As a supplement it is used to treat certain bleeding disorders.[2] This includes warfarin overdose, vitamin K deficiency, and obstructive jaundice.[2] It is also recommended to prevent and treat vitamin K deficiency bleeding in infants.[2] Use is typically recommended by mouth, intramuscular injection or injection under the skin.[2] When given by injection benefits are seen within two hours.[2] Many countries in the world choose intramuscular injections in newborn to keep them safe from severe bleeding (VKDB). It is considered a safe treatment and saves many children from death and severe neurologic deficit every year.[4]
Side effects when given by injection may include pain at the site of injection.[2] Severe allergic reactions may occur when it is injected into a vein or muscle, but this has mainly happened when large doses of a certain type of supplement containing castor oil were given intravenously.[5] Use during pregnancy is considered safe,[6] use is also likely okay during breastfeeding.[7] It works by supplying a required component for making a number of blood clotting factors.[2] Food sources include green vegetables, vegetable oil, and some fruit.[8]
Vitamin K is a fat-soluble vitamin that is stable in air and moisture but decomposes in sunlight.[11] It is a polycyclicaromaticketone, based on 2-methyl-1,4-naphthoquinone, with a 3-phytylsubstituent. 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.
In terms of distribution, phylloquinone typically occurs in higher levels in the liver, heart and pancreas, but in lower levels in the brain, kidneys, and lungs.[14]
The biosynthesis of vitamin K1 via the transformation of chorismate occurs in nine steps.
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:[16][17][18]
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).
^Watson RR (2014). Diet and Exercise in Cystic Fibrosis. Academic Press. p. 187. ISBN9780128005880. from the original on 2016-12-30.
^ abcdefgh"Phytonadione". The American Society of Health-System Pharmacists. from the original on 29 December 2016. Retrieved 8 December 2016.
^World Health Organization (2019). World Health Organization model list of essential medicines: 21st list 2019. Geneva: World Health Organization. hdl:10665/325771. WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO.
^Furman L (27 July 2018). "American Academy of Pediatrics on vitamin k in the newborn period".
^Riegert-Johnson DL, Volcheck GW (October 2002). "The incidence of anaphylaxis following intravenous phytonadione (vitamin K1): a 5-year retrospective review". Annals of Allergy, Asthma & Immunology. 89 (4): 400–406. doi:10.1016/S1081-1206(10)62042-X. PMID 12392385.
^Bailey B (February 2003). "Are there teratogenic risks associated with antidotes used in the acute management of poisoned pregnant women?". Birth Defects Research. Part A, Clinical and Molecular Teratology. 67 (2): 133–140. doi:10.1002/bdra.10007. PMID 12769509.
^"Phytonadione Use During Pregnancy". Drugs.com. from the original on 29 December 2016. Retrieved 29 December 2016.
^"Vitamin K". Office of Dietary Supplements. U.S. National Institutes of Health. 11 February 2016. from the original on 31 December 2016. Retrieved 30 December 2016.
^ abSneader W (2005). Drug Discovery: A History. John Wiley & Sons. p. 243. ISBN9780471899792. from the original on 2016-12-30.
^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): 1105–1117. doi:10.1093/jn/112.6.1105. PMID 7086539.
^Institute of Medicine (US) Panel on Micronutrients. "Dietary Reference Intakes for Vitamin A, Vitamin K, Arsenic, Boron, Chromium, Copper, Iodine, Iron, Manganese, Molybdenum, Nickel, Silicon, Vanadium, and Zinc". Washington (DC): National Academies Press (US). Retrieved 25 November 2021 – via NCBI.
^Itoh S, Iwaki M (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. S2CID 84602152.
^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. S2CID 42983611.
^Bus K, Szterk A (December 2021). "Relationship between Structure and Biological Activity of Various Vitamin K Forms". Foods. 10 (12): 3136. doi:10.3390/foods10123136. PMC8701896. PMID 34945687.
^Basset GJ, Latimer S, Fatihi A, Soubeyrand E, Block A (2017). "Phylloquinone (Vitamin K1): Occurrence, Biosynthesis and Functions". Mini Reviews in Medicinal Chemistry. 17 (12): 1028–1038. doi:10.2174/1389557516666160623082714. PMID 27337968.
