Compounds > pyridoxal isonicotinoyl hydrazone
Page last updated: 2024-10-15

pyridoxal isonicotinoyl hydrazone

Description

pyridoxal isonicotinoyl hydrazone: acts as iron chelating agent [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID135409539
CHEMBL ID103111
SCHEMBL ID801139
MeSH IDM0075533

Synonyms (37)

Synonym
isonicotinic acid, ((3-hydroxy-5-(hydroxymethyl)-2-methyl-4-pyridyl)methylene)hydrazide
nsc 77674
brn 3685006
4-pyridinecarboxylic acid, ((3-hydroxy-5-(hydroxymethyl)-2-methyl-4-pyridinyl)methylene)hydrazide
isonicotinic acid, hydrazide, hydrazone with pyridoxal
n-[(e)-[3-hydroxy-5-(hydroxymethyl)-2-methyl-4-pyridyl]methyleneamino]pyridine-4-carboxamide
isonicotinic acid, [(3-hydroxy-5-hydroxymethyl-2-methyl-4-pyridinyl)methylene]hydrazide
nsc77674
pyridoxal isonicotinoyl hydrazone
737-86-0
ferric pyridoxal isonicotinoyl hydrazone
pyridoxalisonicotinoyl hydrazone
CHEMBL103111
n'-[(e)-[5-(hydroxymethyl)-2-methyl-3-oxopyridin-4-ylidene]methyl]pyridine-4-carbohydrazide
AKOS002083408
unii-xt2mso57qw
xt2mso57qw ,
SCHEMBL801139
pyridoxalisonicotinoylhydrazone
n'-[(e)-[3-hydroxy-5-(hydroxymethyl)-2-methylpyridin-4-yl]methylidene]pyridine-4-carbohydrazide
83706-03-0
BS-17487
unii-9i5aa0jkh0
9I5AA0JKH0 ,
4-pyridinecarboxylic acid, (2e)-((3-hydroxy-5-(hydroxymethyl)-2-methyl-4-pyridinyl)methylene)hydrazide
4-pyridinecarboxylic acid, ((3-hydroxy-5-(hydroxymethyl)-2-methyl-4-pyridinyl)methylene)hydrazide, (e)-
pyridoxal isonicotinoyl hydrazone, (e)-
EX-A2972
n'-((3-hydroxy-5-(hydroxymethyl)-2-methylpyridin-4-yl)methylene)isonicotinohydrazide ,
n-[(e)-[3-hydroxy-5-(hydroxymethyl)-2-methylpyridin-4-yl]methylideneamino]pyridine-4-carboxamide
mfcd00763290
CS-0064264
pyridoxal 4-pyridinyl-acyl hydrazone
DTXSID90877506
HY-114758
4-pyridinecarboxylic acid, 2-[[3-hydroxy-5-(hydroxymethyl)-2-methyl-4-pyridinyl]methylene]hydrazide
Z49547535

Research Excerpts

Overview

Pyridoxal isonicotinoyl hydrazone (PIH) is a lead compound of the aroylhydrazone group of novel iron chelating agents. It is an iron chelator with antioxidant activity, low toxicity and is useful in the experimental treatment of iron-overload diseases.

ExcerptReference
"Pyridoxal isonicotinoyl hydrazone (PIH) is a new tridentate Fe-chelating agent that should be very promising in many pathological states resulting from both an iron-overload and formation of free radicals. "( Cardiac troponin T following repeated administration of pyridoxal isonicotinoyl hydrazone in rabbits.
Adamcová, M; Gersl, V; Hrdina, R; Klimtová, I; Machácková, J; Pelouch, V; Ponka, P; Simůnek, T, 2002)
"Pyridoxal isonicotinoyl hydrazone (PIH) is a lead compound of the aroylhydrazone group of novel iron chelating agents."( HPLC study on stability of pyridoxal isonicotinoyl hydrazone.
Klimes, J; Kovaríková, P; Mokrý, M; Vávrová, K, 2006)
"Pyridoxal isonicotinoyl hydrazone (PIH) is a tridentate Fe-chelating agent that shows high Fe chelation efficacy both in vitro in cell culture models and also in vivo in rats and mice."( Pyridoxal isonicotinoyl hydrazone and its analogs: potential orally effective iron-chelating agents for the treatment of iron overload disease.
Ponka, P; Richardson, DR, 1998)
"Pyridoxal isonicotinoyl hydrazone (PIH) is an iron chelator with antioxidant activity, low toxicity and is useful in the experimental treatment of iron-overload diseases. "( Pyridoxal isonicotinoyl hydrazone (PIH) prevents copper-mediated in vitro free radical formation.
Andrade, RG; Gonçalves, MS; Hermes-Lima, M, 2001)
"Pyridoxal isonicotinoyl hydrazone (PIH) is a highly effective iron chelator. "( Toxicological study of pyridoxal isonicotinoyl hydrazone: acute and subchronic toxicity.
Nakornchai, S; Sookvanichsilp, N; Weerapradist, W, 1991)

Toxicity

ExcerptReference
" The LD50 values of PIH in both species were 5 and 1 g/kg given orally and intraperitoneally, respectively."( Toxicological study of pyridoxal isonicotinoyl hydrazone: acute and subchronic toxicity.
Nakornchai, S; Sookvanichsilp, N; Weerapradist, W, 1991)
" K562 cells loaded with eicosapentaenoic acid, a fatty acid particularly susceptible to oxidation, were also more sensitive to the toxic effects of the Fe complexes, and toxicity was proportional to lipid peroxidation."( The role of oxidative stress in the toxicity of pyridoxal isonicotinoyl hydrazone (PIH) analogues.
Buss, JL; Neuzil, J; Ponka, P, 2002)
" In contrast, PIH was inactive, while SIH was equally toxic toward control and EPA-loaded cells, without causing lipid peroxidation, indicating a much smaller contribution of oxidative stress to the mechanism of toxicity of these analogs."( Oxidative stress mediates toxicity of pyridoxal isonicotinoyl hydrazone analogs.
Buss, JL; Neuzil, J; Ponka, P, 2004)
"Iron (Fe) chelation therapy was initially designed to alleviate the toxic effects of excess Fe evident in Fe-overload diseases."( Future of toxicology--iron chelators and differing modes of action and toxicity: the changing face of iron chelation therapy.
Kalinowski, DS; Richardson, DR, 2007)

