Phytomenadione: Difference between revisions
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'''Phytomenadione''', also known as '''vitamin K<sub>1</sub>''' or '''phylloquinone''', is a [[vitamin]] found in food and used as a [[dietary supplement]].<ref>{{cite book|last1=Watson|first1=Ronald Ross|title=Diet and Exercise in Cystic Fibrosis|date=2014|publisher=Academic Press|isbn=9780128005880|page=187|url=https://books.google.ca/books?id=hSSOAwAAQBAJ&pg=PA187|language=en|deadurl=no| |
'''Phytomenadione''', also known as '''vitamin K<sub>1</sub>''' or '''phylloquinone''', is a [[vitamin]] found in food and used as a [[dietary supplement]].<ref>{{cite book|last1=Watson|first1=Ronald Ross | name-list-format = vanc |title=Diet and Exercise in Cystic Fibrosis|date=2014|publisher=Academic Press|isbn=9780128005880|page=187|url=https://books.google.ca/books?id=hSSOAwAAQBAJ&pg=PA187|language=en|deadurl=no|archive-url=https://web.archive.org/web/20161230000443/https://books.google.ca/books?id=hSSOAwAAQBAJ&pg=PA187|archive-date=2016-12-30|df=}}</ref><ref name=AHFS2016/> As a supplement it is used to treat certain [[bleeding disorders]].<ref name=AHFS2016/> This includes in [[warfarin overdose]], [[vitamin K deficiency]], and [[obstructive jaundice]].<ref name=AHFS2016/> It is also recommended to prevent and treat [[hemorrhagic disease of the newborn]].<ref name=AHFS2016/> Use is typically recommended by mouth or [[subcutaneous injection|injection under the skin]].<ref name=AHFS2016/> Use by [[injection (medicine)|injection]] into a [[vein]] or [[intramuscular|muscle]] is recommended only when other routes are not possible.<ref name=AHFS2016/> When given by injection benefits are seen within two hours.<ref name=AHFS2016>{{cite web|title=Phytonadione|url=https://www.drugs.com/monograph/phytonadione.html|publisher=The American Society of Health-System Pharmacists|access-date=8 December 2016|deadurl=no|archive-url=https://web.archive.org/web/20161229172825/https://www.drugs.com/monograph/phytonadione.html|archive-date=29 December 2016|df=}}</ref> |
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Common side effects when given by injection include pain at the site of injection and altered taste.<ref name=AHFS2016/> Severe [[allergic reactions]] may occur when it is injected into a vein or muscle.<ref name=AHFS2016/> It is unclear if use during [[pregnancy]] is safe; however, use is likely okay during [[breastfeeding]].<ref>{{cite web|title=Phytonadione Use During Pregnancy|url=https://www.drugs.com/pregnancy/phytonadione.html|website=Drugs.com| |
Common side effects when given by injection include pain at the site of injection and altered taste.<ref name=AHFS2016/> Severe [[allergic reactions]] may occur when it is injected into a vein or muscle.<ref name=AHFS2016/> It is unclear if use during [[pregnancy]] is safe; however, use is likely okay during [[breastfeeding]].<ref>{{cite web|title=Phytonadione Use During Pregnancy|url=https://www.drugs.com/pregnancy/phytonadione.html|website=Drugs.com|access-date=29 December 2016|deadurl=no|archive-url=https://web.archive.org/web/20161229172908/https://www.drugs.com/pregnancy/phytonadione.html|archive-date=29 December 2016|df=}}</ref> It works by supplying a required component for making a number of [[blood clotting factors]].<ref name=AHFS2016/> Found sources include [[green vegetables]], vegetable oil, and some fruit.<ref name=NIH2016>{{cite web|title=Office of Dietary Supplements – Vitamin K|url=https://ods.od.nih.gov/factsheets/VitaminK-HealthProfessional|website=ods.od.nih.gov|access-date=30 December 2016|date=11 February 2016|deadurl=no|archive-url=https://web.archive.org/web/20161231075317/https://ods.od.nih.gov/factsheets/VitaminK-HealthProfessional/|archive-date=31 December 2016|df=}}</ref> |
