Page last updated: 2024-12-05

pyrithioxin

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

Description

Pyrithioxin is a synthetic compound with a complex chemical structure, featuring a thiazine ring and a pyrimidine ring. Its synthesis involves a multi-step process, starting with the condensation of 2-amino-4-methylpyrimidine with sulfur monochloride to form a key intermediate. This intermediate is then reacted with 2-chloro-4-phenylthiazole to produce pyrithioxin. The compound has shown various pharmacological effects, including antioxidant, anti-inflammatory, and neuroprotective properties. Research suggests that pyrithioxin might have potential in the treatment of neurodegenerative disorders like Alzheimer's disease, due to its ability to protect neurons from oxidative stress and inflammation. Its specific mechanisms of action remain under investigation, but studies have implicated its interaction with various receptors and enzymes in the nervous system. The compound's ability to cross the blood-brain barrier and its low toxicity profile make it a promising candidate for further research in neuroprotection.'

Pyrithioxin: A neurotropic agent which reduces permeability of blood-brain barrier to phosphate. It has no vitamin B6 activity. [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID14190
CHEMBL ID488093
CHEBI ID135554
SCHEMBL ID150551
MeSH IDM0018266

Synonyms (86)

Synonym
AC-12193
nsc 759229
pyritinolum
unii-ak5q5fzh2r
ak5q5fzh2r ,
piritinolo
3,3'-(dithiodimethylene)bis(5-hydroxy-6-methyl-4-pyridinemethanol)
pyritinolum [inn-latin]
biocefalin
3,3'-(dithiobis(methylene))bis(5-hydroxy-6-methyl-4-pyridinemethanol)
pyritinol [inn:ban:dcf]
einecs 214-150-1
piritinol [inn-spanish]
pyritioxine
4-pyridinemethanol, 3,3'-(dithiobis(methylene))bis(5-hydroxy-6-methyl-
piritinolo [dcit]
4-pyridinemethanol, 3,3'-(dithiodimethylene)bis(5-hydroxy-6-methyl-
pyrithioxin
pyrithioxine hydrochloride
pyrithioxine
5-[[[5-hydroxy-4-(hydroxymethyl)-6-methyl-3-pyridyl]methyldisulfanyl]methyl]-4-(hydroxymethyl)-2-methyl-pyridin-3-ol
vitamin b6 disulfide
piritinol
epocan
pyridoxine disulfide
bonifen
pyridoxine-5-disulfide
bis(4-hydroxymethyl-5-hydroxy-6-methyl-3-pyridylmethyl)disulfide
dipyridoxolyldisulfide
bonol
encefabol
pyritinol
1098-97-1
4-pyridinemethanol, 3,3'-[dithiobis(methylene)]bis[5-hydroxy-6-methyl-
NCGC00166140-01
D02160
pyritinol (inn)
pyrithioxine (jan)
CHEBI:135554
5-[[[5-hydroxy-4-(hydroxymethyl)-6-methylpyridin-3-yl]methyldisulfanyl]methyl]-4-(hydroxymethyl)-2-methylpyridin-3-ol
nsc-759229
CHEMBL488093
AKOS005066380
STK801801
5,5'-(disulfanediyldimethanediyl)bis[4-(hydroxymethyl)-2-methylpyridin-3-ol]
4-(hydroxymethyl)-5-[[[4-(hydroxymethyl)-6-methyl-5-oxidanyl-pyridin-3-yl]methyldisulfanyl]methyl]-2-methyl-pyridin-3-ol
5-[[[5-hydroxy-4-(hydroxymethyl)-6-methyl-3-pyridinyl]methyldisulfanyl]methyl]-4-(hydroxymethyl)-2-methyl-3-pyridinol
A802103
HMS3264M15
nsc759229
pharmakon1600-01505762
smr001550535
pyritinol, pyrithioxin
MLS004712044
FT-0674240
pyritinol [inn]
pyritinol [mi]
pyrithioxine [jan]
pyritinol [who-dd]
S5141
CCG-213980
SCHEMBL150551
BBL028281
SIXLXDIJGIWWFU-UHFFFAOYSA-N
5,5'-(dithiodimethylene)bis[3-hydroxy-4-hydroxymethyl-2-methylpyridine]
5,5'-(dithiodimethylene) bis[3-hydroxy-4-hydroxymethyl-2-methylpyridine]
DTXSID3048362
5,5'-(disulfanediylbis(methylene))bis(4-(hydroxymethyl)-2-methylpyridin-3-ol)
W-108702
5,5'-[disulfanediylbis(methylene)]bis[4-(hydroxymethyl)-2-methyl-3-pyridinol]
HY-B0910
AB00375835_02
sr-01000872772
SR-01000872772-1
5,5'-disulfanediylbis(methylene)bis(4-(hydroxymethyl)-2-methylpyridin-3-ol)
pyrithioxin, analytical standard
SBI-0207045.P001
5,5'-[dithiobis(methylene)]bis[4-(hydroxymethyl)-2-methylpyridin-3-ol]
DB13084
Q416361
mfcd00151477
AS-13595
P2250
BRD-K82181219-001-01-9
HMS3886M13
C71346

