MENADIONE SODIUM BISULFITE

First approved in 1940

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 Search

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	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

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 1447
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 8504	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 1147	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 665	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 Sources: https://pubmed.ncbi.nlm.nih.gov/18392145	unhealthy, 56 – 85 Health Status: unhealthy Age Group: 56 – 85 Sex: M Sources: https://pubmed.ncbi.nlm.nih.gov/18392145	Sources: https://pubmed.ncbi.nlm.nih.gov/18392145

Sourcing

Vendor/Aggregator	ID	URL
AA Blocks	AA00HRXH	http://www.aablocks.com/goods/Goods/detail?id=AA00HRXH
Aaron Chemicals	AR00HSP9	http://www.aaronchem.com/130-37-0
abcr GmbH	AB112063	http://www.abcr.de/shop/en/AB112063
Achemtek	0104-016721	http://www.achemtek.com/130-37-0
AK Scientific, Inc. (AKSCI)	O420	http://www.aksci.com/item_detail.php?cat=O420
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
BioChemPartner	BCP19124	http://www.biochempartner.com/130-37-0-BCP19124
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
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
eNovation Chemicals	D755772	https://www.enovationchem.com/ProductDetails.asp?ProductID=D755772
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/
iChemical	EBD54421	http://www.ichemical.com/products/130-37-0.html?utm_source=PubChem&utm_medium=website&utm_campaign=product%20catalogs
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

PubMed

Title	Date	PubMed
Vitamin K3 (menadione) redox cycling inhibits cytochrome P450-mediated metabolism and inhibits parathion intoxication.	2015-10-01	26212258
Structures of the PutA peripheral membrane flavoenzyme reveal a dynamic substrate-channeling tunnel and the quinone-binding site.	2014-03-04	24550478
NDX-1 protein hydrolyzes 8-oxo-7, 8-dihydrodeoxyguanosine-5'-diphosphate to sanitize oxidized nucleotides and prevent oxidative stress in Caenorhabditis elegans.	2011-12	21873335
Detection of reactive free radicals derived from nucleosides by liquid chromatography coupled to tandem mass spectrometry of DMPO spin trapping adducts.	2006	16810703
[A computer method for assessing the average rate of movement of Paramecium caudatum by a cross-sectional light beam].	2002-02-22	11855298

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 `Mon Mar 31 17:51:50 GMT 2025` Edited by `admin` on `Mon Mar 31 17:51:50 GMT 2025`
Record UNII	6XF3C2HK77
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

MENADIONE SODIUM BISULFITE TRIHYDRATE

Preferred Name

English

MENADIONE SODIUM BISULFITE

Official Name

English

MENADIONE SODIUM BISULFITE [MART.]

Common Name

English

MENADIONE SODIUM SULFONATE

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