^Reumann S (2013). "Biosynthesis of vitamin K1 (phylloquinone) by plant peroxisomes and its integration into signaling molecule synthesis pathways". Peroxisomes and their Key Role in Cellular Signaling and Metabolism. Subcellular Biochemistry. Vol. 69. Springer Netherlands. pp. 213–29. doi:10.1007/978-94-007-6889-5_12. ISBN9789400768888. 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): 5599–5603. Bibcode:2009PNAS..106.5599W. doi:10.1073/pnas.0900738106. PMC2660889. PMID 19321747.
phytomenadione, also, known, vitamin, phylloquinone, vitamin, found, food, used, dietary, supplement, world, health, organization, list, essential, medicines, clinical, datatrade, namesmephyton, othersother, namesvitamin, phytonadione, phylloquinone, phytonadi. Phytomenadione also known as vitamin K1 or phylloquinone is a vitamin found in food and used as a dietary supplement 1 2 It is on the World Health Organization s List of Essential Medicines 3 PhytomenadioneClinical dataTrade namesMephyton othersOther namesVitamin K1 phytonadione phylloquinone E phytonadioneAHFS Drugs comMonographRoutes ofadministrationby mouth subQ IM IVATC codeB02BA01 WHO Legal statusLegal statusUS OTCIdentifiersIUPAC name 2 methyl 3 E 7R 11R 3 7 11 15 tetramethylhexadec 2 enyl naphthalene 1 4 dioneCAS Number84 80 0 YPubChem CID5284607DrugBankDB01022ChemSpider4447652UNIIS5Z3U87QHFKEGGD00148ChEBICHEBI 18067ChEMBLChEMBL1550CompTox Dashboard EPA DTXSID8023472ECHA InfoCard100 001 422Chemical and physical dataFormulaC 31H 46O 2Molar mass450 707 g mol 13D model JSmol Interactive imageSMILES CC1 C C O c2ccccc2C1 O C C C C CCC C H C CCC C H C CCCC C CInChI InChI 1S C31H46O2 c1 22 2 12 9 13 23 3 14 10 15 24 4 16 11 17 25 5 20 21 27 26 6 30 32 28 18 7 8 19 29 28 31 27 33 h7 8 18 20 22 24H 9 17 21H2 1 6H3 b25 20 t23 24 m1 s1 YKey MBWXNTAXLNYFJB NKFFZRIASA NAs a supplement it is used to treat certain bleeding disorders 2 This includes warfarin overdose vitamin K deficiency and obstructive jaundice 2 It is also recommended to prevent and treat vitamin K deficiency bleeding in infants 2 Use is typically recommended by mouth intramuscular injection or injection under the skin 2 When given by injection benefits are seen within two hours 2 Many countries in the world choose intramuscular injections in newborn to keep them safe from severe bleeding VKDB It is considered a safe treatment and saves many children from death and severe neurologic deficit every year 4 Side effects when given by injection may include pain at the site of injection 2 Severe allergic reactions may occur when it is injected into a vein or muscle but this has mainly happened when large doses of a certain type of supplement containing castor oil were given intravenously 5 Use during pregnancy is considered safe 6 use is also likely okay during breastfeeding 7 It works by supplying a required component for making a number of blood clotting factors 2 Food sources include green vegetables vegetable oil and some fruit 8 Phytomenadione was first isolated in 1939 9 In 1943 Edward Doisy and Henrik Dam were given a Nobel Prize for its discovery 9 Contents 1 Terminology 2 Chemistry 3 Biological function 3 1 Animals 3 2 Plants and cyanobacteria 4 Biosynthesis 5 See also 6 References 7 External linksTerminology EditPhytomenadione is often also called phylloquinone vitamin K 10 or phytonadione A stereoisomer of phylloquinone is called vitamin k1 note the difference in capitalization citation needed Chemistry EditThis section needs additional citations for verification Please help improve this article by adding citations to reliable sources in this section Unsourced material may be challenged and removed July 2019 Learn how and when to remove this template message Vitamin K is a fat soluble vitamin that is stable in air and moisture but decomposes in sunlight 11 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 Biological function EditMain article vitamin K Animals Edit 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 In terms of distribution