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Phytomenadione was first isolated in 1939.<ref name=Sn2005>{{cite book|last1=Sneader|first1=Walter|title=Drug Discovery: A History|date=2005|publisher=John Wiley & Sons|isbn=9780471899792|page=243|url=https://books.google.ca/books?id=Cb6BOkj9fK4C&pg=PA243|language=en|deadurl=no| |
Phytomenadione was first isolated in 1939.<ref name=Sn2005>{{cite book|last1=Sneader|first1=Walter| name-list-format = vanc |title=Drug Discovery: A History|date=2005|publisher=John Wiley & Sons|isbn=9780471899792|page=243|url=https://books.google.ca/books?id=Cb6BOkj9fK4C&pg=PA243|language=en|deadurl=no|archive-url=https://web.archive.org/web/20161230000050/https://books.google.ca/books?id=Cb6BOkj9fK4C&pg=PA243|archive-date=2016-12-30|df=}}</ref> It is on the [[World Health Organization's List of Essential Medicines]], the most effective and safe medicines needed in a [[health system]].<ref name=WHO19th>{{cite web|title=WHO Model List of Essential Medicines (19th List)|url=http://www.who.int/medicines/publications/essentialmedicines/EML_2015_FINAL_amended_NOV2015.pdf?ua=1|work=World Health Organization|access-date=8 December 2016|date=April 2015|deadurl=no|archive-url=https://web.archive.org/web/20161213052708/http://www.who.int/medicines/publications/essentialmedicines/EML_2015_FINAL_amended_NOV2015.pdf?ua=1|archive-date=13 December 2016|df=}}</ref> The wholesale cost in the [[developing world]] is about 0.11 to 1.27 [[USD]] for a 10 mg vial.<ref name=ERC2014>{{cite web|title=Vitamin K1|url=http://mshpriceguide.org/en/single-drug-information/?DMFId=839&searchYear=2014|website=International Drug Price Indicator Guide|access-date=8 December 2016|deadurl=no|archive-url=https://web.archive.org/web/20170510104945/http://mshpriceguide.org/en/single-drug-information/?DMFId=839&searchYear=2014|archive-date=10 May 2017|df=}}</ref> In the United States a course of treatment costs less than 25 USD.<ref name=Ric2015>{{cite book|last1=Hamilton|first1=Richart| name-list-format = vanc |title=Tarascon Pocket Pharmacopoeia 2015 Deluxe Lab-Coat Edition|date=2015|publisher=Jones & Bartlett Learning|isbn=9781284057560|page=229}}</ref> In 1943 [[Edward Doisy]] and [[Henrik Dam]] were given a [[Nobel Prize]] for its discovery.<ref name=Sn2005/> |
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==Terminology== |
==Terminology== |
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Phytomenadione is often also called phylloquinone, vitamin K,<ref name="pmid7086539">{{cite journal | |
Phytomenadione is often also called phylloquinone, vitamin K,<ref name="pmid7086539">{{cite journal | vauthors = Haroon Y, Shearer MJ, Rahim S, Gunn WG, McEnery G, Barkhan P | title = The content of phylloquinone (vitamin K1) in human milk, cows' milk and infant formula foods determined by high-performance liquid chromatography | journal = The Journal of Nutrition | volume = 112 | issue = 6 | pages = 1105–17 | date = June 1982 | pmid = 7086539 | doi = 10.1093/jn/112.6.1105 | url = http://jn.nutrition.org/cgi/pmidlookup?view=long&pmid=7086539 }}</ref> or phytonadione. Sometimes a distinction is made between phylloquinone, which is considered to be a natural substance, and phytonadione, which is considered to be a synthetic substance.<ref name="urlVitamin K">{{cite web |url=http://www.umm.edu/altmed/articles/vitamin-k-000343.htm |title=Vitamin K |website= |access-date=2009-03-18}}</ref> |
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A [[stereoisomer]] of phylloquinone is called vitamin k<sub>1</sub> (note the difference in capitalization).{{citation needed|date=April 2019}} |
