pyridoxine
{{Short description|Chemical compound}}
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{{Use dmy dates|date=March 2024}}
{{Infobox drug
| drug_name =
| INN =
| type =
| IUPAC_name = 4,5-Bis(hydroxymethyl)-2-methylpyridin-3-ol
| image = Pyridoxin.svg
| image_class = skin-invert-image
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| image2 = Pyridoxine-from-xtal-3D-bs-17.png
| image_class2 = bg-transparent
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| alt2 =
| caption = Pyridoxine
| pronounce =
| tradename =
| Drugs.com = {{Drugs.com|monograph|pyridoxine-hydrochloride}}
| MedlinePlus =
| licence_EU =
| licence_US =
| DailyMedID = Pyridoxine
| pregnancy_AU =
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| dependency_liability =
| addiction_liability =
| routes_of_administration = By mouth, intravenous (IV), intramuscular (IM), subcutaneous
| class =
| ATCvet =
| ATC_prefix = A11
| ATC_suffix = HA02
| ATC_supplemental =
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| legal_UK = P
| legal_US = OTC
| legal_US_comment = / Rx-only
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| bioavailability =
| protein_bound =
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| onset =
| elimination_half-life = several weeks (see #Metabolism for details)
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| CAS_number = 65-23-6
| CAS_supplemental =
| PubChem = 1054
| PubChemSubstance =
| IUPHAR_ligand =
| DrugBank = DB00165
| ChemSpiderID = 1025
| UNII = KV2JZ1BI6Z
| KEGG = D08454
| ChEBI = 16709
| ChEMBL = 1364
| NIAID_ChemDB =
| synonyms = vitamin B6, pyridoxol{{cite book| vauthors = Dryhurst G | chapter = Electrochemistry of Biologically Important Pyridines |title=Electrochemistry of Biological Molecules |date=2012 |publisher=Elsevier |isbn=978-0-323-14452-0 |page=562 | chapter-url=https://books.google.com/books?id=N2FCSE3TGlgC&pg=PA562 |language=en |url-status=live |archive-url= https://web.archive.org/web/20161230160436/https://books.google.ca/books?id=N2FCSE3TGlgC&pg=PA562 |archive-date=30 December 2016}} pyridoxine hydrochloride
| chemical_formula =
| C=8 | H=11 | N=1 | O=3
| charge=
| molecular_weight =
| SMILES = OCc1cnc(C)c(O)c1CO
| Jmol =
| StdInChI = 1S/C8H11NO3/c1-5-8(12)7(4-11)6(3-10)2-9-5/h2,10-12H,3-4H2,1H3
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = LXNHXLLTXMVWPM-UHFFFAOYSA-N
| density =
| density_notes =
| melting_point = 159 to 162
| melting_high =
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}}
Pyridoxine (PN){{Cite web |title=Vitamin B-6 |url=https://iupac.qmul.ac.uk/misc/B6.html |access-date=2024-09-26 |website=iupac.qmul.ac.uk}} is a form of vitamin B6 found commonly in food and used as a dietary supplement. As a supplement it is used to treat and prevent pyridoxine deficiency, sideroblastic anaemia, pyridoxine-dependent epilepsy, certain metabolic disorders, side effects or complications of isoniazid use, and certain types of mushroom poisoning. It is used by mouth or by injection.
It is usually well tolerated. Occasionally side effects include headache, numbness, and sleepiness. Normal doses are safe during pregnancy and breastfeeding. Pyridoxine is in the vitamin B family of vitamins. It is required by the body to metabolise amino acids, carbohydrates, and lipids.{{cite web|title=Pyridoxine Hydrochloride|url=https://www.drugs.com/monograph/pyridoxine-hydrochloride.html|publisher=The American Society of Health-System Pharmacists|access-date=8 December 2016|url-status=live|archive-url=https://web.archive.org/web/20161230161645/https://www.drugs.com/monograph/pyridoxine-hydrochloride.html|archive-date=30 December 2016}} Sources in the diet include meat, fish, fruit, vegetables, and grain.{{cite web|title=Office of Dietary Supplements - Dietary Supplement Fact Sheet: Vitamin B6|url=https://ods.od.nih.gov/factsheets/VitaminB6-HealthProfessional/|website=ods.od.nih.gov|access-date=30 December 2016|date=11 February 2016|url-status=live|archive-url=https://web.archive.org/web/20161212235920/https://ods.od.nih.gov/factsheets/VitaminB6-HealthProfessional/|archive-date=12 December 2016}}
Medical uses
As a treatment (oral or injection), it is used to treat or prevent pyridoxine deficiency, sideroblastic anaemia, pyridoxine-dependent epilepsy, certain metabolic disorders, side effects of isoniazid treatment and certain types of mushroom poisoning. Isoniazid is an antibiotic used for the treatment of tuberculosis. Common side effect include numbness in the hands and feet.{{cite web|title=Isoniazid|url=https://www.drugs.com/monograph/isoniazid.html|publisher=The American Society of Health-System Pharmacists|access-date=13 August 2021|archive-date=20 December 2016|archive-url=https://web.archive.org/web/20161220231039/https://www.drugs.com/monograph/isoniazid.html|url-status=live}} Co-treatment with vitamin B6 alleviates the numbness.{{cite journal | vauthors = Lheureux P, Penaloza A, Gris M | title = Pyridoxine in clinical toxicology: a review | journal = European Journal of Emergency Medicine | volume = 12 | issue = 2 | pages = 78–85 | date = April 2005 | pmid = 15756083 | doi = 10.1097/00063110-200504000-00007 | s2cid = 39197646 }} Pyridoxine-dependent epilepsy is a type of rare infant epilepsy that does not improve with typical anti-seizure medications.{{cite journal | vauthors = Abend NS, Loddenkemper T | title = Management of pediatric status epilepticus | journal = Current Treatment Options in Neurology | volume = 16 | issue = 7 | pages = 301 | date = July 2014 | pmid = 24909106 | pmc = 4110742 | doi = 10.1007/s11940-014-0301-x }}