phylloquinone typically occurs in higher levels in the liver heart and pancreas but in lower levels in the brain kidneys and lungs 14 Plants and cyanobacteria Edit Vitamin K1 is required for plant photosynthesis where it participates in the Photosystem I electron transport chain 15 Biosynthesis Edit nbsp The biosynthesis of vitamin K1 via the transformation of chorismate occurs in nine steps 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 16 17 18 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 EditMenatetrenone Vitamin K Vitamin K2References Edit Watson RR 2014 Diet and Exercise in Cystic Fibrosis Academic Press p 187 ISBN 9780128005880 Archived from the original on 2016 12 30 a b c d e f g h Phytonadione The American Society of Health System Pharmacists Archived from the original on 29 December 2016 Retrieved 8 December 2016 World Health Organization 2019 World Health Organization model list of essential medicines 21st list 2019 Geneva World Health Organization hdl 10665 325771 WHO MVP EMP IAU 2019 06 License CC BY NC SA 3 0 IGO Furman L 27 July 2018 American Academy of Pediatrics on vitamin k in the newborn period Riegert Johnson DL Volcheck GW October 2002 The incidence of anaphylaxis following intravenous phytonadione vitamin K1 a 5 year retrospective review Annals of Allergy Asthma amp Immunology 89 4 400 406 doi 10 1016 S1081 1206 10 62042 X PMID 12392385 Bailey B February 2003 Are there teratogenic risks associated with antidotes used in the acute management of poisoned pregnant women Birth Defects Research Part A Clinical and Molecular Teratology 67 2 133 140 doi 10 1002 bdra 10007 PMID 12769509 Phytonadione Use During Pregnancy Drugs com Archived from the original on 29 December 2016 Retrieved 29 December 2016 Vitamin K Office of Dietary Supplements U S National Institutes of Health 11 February 2016 Archived from the original on 31 December 2016 Retrieved 30 December 2016 a b Sneader W 2005 Drug Discovery A History John Wiley amp Sons p 243 ISBN 9780471899792 Archived from the original on 2016 12 30 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 1117 doi 10 1093 jn 112 6 1105 PMID 7086539 Institute of Medicine US Panel on Micronutrients Dietary Reference Intakes for Vitamin A Vitamin K Arsenic Boron Chromium Copper Iodine Iron Manganese Molybdenum Nickel Silicon Vanadium and Zinc Washington DC National Academies Press US Retrieved 25 November 2021 via NCBI Itoh S Iwaki M 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 S2CID 84602152 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 S2CID 42983611 Bus K Szterk A December 2021 Relationship between Structure and Biological Activity of Various Vitamin K Forms Foods 10 12 3136 doi 10 3390 foods10123136 PMC 8701896 PMID 34945687 Basset GJ Latimer S Fatihi A Soubeyrand E Block A 2017 Phylloquinone Vitamin K1 Occurrence Biosynthesis and Functions Mini Reviews in Medicinal Chemistry 17 12 1028 1038 doi 10 2174 1389557516666160623082714 PMID 27337968 Reumann S 2013 Biosynthesis of vitamin K1 phylloquinone by plant peroxisomes and its integration into signaling molecule synthesis pathways Peroxisomes and their Key Role in Cellular Signaling and Metabolism Subcellular Biochemistry Vol 69 Springer Netherlands pp 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 5603 Bibcode 2009PNAS 106 5599W doi 10 1073 pnas 0900738106 PMC 2660889 PMID 19321747 Van Oostende C Widhalm JR Furt F Ducluzeau AL Basset GJ 2011 Vitamin K1 Phylloquinone Advances in Botanical Research 59 229 261 doi 10 1016 B978 0 12 385853 5 00001 5 ISBN 9780123858535 External links EditListen to this article 2 minutes source source nbsp This audio file was created from a revision of this article dated 8 September 2012 2012 09 08 and does not reflect subsequent edits Audio help More spoken articles Phytomenadione Drug Information Portal U S National Library of Medicine Portal nbsp Medicine Retrieved from https en wikipedia org w index php title Phytomenadione amp oldid 1171965822, wikipedia, wiki, book, books, library,
