
Aronson, JK; Crotty, B; Jewell, DP; Rosenberg, WM, 1992
)
0.48
"The history, pharmacology, pharmacokinetics, clinical uses and efficacy, adverse effects, drug interactions, and dosage and administration of rectal mesalamine and oral olsalazine in the treatment of inflammatory bowel disease (IBD) are reviewed."( Mesalamine and olsalazine: 5-aminosalicylic acid agents for the treatment of inflammatory bowel disease.
Gales, BJ; Segars, LW, 1992
)
0.83
" Olsalazine-induced diarrhoea usually occurred soon after initiation of olsalazine therapy or dosage increase, was more frequent with higher doses and was usually transient."( Olsalazine. A review of its pharmacodynamic and pharmacokinetic properties, and therapeutic potential in inflammatory bowel disease.
Fitton, A; Wadworth, AN, 1991
)
2.63
"To compare the systemic load of 5-aminosalicylic acid (5-ASA) as a basis for potential long-term toxicity during treatment in usual dosage with olsalazine (Dipentum) and one controlled-release mesalazine preparation (Salofalk) in patients with inactive ulcerative colitis."( Systemic absorption of 5-aminosalicylic acid in patients with inactive ulcerative colitis treated with olsalazine and mesalazine.
Karamanolis, DG; Papatheodoridis, GV; Xourgias, V, 1996
)
0.71
" The dose-response patterns suggested that the active therapeutic moiety for the two drugs appears to be mainly the liberated 5-ASA molecule."( Experimental colitis induced by dextran sulphate sodium in mice: beneficial effects of sulphasalazine and olsalazine.
Axelsson, LG; Bylund-Fellenius, AC; Landström, E, 1998
)
0.51
" This relationship has been applied to the determination of olsalazine in commercial capsule dosage forms."( Determination of olsalazine sodium in pharmaceuticals by differential pulse voltammetry.
Ozkan, SA; Uslu, B; Yilmaz, S, 2001
)
0.89
" Considering the potential therapeutic use in equine colitis, the pharmacokinetics of olsalazine (OLZ) after single oral administration to six horses at a dosage of 30 mg/kg was investigated."( Study of the plasma pharmacokinetics and faecal excretion of the prodrug olsalazine and its metabolites after oral administration to horses.
Knoll, U; Schusser, G; Strauhs, P; Ungemach, FR, 2002
)
0.77
" Mesalazine has been shown equivalent or superior to sulfasalazine, and superior to placebo, with a dose-response benefit, in inducing remission of acute disease."( Role of mesalazine in acute and long-term treatment of ulcerative colitis and its complications.
Schroeder, KW, 2002
)
0.31
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (2)

RoleDescription
prodrugA compound that, on administration, must undergo chemical conversion by metabolic processes before becoming the pharmacologically active drug for which it is a prodrug.
non-steroidal anti-inflammatory drugAn anti-inflammatory drug that is not a steroid. In addition to anti-inflammatory actions, non-steroidal anti-inflammatory drugs have analgesic, antipyretic, and platelet-inhibitory actions. They act by blocking the synthesis of prostaglandins by inhibiting cyclooxygenase, which converts arachidonic acid to cyclic endoperoxides, precursors of prostaglandins.
[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
dicarboxylic acidAny carboxylic acid containing two carboxy groups.
azobenzenesAny member of the wide class of molecules that share the core azobenzene structure, comprising two phenyl rings linked by a N=N double bond, which may have different functional groups extending from the rings.