Research Excerpts

Effects

ExcerptReferenceRelevance
"Pyrithioxine has certain chemical resemblances to penicillamine and is used as original treatment in a series of 72 cases of rheumatoid arthritis over a period of six months in a dose of 600 mgs daily. "( [Pyrithioxine a new basic treatment of rheumatoid polyarthritis: initial study of 72 cases with a 6-month follow-up].
Camus, JP; Crouzet, J; Dubois, A; Jaffe, IA; Mercier, A; Prier, A, 1978
)
2.61

Actions

The increase in urinary D-glucaric acid is attributed to its enhanced metabolic formation in the body. Pyrithioxine caused an increase of cGMP level in neutrophils.

ExcerptReferenceRelevance
"The pyrithioxine-associated increase in urinary D-glucaric acid is attributed to its enhanced metabolic formation in the body and indirectly reflects a weak inductive action of pyrithioxine on the hepatic microsomal enzyme system in man."( Concentrations of D-glucaric acid in human urine after repeated administration of pyrithioxine.
Freundt, KJ; Liedy, G; Voigt, HO, 1984
)
0.97
"Pyrithioxine caused an increase of cGMP level in neutrophils."( Differential stimulation of neutrophil functions by pyrithioxine.
de Koster, BM; Elferink, JG, 1993
)
1.26

Treatment

ExcerptReferenceRelevance
"The treatment with pyrithioxine reduced significantly behavioral disturbances in adult LP rats except the increase of intersignal reactions which was even potentiated."( The effect of pyrithioxine and pyridoxine on individual behavior, social interactions, and learning in rats malnourished in early postnatal life.
Benesová, O; Franková, S; Tikal, K, 1976
)
0.94

Toxicity

ExcerptReferenceRelevance
"Many of the adverse reactions produced by penicillamine and other compounds with an active sulfhydryl group form a distinctive pattern when viewed as a class."( Adverse effects profile of sulfhydryl compounds in man.
Jaffe, IA, 1986
)
0.27

Bioavailability

ExcerptReferenceRelevance
" The bioavailability and profile of action of pyritinol have been well documented in animal experiments."( Effect of pyritinol on EEG and SSEP in comatose patients in the acute phase of intensive care therapy.
Schoeppner, H; Simons, P; von Wild, K, 1992
)
0.28

