WordNet

United States guitar player and singer of the blues (born in 1925) (同)B. B. King, Riley B King
United States woman tennis player (born in 1943) (同)Billie Jean King, Billie Jean Moffitt King
United States charismatic civil rights leader and Baptist minister who campaigned against the segregation of Blacks (1929-1968) (同)Martin Luther King, Martin Luther King Jr.
street names for ketamine (同)jet, super acid, special K, honey oil, green, cat valium, super C
the 11th letter of the Roman alphabet (同)k
any of a group of organic substances essential in small quantities to normal metabolism

PrepTutorEJDIC

Kelvin / Kindergarten / (チェスの)King / kalium(ラテン語)(=potassium)の化学記号
『ビタミン』,栄養素(身体の喜常な機能を維持するために少量ながら必要な有機化合物)

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2013/01/24 00:35:02」(JST)

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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 without the side chain in the 3-position cannot exert all the functions of the K vitamins. Menadione is a vitamin precursor of K₂ which utilizes alkylation to yield menaquinones (MK-n, n=1-13; K₂ vitamers), and 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. Large doses of menadione have been reported to cause adverse outcomes including hemolytic anemia due to G6PD 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 (FDA) 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.

It is used in the treatment of Hypoprothrombinemia

Experimental research

Menadione has been used experimentally as a chemotherapic agent for cancer since 1947.^{[citation needed]} More 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. http://www.plosone.org/article/info:doi/10.1371/journal.pone.0003999.
^ 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. http://molpharm.aspetjournals.org/cgi/pmidlookup?view=long&pmid=15939799.
^ "Vitamin K". http://www.umm.edu/altmed/articles/vitamin-k-000343.htm. 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". J. Nutr. 131 (1): 158S–160S. PMID 11208954. http://jn.nutrition.org/cgi/reprint/131/1/158S.pdf.
^ 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. PMC 2288789. PMID 18392145. http://www.medsci.org/v05p0062.htm.
^ 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". Annals of Oncology. http://annonc.oxfordjournals.org/content/19/suppl_5/v164.full.pdf.
^ 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. http://www.springerlink.com/content/x6712t382565u144/.

UpToDate Contents

全文を閲覧するには購読必要です。 To read the full text you will need to subscribe.

1. ビタミンKの概要 overview of vitamin k
2. ミトコンドリア細胞症における腎病変 renal involvement in the mitochondrial cytopathies
3. ミトコンドリアミオパシー：治療 mitochondrial myopathies treatment

English Journal

The folate precursor para-aminobenzoic acid elicits induced resistance against Cucumber mosaic virus and Xanthomonas axonopodis.

Song GC, Choi HK, Ryu CM.SourceMolecular Phytobacteriology Laboratory, Systems & Synthetic Biology Research Center, KRIBB, Daejeon 305-806, South Korea.
Annals of botany.Ann Bot.2013 May;111(5):925-34. doi: 10.1093/aob/mct049. Epub 2013 Mar 7.
Background and Aims The use of vitamins including vitamin B1, B2 and K3 for the induction of systemic acquired resistance (SAR) to protect crops against plant pathogens has been evaluated previously. The use of vitamins is beneficial because it is cost effective and safe for the environment. The use
PMID 23471007

Reduction of Quinones by NADH Catalyzed by Organoiridium Complexes.

Liu Z, Deeth RJ, Butler JS, Habtemariam A, Newton ME, Sadler PJ.SourceDepartment of Chemistry, University of Warwick, Coventry, CV4 7AL (UK).
Angewandte Chemie (International ed. in English).Angew Chem Int Ed Engl.2013 Apr 8;52(15):4194-7. doi: 10.1002/anie.201300747. Epub 2013 Mar 7.
One electron at a time: Half-sandwich organometallic cyclopentadienyl-Ir(III) complexes containing N,N-chelated ligands can catalyze the reduction of quinones (Q), such as vitamin K3 , to semiquinones (Q(.-) ) by coenzyme NADH. DFT calculations suggest that the mechanism involves hydride transfer
PMID 23471835

Japanese Journal

Taylor法を用いたCO2膨張メタノール中におけるビタミンK3の無限希釈拡散係数

大学院研究年報　理工学研究科篇 (第43号/2013), 2013-07-01
NAID 120005394256

Innovation of Coulometric Analysis, Based on Carbon Felt Electrodes and its Application to Bioelectroanalytical Chemistry

Shunichi Uchiyama
ポーラログラフィー 58(2), 67-73, 2012-09-27
… The various compounds such as L-ascorbic acid, vitamin K3, hydrogen molecule and peroxide have been determined by this novel coulometric method which has been commercialized by three Japanese manufactures so far. …
NAID 10031120424

「ビタミンK3」

Menadione
	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
PubChem	4055
ChemSpider	3915
UNII	723JX6CXY5
DrugBank	DB00170
KEGG	D02335
ChEBI	CHEBI:28869
ChEMBL	CHEMBL590
ATC code	B02BA02
Jmol-3D images	Image 1
	SMILES O=C\2c1c(cccc1)C(=O)/C(=C/2)C ;
	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 ;
Properties
Molecular formula	C11H8O2
Molar mass	172.18 g mol−1
Appearance	Bright yellow crystals
Density	1.225g/cm3
Melting point	105–107 °C
Boiling point	304.5 °C @ 760mmHg
Solubility in water	Insoluble
Hazards
Flash point	113.8 °C
LD50	0.5 g/kg (oral, mouse)
	(verify) (what is: /?); Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
	Infobox references

　　[★]

英: vitamin K3
関: メナジオン

「K」

　　[★]

[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. http://www.plosone.org/article/info:doi/10.1371/journal.pone.0003999.

[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. http://molpharm.aspetjournals.org/cgi/pmidlookup?view=long&pmid=15939799.

[urlVitamin_K-4] "Vitamin K". http://www.umm.edu/altmed/articles/vitamin-k-000343.htm. 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". J. Nutr. 131 (1): 158S–160S. PMID 11208954. http://jn.nutrition.org/cgi/reprint/131/1/158S.pdf.

[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. PMC 2288789. PMID 18392145. http://www.medsci.org/v05p0062.htm.

[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". Annals of Oncology. http://annonc.oxfordjournals.org/content/19/suppl_5/v164.full.pdf.

[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. http://www.springerlink.com/content/x6712t382565u144/.

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案内

vitamin K3