[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)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Cystathionine gamma-lyaseHomo sapiens (human)IC50 (µMol)200.00000.57002.86098.0000AID1680654
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Activation Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Flavin reductase (NADPH)Homo sapiens (human)Kd0.07040.07000.79681.7100AID1815675
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (17)

Processvia Protein(s)Taxonomy
megakaryocyte differentiationFlavin reductase (NADPH)Homo sapiens (human)
heme catabolic processFlavin reductase (NADPH)Homo sapiens (human)
negative regulation of insulin receptor signaling pathwayFlavin reductase (NADPH)Homo sapiens (human)
cysteine metabolic processCystathionine gamma-lyaseHomo sapiens (human)
lipid metabolic processCystathionine gamma-lyaseHomo sapiens (human)
protein-pyridoxal-5-phosphate linkage via peptidyl-N6-pyridoxal phosphate-L-lysineCystathionine gamma-lyaseHomo sapiens (human)
cysteine biosynthetic process via cystathionineCystathionine gamma-lyaseHomo sapiens (human)
cysteine biosynthetic processCystathionine gamma-lyaseHomo sapiens (human)
transsulfurationCystathionine gamma-lyaseHomo sapiens (human)
endoplasmic reticulum unfolded protein responseCystathionine gamma-lyaseHomo sapiens (human)
positive regulation of canonical NF-kappaB signal transductionCystathionine gamma-lyaseHomo sapiens (human)
protein sulfhydrationCystathionine gamma-lyaseHomo sapiens (human)
protein homotetramerizationCystathionine gamma-lyaseHomo sapiens (human)
hydrogen sulfide biosynthetic processCystathionine gamma-lyaseHomo sapiens (human)
positive regulation of aortic smooth muscle cell differentiationCystathionine gamma-lyaseHomo sapiens (human)
cellular response to leukemia inhibitory factorCystathionine gamma-lyaseHomo sapiens (human)
negative regulation of apoptotic signaling pathwayCystathionine gamma-lyaseHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (17)

Processvia Protein(s)Taxonomy
biliverdin reductase (NAD(P)H) activityFlavin reductase (NADPH)Homo sapiens (human)
protein bindingFlavin reductase (NADPH)Homo sapiens (human)
FMN reductase (NAD(P)H) activityFlavin reductase (NADPH)Homo sapiens (human)
peptidyl-cysteine S-nitrosylase activityFlavin reductase (NADPH)Homo sapiens (human)
riboflavin reductase (NADPH) activityFlavin reductase (NADPH)Homo sapiens (human)
FMN reductase (NADPH) activityFlavin reductase (NADPH)Homo sapiens (human)
FMN reductase (NADH) activityFlavin reductase (NADPH)Homo sapiens (human)
biliberdin reductase NAD+ activityFlavin reductase (NADPH)Homo sapiens (human)
biliverdin reductase (NADPH) activityFlavin reductase (NADPH)Homo sapiens (human)
cystathionine gamma-lyase activityCystathionine gamma-lyaseHomo sapiens (human)
protein bindingCystathionine gamma-lyaseHomo sapiens (human)
calmodulin bindingCystathionine gamma-lyaseHomo sapiens (human)
pyridoxal phosphate bindingCystathionine gamma-lyaseHomo sapiens (human)
identical protein bindingCystathionine gamma-lyaseHomo sapiens (human)
L-cystine L-cysteine-lyase (deaminating)Cystathionine gamma-lyaseHomo sapiens (human)
homocysteine desulfhydrase activityCystathionine gamma-lyaseHomo sapiens (human)
L-cysteine desulfhydrase activityCystathionine gamma-lyaseHomo sapiens (human)
selenocystathionine gamma-lyase activityCystathionine gamma-lyaseHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (6)

Processvia Protein(s)Taxonomy
cytoplasmFlavin reductase (NADPH)Homo sapiens (human)
nucleoplasmFlavin reductase (NADPH)Homo sapiens (human)
cytosolFlavin reductase (NADPH)Homo sapiens (human)
plasma membraneFlavin reductase (NADPH)Homo sapiens (human)
intracellular membrane-bounded organelleFlavin reductase (NADPH)Homo sapiens (human)
extracellular exosomeFlavin reductase (NADPH)Homo sapiens (human)
cytosolCystathionine gamma-lyaseHomo sapiens (human)
extracellular exosomeCystathionine gamma-lyaseHomo sapiens (human)
cytoplasmCystathionine gamma-lyaseHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (76)

Assay IDTitleYearJournalArticle
AID1898641Inhibition of amyloid beta (1 to 42) (unknown origin) self aggregation after 24 hrs by thioflavin-T fluorescence method2021European journal of medicinal chemistry, Dec-15, Volume: 226Targeting transthyretin in Alzheimer's disease: Drug discovery of small-molecule chaperones as disease-modifying drug candidates for Alzheimer's disease.