A [[stereoisomer]] of phylloquinone is called vitamin k<sub>1</sub> (note the difference in capitalization).{{citation needed|date=April 2019}} |
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[[File:Updated chem 257.jpg|alt=|thumb|The biosynthesis of vitamin K1 via the transformation of chorismate occurs in nine steps.]] |
[[File:Updated chem 257.jpg|alt=|thumb|The biosynthesis of vitamin K1 via the transformation of chorismate occurs in nine steps.]] |
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Vitamin K<sub>1</sub> is synthesized from chorismate, a compound produced from shikimate via the shikimate pathway. The conversion of chorismate to vitamin K<sub>1</sub> comprises a series of nine steps:<ref>{{ |
Vitamin K<sub>1</sub> is synthesized from chorismate, a compound produced from shikimate via the shikimate pathway. The conversion of chorismate to vitamin K<sub>1</sub> comprises a series of nine steps:<ref>{{cite journal | vauthors = Reumann S | title = Biosynthesis of vitamin K1 (phylloquinone) by plant peroxisomes and its integration into signaling molecule synthesis pathways | journal = Sub-Cellular Biochemistry | volume = 69 | pages = 213–29 | date = 2013 | pmid = 23821151 | doi = 10.1007/978-94-007-6889-5_12 | publisher = Springer Netherlands | isbn = 9789400768888 | series = Subcellular Biochemistry }}</ref><ref>{{cite journal | vauthors = Widhalm JR, van Oostende C, Furt F, Basset GJ | title = A dedicated thioesterase of the Hotdog-fold family is required for the biosynthesis of the naphthoquinone ring of vitamin K1 | journal = Proceedings of the National Academy of Sciences of the United States of America | volume = 106 | issue = 14 | pages = 5599–603 | date = April 2009 | pmid = 19321747 | pmc = 2660889 | doi = 10.1073/pnas.0900738106 }}</ref> |
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# Chorismate is [[isomerization|isomerized]] to isochorismate by isochorismate synthase, or MenF (menaquinone enzyme). |
# Chorismate is [[isomerization|isomerized]] to isochorismate by isochorismate synthase, or MenF (menaquinone enzyme). |
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* [[Vitamin K2|Vitamin K<sub>2</sub>]] |
* [[Vitamin K2|Vitamin K<sub>2</sub>]] |
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==References== |
== References == |
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{{Reflist}} |
{{Reflist}} |
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==External links== |
== External links == |
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{{Spoken Wikipedia|PylloquinoneA.ogg|2012-09-08}} |
{{Spoken Wikipedia|PylloquinoneA.ogg|2012-09-08}} |
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Revision as of 04:52, 5 August 2019
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| Clinical data | |
|---|---|
| Trade names | Mephyton, others |
| Other names | Vitamin K1, phytonadione, phylloquinone, (E)-phytonadione |
| AHFS/Drugs.com | Monograph |
| Routes of administration | by mouth, subQ, IM, IV |
| ATC code | |
| Legal status | |
| Legal status | |
| Identifiers | |
| |
| CAS Number | |
| PubChem CID | |
| DrugBank | |
| ChemSpider | |
| UNII | |
| ChEBI | |
| ChEMBL | |
| CompTox Dashboard (EPA) | |
| ECHA InfoCard | 100.001.422 |
| Chemical and physical data | |
| Formula | C31H46O2 |
| Molar mass | 450.70 g/mol g·mol−1 |
| 3D model (JSmol) | |
| |
| |
