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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

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.

Originator

Approval Year

1940
58
Targets

Targets

Primary TargetPharmacologyConditionPotency
Activator
1430
Substrate
661
Aldose reductase (Gallus gallus)
3
Target ID: Aldose reductase (Gallus gallus)
Inhibitor
8297
 0.025 mM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Phase II
1132
Unknown

Approved Use

Unknown
Primary
Preclinical
Unknown

Approved Use

Unknown
Primary
Phase III
656
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:
https://pubmed.ncbi.nlm.nih.gov/18392145
Page: p.64
unhealthy, 56 – 85
n = 3
Health Status: unhealthy
Condition: Prostate cancer
Age Group: 56 – 85
Sex: M
Population Size: 3
Sources:
https://pubmed.ncbi.nlm.nih.gov/18392145
Page: p.64
Sources:
https://pubmed.ncbi.nlm.nih.gov/18392145
Page: p.64
Sourcing

Sourcing

Vendor/AggregatorIDURL
AA Blocks
AA00HRXH
http://www.aablocks.com/goods/Goods/detail?id=AA00HRXH
AK Scientific, Inc. (AKSCI)
O420
http://www.aksci.com/item_detail.php?cat=O420
Aaron Chemicals
AR00HSP9
http://www.aaronchem.com/130-37-0
Achemtek
0104-016721
http://www.achemtek.com/130-37-0
Ambeed
A142509
https://www.ambeed.com/products/130-37-0.html
Ambinter
Amb16224800
http://www.ambinter.com/reference/16224800
Aurora Fine Chemicals LLC
A12.866.683
http://online.aurorafinechemicals.com/info?ID=A12.866.683
Aurum Pharmatech LLC
A-8168
http://www.Aurumpharmatech.com/Product/ProductDetails/A_8168
BLD Pharm
BD76650
http://www.bldpharm.com/products/130-37-0.html
BOC Sciences
130-37-0
https://www.bocsci.com/menadione-sodium-bisulfite-cas-130-37-0-item-56964.html
BioChemPartner
BCP19124
http://www.biochempartner.com/130-37-0-BCP19124
Chem Scene
CS-6059
http://www.chemscene.com/130-37-0.html
ChemMol
49410551
http://www.chemmol.com/chemmol/49410551.html
Chemspace
CSSB00020648526
https://chem-space.com/CSSB00020648526
Combi-Blocks
QA-2069
http://www.combi-blocks.com/cgi-bin/find.cgi?QA-2069
Finetech
FT-0628195
http://www.finetechnology-ind.com/prod/detail/pub/130-37-0.html
Finetech
FT-0741767
http://www.finetechnology-ind.com/prod/detail/pub/57414-02-5.html
Glentham Life Sciences
GA0934
http://www.glentham.com/products/product/GA0934/
LGC Standards
DRE-C14863200
https://www.lgcstandards.com/US/en/p/DRE-C14863200
MedChem Express
HY-B1897A
https://www.medchemexpress.com/Menadione-bisulfite-sodium.html
MolPort
MolPort-002-543-258
https://www.molport.com/shop/molecule-link/MolPort-002-543-258
MolPort
MolPort-047-483-463
https://www.molport.com/shop/molecule-link/MolPort-047-483-463
MuseChem
I001163
https://www.musechem.com/product/I001163.html
Vitas-M Laboratory
STK700858
http://www.request.vitasmlab.biz/index.php?option=com_search_stk&Itemid=22&stk=STK700858&?utm_source=pubchem&utm_medium=p_search_link&utm_campaign=pubchem_search&utm_content=pubchem_slink
VladaChem
VL163726
https://www.vladachem.com/product.php?products=130-37-0
Yuhao Chemical
LQ0561
http://www.chemyuhao.com/130-37-0.html
abcr GmbH
AB112063
http://www.abcr.de/shop/en/AB112063
eNovation Chemicals
D755772
https://www.enovationchem.com/ProductDetails.asp?ProductID=D755772
iChemical
EBD54421
http://www.ichemical.com/products/130-37-0.html?utm_source=PubChem&utm_medium=website&utm_campaign=product%20catalogs
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
Patents