Bioavailability

ExcerptReference
" Collectively, these findings examining the mechanism of Dp44mT uptake and its distribution and excretion have clinical implications for its bioavailability and uptake in vivo."( Cellular uptake of the antitumor agent Dp44mT occurs via a carrier/receptor-mediated mechanism.
Kalinowski, DS; Menezes, SV; Merlot, AM; Pantarat, N; Richardson, DR; Sahni, S, 2013)

Dosage Studied

ExcerptReference
" A dose-response assay indicated that purified axolotl Tf stimulates growth of cultured blastemal cells at concentrations as low as 100 ng/mL."( Transferrin is necessary and sufficient for the neural effect on growth in amphibian limb regeneration blastemas.
Connell, E; Hsu, C; Mescher, AL; Overton, B; Patel, C, 1997)
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (20)

Assay IDTitleYearJournalArticle
AID16358% distribution of the radioiron in rat liver followed by intravenous injection of chelating agent1983Journal of medicinal chemistry, Feb, Volume: 26, Issue:2
Syntheses of iron bis(pyridoxal isonicotinoylhydrazone)s and the in vivo iron-removal properties of some pyridoxal derivatives.
AID16360% distribution of the radioiron in rat spleen followed by intravenous injection of chelating agent1983Journal of medicinal chemistry, Feb, Volume: 26, Issue:2
Syntheses of iron bis(pyridoxal isonicotinoylhydrazone)s and the in vivo iron-removal properties of some pyridoxal derivatives.
AID303516Effect on iron efflux in human SK-N-MC cells assessed as cellular iron release2007Journal of medicinal chemistry, Nov-29, Volume: 50, Issue:24
Design, synthesis, and characterization of new iron chelators with anti-proliferative activity: structure-activity relationships of novel thiohydrazone analogues.
AID16356% distribution of the radioiron in rat kidney followed by intravenous injection of chelating agent1983Journal of medicinal chemistry, Feb, Volume: 26, Issue:2
Syntheses of iron bis(pyridoxal isonicotinoylhydrazone)s and the in vivo iron-removal properties of some pyridoxal derivatives.
AID312543Inhibition of [59Fe]uptake from human transferrin in SK-MN-C cells relative to control2008Journal of medicinal chemistry, Jan-24, Volume: 51, Issue:2
Structure-activity relationships of novel iron chelators for the treatment of iron overload disease: the methyl pyrazinylketone isonicotinoyl hydrazone series.
AID292409Inhibition of iron uptake from transferrin in SK-N-MC cells at 50 uM relative to control2007Journal of medicinal chemistry, Jul-26, Volume: 50, Issue:15
Design, synthesis, and characterization of novel iron chelators: structure-activity relationships of the 2-benzoylpyridine thiosemicarbazone series and their 3-nitrobenzoyl analogues as potent antitumor agents.
AID370487Induction of iron mobilization in 59Fe]transferrin labeled human SK-N-MC cells assessed as iron release at 25 uM after 3 hrs by gamma scintillation counter2009Journal of medicinal chemistry, Mar-12, Volume: 52, Issue:5
2-Acetylpyridine thiosemicarbazones are potent iron chelators and antiproliferative agents: redox activity, iron complexation and characterization of their antitumor activity.
AID16364% excretion of radioiron determined in feces of rat followed by intravenous injection of transferrin pre-incubated with 10 mg of chelating agent1983Journal of medicinal chemistry, Feb, Volume: 26, Issue:2
Syntheses of iron bis(pyridoxal isonicotinoylhydrazone)s and the in vivo iron-removal properties of some pyridoxal derivatives.
AID439758Iron chelating activity in rat assessed as faecal iron excretion at 25 to 100 mg/kg, po administered as single dose relative to basal level2009Journal of medicinal chemistry, Sep-10, Volume: 52, Issue:17
Thiosemicarbazones from the old to new: iron chelators that are more than just ribonucleotide reductase inhibitors.
AID16362% excretion of ferritin determined in faces of rat followed by intravenous injection of chelating agent1983Journal of medicinal chemistry, Feb, Volume: 26, Issue:2
Syntheses of iron bis(pyridoxal isonicotinoylhydrazone)s and the in vivo iron-removal properties of some pyridoxal derivatives.
AID16363% excretion of ferritin determined in urine of rat followed by intravenous injection of chelating agent1983Journal of medicinal chemistry, Feb, Volume: 26, Issue:2
Syntheses of iron bis(pyridoxal isonicotinoylhydrazone)s and the in vivo iron-removal properties of some pyridoxal derivatives.
AID16361% distribution of the radioiron in rat spleen followed by intravenous injection of transferrin pre-incubated with 10 mg of chelating agent1983Journal of medicinal chemistry, Feb, Volume: 26, Issue:2
Syntheses of iron bis(pyridoxal isonicotinoylhydrazone)s and the in vivo iron-removal properties of some pyridoxal derivatives.
AID16354% distribution of the radioiron in blood of rat followed by intravenous injection of chelating agent1983Journal of medicinal chemistry, Feb, Volume: 26, Issue:2
Syntheses of iron bis(pyridoxal isonicotinoylhydrazone)s and the in vivo iron-removal properties of some pyridoxal derivatives.
AID16359% distribution of the radioiron in rat liver followed by intravenous injection of transferrin preincubated with 10 mg of chelating agent1983Journal of medicinal chemistry, Feb, Volume: 26, Issue:2
Syntheses of iron bis(pyridoxal isonicotinoylhydrazone)s and the in vivo iron-removal properties of some pyridoxal derivatives.
AID303517Inhibition of cellular iron uptake from 59Fe]transferrin in human SK-N-MC cells at 50 uM relative to control2007Journal of medicinal chemistry, Nov-29, Volume: 50, Issue:24
Design, synthesis, and characterization of new iron chelators with anti-proliferative activity: structure-activity relationships of novel thiohydrazone analogues.
AID16357% distribution of the radioiron in rat kidney followed by intravenous injection of transferrin pre-incubated with 10 mg of chelating agent1983Journal of medicinal chemistry, Feb, Volume: 26, Issue:2
Syntheses of iron bis(pyridoxal isonicotinoylhydrazone)s and the in vivo iron-removal properties of some pyridoxal derivatives.
AID16355% distribution of the radioiron in blood of rats followed by intravenous injection of transferrin pre-incubated with 10 mg of chelating agent1983Journal of medicinal chemistry, Feb, Volume: 26, Issue:2
Syntheses of iron bis(pyridoxal isonicotinoylhydrazone)s and the in vivo iron-removal properties of some pyridoxal derivatives.
AID370489Reduction of cellular iron uptake from 59Fe]transferrin in human SK-N-MC cells at 25 uM after 3 hrs relative to control2009Journal of medicinal chemistry, Mar-12, Volume: 52, Issue:5
2-Acetylpyridine thiosemicarbazones are potent iron chelators and antiproliferative agents: redox activity, iron complexation and characterization of their antitumor activity.
AID312542Induction of intracellular iron mobilization in human SK-MN-C cells relative to control2008Journal of medicinal chemistry, Jan-24, Volume: 51, Issue:2
Structure-activity relationships of novel iron chelators for the treatment of iron overload disease: the methyl pyrazinylketone isonicotinoyl hydrazone series.
AID16365% excretion of radioiron determined in urine of rat followed by intravenous injection of transferrin preincubated with 10 mg of chelating agent1983Journal of medicinal chemistry, Feb, Volume: 26, Issue:2
Syntheses of iron bis(pyridoxal isonicotinoylhydrazone)s and the in vivo iron-removal properties of some pyridoxal derivatives.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (96)