AID237585Tested for fraction of oral dose absorbed orally in humans2005Journal of medicinal chemistry, May-05, Volume: 48, Issue:9
Calculating virtual log P in the alkane/water system (log P(N)(alk)) and its derived parameters deltalog P(N)(oct-alk) and log D(pH)(alk).
AID444055Fraction absorbed in human2010Journal of medicinal chemistry, Feb-11, Volume: 53, Issue:3
Physicochemical space for optimum oral bioavailability: contribution of human intestinal absorption and first-pass elimination.
AID588214FDA HLAED, liver enzyme composite activity2004Current drug discovery technologies, Dec, Volume: 1, Issue:4
Assessment of the health effects of chemicals in humans: II. Construction of an adverse effects database for QSAR modeling.
AID1079934Highest frequency of acute liver toxicity observed during clinical trials, expressed as a percentage. [column '% AIGUE' in source]
AID588219FDA HLAED, gamma-glutamyl transferase (GGT) increase2004Current drug discovery technologies, Dec, Volume: 1, Issue:4
Assessment of the health effects of chemicals in humans: II. Construction of an adverse effects database for QSAR modeling.
AID1221963Transporter substrate index ratio of permeability from apical to basolateral side in human Caco2 cells at 10 uM up to 120 mins by HPLC-MC analysis in presence of 1 uM of P-gp inhibitor LY3359792011Drug metabolism and disposition: the biological fate of chemicals, Feb, Volume: 39, Issue:2
Attenuation of intestinal absorption by major efflux transporters: quantitative tools and strategies using a Caco-2 model.
AID476929Human intestinal absorption in po dosed human2010European journal of medicinal chemistry, Mar, Volume: 45, Issue:3
Neural computational prediction of oral drug absorption based on CODES 2D descriptors.
AID1221958Efflux ratio of permeability from apical to basolateral side over basolateral to apical side of human Caco2 cells at 10 uM up to 120 mins by HPLC-MC analysis2011Drug metabolism and disposition: the biological fate of chemicals, Feb, Volume: 39, Issue:2
Attenuation of intestinal absorption by major efflux transporters: quantitative tools and strategies using a Caco-2 model.
AID444057Fraction escaping hepatic elimination in human2010Journal of medicinal chemistry, Feb-11, Volume: 53, Issue:3
Physicochemical space for optimum oral bioavailability: contribution of human intestinal absorption and first-pass elimination.
AID236268Fraction absorbed in human intestine after oral administration compound was measured2005Journal of medicinal chemistry, Jan-27, Volume: 48, Issue:2
Exploring the role of different drug transport routes in permeability screening.
AID1815673Binding affinity to human N-terminal His6-tagged and thrombin cleavage fused BLVRB expressed in Escherichia coli BL21 (DE3) assessed as change in entropy by isothermal titration calorimetry2022Journal of medicinal chemistry, 02-10, Volume: 65, Issue:3
Repositioning Food and Drug Administration-Approved Drugs for Inhibiting Biliverdin IXβ Reductase B as a Novel Thrombocytopenia Therapeutic Target.
AID1221957Apparent permeability from basolateral to apical side of human Caco2 cells at 10 uM up to 120 mins by HPLC-MC analysis2011Drug metabolism and disposition: the biological fate of chemicals, Feb, Volume: 39, Issue:2
Attenuation of intestinal absorption by major efflux transporters: quantitative tools and strategies using a Caco-2 model.
AID1898640Neuroprotective activity against amyloid beta (1 to 42 residues)-induced cell injury in human SH-SY5Y cells assessed as reduction in caspase 3 level2021European journal of medicinal chemistry, Dec-15, Volume: 226Targeting transthyretin in Alzheimer's disease: Drug discovery of small-molecule chaperones as disease-modifying drug candidates for Alzheimer's disease.
