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Menadione is a synthetic chemical compound sometimes used as a nutritional supplement because of its vitamin K activity. It is an analog of 1,4-naphthoquinone with a methyl group in the 2-position.^[2]

Terminology

It is sometimes called vitamin K₃,^[3] although derivatives of naphthoquinone are not naturally occurring chemicals and therefore do not qualify as vitamins, and without the side chain in the 2-position they cannot exert all the functions of the K vitamins. Menadione is metabolized by the human body into K₂ which uses alkylation to yield menaquinones (MK-n, n=1-13; K₂ vitamers), hence is better classified as a provitamin.

It is also known as "menaphthone".^[4]

Uses

Despite the fact that it can serve as a precursor to various types of vitamin K, menadione is generally not used as a nutritional supplement in economically developed countries. Menadione for human use at pharmaceutical strength is available in some countries with large lower income populations.^{[citation needed]} It is used in the treatment of hypoprothrombinemia outside of the United States.

Toxicity

Large doses of menadione have been reported to cause adverse outcomes including hemolytic anemia due to glucose-6-phosphate dehydrogenase deficiency, neonatal brain or liver damage, or neonatal death in some rare cases. In the United States, menadione supplements are banned by the U.S. Food and Drug Administration because of their potential toxicity in human use.

Low-dose menadione is still used as an inexpensive micronutrient for livestock in many countries. Forms of menadione are also included in some pet foods in developed countries as a source of vitamin K. These doses have yielded no reported cases of toxicity from menadione in livestock or pets.

Experimental research

Recently, menadione in combination with vitamin C is being studied as a potential treatment for prostate cancer.^[5]^[6]

A menadione topical lotion was recently developed to reduce epidermal growth factor receptor inhibitor-related side effects, by the prevention of skin toxicities that result from inhibition of protein kinases by drugs such as erlotinib (Tarceva) and cetuximab (Erbitux).^[7]^[8]

References

^ The Merck Index, 11th Edition, 5714
^ Castro FA, Mariani D, Panek AD, Eleutherio EC, Pereira MD (2008). Fox, Debbie, ed. "Cytotoxicity Mechanism of Two Naphthoquinones (Menadione and Plumbagin) in Saccharomyces cerevisiae". PLoS ONE 3 (12): e3999. doi:10.1371/journal.pone.0003999. PMC 2600608. PMID 19098979.
^ Scott GK, Atsriku C, Kaminker P, et al. (September 2005). "Vitamin K3 (menadione)-induced oncosis associated with keratin 8 phosphorylation and histone H3 arylation". Mol. Pharmacol. 68 (3): 606–15. doi:10.1124/mol.105.013474. PMID 15939799.
^ "Vitamin K". Retrieved 2009-03-18.
^ James M. Jamison, Jacques Gilloteaux, Henryk S. Taper and Jack L. Summers (2001). "Evaluation of the In Vitro and In Vivo Antitumor Activities of Vitamin C and K-3 Combinations against Human Prostate Cancer" (PDF). J. Nutr. 131 (1): 158S–160S. PMID 11208954.
^ Tareen B, Summers JL, Jamison JM, Neal DR, McGuire K, Gerson L, Diokno A (2008). "A 12 Week, Open Label, Phase I/IIa Study Using Apatone® for the Treatment of Prostate Cancer Patients Who Have Failed Standard Therapy". Int J Med Sci 5 (2): 62–67. doi:10.7150/ijms.5.62. PMC 2288789. PMID 18392145.
^ R. Perez-Soler, Y. Ling, Y. Zou, S.R. Deitcher (2008). "Local Rescue of Skin Toxicities Secondary to Kinase Inhibitor (KI) Therapy with Topical Menadione" (PDF). Annals of Oncology. doi:10.1093/annonc/mdn346.
^ Tianhong Li and Roman Perez-Soler (2009). "Skin toxicities associated with epidermal growth factor receptor inhibitors". Targeted Oncology 4 (2): 107–119. doi:10.1007/s11523-009-0114-0. PMID 19452131.