TimeframeStudies, This Drug (%)All Drugs %
pre-199030 (31.25)18.7374
1990's28 (29.17)18.2507
2000's31 (32.29)29.6817
2010's5 (5.21)24.3611
2020's2 (2.08)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials2 (2.08%)5.53%
Reviews9 (9.38%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other85 (88.54%)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
Chelation Therapy of Iron Overload With Oral Pyridoxal Isonicotinoyl Hydrazone[NCT00000588]Phase 2120 participants (Actual)Interventional1989-06-05Completed
[information is prepared from clinicaltrials.gov, extracted Sep-2024]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
dimethyl sulfoxide
Dimethyl Sulfoxide: A highly polar organic liquid, that is used widely as a chemical solvent. Because of its ability to penetrate biological membranes, it is used as a vehicle for topical application of pharmaceuticals. It is also used to protect tissue during CRYOPRESERVATION. Dimethyl sulfoxide shows a range of pharmacological activity including analgesia and anti-inflammation.. dimethyl sulfoxide : A 2-carbon sulfoxide in which the sulfur atom has two methyl substituents.		2.3920sulfoxide;
volatile organic compound		alkylating agent;
antidote;
Escherichia coli metabolite;
geroprotector;
MRI contrast agent;
non-narcotic analgesic;
polar aprotic solvent;
radical scavenger
glycine
[no description available]		1.9610alpha-amino acid;
amino acid zwitterion;
proteinogenic amino acid;
serine family amino acid		EC 2.1.2.1 (glycine hydroxymethyltransferase) inhibitor;
fundamental metabolite;
hepatoprotective agent;
micronutrient;
neurotransmitter;
NMDA receptor agonist;
nutraceutical
pyridoxal
[no description available]		11.97902hydroxymethylpyridine;
methylpyridines;
monohydroxypyridine;
pyridinecarbaldehyde;
vitamin B6		cofactor;
Escherichia coli metabolite;
human metabolite;
mouse metabolite;
Saccharomyces cerevisiae metabolite
pyridoxal phosphate
Pyridoxal Phosphate: This is the active form of VITAMIN B 6 serving as a coenzyme for synthesis of amino acids, neurotransmitters (serotonin, norepinephrine), sphingolipids, aminolevulinic acid. During transamination of amino acids, pyridoxal phosphate is transiently converted into pyridoxamine phosphate (PYRIDOXAMINE).. pyridoxal 5'-phosphate : The monophosphate ester obtained by condensation of phosphoric acid with the primary hydroxy group of pyridoxal.		2.3520methylpyridines;
monohydroxypyridine;
pyridinecarbaldehyde;
vitamin B6 phosphate		coenzyme;
cofactor;
EC 2.7.7.7 (DNA-directed DNA polymerase) inhibitor;
Escherichia coli metabolite;
human metabolite;
mouse metabolite;
Saccharomyces cerevisiae metabolite
1,10-phenanthroline
1,10-phenanthroline: RN given refers to parent cpd; inhibits Zn-dependent metalloproteinases		1.9610phenanthrolineEC 2.7.1.1 (hexokinase) inhibitor;
EC 3.4.19.3 (pyroglutamyl-peptidase I) inhibitor
2,2'-dipyridyl
2,2'-Dipyridyl: A reagent used for the determination of iron.. 2,2'-bipyridine : A bipyridine in which the two pyridine moieties are linked by a bond between positions C-2 and C-2'.		2.6630bipyridinechelator;
ferroptosis inhibitor
5,5-dimethyl-1-pyrroline-1-oxide
5,5-dimethyl-1-pyrroline-1-oxide: do not confuse with DMPO (4',5'-dihydroxy-7-methoxy-4-phenyl-5,2'-oxidocoumarin). 5,5-dimethyl-1-pyrroline N-oxide : A member of the class of 1-pyrroline nitrones (1-pyrroline N-oxides) resulting from the formal N-oxidation of 5,5-dimethyl-1-pyrroline. Used as a spin trap for the study of radicals formed by enzymatic acetaldehyde oxidation.		2101-pyrroline nitronesneuroprotective agent;
spin trapping reagent
acetohydroxamic acid
acetohydroxamic acid: urease inhibitor. oxime : Compounds of structure R2C=NOH derived from condensation of aldehydes or ketones with hydroxylamine. Oximes from aldehydes may be called aldoximes; those from ketones may be called ketoximes.. N-hydroxyacetimidic acid : A carbohydroximic acid consisting of acetimidic acid having a hydroxy group attached to the imide nitrogen.. acetohydroxamic acid : A member of the class of acetohydroxamic acids that is acetamide in which one of the amino hydrogens has been replaced by a hydroxy group.		1.9710acetohydroxamic acids;
carbohydroximic acid		algal metabolite;
EC 3.5.1.5 (urease) inhibitor
deferiprone
Deferiprone: A pyridone derivative and iron chelator that is used in the treatment of IRON OVERLOAD in patients with THALASSEMIA.. deferiprone : A member of the class of 4-pyridones that is pyridin-4(1H)-one substituted at positions 1 and 2 by methyl groups and at position 3 by a hydroxy group. A lipid-soluble iron-chelator used for treatment of thalassaemia.		4.87604-pyridonesiron chelator;
protective agent
deferoxamine
Deferoxamine: Natural product isolated from Streptomyces pilosus. It forms iron complexes and is used as a chelating agent, particularly in the mesylate form.. desferrioxamine B : An acyclic desferrioxamine that is butanedioic acid in which one of the carboxy groups undergoes formal condensation with the primary amino group of N-(5-aminopentyl)-N-hydroxyacetamide and the second carboxy group undergoes formal condensation with the hydroxyamino group of N(1)-(5-aminopentyl)-N(1)-hydroxy-N(4)-[5-(hydroxyamino)pentyl]butanediamide. It is a siderophore native to Streptomyces pilosus biosynthesised by the DesABCD enzyme cluster as a high affinity Fe(III) chelator.		6.09230acyclic desferrioxaminebacterial metabolite;