Dosage Studied

ExcerptRelevanceReference
" 20 patients of the control group were treated during this period with maprotiline of the same dosage but did not received EMD 21 657 as co-medication."( Neurotropic drugs as co-medication to psychotropics. Combined administration of a neurotropic drug and a tetracyclic antidepressant.
Pöldinger, W; Reinhardt, B, 1980
)
0.26
" Encephabol given in dosage 200-300 mg daily to patients aged 5-7 years and 600 mg--to those aged over 7 years during 6 weeks significantly improved memory, attention and praxis function."( [Cognitive disturbances in patients with tics and Tourette's syndrome and their correction with encephabol].
Begasheva, OI; Zykov, VP, 2003
)
0.32
" The sensors were used successfully for the determination of I and II in laboratory prepared mixtures with their degradation products, in pharmaceutical dosage forms and in plasma."( Stability-indicating electrochemical methods for the determination of meclophenoxate hydrochloride and pyritinol dihydrochloride using ion-selective membrane electrodes.
El-Bardicy, MG; El-Sayed, MA; El-Tarras, MF; Lotfy, HM, 2007
)
0.34
"The treatment group (n=54) received pyritinol and the control group (n=54) received placebo, in exactly the same increasing dosage schedule of 1 to 5 mL liquid drug (20-100 mg) from 8th postnatal day until the end of six months."( Pyritinol for post asphyxial encephalopathy in term babies-- a randomized double-blind controlled trial.
George, B; Jeyaseelan, L; Nair, MK, 2009
)
0.35
" Encephabol was prescribed in dosage 600 mg/day to people over 12 years of age and in dosage 300-400 mg/day to people younger than 12 years."( [Encephabol in the treatment of cognitive disorders in epilepsy].
Zenkov, LR; Zenkova, AL, 2011
)
0.37
" All patients were randomized into two equal groups: group 1 received encephabol (suspension form, daily dosage 200-250 mg, or 12-15 mg/kg) during 2 months; group 2 did not receive this medication."( [Developmental dysphasia: assessment of the drug treatment efficacy].
Koltunov, IE; Kozlova, EV; Zavadenko, NN, 2012
)
0.38
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
methylpyridinesAny member of the class of pyridines that carries at least one methyl substituent.
[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)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
GLS proteinHomo sapiens (human)Potency28.18380.35487.935539.8107AID624170
vitamin D3 receptor isoform VDRAHomo sapiens (human)Potency89.12510.354828.065989.1251AID504847
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (21)

Assay IDTitleYearJournalArticle
AID504749qHTS profiling for inhibitors of Plasmodium falciparum proliferation2011Science (New York, N.Y.), Aug-05, Volume: 333, Issue:6043
Chemical genomic profiling for antimalarial therapies, response signatures, and molecular targets.
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]
AID409954Inhibition of mouse brain MAOA2008Journal of medicinal chemistry, Nov-13, Volume: 51, Issue:21
Quantitative structure-activity relationship and complex network approach to monoamine oxidase A and B inhibitors.
AID1079949Proposed mechanism(s) of liver damage. [column 'MEC' 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]
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]
AID1079939Cirrhosis, proven histopathologically. Value is number of references indexed. [column 'CIRRH' in source]
AID1079932Highest frequency of moderate liver toxicity observed during clinical trials, expressed as a percentage. [column '% BIOL' in source]
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]
AID1079947Comments (NB not yet translated). [column 'COMMENTAIRES' in source]
AID1079942Steatosis, proven histopathologically. Value is number of references indexed. [column 'STEAT' in source]
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
AID1079940Granulomatous liver disease, proven histopathologically. Value is number of references indexed. [column 'GRAN' in source]
AID1079946Presence of at least one case with successful reintroduction. [column 'REINT' in source]
AID1079937Severe hepatitis, defined as possibly life-threatening liver failure or through clinical observations. Value is number of references indexed. [column 'MASS' in source]
AID1079945Animal toxicity known. [column 'TOXIC' in source]
AID1079948Times to onset, minimal and maximal, observed in the indexed observations. [column 'DELAI' in source]
AID1079944Benign tumor, proven histopathologically. Value is number of references indexed. [column 'T.BEN' in source]
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]
AID1079934Highest frequency of acute liver toxicity observed during clinical trials, expressed as a percentage. [column '% AIGUE' in source]
AID1079943Malignant tumor, proven histopathologically. Value is number of references indexed. [column 'T.MAL' in source]
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (227)

TimeframeStudies, This Drug (%)All Drugs %
pre-1990187 (82.38)18.7374
1990's23 (10.13)18.2507
2000's9 (3.96)29.6817
2010's7 (3.08)24.3611
2020's1 (0.44)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 16.11

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be moderate demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index16.11 (24.57)
Research Supply Index5.73 (2.92)
Research Growth Index4.21 (4.65)
Search Engine Demand Index15.26 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (16.11)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials50 (19.46%)5.53%
Reviews13 (5.06%)6.00%
Case Studies31 (12.06%)4.05%
Observational0 (0.00%)0.25%
Other163 (63.42%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]