AID1079935Cytolytic liver toxicity, either proven histopathologically or where the ratio of maximal ALT or AST activity above normal to that of Alkaline Phosphatase is > 5 (see ACUTE). Value is number of references indexed. [column 'CYTOL' in source]
AID1079941Liver damage due to vascular disease: peliosis hepatitis, hepatic veno-occlusive disease, Budd-Chiari syndrome. Value is number of references indexed. [column 'VASC' in source]
AID588220Literature-mined public compounds from Kruhlak et al phospholipidosis modelling dataset2008Toxicology mechanisms and methods, , Volume: 18, Issue:2-3
Development of a phospholipidosis database and predictive quantitative structure-activity relationship (QSAR) models.
AID588217FDA HLAED, serum glutamic pyruvic transaminase (SGPT) increase2004Current drug discovery technologies, Dec, Volume: 1, Issue:4
Assessment of the health effects of chemicals in humans: II. Construction of an adverse effects database for QSAR modeling.
AID236913Permeability Coefficient in Caco-2 cell culture model2005Journal of medicinal chemistry, Jan-27, Volume: 48, Issue:2
Exploring the role of different drug transport routes in permeability screening.
AID1221960Apparent permeability from apical to basolateral side of human Caco2 cells at 10 uM up to 120 mins by HPLC-MC analysis in presence of 1 uM of P-gp inhibitor LY3359792011Drug metabolism and disposition: the biological fate of chemicals, Feb, Volume: 39, Issue:2
Attenuation of intestinal absorption by major efflux transporters: quantitative tools and strategies using a Caco-2 model.
AID1221982Fraction absorbed in human2011Drug metabolism and disposition: the biological fate of chemicals, Feb, Volume: 39, Issue:2
Attenuation of intestinal absorption by major efflux transporters: quantitative tools and strategies using a Caco-2 model.
AID592681Apparent permeability across human Caco2 cell membrane after 2 hrs by LC-MS/MS analysis2011Bioorganic & medicinal chemistry, Apr-15, Volume: 19, Issue:8
QSAR-based permeability model for drug-like compounds.
AID540210Clearance in human after iv administration2008Drug metabolism and disposition: the biological fate of chemicals, Jul, Volume: 36, Issue:7
Trend analysis of a database of intravenous pharmacokinetic parameters in humans for 670 drug compounds.
AID1474167Liver toxicity in human assessed as induction of drug-induced liver injury by measuring verified drug-induced liver injury concern status2016Drug discovery today, Apr, Volume: 21, Issue:4
DILIrank: the largest reference drug list ranked by the risk for developing drug-induced liver injury in humans.
AID567091Drug absorption in human assessed as human intestinal absorption rate2011European journal of medicinal chemistry, Jan, Volume: 46, Issue:1
Prediction of drug intestinal absorption by new linear and non-linear QSPR.
AID710746Drug metabolism in Sprague-Dawley rat cecal contents assessed as accumulation of colonic bacteria-mediated final reduction product level at 2 mM2012Journal of medicinal chemistry, Dec-13, Volume: 55, Issue:23
Bacterial reduction as means for colonic drug delivery: can other chemical groups provide an alternative to the azo bond?
AID1815672Binding affinity to human N-terminal His6-tagged and thrombin cleavage fused BLVRB expressed in Escherichia coli BL21 (DE3) assessed as change in enthalpy by isothermal titration calorimetry2022Journal of medicinal chemistry, 02-10, Volume: 65, Issue:3
Repositioning Food and Drug Administration-Approved Drugs for Inhibiting Biliverdin IXβ Reductase B as a Novel Thrombocytopenia Therapeutic Target.
AID19419Partition coefficient (logD7.4)1998Journal of medicinal chemistry, Mar-26, Volume: 41, Issue:7
Physicochemical high throughput screening: parallel artificial membrane permeation assay in the description of passive absorption processes.
AID540209Volume of distribution at steady state in human after iv administration2008Drug metabolism and disposition: the biological fate of chemicals, Jul, Volume: 36, Issue:7
Trend analysis of a database of intravenous pharmacokinetic parameters in humans for 670 drug compounds.