ferroptosis inhibitor;
iron chelator;
siderophore
pentetic acid
Pentetic Acid: An iron chelating agent with properties like EDETIC ACID. DTPA has also been used as a chelator for other metals, such as plutonium.		1.9810pentacarboxylic acidcopper chelator
hydroxyurea
[no description available]		210one-carbon compound;
ureas		antimetabolite;
antimitotic;
antineoplastic agent;
DNA synthesis inhibitor;
EC 1.17.4.1 (ribonucleoside-diphosphate reductase) inhibitor;
genotoxin;
immunomodulator;
radical scavenger;
teratogenic agent
isoniazid
Hydra: A genus of freshwater polyps in the family Hydridae, order Hydroida, class HYDROZOA. They are of special interest because of their complex organization and because their adult organization corresponds roughly to the gastrula of higher animals.. hydrazide : Compounds derived from oxoacids RkE(=O)l(OH)m (l =/= 0) by replacing -OH by -NRNR2 (R groups are commonly H). (IUPAC).		11.97902carbohydrazideantitubercular agent;
drug allergen
ethylmaleimide
Ethylmaleimide: A sulfhydryl reagent that is widely used in experimental biochemical studies.		1.9710maleimidesanticoronaviral agent;
EC 1.3.1.8 [acyl-CoA dehydrogenase (NADP(+))] inhibitor;
EC 2.1.1.122 [(S)-tetrahydroprotoberberine N-methyltransferase] inhibitor;
EC 2.7.1.1 (hexokinase) inhibitor
protoporphyrin ix
protoporphyrin IX: RN given refers to parent cpd; structure in Merck Index, 9th ed, #7685. protoporphyrin : A cyclic tetrapyrrole that consists of porphyrin bearing four methyl substituents at positions 3, 8, 13 and 17, two vinyl substituents at positions 7 and 12 and two 2-carboxyethyl substituents at positions 2 and 18. The parent of the class of protoporphyrins.		2.4120
succinylacetone
succinylacetone: inhibitor of heme biosynthesis. 4,6-dioxoheptanoic acid : A dioxo monocarboxylic acid that is heptanoic acid in which oxo groups replace the hydrogens at positions 4 and 6. It is an abnormal metabolite of the tyrosine metabolic pathway and a marker for type 1 tyrosinaemia.		1.9610beta-diketone;
dioxo monocarboxylic acid		human metabolite
suramin
Suramin: A polyanionic compound with an unknown mechanism of action. It is used parenterally in the treatment of African trypanosomiasis and it has been used clinically with diethylcarbamazine to kill the adult Onchocerca. (From AMA Drug Evaluations Annual, 1992, p1643) It has also been shown to have potent antineoplastic properties.. suramin : A member of the class of phenylureas that is urea in which each of the amino groups has been substituted by a 3-({2-methyl-5-[(4,6,8-trisulfo-1-naphthyl)carbamoyl]phenyl}carbamoyl)phenyl group. An activator of both the rabbit skeletal muscle RyR1 and sheep cardiac RyR2 isoform ryanodine receptor channels, it has been used for the treatment of human African trypanosomiasis for over 100 years.		1.9610naphthalenesulfonic acid;
phenylureas;
secondary carboxamide		angiogenesis inhibitor;
antinematodal drug;
antineoplastic agent;
apoptosis inhibitor;
EC 2.7.11.13 (protein kinase C) inhibitor;
GABA antagonist;
GABA-gated chloride channel antagonist;
purinergic receptor P2 antagonist;
ryanodine receptor agonist;
trypanocidal drug
thymidine
[no description available]		2.6830pyrimidine 2'-deoxyribonucleosideEscherichia coli metabolite;
human metabolite;
metabolite;
mouse metabolite
uridine
[no description available]		210uridinesdrug metabolite;
fundamental metabolite;
human metabolite
edetic acid
Edetic Acid: A chelating agent that sequesters a variety of polyvalent cations such as CALCIUM. It is used in pharmaceutical manufacturing and as a food additive.		2.7330ethylenediamine derivative;
polyamino carboxylic acid;
tetracarboxylic acid		anticoagulant;
antidote;
chelator;
copper chelator;
geroprotector
leucine
Leucine: An essential branched-chain amino acid important for hemoglobin formation.. leucine : A branched-chain amino acid that consists of glycine in which one of the hydrogens attached to the alpha-carbon is substituted by an isobutyl group.		210amino acid zwitterion;
L-alpha-amino acid;
leucine;
proteinogenic amino acid;
pyruvate family amino acid		algal metabolite;
Escherichia coli metabolite;
human metabolite;
mouse metabolite;
plant metabolite;
Saccharomyces cerevisiae metabolite
methionine
Methionine: A sulfur-containing essential L-amino acid that is important in many body functions.. methionine : A sulfur-containing amino acid that is butyric acid bearing an amino substituent at position 2 and a methylthio substituent at position 4.		1.9710aspartate family amino acid;
L-alpha-amino acid;
methionine zwitterion;
methionine;
proteinogenic amino acid		antidote to paracetamol poisoning;
human metabolite;
micronutrient;
mouse metabolite;
nutraceutical
cycloheximide
Cycloheximide: Antibiotic substance isolated from streptomycin-producing strains of Streptomyces griseus. It acts by inhibiting elongation during protein synthesis.. cycloheximide : A dicarboximide that is 4-(2-hydroxyethyl)piperidine-2,6-dione in which one of the hydrogens attached to the carbon bearing the hydroxy group is replaced by a 3,5-dimethyl-2-oxocyclohexyl group. It is an antibiotic produced by the bacterium Streptomyces griseus.		1.9710antibiotic fungicide;
cyclic ketone;
dicarboximide;
piperidine antibiotic;
piperidones;
secondary alcohol		anticoronaviral agent;
bacterial metabolite;
ferroptosis inhibitor;
neuroprotective agent;
protein synthesis inhibitor
cytarabine
