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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
Structure of MENADIONE SODIUM BISULFITE

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

HIDE SMILES / InChI

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 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 Na
Molecular Weight 22.9898
Charge 1
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
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.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: Aldose reductase (Gallus gallus)
0.025 mM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Doses

Doses

DosePopulationAdverse events​
10 mg 10 times / day multiple, oral
Highest studied dose
Dose: 10 mg, 10 times / day
Route: oral
Route: multiple
Dose: 10 mg, 10 times / day
Co-administed with::
Vitamin C, p.o(500 mg; 10 times/day)
Sources: Page: p.64
unhealthy, 56 – 85
n = 3
Health Status: unhealthy
Condition: Prostate cancer
Age Group: 56 – 85
Sex: M
Population Size: 3
Sources: Page: p.64
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Detection of reactive free radicals derived from nucleosides by liquid chromatography coupled to tandem mass spectrometry of DMPO spin trapping adducts.
2006
NDX-1 protein hydrolyzes 8-oxo-7, 8-dihydrodeoxyguanosine-5'-diphosphate to sanitize oxidized nucleotides and prevent oxidative stress in Caenorhabditis elegans.
2011 Dec
Vitamin K3 (menadione) redox cycling inhibits cytochrome P450-mediated metabolism and inhibits parathion intoxication.
2015 Oct 1
Patents

Sample Use Guides

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
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
by admin
on Wed Jul 05 22:46:46 UTC 2023
Edited
by admin
on Wed Jul 05 22:46:46 UTC 2023
Record UNII
6XF3C2HK77
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
MENADIONE SODIUM BISULFITE
MART.  
USP  
Official Name English
MENADIONE SODIUM BISULFITE [MART.]
Common Name English
MENADIONE SODIUM SULFONATE
Common Name English
MENADIONE SODIUM BISULFITE TRIHYDRATE
MI   WHO-DD  
Common Name English
HYKINONE
Brand Name English
MENADIONE SODIUM BISULFITE TRIHYDRATE [MI]
Common Name English
MENADIONE SODIUM SULPHONATE
Common Name English
Menadione sodium bisulfite trihydrate [WHO-DD]
Common Name English
2-NAPHTHALENESULFONIC ACID, 1,2,3,4-TETRAHYDRO-2-METHYL-1,4-DIOXO-, SODIUM SALT, TRIHYDRATE
Common Name English
KLOTOGEN
Brand Name English
2-NAPHTHALENESULFONIC ACID, 1,2,3,4-TETRAHYDRO-2-METHYL-1,4-DIOXO-, SODIUM SALT, HYDRATE (1:1:3)
Common Name English
Sodium 1,2,3,4-tetrahydro-2-methyl-1,4-dioxo-2-naphthalenesulfonate trihydrate
Systematic Name English
K-THROMBIN
Brand Name English
MENAPHTHONE SODIUM BISULFITE
Common Name English
MENADIONE SODIUM BISULPHITE
Common Name English
Classification Tree Code System Code
FDA ORPHAN DRUG 392513
Created by admin on Wed Jul 05 22:46:46 UTC 2023 , Edited by admin on Wed Jul 05 22:46:46 UTC 2023
EU-Orphan Drug EU/3/14/1308
Created by admin on Wed Jul 05 22:46:46 UTC 2023 , Edited by admin on Wed Jul 05 22:46:46 UTC 2023
FDA ORPHAN DRUG 395413
Created by admin on Wed Jul 05 22:46:46 UTC 2023 , Edited by admin on Wed Jul 05 22:46:46 UTC 2023
FDA ORPHAN DRUG 394313
Created by admin on Wed Jul 05 22:46:46 UTC 2023 , Edited by admin on Wed Jul 05 22:46:46 UTC 2023
NCI_THESAURUS C26017
Created by admin on Wed Jul 05 22:46:46 UTC 2023 , Edited by admin on Wed Jul 05 22:46:46 UTC 2023
FDA ORPHAN DRUG 236606
Created by admin on Wed Jul 05 22:46:46 UTC 2023 , Edited by admin on Wed Jul 05 22:46:46 UTC 2023
FDA ORPHAN DRUG 429014
Created by admin on Wed Jul 05 22:46:46 UTC 2023 , Edited by admin on Wed Jul 05 22:46:46 UTC 2023
FDA ORPHAN DRUG 430114
Created by admin on Wed Jul 05 22:46:46 UTC 2023 , Edited by admin on Wed Jul 05 22:46:46 UTC 2023
Code System Code Type Description
FDA UNII
6XF3C2HK77
Created by admin on Wed Jul 05 22:46:46 UTC 2023 , Edited by admin on Wed Jul 05 22:46:46 UTC 2023
PRIMARY
CAS
6147-37-1
Created by admin on Wed Jul 05 22:46:46 UTC 2023 , Edited by admin on Wed Jul 05 22:46:46 UTC 2023
PRIMARY
SMS_ID
300000031168
Created by admin on Wed Jul 05 22:46:46 UTC 2023 , Edited by admin on Wed Jul 05 22:46:46 UTC 2023
PRIMARY
MERCK INDEX
M7169
Created by admin on Wed Jul 05 22:46:46 UTC 2023 , Edited by admin on Wed Jul 05 22:46:46 UTC 2023
PRIMARY
DRUG CENTRAL
1684
Created by admin on Wed Jul 05 22:46:46 UTC 2023 , Edited by admin on Wed Jul 05 22:46:46 UTC 2023
PRIMARY
PUBCHEM
23677974
Created by admin on Wed Jul 05 22:46:46 UTC 2023 , Edited by admin on Wed Jul 05 22:46:46 UTC 2023
PRIMARY
NCI_THESAURUS
C83928
Created by admin on Wed Jul 05 22:46:46 UTC 2023 , Edited by admin on Wed Jul 05 22:46:46 UTC 2023
PRIMARY
EPA CompTox
DTXSID10977032
Created by admin on Wed Jul 05 22:46:46 UTC 2023 , Edited by admin on Wed Jul 05 22:46:46 UTC 2023
PRIMARY
RXCUI
52551
Created by admin on Wed Jul 05 22:46:46 UTC 2023 , Edited by admin on Wed Jul 05 22:46:46 UTC 2023
PRIMARY RxNorm
CHEBI
63928
Created by admin on Wed Jul 05 22:46:46 UTC 2023 , Edited by admin on Wed Jul 05 22:46:46 UTC 2023
PRIMARY
ChEMBL
CHEMBL1159684
Created by admin on Wed Jul 05 22:46:46 UTC 2023 , Edited by admin on Wed Jul 05 22:46:46 UTC 2023
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
ANHYDROUS->SOLVATE