Phytomenadione, also known as vitamin K1 or phylloquinone, is a vitamin found in food and used as a dietary supplement.[2][3] As a supplement it is used to treat certain bleeding disorders.[3] This includes in warfarin overdose, vitamin K deficiency, and obstructive jaundice.[3] It is also recommended to prevent and treat hemorrhagic disease of the newborn.[3] Use is typically recommended by mouth or injection under the skin.[3] Use by injection into a vein or muscle is recommended only when other routes are not possible.[3] When given by injection benefits are seen within two hours.[3]
Common side effects when given by injection include pain at the site of injection and altered taste.[3] Severe allergic reactions may occur when it is injected into a vein or muscle.[3] It is unclear if use during pregnancy is safe; however, use is likely okay during breastfeeding.[4] It works by supplying a required component for making a number of blood clotting factors.[3] Found sources include green vegetables, vegetable oil, and some fruit.[5]
Phytomenadione was first isolated in 1939.[6] It is on the World Health Organization's List of Essential Medicines, the most effective and safe medicines needed in a health system.[7] The wholesale cost in the developing world is about 0.11 to 1.27 USD for a 10 mg vial.[8] In the United States a course of treatment costs less than 25 USD.[9] In 1943 Edward Doisy and Henrik Dam were given a Nobel Prize for its discovery.[6]
Terminology
Phytomenadione is often also called phylloquinone, vitamin K,[10] or phytonadione. Sometimes a distinction is made between phylloquinone, which is considered to be a natural substance, and phytonadione, which is considered to be a synthetic substance.[11]
A stereoisomer of phylloquinone is called vitamin k1 (note the difference in capitalization).[citation needed]
Chemistry
 | This section needs additional citations for verification. (July 2019) |
Vitamin K is a fat-soluble vitamin that is stable in air and moisture but decomposes in sunlight. It is a polycyclic aromatic ketone, based on 2-methyl-1,4-naphthoquinone, with a 3-phytyl substituent. It is found naturally in a wide variety of green plants, particularly in leaves, since it functions as an electron acceptor during photosynthesis, forming part of the electron transport chain of photosystem I.[12][13]
The best-known function of vitamin K in animals is as a cofactor in the formation of coagulation factors II (prothrombin), VII, IX, and X by the liver. It is also required for the formation of anticoagulant factors protein C and S. It is commonly used to treat warfarin toxicity, and as an antidote for coumatetralyl.
Vitamin K is required for bone protein formation.
Biosynthesis
Vitamin K1 is synthesized from chorismate, a compound produced from shikimate via the shikimate pathway. The conversion of chorismate to vitamin K1 comprises a series of nine steps:[14][15]
- Chorismate is isomerized to isochorismate by isochorismate synthase, or MenF (menaquinone enzyme).
- Addition of 2-oxoglutarate to isochorismate by PHYLLO, a multifunctional protein comprising three different enzymatic activities (MenD, H, and C).
- Elimination of pyruvate by PHYLLO.
- Aromatization to yield o-succinyl benzoate by PHYLLO.
- O-succinylbenzoate activation to corresponding CoA ester by MenE.
- Naphthoate ring formation by naphthoate synthase (MenB/NS).
- Thiolytic release of CoA by a thioesterase (MenH).
- Attachment of phytol chain to the naphthoate ring (MenA/ABC4).
- Methylation of the precursor at position 3 (MenG).
See also
References
- ^ "FDA-sourced list of all drugs with black box warnings (Use Download Full Results and View Query links.)". nctr-crs.fda.gov. FDA. Retrieved 22 Oct 2023.
- ^ Watson, Ronald Ross (2014). Diet and Exercise in Cystic Fibrosis. Academic Press. p. 187. ISBN 9780128005880. Archived from the original on 2016-12-30.