[no description available]		1.9710beta-D-arabinoside;
monosaccharide derivative;
pyrimidine nucleoside		antimetabolite;
antineoplastic agent;
antiviral agent;
immunosuppressive agent
phenylhydrazine
[no description available]		210phenylhydrazinesxenobiotic
2-naphthol
2-naphthol: RN given refers to parent cpd. 2-naphthol : A naphthol carrying a hydroxy group at position 2.. naphthols : Any hydroxynaphthalene derivative that has a single hydroxy substituent.		1.9910naphtholantinematodal drug;
genotoxin;
human urinary metabolite;
human xenobiotic metabolite;
mouse metabolite;
radical scavenger
nitrilotriacetic acid
Nitrilotriacetic Acid: A derivative of acetic acid, N(CH2COOH)3. It is a complexing (sequestering) agent that forms stable complexes with Zn2+. (From Miall's Dictionary of Chemistry, 5th ed.)		2.6830NTA;
tricarboxylic acid		carcinogenic agent;
nephrotoxic agent
hydrazine
diamine : Any polyamine that contains two amino groups.		7.2110azane;
hydrazines		EC 4.3.1.10 (serine-sulfate ammonia-lyase) inhibitor
salicylaldehyde isonicotinoyl hydrazone
salicylaldehyde isonicotinoyl hydrazone: structure in first source		8.360
malondialdehyde
Malondialdehyde: The dialdehyde of malonic acid.. malonaldehyde : A dialdehyde that is propane substituted by two oxo groups at the terminal carbon atoms respectively. A biomarker of oxidative damage to lipids caused by smoking, it exists in vivo mainly in the enol form.		1.9910dialdehydebiomarker
buthionine sulfoximine
Buthionine Sulfoximine: A synthetic amino acid that depletes glutathione by irreversibly inhibiting gamma-glutamylcysteine synthetase. Inhibition of this enzyme is a critical step in glutathione biosynthesis. It has been shown to inhibit the proliferative response in human T-lymphocytes and inhibit macrophage activation. (J Biol Chem 1995;270(33):1945-7). 2-amino-4-(S-butylsulfonimidoyl)butanoic acid : A non-proteinogenic alpha-amino acid that is homocysteine in which the thiol group carries an oxo, imino and butyl groups.. S-butyl-DL-homocysteine (S,R)-sulfoximine : A sulfoximide that is the sulfoximine derivative of an analogue of DL-methionine in which the S-methyl group is replaced by S-butyl.		2.0210diastereoisomeric mixture;
homocysteines;
non-proteinogenic alpha-amino acid;
sulfoximide		EC 6.3.2.2 (glutamate--cysteine ligase) inhibitor;
ferroptosis inducer
copper sulfate
Copper Sulfate: A sulfate salt of copper. It is a potent emetic and is used as an antidote for poisoning by phosphorus. It also can be used to prevent the growth of algae.. copper(II) sulfate : A metal sulfate compound having copper(2+) as the metal ion.		210metal sulfateemetic;
fertilizer;
sensitiser
ammonium chloride
Ammonium Chloride: An acidifying agent that has expectorant and diuretic effects. Also used in etching and batteries and as a flux in electroplating.. ammonium chloride : An inorganic chloride having ammonium as the counterion.		1.9810ammonium salt;
inorganic chloride		ferroptosis inhibitor
ferric nitrilotriacetate
ferric nitrilotriacetate: induces diabetes in animals (iron loading)		2.420iron chelatecarcinogenic agent;
mutagen
daunorubicin
Daunorubicin: A very toxic anthracycline aminoglycoside antineoplastic isolated from Streptomyces peucetius and others, used in treatment of LEUKEMIA and other NEOPLASMS.. anthracycline : Anthracyclines are polyketides that have a tetrahydronaphthacenedione ring structure attached by a glycosidic linkage to the amino sugar daunosamine.. daunorubicin : A natural product found in Actinomadura roseola.		7.4420aminoglycoside antibiotic;
anthracycline;
p-quinones;
tetracenequinones		antineoplastic agent;
bacterial metabolite
razoxane
Razoxane: An antimitotic agent with immunosuppressive properties.		2.0310N-alkylpiperazine
transferrin
Transferrin: An iron-binding beta1-globulin that is synthesized in the LIVER and secreted into the blood. It plays a central role in the transport of IRON throughout the circulation. A variety of transferrin isoforms exist in humans, including some that are considered markers for specific disease states.		9.5240
ferrozine
Ferrozine: A ferroin compound that forms a stable magenta-colored solution with the ferrous ion. The complex has an absorption peak at 562 nm and is used as a reagent and indicator for iron.		2.0210
ferric citrate
ferric citrate: RN given refers to Fe(+3)[1:1] salt. iron(III) citrate : An iron chelate resulting from the combination of iron(3+) and citrate(3-).		2.4120iron chelateanti-anaemic agent;
nutraceutical
gallium nitrate
gallium nitrate: RN given refers to parent cpd		7.3920
1,7-phenanthroline
[no description available]		2.3720phenanthroline
triazoles
Triazoles: Heterocyclic compounds containing a five-membered ring with two carbon atoms and three nitrogen atoms with the molecular formula C2H3N3.. triazoles : An azole in which the five-membered heterocyclic aromatic skeleton contains three N atoms and two C atoms.		2.02101,2,3-triazole
bathophenanthroline
4,7-diphenyl-1,10-phenanthroline : A member of the class of phenanthrolines that is 1,10-phenanthroline bearing two phenyl substituents at positions 4 and 7.		1.9710benzenes;
phenanthrolines		chelator
vitamin b 6