Patents

JP2009533384A
5
JP2010509991A
41
JP2010540159A
31
JPH00324002A
3
JPH0324002A
3
JPS62190101A
3
JPS62192302A
3
US4577019 A
3

Sample Use Guides

In Vivo Use Guide
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).
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 Fri Dec 15 15:15:28 GMT 2023 , Edited by admin on Fri Dec 15 15:15:28 GMT 2023
EU-Orphan Drug EU/3/14/1308
Created by admin on Fri Dec 15 15:15:28 GMT 2023 , Edited by admin on Fri Dec 15 15:15:28 GMT 2023
FDA ORPHAN DRUG 395413
Created by admin on Fri Dec 15 15:15:28 GMT 2023 , Edited by admin on Fri Dec 15 15:15:28 GMT 2023
FDA ORPHAN DRUG 394313
Created by admin on Fri Dec 15 15:15:28 GMT 2023 , Edited by admin on Fri Dec 15 15:15:28 GMT 2023
NCI_THESAURUS C26017
Created by admin on Fri Dec 15 15:15:28 GMT 2023 , Edited by admin on Fri Dec 15 15:15:28 GMT 2023
FDA ORPHAN DRUG 236606
Created by admin on Fri Dec 15 15:15:28 GMT 2023 , Edited by admin on Fri Dec 15 15:15:28 GMT 2023
FDA ORPHAN DRUG 429014
Created by admin on Fri Dec 15 15:15:28 GMT 2023 , Edited by admin on Fri Dec 15 15:15:28 GMT 2023
FDA ORPHAN DRUG 430114
Created by admin on Fri Dec 15 15:15:28 GMT 2023 , Edited by admin on Fri Dec 15 15:15:28 GMT 2023
Code System Code Type Description
FDA UNII
6XF3C2HK77
Created by admin on Fri Dec 15 15:15:28 GMT 2023 , Edited by admin on Fri Dec 15 15:15:28 GMT 2023
PRIMARY
CAS
6147-37-1
Created by admin on Fri Dec 15 15:15:28 GMT 2023 , Edited by admin on Fri Dec 15 15:15:28 GMT 2023
PRIMARY
SMS_ID
300000031168
Created by admin on Fri Dec 15 15:15:28 GMT 2023 , Edited by admin on Fri Dec 15 15:15:28 GMT 2023
PRIMARY
MERCK INDEX
m7169
Created by admin on Fri Dec 15 15:15:28 GMT 2023 , Edited by admin on Fri Dec 15 15:15:28 GMT 2023
PRIMARY
DRUG CENTRAL
1684
Created by admin on Fri Dec 15 15:15:28 GMT 2023 , Edited by admin on Fri Dec 15 15:15:28 GMT 2023
PRIMARY
PUBCHEM
23677974
Created by admin on Fri Dec 15 15:15:28 GMT 2023 , Edited by admin on Fri Dec 15 15:15:28 GMT 2023
PRIMARY
NCI_THESAURUS
C83928
Created by admin on Fri Dec 15 15:15:28 GMT 2023 , Edited by admin on Fri Dec 15 15:15:28 GMT 2023
PRIMARY
EPA CompTox
DTXSID10977032
Created by admin on Fri Dec 15 15:15:28 GMT 2023 , Edited by admin on Fri Dec 15 15:15:28 GMT 2023
PRIMARY
RXCUI
52551
Created by admin on Fri Dec 15 15:15:28 GMT 2023 , Edited by admin on Fri Dec 15 15:15:28 GMT 2023
PRIMARY RxNorm
CHEBI
63928
Created by admin on Fri Dec 15 15:15:28 GMT 2023 , Edited by admin on Fri Dec 15 15:15:28 GMT 2023
PRIMARY
ChEMBL
CHEMBL1159684
Created by admin on Fri Dec 15 15:15:28 GMT 2023 , Edited by admin on Fri Dec 15 15:15:28 GMT 2023
PRIMARY
PARENT (SALT/SOLVATE)
Structure of MENADIONE BISULFITE
NIH
NCATS
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HHS VULNERABILITY DISCLOSURE
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