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Identification
Name Biperiden
Accession Number DB00810 (APRD00725)
Type small molecule
Groups approved
Description

A muscarinic antagonist that has effects in both the central and peripheral nervous systems. It has been used in the treatment of arteriosclerotic, idiopathic, and postencephalitic parkinsonism. It has also been used to alleviate extrapyramidal symptoms induced by phenothiazine derivatives and reserpine. [PubChem]
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  • Beperiden
  • Biperiden [Usan:Ban:Inn:Jan]
  • Biperiden Hydrochloride
  • Biperidene [INN-French]
  • Biperidene Hydrochloride
  • Biperideno [INN-Spanish]
  • Biperidenum [INN-Latin]
  • Biperidine
  • Biperidine Hydrochloride
Brand names
  • Akineton
  • Akinophyl
Brand name mixtures Not Available
Categories
  • Antiparkinson Agents
  • Antidyskinetics
  • Muscarinic Antagonists
  • Parasympatholytics
CAS number 514-65-8
Weight Average: 311.4611
Monoisotopic: 311.224914555
Chemical Formula C21H29NO
InChI Key InChIKey=YSXKPIUOCJLQIE-UHFFFAOYSA-N
InChI
InChI=1S/C21H29NO/c23-21(19-7-3-1-4-8-19,11-14-22-12-5-2-6-13-22)20-16-17-9-10-18(20)15-17/h1,3-4,7-10,17-18,20,23H,2,5-6,11-16H2
Plain Text
IUPAC Name
1-{bicyclo[2.2.1]hept-5-en-2-yl}-1-phenyl-3-(piperidin-1-yl)propan-1-ol
SMILES
OC(CCN1CCCCC1)(C1CC2CC1C=C2)C1=CC=CC=C1
Plain Text
Mass Spec show (7.7 KB)
Taxonomy
Kingdom Organic
Classes
  • Cumenes and Derivatives
  • Phenylpropylamines
Substructures
  • Hydroxy Compounds
  • Alkanes and Alkenes
  • Benzyl Alcohols and Derivatives
  • Benzene and Derivatives
  • Cumenes and Derivatives
  • Aliphatic and Aryl Amines
  • Alcohols and Polyols
  • Heterocyclic compounds
  • Aromatic compounds
  • Phenylpropylamines
  • Cyclohexenes and Derivatives
  • Piperidines
Pharmacology
Indication For use as an adjunct in the therapy of all forms of parkinsonism and control of extrapyramidal disorders secondary to neuroleptic drug therapy.
Pharmacodynamics Biperiden is a weak peripheral anticholinergic agent. It has, therefore, some antisecretory, antispasmodic and mydriatic effects. In addition, biperiden possesses nicotinolytic activity. The parenteral form of biperiden is an effective and reliable agent for the treatment of acute episodes of extrapyramidal disturbances sometimes seen during treatment with neuroleptic agents. Akathisia, akinesia, dyskinetic tremors, rigor, oculogyric crisis, spasmodic torticollis, and profuse sweating are markedly reduced or eliminated. With parenteral biperiden, these drug-induced disturbances are rapidly brought under control.
Mechanism of action Parkinsonism is thought to result from an imbalance between the excitatory (cholinergic) and inhibitory (dopaminergic) systems in the corpus striatum. The mechanism of action of centrally active anticholinergic drugs such as biperiden is considered to relate to competitive antagonism of acetylcholine at cholinergic receptors in the corpus striatum, which then restores the balance.
Absorption 87% bioavailability
Volume of distribution Not Available
Protein binding 60%
Metabolism

