Pyritinol

Structural formula
General
Non-proprietary name	Pyritinol
other names	1,2-bis (3-Hydroxy-4-hydroxymethyl-2-methylpyridin-5-ylmethyl) disulfane Pyrithioxine
Molecular formula	C 16 H 20 N 2 O 4 S 2
External identifiers / databases
CAS number 1098-97-1 10049-83-9 (dihydrochloride monohydrate) EC number 214-150-1 ECHA InfoCard 100.012.864 PubChem 14190 ChemSpider 13561 DrugBank DB13084 Wikidata Q416361
Drug information
ATC code	N06 BX02
Drug class	Anti-dementia
properties
Molar mass	368.47 g mol −1
Physical state	firmly
Melting point	216-217 ° C
safety instructions
Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed GHS labeling of hazardous substances danger H and P phrases H: 315-318-335 P: 261-380-305 + 351 + 338
Toxicological data	115 mg kg −1 ( LD 50 ,  mouse ,  iv ) 6000 mg kg −1 ( LD 50 ,  rat ,  oral , hydrochloride monohydrate) 300 mg kg −1 ( LD 50 ,  rat ,  iv , dihydrochloride monohydrate) 5786 mg kg −1 ( LD 50 ,  mouse ,  oral , dihydrochloride monohydrate) 211 mg kg −1 ( LD 50 ,  mouse ,  iv , dihydrochloride monohydrate)
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Pyritinol (trade name: Encephabol , manufactured by Merck KGaA ) is a drug , known as anti-dementia drug for the treatment of senile dementia is used.

synthesis

The compound can be prepared from pyridoxine in a three-step synthesis . The first step is the conversion of pyridoxine hydrochloride in concentrated hydrobromic acid to the corresponding bromine compound. This is then reacted with potassium ethyl xanthate . The target compound is produced by the dimerization of the xanthate obtained in the presence of ammonia .

Pharmacokinetics

The pyridoxine residues (vitamin B6) resulting from the cleavage at the disulfide bridge are pharmacologically effective . The elimination half-life is approximately 6 hours, with a range of 2.5 to 8 hours. The availability is over 80%. After oral administration (in tablet form), the maximum effect is reached after approx. 30 to 60 minutes. The active ingredient crosses the blood-brain barrier and accumulates in the gray matter. Over 70% of the active substance and the pharmacologically active metabolites and their conjugates are excreted within 24 hours via the kidneys and 5% with the faeces . No accumulation of pyritinol was observed in the organism.

history

The drug Encephabol from Merck with the active ingredient pyritinol was brought onto the market in Germany on May 15, 1963. It was recommended for the treatment of organic brain damage in children. Years before it was approved, it was tested on children, especially children in homes .

Web links

• Pharmaceutical information. Pyritinol. University of Innsbruck, November 27, 1996. 

Individual evidence

1. ↑ G. Quadbeck, HR Landmann, W. Sachsse, I. Schmidt: The influence of pyrithioxin on the blood-brain barrier . In: Pharmacology . tape 7 , no. 3 , July 1, 2004, p. 144 , doi : 10.1159 / 000135213 .
2. ↑ B. Paul, W. Korytnyk: Selective esterifications and acyl rearrangements in vitamin B6 . In: Tetrahedron , 25 (1969) 1071-1087, doi: 10.1016 / S0040-4020 (01) 82680-6 .
3. ↑ ^{a b c} data sheet pyritinol from Sigma-Aldrich , accessed on October 18, 2016 ( PDF ).
4. ^ ^{A b c d e} A. Kleemann , J. Engel, B. Kutscher, D. Reichert: Pharmaceutical Substances - Synthesis, Patents, Applications. 4th edition. Thieme 2001, ISBN 3-13-115134-X .
5. ↑ G. McCasland, L. Gottwald, A. Furst: 4,5-Dihalo and 3-Amino Analogs of Pyridoxine. New Route to 4-Deoxypyridoxine . In: J. Org. Chem. , 26, 1961, pp. 3541-3543, doi: 10.1021 / jo01067a622 .
6. ↑ Patents DE 1,135,460 (E. Merck AG 1958); U.S. 3,010,966 (E. Merck AG 1961).
7. ↑ Sylvia Wagner: docserv.uni-duesseldorf.de (PDF) Dissertation
8. ↑ spiegel.de

This article is about a health issue. It is not used for self-diagnosis and does not replace a diagnosis by a doctor. Please note the information on health issues !