External links

Menadione in the Pesticide Properties DataBase (PPDB)

English Journal

Demonstration of maximum solubilization in a polyoxyethylene alkyl ether series of non-ionic surfactants.

Elworthy PH, Patel MS.AbstractThe solubilization of azobenzene, menaphthone, cortisone acetate, and griseofulvin was measured in a series of non-ionic surfactants of structure CH3[CH2](m-1) [OCH2CH2]1.25m OH, where m varied from 8 to 18. Maximum solubilization occurs when m = 16 (the hexadecyl alkyl ether). This is explained in terms of changes in the oxyethylene mantle close to the micelle core/mantle interface, which appears to be the main locus of solubilization. Micellar properties of CH3[CH2]17[OCH2CH2]22OH are also reported and discussed.
The Journal of pharmacy and pharmacology.J Pharm Pharmacol.1982 Sep;34(9):543-6.
The solubilization of azobenzene, menaphthone, cortisone acetate, and griseofulvin was measured in a series of non-ionic surfactants of structure CH3[CH2](m-1) [OCH2CH2]1.25m OH, where m varied from 8 to 18. Maximum solubilization occurs when m = 16 (the hexadecyl alkyl ether). This is explained in
PMID 6127376

Effects of structural variations of non-ionic surfactants on micellar properties and solubilization: variation of oxyethylene content on properties of C22 monoethers.

Arnarson T, Elworthy PH.AbstractStudies on erucyl alcohol ethoxylated with 40 and 47 units, and on behenyl alcohol ethoxylated with 33 and 43 units, gave values of 106, 101, 271, and 304 (all X 10(3)) for the micellar weight, 51,42,152, and 137 for the aggregation numbers, and 257,362,209, and 311 moles water mol-1 surfactant for the micellar hydration, respectively. Measurements of the solubilization of azobenzene, cortisone acetate, griseofulvin, sulphadiazine, phenylbutazone, betamethasone, tolbutamide, and menaphthone showed that the erucyl derivatives were better solubilizers than the behenyl compounds, and that solubilization increased as the polyoxyethylene chain was shortened; this change was more pronounced with the erucyl compounds.
The Journal of pharmacy and pharmacology.J Pharm Pharmacol.1982 Feb;34(2):87-9.
Studies on erucyl alcohol ethoxylated with 40 and 47 units, and on behenyl alcohol ethoxylated with 33 and 43 units, gave values of 106, 101, 271, and 304 (all X 10(3)) for the micellar weight, 51,42,152, and 137 for the aggregation numbers, and 257,362,209, and 311 moles water mol-1 surfactant for
PMID 6121886

Effects of structural variations on non-ionic surfactants on micellar properties and solubilization: surfactants containing very long hydrocarbon chains.

Arnarson T, Elworthy PH.AbstractPolyoxyethylene mono-ethers of dotriacontanol (C32E41) and 4,9-dimethyltritriacontanol (C35E40) have been synthesized. The micellar weights in water at 298K were 4.82 x 10(5) and 5.90 x 10(5), the aggregation numbers 212 and 260, and the levels of hydration 290 and 283 mol water mol-1 surfactant, respectively. The solubilization of azobenzene, cortisone acetate, griseofulvin, sulphadiazine, phenylbutazone, betamethasone, tolbutamide, and menaphthone was studied in 2% solutions of the above surfactants. The presence of large micelles did not result in increased solubilization; C32E41 and C35E40 had a lower solubilizing capacity than that of cetomacrogol.
The Journal of pharmacy and pharmacology.J Pharm Pharmacol.1981 Mar;33(3):141-4.
Polyoxyethylene mono-ethers of dotriacontanol (C32E41) and 4,9-dimethyltritriacontanol (C35E40) have been synthesized. The micellar weights in water at 298K were 4.82 x 10(5) and 5.90 x 10(5), the aggregation numbers 212 and 260, and the levels of hydration 290 and 283 mol water mol-1 surfactant, re
PMID 6116753

