Editing Pyritinol

{{Short description|Chemical compound}}
{{Infobox drug
| Verifiedfields = changed
| verifiedrevid = 464377508
| IUPAC_name = 5,5'-[dithiobis(methylene)]bis[4-(hydroxymethyl)-2-methylpyridin-3-ol]
| image = Pyritinol.svg
| image_class = skin-invert-image

<!--Clinical data-->
| tradename =  
| pregnancy_category =  
| legal_status =  
| routes_of_administration =

<!--Pharmacokinetic data-->
| bioavailability =  
| metabolism =  
| elimination_half-life = 2.5 hours
| excretion =

<!--Identifiers-->
| CAS_number_Ref = {{cascite|changed|??}}
| CAS_number = 1098-97-1
| ATC_prefix = N06
| ATC_suffix = BX02
| PubChem = 14190
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 13561
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = AK5Q5FZH2R
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = D02160
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 488093

<!--Chemical data-->
| C=16 | H=20 | N=2 | O=4 | S=2 
| smiles = Oc1c(c(cnc1C)CSSCc2c(c(O)c(nc2)C)CO)CO
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C16H20N2O4S2/c1-9-15(21)13(5-19)11(3-17-9)7-23-24-8-12-4-18-10(2)16(22)14(12)6-20/h3-4,19-22H,5-8H2,1-2H3
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = SIXLXDIJGIWWFU-UHFFFAOYSA-N
}}

'''Pyritinol''' also called pyridoxine disulfide or pyrithioxine (European drug names Encephabol, Encefabol, Cerbon 6) is a semi-synthetic water-soluble analog of [[vitamin B6|vitamin B<sub>6</sub>]] (Pyridoxine HCl). It was produced in 1961 by Merck Laboratories by bonding 2 vitamin B<sub>6</sub> compounds ([[pyridoxine]]) together with a disulfide bridge. Since the 1970s, it has been a prescription and OTC drug in several countries for cognitive disorders, rheumatoid arthritis,<ref>{{cite journal | vauthors = Lemmel EM | title = Comparison of pyritinol and auranofin in the treatment of rheumatoid arthritis. The European Multicentre Study Group | journal = British Journal of Rheumatology | volume = 32 | issue = 5 | pages = 375–82 | date = May 1993 | pmid = 8495257 | doi = 10.1093/rheumatology/32.5.375 }}</ref> and learning disorders in children. Since the early 1990s it has been sold as a [[nootropic]] [[dietary supplement]] in the United States.

== Availability ==
It is approved for "symptomatic treatment of chronically impaired brain function in dementia syndromes" and for "supportive treatment of sequelae of craniocerebral trauma" in various European countries, including Austria, Germany, France, Italy, Portugal, and Greece. In France it is also approved for [[rheumatoid arthritis]] as a [[DMARD|disease modifying drug]], on the basis of the results of clinical trials. In many countries it is available over the counter and is widely advertised on the internet as being for "memory disturbances."{{citation needed|date=December 2019}}

== Adverse effects ==
Adverse effects include nausea, headache,<ref>{{cite journal | vauthors = Nachbar F, Korting HC, Vogl T | title = Erythema multiforme-like eruption in association with severe headache following pyritinol | journal = Dermatology | volume = 187 | issue = 1 | pages = 42–6 | date = 1993 | pmid = 8324277 | doi = 10.1159/000247196 }}</ref> and rarely allergic reaction (mild skin reactions).<ref>{{cite book |title=Unwanted Effects of Cosmetics and Drugs Used in Dermatology | vauthors = de Groot AC, Nater JP, Weyland JW | publisher = Elsevier | date = 1994 | isbn = 978-0-444-89775-6 | page = 307 }}</ref>  A 2004 survey of six case reports suggested a link between pyritinol and severe [[cholestatic]] [[hepatitis]] when on several drugs for certain diseases.<ref>{{cite journal | vauthors = Maria V, Albuquerque A, Loureiro A, Sousa A, Victorino R | title = Severe cholestatic hepatitis induced by pyritinol | journal = BMJ | volume = 328 | issue = 7439 | pages = 572–4 | date = March 2004 | pmid = 15001508 | pmc = 381054 | doi = 10.1136/bmj.328.7439.572 }}</ref>

Other rare side effects: acute pancreatitis<ref>{{cite journal | vauthors = Straumann A, Bauer M, Pichler WJ, Pirovino M | title = Acute pancreatitis due to pyritinol: an immune-mediated phenomenon | journal = Gastroenterology | volume = 115 | issue = 2 | pages = 452–4 | date = August 1998 | pmid = 9679051 | doi = 10.1016/S0016-5085(98)70212-4 | doi-access = free }}</ref> and photoallergic eruption.<ref>{{cite journal | vauthors = Tanaka M, Niizeki H, Shimizu S, Miyakawa S | title = Photoallergic drug eruption due to pyridoxine hydrochloride | journal = The Journal of Dermatology | volume = 23 | issue = 10 | pages = 708–9 | date = October 1996 | pmid = 8973037 | doi = 10.1111/j.1346-8138.1996.tb02685.x | s2cid = 28810619 }}</ref>

== See also ==
* [[Emoxypine]]
* [[Pirisudanol]]
* [[Sulbutiamine]]

==References==
{{Reflist}}

==External links==
*{{Commons category-inline}}

{{Stimulants}}{{Vitamins}}

[[Category:Antioxidants]]
[[Category:Nootropics]]
[[Category:Organic disulfides]]
[[Category:Hydroxypyridines]]
[[Category:Primary alcohols]]