Pyridoxine in combination with doxylamine is used as a treatment for morning sickness in pregnant women.{{cite journal | vauthors = Anh NH, Kim SJ, Long NP, Min JE, Yoon YC, Lee EG, Kim M, Kim TJ, Yang YY, Son EY, Yoon SJ, Diem NC, Kim HM, Kwon SW | title = Ginger on Human Health: A Comprehensive Systematic Review of 109 Randomized Controlled Trials | journal = Nutrients | volume = 12 | issue = 1 | pages = 157 | date = January 2020 | pmid = 31935866 | pmc = 7019938 | doi = 10.3390/nu12010157 | doi-access = free }}
Side effects
It is usually well tolerated, though overdose toxicity is possible. Occasionally side effects include headache, numbness, and sleepiness. Pyridoxine overdose can cause a peripheral sensory neuropathy characterized by poor coordination, numbness, and decreased sensation to touch, temperature, and vibration.{{Cite web|title=Pyridoxine deficiency and toxicity|work=MedLink Neurology|url=https://www.medlink.com/article/pyridoxine_deficiency_and_toxicity|access-date=14 December 2020|publisher=www.medlink.com|archive-date=19 July 2020|archive-url=https://web.archive.org/web/20200719043247/https://www.medlink.com/article/pyridoxine_deficiency_and_toxicity|url-status=live}} Healthy human blood levels of pyridoxine are 2.1–21.7 ng/mL. Normal doses are safe during pregnancy and breastfeeding.
Mechanism
Metabolism
The half-life of pyridoxine varies according to different sources: one source suggests that the half-life of pyridoxine is up to 20 days,{{cite book|doi=10.1007/978-3-319-20790-2_174-1|quote=The half-life of pyridoxine is up to 20 days. |chapter=Pyridoxine |title=Critical Care Toxicology |date=2016 | vauthors = Kennedy A, Schaeffer T |pages=1–4 |isbn=978-3-319-20790-2 }} while another source indicates half-life of vitamin B6 is in range of 25 to 33 days.{{cite book |title=Assessment of vitamin B6 intake in relation to tolerable upper intake levels. Opinion of the Panel on Nutrition, Dietetic Products, Novel Food and Allergy of the Norwegian Scientific Committee for Food Safety |isbn=978-82-8259-260-4 |location=Oslo, Norway |url=https://vkm.no/download/18.645b840415d03a2fe8f2653d/1499330353450/087ba2170f.pdf |access-date=7 December 2019 |archive-url=https://web.archive.org/web/20191117011203/https://vkm.no/download/18.645b840415d03a2fe8f2653d/1499330353450/087ba2170f.pdf |archive-date=17 November 2019 | quote=Eighty to ninety percent of vitamin B6 in the body is found in muscles and estimated body stores in adults amount to about 170 mg with a half-life of 25-33 days.}} After considering the different sources, it can be concluded that the half-life of pyridoxine is typically measured in several weeks.
History
Pyridoxine was discovered in 1934, isolated in 1938, and first made in 1939.{{cite book|vauthors=Squires VR|title=The Role of Food, Agriculture, Forestry and Fisheries in Human Nutrition - Volume IV|date=2011|publisher=EOLSS Publications|isbn=978-1-84826-195-2|page=121|url=https://books.google.com/books?id=VJWoCwAAQBAJ&pg=PA121|language=en|access-date=30 June 2020|archive-date=11 January 2023|archive-url=https://web.archive.org/web/20230111085247/https://books.google.com/books?id=VJWoCwAAQBAJ&pg=PA121|url-status=live}}{{cite book|vauthors=Harris H|title=Advances in Human Genetics 6|date=2012|publisher=Springer Science & Business Media|isbn=978-1-4615-8264-9|page=39|url=https://books.google.com/books?id=UJ0KCAAAQBAJ&pg=PA39|access-date=30 June 2020|archive-date=14 January 2023|archive-url=https://web.archive.org/web/20230114034224/https://books.google.com/books?id=UJ0KCAAAQBAJ&pg=PA39|url-status=live}} It is on the World Health Organization's List of Essential Medicines.{{cite book | vauthors = ((World Health Organization)) | title = World Health Organization model list of essential medicines: 21st list 2019 | year = 2019 | hdl = 10665/325771 | author-link = World Health Organization | publisher = World Health Organization | location = Geneva | id = WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO | hdl-access=free }} Pyridoxine is available both as a generic medication and over the counter product. Foods, such as breakfast cereal have pyridoxine added in some countries.
References
{{Reflist}}
External links
- {{Commons category-inline}}
- {{cite web| url = https://druginfo.nlm.nih.gov/drugportal/name/pyridoxine | publisher = U.S. National Library of Medicine| work = Drug Information Portal| title = Pyridoxine }}
- {{cite web | url = http://gmd.mpimp-golm.mpg.de/Spectrums/73e34958-2680-41b1-a8d7-40e1650703bc.aspx | title = Pyridoxine mass spectrum | work = Golm Metabolome Database }}
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Category:World Health Organization essential medicines