Vitamin B 6: VITAMIN B 6 refers to several PICOLINES (especially PYRIDOXINE; PYRIDOXAL; & PYRIDOXAMINE) that are efficiently converted by the body to PYRIDOXAL PHOSPHATE which is a coenzyme for synthesis of amino acids, neurotransmitters (serotonin, norepinephrine), sphingolipids, and aminolevulinic acid. During transamination of amino acids, pyridoxal phosphate is transiently converted into PYRIDOXAMINE phosphate. Although pyridoxine and Vitamin B 6 are still frequently used as synonyms, especially by medical researchers, this practice is erroneous and sometimes misleading (EE Snell; Ann NY Acad Sci, vol 585 pg 1, 1990). Most of vitamin B6 is eventually degraded to PYRIDOXIC ACID and excreted in the urine.		2.2110
hydroxyl radical
Hydroxyl Radical: The univalent radical OH. Hydroxyl radical is a potent oxidizing agent.		3.150oxygen hydride;
oxygen radical;
reactive oxygen species
fenton's reagent
Fenton's reagent: used for oxidizing sugars & alcohols		2.4220
fe(iii)-edta
Fe(III)-EDTA: iron fortifying agent; RN given refers to parent cpd		2.0110iron coordination entity
deferasirox
Deferasirox: A triazole and benzoate derivative that acts as a selective iron chelator. It is used in the management of chronic IRON OVERLOAD due to blood transfusion or non-transfusion dependent THALASSEMIA.. deferasirox : A member of the class of triazoles, deferasirox is 1,2,4-triazole substituted by a 4-carboxyphenyl group at position 1 and by 2-hydroxyphenyl groups at positions 3 and 5. An orally active iron chelator, it is used to manage chronic iron overload in patients receiving long-term blood transfusions.		2.0210benzoic acids;
monocarboxylic acid;
phenols;
triazoles		iron chelator
2-pyridylcarboxaldehyde benzoylhydrazone
2-pyridylcarboxaldehyde benzoylhydrazone: structure in first source		2.0410
gallium
Gallium: A rare, metallic element designated by the symbol, Ga, atomic number 31, and atomic weight 69.72.. gallium atom : A metallic element predicted as eka-aluminium by Mendeleev in 1870 and discovered by Paul-Emile Lecoq de Boisbaudran in 1875. Named in honour of France (Latin Gallia) and perhaps also from the Latin gallus cock, a translation of Lecoq.		3.0850boron group element atom
deoxyribose
[no description available]		2.9240deoxypentosehuman metabolite;
mouse metabolite;
Saccharomyces cerevisiae metabolite
2-pyridylcarboxaldehyde isonicotinoylhydrazone
2-pyridylcarboxaldehyde isonicotinoylhydrazone: structure in first source		2.4420
2-acetylpyridine thiosemicarbazone
2-acetylpyridine thiosemicarbazone: RN given refers to parent cpd		3.5520
2-acetylpyridine-4-methyl-3-thiosemicarbazone
[no description available]		2.0510
3-aminopyridine-2-carboxaldehyde thiosemicarbazone
3-aminopyridine-2-carboxaldehyde thiosemicarbazone: a neuroprotective agent; structure given in first source		4.2350
di-2-pyridylketone-4,4-dimethyl-3-thiosemicarbazone
[no description available]		4.2450
di-2-pyridyl ketone isonicotinoyl hydrazone
di-2-pyridyl ketone isonicotinoyl hydrazone: a chelating agent; structure in first source		2.0410
heme
Heme: The color-furnishing portion of hemoglobin. It is found free in tissues and as the prosthetic group in many hemeproteins.. ferroheme : Any iron(II)--porphyrin coordination complex.. ferroheme b : Heme b in which the iron has oxidation state +2.. heme : A heme is any tetrapyrrolic chelate of iron.		3.0950
ascorbic acid
Ascorbic Acid: A six carbon compound related to glucose. It is found naturally in citrus fruits and many vegetables. Ascorbic acid is an essential nutrient in human diets, and necessary to maintain connective tissue and bone. Its biologically active form, vitamin C, functions as a reducing agent and coenzyme in several metabolic pathways. Vitamin C is considered an antioxidant.. L-ascorbic acid : The L-enantiomer of ascorbic acid and conjugate acid of L-ascorbate.. L-ascorbate : The L-enantiomer of ascorbate and conjugate base of L-ascorbic acid, arising from selective deprotonation of the 3-hydroxy group. Required for a range of essential metabolic reactions in all animals and plants.. vitamin C : Any member of a group of vitamers that belong to the chemical structural class called butenolides that exhibit biological activity against vitamin C deficiency in animals. The vitamers include L-ascorbic acid and its salt, ionized and oxidized forms.		3.1250ascorbic acid;
vitamin C		coenzyme;
cofactor;
flour treatment agent;
food antioxidant;
food colour retention agent;
geroprotector;
plant metabolite;
skin lightening agent
epidermal growth factor
Epidermal Growth Factor: A 6-kDa polypeptide growth factor initially discovered in mouse submaxillary glands. Human epidermal growth factor was originally isolated from urine based on its ability to inhibit gastric secretion and called urogastrone. Epidermal growth factor exerts a wide variety of biological effects including the promotion of proliferation and differentiation of mesenchymal and EPITHELIAL CELLS. It is synthesized as a transmembrane protein which can be cleaved to release a soluble active form.		1.9710
hypoxanthine
[no description available]		1.9910nucleobase analogue;
oxopurine;
purine nucleobase		fundamental metabolite
rifampin
Rifampin: A semisynthetic antibiotic produced from Streptomyces mediterranei. It has a broad antibacterial spectrum, including activity against several forms of Mycobacterium. In susceptible organisms it inhibits DNA-dependent RNA polymerase activity by forming a stable complex with the enzyme. It thus suppresses the initiation of RNA synthesis. Rifampin is bactericidal, and acts on both intracellular and extracellular organisms. (From Gilman et al., Goodman and Gilman's The Pharmacological Basis of Therapeutics, 9th ed, p1160)		2.2110cyclic ketal;