AID588216FDA HLAED, serum glutamic oxaloacetic transaminase (SGOT) increase2004Current drug discovery technologies, Dec, Volume: 1, Issue:4
Assessment of the health effects of chemicals in humans: II. Construction of an adverse effects database for QSAR modeling.
AID1079942Steatosis, proven histopathologically. Value is number of references indexed. [column 'STEAT' in source]
AID1474166Liver toxicity in human assessed as induction of drug-induced liver injury by measuring severity class index2016Drug discovery today, Apr, Volume: 21, Issue:4
DILIrank: the largest reference drug list ranked by the risk for developing drug-induced liver injury in humans.
AID1079933Acute liver toxicity defined via clinical observations and clear clinical-chemistry results: serum ALT or AST activity > 6 N or serum alkaline phosphatases activity > 1.7 N. This category includes cytolytic, choleostatic and mixed liver toxicity. Value is
AID18847Percent of drug absorbed by human intestine after oral administration2000Journal of medicinal chemistry, Oct-05, Volume: 43, Issue:20
Fast calculation of molecular polar surface area as a sum of fragment-based contributions and its application to the prediction of drug transport properties.
AID15120Percent of the drug absorbed after administration to humans was determined1999Journal of medicinal chemistry, May-20, Volume: 42, Issue:10
Molecular hashkeys: a novel method for molecular characterization and its application for predicting important pharmaceutical properties of molecules.
AID1898637Binding affinity to wild type TTR/Amyloid beta (1 to 40 residues) binary complex (unknown origin) assessed as Gibbs free energy change for binary complex by isothermal titration calorimetry2021European journal of medicinal chemistry, Dec-15, Volume: 226Targeting transthyretin in Alzheimer's disease: Drug discovery of small-molecule chaperones as disease-modifying drug candidates for Alzheimer's disease.
AID1680654Inhibition of human CSE using L-Cys as the substrate by tandem well based HTS assay2019Journal of medicinal chemistry, 02-14, Volume: 62, Issue:3
Discovery of a Bioactive Inhibitor with a New Scaffold for Cystathionine γ-Lyase.
AID540213Half life in human after iv administration2008Drug metabolism and disposition: the biological fate of chemicals, Jul, Volume: 36, Issue:7
Trend analysis of a database of intravenous pharmacokinetic parameters in humans for 670 drug compounds.
AID1079943Malignant tumor, proven histopathologically. Value is number of references indexed. [column 'T.MAL' in source]
AID444054Oral bioavailability in human2010Journal of medicinal chemistry, Feb-11, Volume: 53, Issue:3
Physicochemical space for optimum oral bioavailability: contribution of human intestinal absorption and first-pass elimination.
AID1815675Binding affinity to human N-terminal His6-tagged and thrombin cleavage fused BLVRB expressed in Escherichia coli BL21 (DE3) assessed as dissociation constant by isothermal titration calorimetry2022Journal of medicinal chemistry, 02-10, Volume: 65, Issue:3
Repositioning Food and Drug Administration-Approved Drugs for Inhibiting Biliverdin IXβ Reductase B as a Novel Thrombocytopenia Therapeutic Target.
AID588215FDA HLAED, alkaline phosphatase increase2004Current drug discovery technologies, Dec, Volume: 1, Issue:4
Assessment of the health effects of chemicals in humans: II. Construction of an adverse effects database for QSAR modeling.
AID444051Total clearance in human2010Journal of medicinal chemistry, Feb-11, Volume: 53, Issue:3
Physicochemical space for optimum oral bioavailability: contribution of human intestinal absorption and first-pass elimination.
AID444056Fraction escaping gut-wall elimination in human2010Journal of medicinal chemistry, Feb-11, Volume: 53, Issue:3
Physicochemical space for optimum oral bioavailability: contribution of human intestinal absorption and first-pass elimination.
AID1079938Chronic liver disease either proven histopathologically, or through a chonic elevation of serum amino-transferase activity after 6 months. Value is number of references indexed. [column 'CHRON' in source]
AID1221956Apparent permeability from apical to basolateral side of human Caco2 cells at 10 uM up to 120 mins by HPLC-MC analysis2011Drug metabolism and disposition: the biological fate of chemicals, Feb, Volume: 39, Issue:2
Attenuation of intestinal absorption by major efflux transporters: quantitative tools and strategies using a Caco-2 model.
