Synonym
Menadione; Vitamin K3; 2-Methyl-1,4-naphthoquinone; Menaphthone; Thyloquinone; Vitamin K3 sodium bisulfite; Vicasol; Vikasol;Menadione bisulfite;
IUPAC/Chemical Name
2-methylnaphthalene-1,4-dione
InChi Key
MJVAVZPDRWSRRC-UHFFFAOYSA-N
InChi Code
InChI=1S/C11H8O2/c1-7-6-10(12)8-4-2-3-5-9(8)11(7)13/h2-6H,1H3
SMILES Code
CC1=CC(=O)C2=CC=CC=C2C1=O
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO, not in water
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
Biological target:
Menadione, a naphthoquinone, can be converted to active vitamin K2 in vivo.
In vitro activity:
Conjunctival fibroblasts were incubated for 24 hours. An artificial wound was made and the cells were incubated with fresh medium plus doses of vitamin K3 to be tested. Fibroblast mitogenic activity was statistically decreased in all vitamin K groups; statistical differences were found among vitamin K3 1 mg/mL and higher doses too. Vitamin K3 is able to inhibit fibroblast proliferation.
Reference: ScientificWorldJournal. 2014 Jan 8;2014:916713. https://pubmed.ncbi.nlm.nih.gov/24523654/
In vivo activity:
In the second animal model, until day 300, CDC25B mRNA and protein expression levels were slightly lower in primates of the MNU (N-Methyl-N-nitrosourea) + MD (menadione) group compared to animals of the MNU group. However, at day 960 both expression levels were around 40% lower in the animals treated with MD (Figure 4). The animal of MNU group that was treated with MD after tumor development presented a considerable decrease in CDC25B mRNA and protein expression levels at the time of surgical tumor extraction when compared to day 990 and to the nontreated animal (Figure 4).
Reference: Therap Adv Gastroenterol. 2020 Jan 11;13:1756284819895435. https://pubmed.ncbi.nlm.nih.gov/35392297/
|
Solvent |
mg/mL |
mM |
| Solubility |
| Ethanol |
22.0 |
127.77 |
| Water |
0.1 |
0.58 |
| DMSO |
34.7 |
201.34 |
| DMF |
30.0 |
174.23 |
| DMF:PBS (pH 7.2) (1:1) |
0.5 |
2.90 |
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.
Preparing Stock Solutions
The following data is based on the
product
molecular weight
172.18
Batch specific molecular weights may vary
from batch to batch
due to the degree of hydration, which will
affect the solvent
volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass |
1 mg |
5 mg |
10 mg |
| 1 mM |
1.15 mL |
5.76 mL |
11.51 mL |
| 5 mM |
0.23 mL |
1.15 mL |
2.3 mL |
| 10 mM |
0.12 mL |
0.58 mL |
1.15 mL |
| 50 mM |
0.02 mL |
0.12 mL |
0.23 mL |
Formulation protocol:
1. Pinilla I, Izaguirre LB, Gonzalvo FJ, Piazuelo E, Garcia-Gonzalez MA, Sanchez-Cano AI, Sopeña F. In vitro vitamin K3 effect on conjunctival fibroblast migration and proliferation. ScientificWorldJournal. 2014 Jan 8;2014:916713. doi: 10.1155/2014/916713. PMID: 24523654; PMCID: PMC3910386.
2. Scott GK, Atsriku C, Kaminker P, Held J, Gibson B, Baldwin MA, Benz CC. Vitamin K3 (menadione)-induced oncosis associated with keratin 8 phosphorylation and histone H3 arylation. Mol Pharmacol. 2005 Sep;68(3):606-15. doi: 10.1124/mol.105.013474. Epub 2005 Jun 6. PMID: 15939799.
