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Details

Stereochemistry RACEMIC
Molecular Formula C11H9O5S.Na
Molecular Weight 276.241
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of MENADIONE SODIUM BISULFITE ANHYDROUS

SMILES

[Na+].CC1(CC(=O)C2=CC=CC=C2C1=O)S([O-])(=O)=O

InChI

InChIKey=XDPFHGWVCTXHDX-UHFFFAOYSA-M
InChI=1S/C11H10O5S.Na/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);/q;+1/p-1

HIDE SMILES / InChI

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

Molecular Formula C11H9O5S
Molecular Weight 253.251
Charge -1
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

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
[A computer method for assessing the average rate of movement of Paramecium caudatum by a cross-sectional light beam].
2002 Jan-Feb
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
Structures of the PutA peripheral membrane flavoenzyme reveal a dynamic substrate-channeling tunnel and the quinone-binding site.
2014 Mar 4
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 Fri Dec 15 18:32:35 GMT 2023
Edited
by admin
on Fri Dec 15 18:32:35 GMT 2023
Record UNII
97K34V88SA
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
MENADIONE SODIUM BISULFITE ANHYDROUS
MI  
Common Name English
menadione sodium bisulfite [INN]
Common Name English
MENADIONE SODIUM BISULFITE [MI]
Common Name English
MENAPHTHONE SODIUM BISULFITE ANHYDROUS
Common Name English
2-NAPHTHALENESULFONIC ACID, 1,2,3,4-TETRAHYDRO-2-METHYL-1,4-DIOXO-, SODIUM SALT
Common Name English
KAVITAMIN
Common Name English
MSBC
Common Name English
Menadione sodium bisulfite [WHO-DD]
Common Name English
2,3-DIHYDRO-2-METHYL-1,4-NAPHTHOQUINONE-2-SULFONATE SODIUM
Systematic Name English
VITAMIN K3 SODIUM BISULFITE
Common Name English
Code System Code Type Description
EPA CompTox
DTXSID0040547
Created by admin on Fri Dec 15 18:32:35 GMT 2023 , Edited by admin on Fri Dec 15 18:32:35 GMT 2023
PRIMARY
PUBCHEM
23665888
Created by admin on Fri Dec 15 18:32:35 GMT 2023 , Edited by admin on Fri Dec 15 18:32:35 GMT 2023
PRIMARY
EVMPD
SUB08735MIG
Created by admin on Fri Dec 15 18:32:35 GMT 2023 , Edited by admin on Fri Dec 15 18:32:35 GMT 2023
PRIMARY
NCI_THESAURUS
C175728
Created by admin on Fri Dec 15 18:32:35 GMT 2023 , Edited by admin on Fri Dec 15 18:32:35 GMT 2023
PRIMARY
CHEBI
63928
Created by admin on Fri Dec 15 18:32:35 GMT 2023 , Edited by admin on Fri Dec 15 18:32:35 GMT 2023
PRIMARY
FDA UNII
97K34V88SA
Created by admin on Fri Dec 15 18:32:35 GMT 2023 , Edited by admin on Fri Dec 15 18:32:35 GMT 2023
PRIMARY
EVMPD
SUB96096
Created by admin on Fri Dec 15 18:32:35 GMT 2023 , Edited by admin on Fri Dec 15 18:32:35 GMT 2023
PRIMARY
SMS_ID
100000092336
Created by admin on Fri Dec 15 18:32:35 GMT 2023 , Edited by admin on Fri Dec 15 18:32:35 GMT 2023
PRIMARY
MERCK INDEX
m7169
Created by admin on Fri Dec 15 18:32:35 GMT 2023 , Edited by admin on Fri Dec 15 18:32:35 GMT 2023
PRIMARY
INN
4206
Created by admin on Fri Dec 15 18:32:35 GMT 2023 , Edited by admin on Fri Dec 15 18:32:35 GMT 2023
PRIMARY
CAS
130-37-0
Created by admin on Fri Dec 15 18:32:35 GMT 2023 , Edited by admin on Fri Dec 15 18:32:35 GMT 2023
PRIMARY
ECHA (EC/EINECS)
204-987-0
Created by admin on Fri Dec 15 18:32:35 GMT 2023 , Edited by admin on Fri Dec 15 18:32:35 GMT 2023
PRIMARY
Related Record Type Details
SOLVATE->ANHYDROUS
PARENT -> SALT/SOLVATE