hydrazone;
N-iminopiperazine;
N-methylpiperazine;
rifamycins;
semisynthetic derivative;
zwitterion		angiogenesis inhibitor;
antiamoebic agent;
antineoplastic agent;
antitubercular agent;
DNA synthesis inhibitor;
EC 2.7.7.6 (RNA polymerase) inhibitor;
Escherichia coli metabolite;
geroprotector;
leprostatic drug;
neuroprotective agent;
pregnane X receptor agonist;
protein synthesis inhibitor
2-hydroxy-1-naphthylaldehyde isonicotinoyl hydrazone
2-hydroxy-1-naphthylaldehyde isonicotinoyl hydrazone: structure in first source		4.3860
salicylaldehyde benzoyl hydrazone
salicylaldehyde benzoyl hydrazone: structure given in first source		7.4120
allopurinol
Allopurinol: A XANTHINE OXIDASE inhibitor that decreases URIC ACID production. It also acts as an antimetabolite on some simpler organisms.. allopurinol : A bicyclic structure comprising a pyrazole ring fused to a hydroxy-substituted pyrimidine ring.		1.9910nucleobase analogue;
organic heterobicyclic compound		antimetabolite;
EC 1.17.3.2 (xanthine oxidase) inhibitor;
gout suppressant;
radical scavenger
pyridoxal 4-methoxybenzoyl hydrazone
pyridoxal 4-methoxybenzoyl hydrazone: structure given in first source		1.9710
ConditionIndicatedRelationship StrengthStudiesTrials
Iron Overload
An excessive accumulation of iron in the body due to a greater than normal absorption of iron from the gastrointestinal tract or from parenteral injection. This may arise from idiopathic hemochromatosis, excessive iron intake, chronic alcoholism, certain types of refractory anemia, or transfusional hemosiderosis. (From Churchill's Illustrated Medical Dictionary, 1989)		05.2280
Brain Hemorrhage, Cerebral
[description not available]		02.3110
Innate Inflammatory Response
[description not available]		02.3110
Cerebral Hemorrhage
Bleeding into one or both CEREBRAL HEMISPHERES including the BASAL GANGLIA and the CEREBRAL CORTEX. It is often associated with HYPERTENSION and CRANIOCEREBRAL TRAUMA.		02.3110
Inflammation
A pathological process characterized by injury or destruction of tissues caused by a variety of cytologic and chemical reactions. It is usually manifested by typical signs of pain, heat, redness, swelling, and loss of function.		07.3110
Acute Liver Injury, Drug-Induced
[description not available]		02.4820
Liver Steatosis
[description not available]		02.2510
Fatty Liver
Lipid infiltration of the hepatic parenchymal cells resulting in a yellow-colored liver. The abnormal lipid accumulation is usually in the form of TRIGLYCERIDES, either as a single large droplet or multiple small droplets. Fatty liver is caused by an imbalance in the metabolism of FATTY ACIDS.		02.2510
Necrosis
The death of cells in an organ or tissue due to disease, injury or failure of the blood supply.		02.2510
Chemical and Drug Induced Liver Injury
A spectrum of clinical liver diseases ranging from mild biochemical abnormalities to ACUTE LIVER FAILURE, caused by drugs, drug metabolites, herbal and dietary supplements and chemicals from the environment.		02.4820
Hepatocellular Carcinoma
[description not available]		02.2110
Carcinoma, Hepatocellular
A primary malignant neoplasm of epithelial liver cells. It ranges from a well-differentiated tumor with EPITHELIAL CELLS indistinguishable from normal HEPATOCYTES to a poorly differentiated neoplasm. The cells may be uniform or markedly pleomorphic, or form GIANT CELLS. Several classification schemes have been suggested.		02.2110
Atrophy, Muscle
[description not available]		02.0810
Aging
The gradual irreversible changes in structure and function of an organism that occur as a result of the passage of time.		02.4220
Muscle Contraction
A process leading to shortening and/or development of tension in muscle tissue. Muscle contraction occurs by a sliding filament mechanism whereby actin filaments slide inward among the myosin filaments.		02.0810
Muscular Atrophy
Derangement in size and number of muscle fibers occurring with aging, reduction in blood supply, or following immobilization, prolonged weightlessness, malnutrition, and particularly in denervation.		02.0810
Sarcopenia
Progressive decline in muscle mass due to aging which results in decreased functional capacity of muscles.		02.0810
Sensitivity and Specificity
Binary classification measures to assess test results. Sensitivity or recall rate is the proportion of true positives. Specificity is the probability of correctly determining the absence of a condition. (From Last, Dictionary of Epidemiology, 2d ed)		02.0510
Benign Neoplasms
[description not available]		04.4850
Injury, Myocardial Reperfusion
[description not available]		02.0610
Neoplasms
New abnormal growth of tissue. Malignant neoplasms show a greater degree of anaplasia and have the properties of invasion and metastasis, compared to benign neoplasms.		04.4850
Anemia, Cooley's
[description not available]		02.0210
beta-Thalassemia
A disorder characterized by reduced synthesis of the beta chains of hemoglobin. There is retardation of hemoglobin A synthesis in the heterozygous form (thalassemia minor), which is asymptomatic, while in the homozygous form (thalassemia major, Cooley's anemia, Mediterranean anemia, erythroblastic anemia), which can result in severe complications and even death, hemoglobin A synthesis is absent.		02.0210