3. Bona AB, Calcagno DQ, Ribeiro HF, Muniz JAPC, Pinto GR, Rocha CAM, Lacreta Junior ACC, de Assumpção PP, Herranz JAR, Burbano RR. Menadione reduces CDC25B expression and promotes tumor shrinkage in gastric cancer. Therap Adv Gastroenterol. 2020 Jan 11;13:1756284819895435. doi: 10.1177/1756284819895435. PMID: 35392297; PMCID: PMC8981514.
4. Kapadia GJ, Soares IAO, Rao GS, Badoco FR, Furtado RA, Correa MB, Tavares DC, Cunha WR, Magalhães LG. Antiparasitic activity of menadione (vitamin K3) against Schistosoma mansoni in BABL/c mice. Acta Trop. 2017 Mar;167:163-173. doi: 10.1016/j.actatropica.2016.12.001. Epub 2016 Dec 23. PMID: 28017859.
In vitro protocol:
1. Pinilla I, Izaguirre LB, Gonzalvo FJ, Piazuelo E, Garcia-Gonzalez MA, Sanchez-Cano AI, Sopeña F. In vitro vitamin K3 effect on conjunctival fibroblast migration and proliferation. ScientificWorldJournal. 2014 Jan 8;2014:916713. doi: 10.1155/2014/916713. PMID: 24523654; PMCID: PMC3910386.
2. Scott GK, Atsriku C, Kaminker P, Held J, Gibson B, Baldwin MA, Benz CC. Vitamin K3 (menadione)-induced oncosis associated with keratin 8 phosphorylation and histone H3 arylation. Mol Pharmacol. 2005 Sep;68(3):606-15. doi: 10.1124/mol.105.013474. Epub 2005 Jun 6. PMID: 15939799.
In vivo protocol:
1. Bona AB, Calcagno DQ, Ribeiro HF, Muniz JAPC, Pinto GR, Rocha CAM, Lacreta Junior ACC, de Assumpção PP, Herranz JAR, Burbano RR. Menadione reduces CDC25B expression and promotes tumor shrinkage in gastric cancer. Therap Adv Gastroenterol. 2020 Jan 11;13:1756284819895435. doi: 10.1177/1756284819895435. PMID: 35392297; PMCID: PMC8981514.
2. Kapadia GJ, Soares IAO, Rao GS, Badoco FR, Furtado RA, Correa MB, Tavares DC, Cunha WR, Magalhães LG. Antiparasitic activity of menadione (vitamin K3) against Schistosoma mansoni in BABL/c mice. Acta Trop. 2017 Mar;167:163-173. doi: 10.1016/j.actatropica.2016.12.001. Epub 2016 Dec 23. PMID: 28017859.
1: Halilovic A, Schmedt T, Benischke AS, Hamill CE, Chen Y, Santos JH, Jurkunas UV. Menadione-induced DNA damage leads to mitochondrial dysfunction and fragmentation during rosette formation in Fuchs Endothelial Corneal Dystrophy. Antioxid Redox Signal. 2016 Mar 2. [Epub ahead of print] PubMed PMID: 26935406.
2: Tofolean IT, Ganea C, Ionescu D, Filippi A, Garaiman A, Goicea A, Gaman MA, Dimancea A, Baran I. Cellular determinants involving mitochondrial dysfunction, oxidative stress and apoptosis correlate with the synergic cytotoxicity of epigallocatechin-3-gallate and menadione in human leukemia Jurkat T cells. Pharmacol Res. 2016 Jan;103:300-17. doi: 10.1016/j.phrs.2015.12.013. Epub 2015 Dec 11. PubMed PMID: 26687095.
3: Arslan M, Sevgiler Y, Buyukleyla M, Yardimci M, Yilmaz M, Rencuzogullari E. Sex-related effects of imidacloprid modulated by piperonyl butoxide and menadione in rats. Part II: genotoxic and cytotoxic potential. Drug Chem Toxicol. 2016 Jan;39(1):81-6. doi: 10.3109/01480545.2015.1029049. Epub 2015 Sep 25. PubMed PMID: 25826181.
