関: pyrithioxin、pyrithioxine

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2016/01/14 10:35:30」(JST)

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Pyritinol also called pyridoxine disulfide or pyrithioxine (European drug names Encephabol, Encefabol, Cerbon 6) is a semi-synthetic water-soluble analog of vitamin B₆ (Pyridoxine HCl). It was produced in 1961 by Merck Laboratories by bonding 2 vitamin B₆ compounds (pyridoxine) together with a disulfide bridge. Since the 1970s, it has been a prescription and OTC drug in several countries for cognitive disorders and learning disorders in children. Since the early 1990s it has been sold as a nootropic dietary supplement in the United States.

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 disease modifying drug, on the basis of the results of clinical trials.

It is not licensed for use in the United Kingdom, but in many countries it is available over the counter and is widely advertised on the internet as being for "memory disturbances." From the known sales data, it is estimated that more than 100 000 individuals in European Union countries have taken pyritinol in the past five years.

One small study, with 12 subjects given pyritinol, showed an improvement in performance on tests of reaction time, but not on memory tests.^[1]

Some studies have found large doses of Pyritinol can help to reduce hangovers.^[2]

Adverse effects

Adverse effects include nausea, headache,^[3] and rarely allergic reaction (mild skin reactions).^[4] A 2004 survey of six case reports suggested a link between pyritinol and severe cholestatic hepatitis when on several drugs for certain diseases.^[5]

Other rare side effects: acute pancreatitis^[6] and photoallergic eruption.^[7]

References

^ Hindmarch I, Coleston DM, Kerr JS (1990). "Psychopharmacological effects of pyritinol in normal volunteers". Neuropsychobiology 24 (3): 159–64. doi:10.1159/000119478. PMID 2135070.
^ Wiese JG, Shlipak MG, Browner WS (June 2000). "The alcohol hangover". Annals of Internal Medicine 132 (11): 897–902. doi:10.7326/0003-4819-132-11-200006060-00008. PMID 10836917.
^ Nachbar, et.al., F (1993). "Erythema multiforme-like eruption in association with severe headache following pyritinol". Dermatology 187 (1): 42-6.
^ Unwanted Effects of Cosmetics and Drugs Used in Dermatology, Issue 282 By Anton C. de Groot, Johan Pieter Nater, J. Willem Weyland
^ Maria V, Albuquerque A, Loureiro A, Sousa A, Victorino R (March 2004). "Severe cholestatic hepatitis induced by pyritinol". BMJ (Clinical Research Ed.) 328 (7439): 572–4. doi:10.1136/bmj.328.7439.572. PMC 381054. PMID 15001508.
^ Straumann A, Bauer M, Pichler WJ, Pirovino M (August 1998). "Acute pancreatitis due to pyritinol: an immune-mediated phenomenon". Gastroenterology 115 (2): 452–4. doi:10.1016/S0016-5085(98)70212-4. PMID 9679051.
^ Tanaka M, Niizeki H, Shimizu S, Miyakawa S (October 1996). "Photoallergic drug eruption due to pyridoxine hydrochloride". The Journal of Dermatology 23 (10): 708–9. PMID 8973037.

English Journal

The protective effects of Cyperus rotundus on behavior and cognitive function in a rat model of hypoxia injury.

Jebasingh D1, Devavaram Jackson D, Venkataraman S, Adeghate E, Starling Emerald B.
Pharmaceutical biology.Pharm Biol.2014 Dec;52(12):1558-69. doi: 10.3109/13880209.2014.908395. Epub 2014 Jul 15.
PMID 25026346

Vinpocetine and pyritinol: a new model for blood rheological modulation in cerebrovascular disorders—a randomized controlled clinical study.

Alkuraishy HM1, Al-Gareeb AI1, Albuhadilly AK2.
BioMed research international.Biomed Res Int.2014;2014:324307. doi: 10.1155/2014/324307. Epub 2014 Dec 7.
PMID 25548768

[Developmental dysphasia: assessment of the drug treatment efficacy].

Zavadenko NN, Kozlova EV, Koltunov IE.
Zhurnal nevrologii i psikhiatrii imeni S.S. Korsakova.Zh Nevrol Psikhiatr Im S S Korsakova.2012;112(7 Pt 2):90-5.
To assess the efficacy of treatment with encephabol, we examined 40 children, aged from 3 to 5 years, with developmental dysphasia. All patients were randomized into two equal groups: group 1 received encephabol (suspension form, daily dosage 200-250 mg, or 12-15 mg/kg) during 2 months; group 2 did
PMID 23330199

Japanese Journal

Stability Indicating Electrochemical Methods for the Determination of Meclophenoxate Hydrochloride and Pyritinol Dihydrochloride Using Ion-Selective Membrane Electrodes

El-Bardicy Mohammad Galal,Lotfy Hayam Mahmoud,El-Sayed Mohammad Abdalla [他],El-TARRAS Mohammad Fayez
藥學雜誌 127(1), 201-208, 2007-01-01
… The construction and electrochemical response characteristics of polyvinyl chloride (PVC) membrane sensors for the determination of meclophenoxate hydrochloride (I) and pyritinol dihydrochloride (II) in presence of their degradation products are described. … Three PVC sensors were fabricated for each drug, i.e. meclophenoxate tetraphenyl borate (meclo-TPB), meclophenoxate reineckate (meclo-RNC) and meclophenoxate β-cyclodextrin (meclo-β-CD), and the same was done for pyritinol (pyrit-TPB), (pyrit-RNC) and (pyrit-β-CD). …
NAID 110006155026

Acute pancreatitis due to pyritinol : an immune-mediated phenomenon

STRAUMANN A
Gastroenterology 115, 452-454, 1998
NAID 30023000193

Long-term effects of phosphatidylserine, pyritinol, and cognitive training in Alzheimer's disease. A neuropsychological, EEG, and PET investigation

HEISS W. D.
Dementia 5, 88-98, 1994
NAID 30028861483

「pyrithioxin」

Pyritinol
Systematic (IUPAC) name
	5,5'-[dithiobis(methylene)]bis[4-(hydroxymethyl)-2-methylpyridin-3-ol]
Pharmacokinetic data
Biological half-life	2.5 hours
Identifiers
CAS Number	1098-97-1
ATC code	N06BX02
PubChem	CID: 14190
ChemSpider	13561
UNII	AK5Q5FZH2R
KEGG	D02160
ChEMBL	CHEMBL488093
Chemical data
Formula	C16H20N2O4S2
Molecular mass	368.473
	SMILES Oc1c(c(cnc1C)CSSCc2c(c(O)c(nc2)C)CO)CO ;
	InChI InChI=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 ; Key:SIXLXDIJGIWWFU-UHFFFAOYSA-N ;
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