Cancer of Lung
[description not available]		02.0310
Lung Neoplasms
Tumors or cancer of the LUNG.		02.0310
Cardiac Diseases
[description not available]		02.0410
Heart Diseases
Pathological conditions involving the HEART including its structural and functional abnormalities.		02.0410
Pregnancy
The status during which female mammals carry their developing young (EMBRYOS or FETUSES) in utero before birth, beginning from FERTILIZATION to BIRTH.		02.3720
Neuroblastoma
A common neoplasm of early childhood arising from neural crest cells in the sympathetic nervous system, and characterized by diverse clinical behavior, ranging from spontaneous remission to rapid metastatic progression and death. This tumor is the most common intraabdominal malignancy of childhood, but it may also arise from thorax, neck, or rarely occur in the central nervous system. Histologic features include uniform round cells with hyperchromatic nuclei arranged in nests and separated by fibrovascular septa. Neuroblastomas may be associated with the opsoclonus-myoclonus syndrome. (From DeVita et al., Cancer: Principles and Practice of Oncology, 5th ed, pp2099-2101; Curr Opin Oncol 1998 Jan;10(1):43-51)		01.9810
Malignant Melanoma
[description not available]		02.3820
Melanoma
A malignant neoplasm derived from cells that are capable of forming melanin, which may occur in the skin of any part of the body, in the eye, or, rarely, in the mucous membranes of the genitalia, anus, oral cavity, or other sites. It occurs mostly in adults and may originate de novo or from a pigmented nevus or malignant lentigo. Melanomas frequently metastasize widely, and the regional lymph nodes, liver, lungs, and brain are likely to be involved. The incidence of malignant skin melanomas is rising rapidly in all parts of the world. (Stedman, 25th ed; from Rook et al., Textbook of Dermatology, 4th ed, p2445)		02.3820
Asphyxia Neonatorum
Respiratory failure in the newborn. (Dorland, 27th ed)		01.9910
Disease Models, Animal
Naturally-occurring or experimentally-induced animal diseases with pathological processes analogous to human diseases.		01.9910
Day Blindness
[description not available]		01.9910
Leukemia, Lymphocytic
[description not available]		01.9910
Leukemia, Lymphoid
Leukemia associated with HYPERPLASIA of the lymphoid tissues and increased numbers of circulating malignant LYMPHOCYTES and lymphoblasts.		01.9910
(pPNET) Peripheral Primitive Neuroectodermal Tumors
[description not available]		0210
Neuroectodermal Tumors, Primitive, Peripheral
A group of highly cellular primitive round cell neoplasms which occur extracranially in soft tissue and bone and are derived from embryonal neural crest cells. These tumors occur primarily in children and adolescents and share a number of characteristics with EWING SARCOMA.		0210
Friedreich Disease
[description not available]		0210
Friedreich Ataxia
An autosomal recessive disease, usually of childhood onset, characterized pathologically by degeneration of the spinocerebellar tracts, posterior columns, and to a lesser extent the corticospinal tracts. Clinical manifestations include GAIT ATAXIA, pes cavus, speech impairment, lateral curvature of spine, rhythmic head tremor, kyphoscoliosis, congestive heart failure (secondary to a cardiomyopathy), and lower extremity weakness. Most forms of this condition are associated with a mutation in a gene on chromosome 9, at band q13, which codes for the mitochondrial protein frataxin. (From Adams et al., Principles of Neurology, 6th ed, p1081; N Engl J Med 1996 Oct 17;335(16):1169-75) The severity of Friedreich ataxia associated with expansion of GAA repeats in the first intron of the frataxin gene correlates with the number of trinucleotide repeats. (From Durr et al, N Engl J Med 1996 Oct 17;335(16):1169-75)		0210
Body Weight
The mass or quantity of heaviness of an individual. It is expressed by units of pounds or kilograms.		01.9710
Thalassemias
[description not available]		05.1911
Thalassemia
A group of hereditary hemolytic anemias in which there is decreased synthesis of one or more hemoglobin polypeptide chains. There are several genetic types with clinical pictures ranging from barely detectable hematologic abnormality to severe and fatal anemia.		05.1911
Acute Promyelocytic Leukemia
[description not available]		01.9710
Leukemia, Promyelocytic, Acute
An acute myeloid leukemia in which abnormal PROMYELOCYTES predominate. It is frequently associated with DISSEMINATED INTRAVASCULAR COAGULATION.		01.9710
Di Guglielmo Disease
[description not available]		02.3720
Leukemia, Erythroblastic, Acute
A myeloproliferative disorder characterized by neoplastic proliferation of erythroblastic and myeloblastic elements with atypical erythroblasts and myeloblasts in the peripheral blood.		02.3720
Anemia, Hypochromic
Anemia characterized by a decrease in the ratio of the weight of hemoglobin to the volume of the erythrocyte, i.e., the mean corpuscular hemoglobin concentration is less than normal. The individual cells contain less hemoglobin than they could have under optimal conditions. Hypochromic anemia may be caused by iron deficiency from a low iron intake, diminished iron absorption, or excessive iron loss. It can also be caused by infections or other diseases, therapeutic drugs, lead poisoning, and other conditions. (Stedman, 25th ed; from Miale, Laboratory Medicine: Hematology, 6th ed, p393)		01.9710