AID588218FDA HLAED, lactate dehydrogenase (LDH) increase2004Current drug discovery technologies, Dec, Volume: 1, Issue:4
Assessment of the health effects of chemicals in humans: II. Construction of an adverse effects database for QSAR modeling.
AID1079946Presence of at least one case with successful reintroduction. [column 'REINT' in source]
AID1079947Comments (NB not yet translated). [column 'COMMENTAIRES' in source]
AID1221962Efflux ratio of permeability from apical to basolateral side over basolateral to apical side of human Caco2 cells at 10 uM up to 120 mins by HPLC-MC analysis in presence of 1 uM of P-gp inhibitor LY3359792011Drug metabolism and disposition: the biological fate of chemicals, Feb, Volume: 39, Issue:2
Attenuation of intestinal absorption by major efflux transporters: quantitative tools and strategies using a Caco-2 model.
AID20050Human absorption A (%)1998Journal of medicinal chemistry, Mar-26, Volume: 41, Issue:7
Physicochemical high throughput screening: parallel artificial membrane permeation assay in the description of passive absorption processes.
AID444053Renal clearance in human2010Journal of medicinal chemistry, Feb-11, Volume: 53, Issue:3
Physicochemical space for optimum oral bioavailability: contribution of human intestinal absorption and first-pass elimination.
AID1898639Binding affinity to wild type TTR/Amyloid beta (1 to 40 residues) binary complex (unknown origin) assessed as change in entropy for binary complex by isothermal titration calorimetry2021European journal of medicinal chemistry, Dec-15, Volume: 226Targeting transthyretin in Alzheimer's disease: Drug discovery of small-molecule chaperones as disease-modifying drug candidates for Alzheimer's disease.
AID1079937Severe hepatitis, defined as possibly life-threatening liver failure or through clinical observations. Value is number of references indexed. [column 'MASS' in source]
AID1079949Proposed mechanism(s) of liver damage. [column 'MEC' in source]
AID1079939Cirrhosis, proven histopathologically. Value is number of references indexed. [column 'CIRRH' in source]
AID1815674Binding affinity to human N-terminal His6-tagged and thrombin cleavage fused BLVRB expressed in Escherichia coli BL21 (DE3) assessed as change in gibbs free energy by isothermal titration calorimetry2022Journal of medicinal chemistry, 02-10, Volume: 65, Issue:3
Repositioning Food and Drug Administration-Approved Drugs for Inhibiting Biliverdin IXβ Reductase B as a Novel Thrombocytopenia Therapeutic Target.
AID1221964Transporter substrate index ratio of permeability from basolateral to apical side in human Caco2 cells at 10 uM up to 120 mins by HPLC-MC analysis in presence of 1 uM of P-gp inhibitor LY3359792011Drug metabolism and disposition: the biological fate of chemicals, Feb, Volume: 39, Issue:2
Attenuation of intestinal absorption by major efflux transporters: quantitative tools and strategies using a Caco-2 model.
AID1079948Times to onset, minimal and maximal, observed in the indexed observations. [column 'DELAI' in source]
AID444052Hepatic clearance in human2010Journal of medicinal chemistry, Feb-11, Volume: 53, Issue:3
Physicochemical space for optimum oral bioavailability: contribution of human intestinal absorption and first-pass elimination.
AID1898638Binding affinity to wild type TTR/Amyloid beta (1 to 40 residues) binary complex (unknown origin) assessed as change in enthalpy binary by isothermal titration calorimetry2021European journal of medicinal chemistry, Dec-15, Volume: 226Targeting transthyretin in Alzheimer's disease: Drug discovery of small-molecule chaperones as disease-modifying drug candidates for Alzheimer's disease.
