MENADIONE BISULFITE

First approved in 1940

Details

Stereochemistry	RACEMIC
Molecular Formula	C11H10O5S
Molecular Weight	254.259
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC1(CC(=O)C2=CC=CC=C2C1=O)S(O)(=O)=O

InChI

InChIKey=WIXFIQKTHUVFDI-UHFFFAOYSA-N

InChI=1S/C11H10O5S/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)

HIDE SMILES / InChI

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	( + / - )

Description
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	Potency
Heme oxygenase 1 15 Target ID: CHEMBL5035 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11081416	Activator 1430
NQO1 protein 3 Target ID: CHEMBL2169730 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9324955	Substrate 661
Aldose reductase (Gallus gallus) 3 Target ID: Aldose reductase (Gallus gallus) Sources: https://www.ncbi.nlm.nih.gov/pubmed/3927923	Inhibitor 8297	0.025 mM [Ki]

Conditions

Condition	Modality	Highest Phase	Product
Vomiting of pregnancy 3 Sources: https://www.ncbi.nlm.nih.gov/pubmed/14952541	Primary	Phase II 1132	Unknown Approved Use Unknown
Organophosphorus pesticides intoxication 3 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26212258	Primary	Preclinical	Unknown Approved Use Unknown
Dicumarol toxicity 3 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18935165	Primary	Phase III 656	Unknown Approved Use Unknown

Doses

Dose	Population	Adverse 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

Vendor/Aggregator	ID	URL
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

Title	Date	PubMed
[A computer method for assessing the average rate of movement of Paramecium caudatum by a cross-sectional light beam].	2002 Jan-Feb	11855298
Detection of reactive free radicals derived from nucleosides by liquid chromatography coupled to tandem mass spectrometry of DMPO spin trapping adducts.	2006	16810703
NDX-1 protein hydrolyzes 8-oxo-7, 8-dihydrodeoxyguanosine-5'-diphosphate to sanitize oxidized nucleotides and prevent oxidative stress in Caenorhabditis elegans.	2011 Dec	21873335
Structures of the PutA peripheral membrane flavoenzyme reveal a dynamic substrate-channeling tunnel and the quinone-binding site.	2014 Mar 4	24550478
Vitamin K3 (menadione) redox cycling inhibits cytochrome P450-mediated metabolism and inhibits parathion intoxication.	2015 Oct 1	26212258

Patents

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).

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:55:57 UTC 2023` Edited by `admin` on `Fri Dec 15 15:55:57 UTC 2023`
Record UNII	I2BE1ZEN8I
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

MENADIONE BISULFITE

Common Name

English

2-NAPHTHALENESULFONIC ACID, 1,2,3,4-TETRAHYDRO-2-METHYL-1,4-DIOXO-

Common Name

English

Code System Code Type Description

FDA UNII

I2BE1ZEN8I