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リンク元

「メナフトン」

Menadione^[1]
Names
	IUPAC name 2-Methylnaphthalene-1,4-dione
	Other names Menaphthone; Vitamin K3; β-Methyl-1,4-naphthoquinone; 2-Methyl-1,4-naphthodione; 2-Methyl-1,4-naphthoquinone
Identifiers
CAS Number	58-27-5
ChEBI	CHEBI:28869
ChEMBL	ChEMBL590
ChemSpider	3915
DrugBank	DB00170
Jmol interactive 3D	Image
KEGG	D02335
PubChem	4055
UNII	723JX6CXY5
	InChI InChI=1S/C11H8O2/c1-7-6-10(12)8-4-2-3-5-9(8)11(7)13/h2-6H,1H3 Key: MJVAVZPDRWSRRC-UHFFFAOYSA-N ; InChI=1/C11H8O2/c1-7-6-10(12)8-4-2-3-5-9(8)11(7)13/h2-6H,1H3 Key: MJVAVZPDRWSRRC-UHFFFAOYAY ;
	SMILES O=C\2c1c(cccc1)C(=O)/C(=C/2)C ;
Properties
Chemical formula	C11H8O2
Molar mass	172.18 g·mol−1
Appearance	Bright yellow crystals
Density	1.225g/cm3
Melting point	105 to 107 °C (221 to 225 °F; 378 to 380 K)
Boiling point	304.5 °C (580.1 °F; 577.6 K) @ 760mmHg
Solubility in water	Insoluble
Pharmacology
ATC code	B02BA02
Hazards
Flash point	113.8 °C (236.8 °F; 386.9 K)
	Lethal dose or concentration (LD, LC):
LD50 (Median dose)	0.5 g/kg (oral, mouse)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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	Infobox references

　　[★]

英: menaphthone
関: メナジオン

[1] The Merck Index, 11th Edition, 5714

[pmid19098979-2] Castro FA, Mariani D, Panek AD, Eleutherio EC, Pereira MD (2008). Fox, Debbie, ed. "Cytotoxicity Mechanism of Two Naphthoquinones (Menadione and Plumbagin) in Saccharomyces cerevisiae". PLoS ONE 3 (12): e3999. doi:10.1371/journal.pone.0003999. PMC 2600608. PMID 19098979.

[pmid15939799-3] Scott GK, Atsriku C, Kaminker P, et al. (September 2005). "Vitamin K3 (menadione)-induced oncosis associated with keratin 8 phosphorylation and histone H3 arylation". Mol. Pharmacol. 68 (3): 606–15. doi:10.1124/mol.105.013474. PMID 15939799.

[urlVitamin_K-4] "Vitamin K". Retrieved 2009-03-18.

[5] James M. Jamison, Jacques Gilloteaux, Henryk S. Taper and Jack L. Summers (2001). "Evaluation of the In Vitro and In Vivo Antitumor Activities of Vitamin C and K-3 Combinations against Human Prostate Cancer" (PDF). J. Nutr. 131 (1): 158S–160S. PMID 11208954.

[6] Tareen B, Summers JL, Jamison JM, Neal DR, McGuire K, Gerson L, Diokno A (2008). "A 12 Week, Open Label, Phase I/IIa Study Using Apatone® for the Treatment of Prostate Cancer Patients Who Have Failed Standard Therapy". Int J Med Sci 5 (2): 62–67. doi:10.7150/ijms.5.62. PMC 2288789. PMID 18392145.

[7] R. Perez-Soler, Y. Ling, Y. Zou, S.R. Deitcher (2008). "Local Rescue of Skin Toxicities Secondary to Kinase Inhibitor (KI) Therapy with Topical Menadione" (PDF). Annals of Oncology. doi:10.1093/annonc/mdn346.

[8] Tianhong Li and Roman Perez-Soler (2009). "Skin toxicities associated with epidermal growth factor receptor inhibitors". Targeted Oncology 4 (2): 107–119. doi:10.1007/s11523-009-0114-0. PMID 19452131.

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menaphthone