Biperiden

Structural formula
	Racemate (1: 1 mixture of the structures given above)
General
Non-proprietary name	Biperiden
other names	(1 RS , 2 SR , 4 RS ) -1- [bicyclo [2.2.1] hept-5-en-2-yl] -1-phenyl-3-piperidinopropanol; (1 R * , 2 S * , 4 R * ) 1- [Bicyclo [2.2.1] hept-5-en-2-yl] -1-phenyl-3-piperidinopropanol;
Molecular formula	C 21 H 29 NO
External identifiers / databases
ECHA InfoCard	100.007.441
PubChem	2381
DrugBank	DB00810
Wikidata	Q414914
Drug information
ATC code	N04 AA02
Drug class	Anticholinergics; Anti-Parkinson drugs;
properties
Molar mass	311.46 g · mol -1
Melting point	101 ° C (Biperiden) ; about 280 ° C, with decomposition (Biperiden hydrochloride) ;
safety instructions
	Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed
GHS labeling of hazardous substances Caution
H and P phrases	H: 302-319
	P: 305 + 351 + 338
Toxicological data	750 mg kg −1 ( LD 50 , rat , oral )
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Biperiden is a drug from the group of anticholinergics and is used as an antiparkinson agent. Biperiden is also used to treat the often severe extrapyramidal side effects such as body stiffness, fixed gaze and akathisia that many antipsychotics can cause above a certain dose. The active ingredient has been marketed under the trade name Akineton ^® since 1953.

Biperiden was first synthesized by the German chemist Wilfried Klavehn on behalf of Knoll AG (Germany). In March 1953 the drug was patented and sold under the name Akineton. There are now numerous generic drugs that are available in tablet form (both retarded and non-retarded) or as a solution for injection.

Mechanism of action

Biperiden inhibits cholinergic receptors. Biperiden also acts as a FIASMA (functional inhibitor of acid sphingomyelinase ).

Side effects and warnings

The therapeutic dose is between 2 and 16 mg, always starting with a low initial dose. Typical side effects are dry mouth, dizziness, nausea and tachycardia . The drug lowers the seizure threshold and is therefore in an existing epilepsy contraindicated, further, it may be an increase in intraocular pressure, which if left untreated glaucoma can lead.

Can biperiden responsiveness even when used as intended so far as change that the ability to drive and the ability to be impaired to drive or operate machinery.

Biperiden occasionally causes restlessness, anxiety, excitement and confusion (risk of disorientation) and hallucinations , especially if the initial dose is too high or overdosage . An unnaturally elevated mood can also occur, so that the active ingredient is not infrequently misused. The symptoms of biperiden poisoning are similar to those of atropine , it can cause circulatory failure and respiratory paralysis.

Stereoisomerism

Biperiden contains three different stereocenters. Theoretically there are 2 ³ = 8 stereoisomers . The drug Biperiden is a racemate (1: 1 mixture of isomers) of the (1 R , 2 S , 4 R ) form and the (1 S , 2 R , 4 S ) form.

Trade names

Biperiden is commercially available in Germany, Austria and Switzerland under the name Akineton and, with the exception of Switzerland, as a generic.

Individual evidence

^ The Merck Index. An Encyclopaedia of Chemicals, Drugs and Biologicals. 14th edition, 2006, p. 204, ISBN 978-0-911910-00-1 .
↑ European Pharmacopoeia, Deutscher Apotheker Verlag Stuttgart, 6th edition, 2008, pp. 1826–1828, ISBN 978-3-7692-3962-1 .
↑ ^a ^b Biperiden data sheet at Sigma-Aldrich , accessed on March 13, 2011 ( PDF ).

↑ Data sheet BIPERIDEN HYDROCHLORIDE CRS (PDF) at EDQM , accessed on July 5, 2008.

↑ ^a ^b Instructions for use neuraxpharm: Biperiden 2mg tablets ( Memento of the original from June 12, 2015 in the Internet Archive ) Info: The archive link has been inserted automatically and has not yet been checked. Please check the original and archive link according to the instructions and then remove this notice. @1@ 2
↑ Kornhuber J, Muehlbacher M, Trapp S, Pechmann S, Friedl A, Reichel M, Mühle C, Terfloth L, Groemer T, Spitzer G, Liedl K, Gulbins E, Tripal P: Identification of novel functional inhibitors of acid sphingomyelinase . In: PLoS ONE . 6, No. 8, 2011, p. E23852. doi : 10.1371 / journal.pone.0023852 .

[MerckIndex-1] The Merck Index. An Encyclopaedia of Chemicals, Drugs and Biologicals. 14th edition, 2006, p. 204, ISBN 978-0-911910-00-1 .

[EuropäischesArzneibuch-2] European Pharmacopoeia, Deutscher Apotheker Verlag Stuttgart, 6th edition, 2008, pp. 1826–1828, ISBN 978-3-7692-3962-1 .

[Sigma-3] Biperiden data sheet at Sigma-Aldrich , accessed on March 13, 2011 ( PDF ).

[Ph._Eur.-4] Data sheet BIPERIDEN HYDROCHLORIDE CRS (PDF) at EDQM , accessed on July 5, 2008.

[Gebrauchsinformation_neuraxpharm-5] Instructions for use neuraxpharm: Biperiden 2mg tablets ( Memento of the original from June 12, 2015 in the Internet Archive ) Info: The archive link has been inserted automatically and has not yet been checked. Please check the original and archive link according to the instructions and then remove this notice. @1@ 2

[pmid18504571-6] Kornhuber J, Muehlbacher M, Trapp S, Pechmann S, Friedl A, Reichel M, Mühle C, Terfloth L, Groemer T, Spitzer G, Liedl K, Gulbins E, Tripal P: Identification of novel functional inhibitors of acid sphingomyelinase . In: PLoS ONE . 6, No. 8, 2011, p. E23852. doi : 10.1371 / journal.pone.0023852 .