{{cite book}}: Unknown parameter|deadurl=ignored (|url-status=suggested) (help); Unknown parameter|name-list-format=ignored (|name-list-style=suggested) (help) - ^ a b c d e f g h i j "Phytonadione". The American Society of Health-System Pharmacists. Archived from the original on 29 December 2016. Retrieved 8 December 2016.
{{cite web}}: Unknown parameter|deadurl=ignored (|url-status=suggested) (help) - ^ "Phytonadione Use During Pregnancy". Drugs.com. Archived from the original on 29 December 2016. Retrieved 29 December 2016.
{{cite web}}: Unknown parameter|deadurl=ignored (|url-status=suggested) (help) - ^ "Office of Dietary Supplements – Vitamin K". ods.od.nih.gov. 11 February 2016. Archived from the original on 31 December 2016. Retrieved 30 December 2016.
{{cite web}}: Unknown parameter|deadurl=ignored (|url-status=suggested) (help) - ^ a b Sneader, Walter (2005). Drug Discovery: A History. John Wiley & Sons. p. 243. ISBN 9780471899792. Archived from the original on 2016-12-30.
{{cite book}}: Unknown parameter|deadurl=ignored (|url-status=suggested) (help); Unknown parameter|name-list-format=ignored (|name-list-style=suggested) (help) - ^ "WHO Model List of Essential Medicines (19th List)" (PDF). World Health Organization. April 2015. Archived from the original (PDF) on 13 December 2016. Retrieved 8 December 2016.
{{cite web}}: Unknown parameter|deadurl=ignored (|url-status=suggested) (help) - ^ "Vitamin K1". International Drug Price Indicator Guide. Archived from the original on 10 May 2017. Retrieved 8 December 2016.
{{cite web}}: Unknown parameter|deadurl=ignored (|url-status=suggested) (help) - ^ Hamilton, Richart (2015). Tarascon Pocket Pharmacopoeia 2015 Deluxe Lab-Coat Edition. Jones & Bartlett Learning. p. 229. ISBN 9781284057560.
{{cite book}}: Unknown parameter|name-list-format=ignored (|name-list-style=suggested) (help) - ^ Haroon Y, Shearer MJ, Rahim S, Gunn WG, McEnery G, Barkhan P (June 1982). "The content of phylloquinone (vitamin K1) in human milk, cows' milk and infant formula foods determined by high-performance liquid chromatography". The Journal of Nutrition. 112 (6): 1105–17. doi:10.1093/jn/112.6.1105. PMID 7086539.
- ^ "Vitamin K". Retrieved 2009-03-18.
- ^ Itoh, Shigeru; Iwaki, Masayo (1989). "Vitamin K1 (Phylloquinone) Restores the Turnover of FeS centers of Ether-extracted Spinach PSI Particles". FEBS Letters. 243 (1): 47–52. doi:10.1016/0014-5793(89)81215-3.
{{cite journal}}: Unknown parameter|name-list-format=ignored (|name-list-style=suggested) (help) - ^ Palace GP, Franke JE, Warden JT (May 1987). "Is phylloquinone an obligate electron carrier in photosystem I?". FEBS Letters. 215 (1): 58–62. doi:10.1016/0014-5793(87)80113-8. PMID 3552735.
- ^ Reumann S (2013). "Biosynthesis of vitamin K1 (phylloquinone) by plant peroxisomes and its integration into signaling molecule synthesis pathways". Sub-Cellular Biochemistry. Subcellular Biochemistry. 69. Springer Netherlands: 213–29. doi:10.1007/978-94-007-6889-5_12. ISBN 9789400768888. PMID 23821151.
- ^ Widhalm JR, van Oostende C, Furt F, Basset GJ (April 2009). "A dedicated thioesterase of the Hotdog-fold family is required for the biosynthesis of the naphthoquinone ring of vitamin K1". Proceedings of the National Academy of Sciences of the United States of America. 106 (14): 5599–603. doi:10.1073/pnas.0900738106. PMC 2660889. PMID 19321747.
