Details
Stereochemistry | RACEMIC |
Molecular Formula | C11H9O5S.Na.3H2O |
Molecular Weight | 330.287 |
Optical Activity | ( + / - ) |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
O.O.O.[Na+].CC1(CC(=O)C2=CC=CC=C2C1=O)S([O-])(=O)=O
InChI
InChIKey=SRPZAZGARCFWTO-UHFFFAOYSA-M
InChI=1S/C11H10O5S.Na.3H2O/c1-11(17(14,15)16)6-9(12)7-4-2-3-5-8(7)10(11)13;;;;/h2-5H,6H2,1H3,(H,14,15,16);;3*1H2/q;+1;;;/p-1
Molecular Formula | C11H10O5S |
Molecular Weight | 254.259 |
Charge | 0 |
Count |
|
Stereochemistry | RACEMIC |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Optical Activity | ( + / - ) |
Molecular Formula | H2O |
Molecular Weight | 18.0153 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
Molecular Formula | Na |
Molecular Weight | 22.98976928 |
Charge | 1 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/14952541Curator's Comment: description was created based on several sources, including:
https://www.ncbi.nlm.nih.gov/pubmed/3927923 | https://www.ncbi.nlm.nih.gov/pubmed/18935165 | https://www.ncbi.nlm.nih.gov/pubmed/26212258
Sources: https://www.ncbi.nlm.nih.gov/pubmed/14952541
Curator's Comment: description was created based on several sources, including:
https://www.ncbi.nlm.nih.gov/pubmed/3927923 | https://www.ncbi.nlm.nih.gov/pubmed/18935165 | https://www.ncbi.nlm.nih.gov/pubmed/26212258
Menadione bisulfite is a water-soluble analog of Vitamin K3. Pharmacologic studies on menadione bisulfate indicad that its toxicity is relatively low. In man, doses approximately ten times as great as those generally recommended for therapeutic use, given daily for a period of one week. Redox cycling compounds, such as menadione, have the potential to effectively mitigate the toxicity of organophosphorus pesticides including parathion. Menadione bisulfite behaved as a competitive inhibitor of chicken muscle aldose reductase.
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL5035 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11081416 |
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Target ID: CHEMBL2169730 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9324955 |
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Target ID: Aldose reductase (Gallus gallus) Sources: https://www.ncbi.nlm.nih.gov/pubmed/3927923 |
0.025 mM [Ki] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
---|---|---|
NDX-1 protein hydrolyzes 8-oxo-7, 8-dihydrodeoxyguanosine-5'-diphosphate to sanitize oxidized nucleotides and prevent oxidative stress in Caenorhabditis elegans. | 2011 Dec |
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Structures of the PutA peripheral membrane flavoenzyme reveal a dynamic substrate-channeling tunnel and the quinone-binding site. | 2014 Mar 4 |
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Vitamin K3 (menadione) redox cycling inhibits cytochrome P450-mediated metabolism and inhibits parathion intoxication. | 2015 Oct 1 |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/14952541
5 mg. Therapy, averaging thirty days, was continued until the withdrawal of metlication produced no recurrence of symptoms.
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/2250668
Addition of menadione bisulfite (3 mM) alone to the perfusate increased oxygen uptake by 20-30 uM/g/hr. In the presence of ethanol, maximal increases in oxygen uptake due to menadione bisulfite were much larger (about 90 uM/g/hr), and lactate dehydrogenase release occurred earlier and reached higher maximal values (330 units/g/hr).
Substance Class |
Chemical
Created
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admin
on
Edited
Mon Mar 31 17:51:50 GMT 2025
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Mon Mar 31 17:51:50 GMT 2025
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Record UNII |
6XF3C2HK77
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Record Status |
Validated (UNII)
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Classification Tree | Code System | Code | ||
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FDA ORPHAN DRUG |
392513
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EU-Orphan Drug |
EU/3/14/1308
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FDA ORPHAN DRUG |
395413
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FDA ORPHAN DRUG |
394313
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NCI_THESAURUS |
C26017
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FDA ORPHAN DRUG |
236606
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FDA ORPHAN DRUG |
429014
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FDA ORPHAN DRUG |
430114
Created by
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6XF3C2HK77
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6147-37-1
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300000031168
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m7169
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1684
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23677974
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C83928
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DTXSID10977032
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52551
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63928
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CHEMBL1159684
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Related Record | Type | Details | ||
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PARENT -> SALT/SOLVATE | |||
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ANHYDROUS->SOLVATE |