AID1079940Granulomatous liver disease, proven histopathologically. Value is number of references indexed. [column 'GRAN' in source]
AID1079932Highest frequency of moderate liver toxicity observed during clinical trials, expressed as a percentage. [column '% BIOL' in source]
AID1079931Moderate liver toxicity, defined via clinical-chemistry results: ALT or AST serum activity 6 times the normal upper limit (N) or alkaline phosphatase serum activity of 1.7 N. Value is number of references indexed. [column 'BIOL' in source]
AID1079945Animal toxicity known. [column 'TOXIC' in source]
AID1221965Transporter substrate index of efflux ratio in human Caco2 cells at 10 uM up to 120 mins by HPLC-MC analysis in presence of 1 uM of P-gp inhibitor LY3359792011Drug metabolism and disposition: the biological fate of chemicals, Feb, Volume: 39, Issue:2
Attenuation of intestinal absorption by major efflux transporters: quantitative tools and strategies using a Caco-2 model.
AID1079944Benign tumor, proven histopathologically. Value is number of references indexed. [column 'T.BEN' in source]
AID1898636Binding affinity to wild type TTR/Amyloid beta (1 to 40 residues) binary complex (unknown origin) assessed as complex dissociation constant by isothermal titration calorimetry2021European journal of medicinal chemistry, Dec-15, Volume: 226Targeting transthyretin in Alzheimer's disease: Drug discovery of small-molecule chaperones as disease-modifying drug candidates for Alzheimer's disease.
AID236916Percentage of mass balance in hexadecane membranes model2005Journal of medicinal chemistry, Jan-27, Volume: 48, Issue:2
Exploring the role of different drug transport routes in permeability screening.
AID236914Permeability Coefficient in hexadecane membranes model2005Journal of medicinal chemistry, Jan-27, Volume: 48, Issue:2
Exploring the role of different drug transport routes in permeability screening.
AID1079936Choleostatic liver toxicity, either proven histopathologically or where the ratio of maximal ALT or AST activity above normal to that of Alkaline Phosphatase is < 2 (see ACUTE). Value is number of references indexed. [column 'CHOLE' in source]
AID236912Permeability Coefficient in 2/4/A1 cell model2005Journal of medicinal chemistry, Jan-27, Volume: 48, Issue:2
Exploring the role of different drug transport routes in permeability screening.
AID455986Permeability across human Caco-2 cells2009Bioorganic & medicinal chemistry, Oct-01, Volume: 17, Issue:19
Computational modeling of novel inhibitors targeting the Akt pleckstrin homology domain.
AID540212Mean residence time in human after iv administration2008Drug metabolism and disposition: the biological fate of chemicals, Jul, Volume: 36, Issue:7
Trend analysis of a database of intravenous pharmacokinetic parameters in humans for 670 drug compounds.
AID1221961Apparent permeability from basolateral to apical side of human Caco2 cells at 10 uM up to 120 mins by HPLC-MC analysis in presence of 1 uM of P-gp inhibitor LY3359792011Drug metabolism and disposition: the biological fate of chemicals, Feb, Volume: 39, Issue:2
Attenuation of intestinal absorption by major efflux transporters: quantitative tools and strategies using a Caco-2 model.
AID444058Volume of distribution at steady state in human2010Journal of medicinal chemistry, Feb-11, Volume: 53, Issue:3
Physicochemical space for optimum oral bioavailability: contribution of human intestinal absorption and first-pass elimination.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (215)

TimeframeStudies, This Drug (%)All Drugs %
pre-199069 (32.09)18.7374
1990's78 (36.28)18.2507
2000's29 (13.49)29.6817
2010's28 (13.02)24.3611
2020's11 (5.12)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 51.29

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 Index51.29 (24.57)
Research Supply Index5.63 (2.92)
Research Growth Index4.52 (4.65)
Search Engine Demand Index81.88 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (51.29)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials52 (23.11%)5.53%
Reviews20 (8.89%)6.00%
Case Studies15 (6.67%)4.05%
Observational0 (0.00%)0.25%
Other138 (61.33%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Clinical Trials (1)

Trial Overview

TrialPhaseEnrollmentStudy TypeStart DateStatus
[NCT00004288]Phase 24 participants Interventional1996-05-31Completed
[information is prepared from clinicaltrials.gov, extracted Sep-2024]