The metabolism of biperiden is not completely understood, but does involve hydroxylation.
Route of elimination Not Available
Half life Not Available
Clearance Not Available
Toxicity LD50=760 mg/kg (Orally in rats). Signs of overdose include dilated and sluggish pupils, warm, dry skin, facial flushing, decreased secretions of the mouth, pharynx, nose, and bronchi, foul-smelling breath, elevated temperature, tachycardia, cardiac arrhythmias, decreased bowel sounds, urinary retention, delirium, disorientation, anxiety, hallucinations, illusions, confusion, incoherence, agitation, hyperactivity, ataxia, loss of memory, paranoia, combativeness, and seizures.
Affected organisms
  • Humans and other mammals
Pathways Not Available
Pharmacoeconomics
Manufacturers
  • Abbott laboratories
Packagers
Dosage forms
Form Route Strength
Tablet Oral
Prices Not Available
Patents Not Available
Properties
State solid
Melting point 114 oC
Experimental Properties
Property Value Source
water solubility 25.1 mg/L PhysProp
logP 4.1 PhysProp
Predicted Properties
Property Value Source
water solubility 4.26e-03 g/l ALOGPS
logP 4.28 ALOGPS
logP 3.54 ChemAxon Molconvert
logS -4.86 ALOGPS
pKa ChemAxon Molconvert
hydrogen acceptor count 2 ChemAxon Molconvert
hydrogen donor count 1 ChemAxon Molconvert
polar surface area 23.47 ChemAxon Molconvert
rotatable bond count 5 ChemAxon Molconvert
refractivity 97.02 ChemAxon Molconvert
polarizability 36.74 ChemAxon Molconvert
References
Synthesis Reference Not Available
General Reference
  1. Nishiyama K, Mizuno T, Sakuta M, Kurisaki H: Chronic dementia in Parkinson’s disease treated by anticholinergic agents. Neuropsychological and neuroradiological examination. Adv Neurol. 1993;60:479-83. Pubmed
External Links
Resource Link
KEGG Drug D00779 Link_out
KEGG Compound C07941 Link_out
PubChem Compound 2381 Link_out
PubChem Substance 46508325 Link_out
ChemSpider 2289 Link_out
BindingDB 50240680 Link_out
ChEBI 3112 Link_out
ChEMBL 3112 Link_out
Therapeutic Targets Database DAP001125 Link_out
PharmGKB PA448626 Link_out
Drug Product Database 124982 Link_out
RxList http://www.rxlist.com/cgi/generic2/biperiden.htm Link_out
Drugs.com http://www.drugs.com/cdi/biperiden.html Link_out
Wikipedia http://en.wikipedia.org/wiki/Biperiden Link_out
ATC Codes
  • N04AA02
AHFS Codes
  • 12:08.04
PDB Entries Not Available
FDA label Not Available
MSDS Not Available
Interactions
Drug Interactions Not Available
Food Interactions
  • Avoid alcohol.
  • Take with food.
Targets

1. Muscarinic acetylcholine receptor M1

Pharmacological action: yes
Actions: antagonist

The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the action of G proteins. Primary transducing effect is Pi turnover

Organism class: human
UniProt ID: P11229 Link_out
Gene: CHRM1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed
  3. Hosoi R, Kobayashi K, Watanabe Y, Inoue O: Evaluation of in vivo binding properties of 3H-NMPB and 3H-QNB in mouse brain. J Neural Transm. 1999;106(7-8):583-92. Pubmed
  4. Pehl C, Wendl B, Kaess H, Pfeiffer A: Effects of two anticholinergic drugs, trospium chloride and biperiden, on motility and evoked potentials of the oesophagus. Aliment Pharmacol Ther. 1998 Oct;12(10):979-84. Pubmed
  5. Eltze M: Multiple mechanisms of action: the pharmacological profile of budipine. J Neural Transm Suppl. 1999;56:83-105. Pubmed
  6. Eltze M, Galvan M: Involvement of muscarinic M2 and M3, but not of M1 and M4 receptors in vagally stimulated contractions of rabbit bronchus/trachea. Pulm Pharmacol. 1994 Apr;7(2):109-20. Pubmed
  7. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed

2. Neuronal acetylcholine receptor subunit alpha-2

Pharmacological action: yes
Actions: antagonist

After binding acetylcholine, the AChR responds by an extensive change in conformation that affects all subunits and leads to opening of an ion-conducting channel across the plasma membrane

Organism class: human
UniProt ID: Q15822 Link_out
Gene: CHRNA2 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed
Enzymes

1. Cytochrome P450 2D6

Actions: inhibitor

Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic antidepressants

UniProt ID: P10635 Link_out
Gene: CYP2D6 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed
Transporters

1. Multidrug resistance protein 1

Actions: inhibitor

Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells

UniProt ID: P08183 Link_out
Gene: ABCB1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Mahar Doan KM, Humphreys JE, Webster LO, Wring SA, Shampine LJ, Serabjit-Singh CJ, Adkison KK, Polli JW: Passive permeability and P-glycoprotein-mediated efflux differentiate central nervous system (CNS) and non-CNS marketed drugs. J Pharmacol Exp Ther. 2002 Dec;303(3):1029-37. Pubmed
Comments
Drug created on June 13, 2005 07:24 / Updated on April 19, 2011 15:06

This project is supported by Genome Alberta & Genome Canada, a not-for-profit organization that is leading Canada's national genomics strategy with $600 million in funding from the federal government. This project is also supported in part by GenomeQuest, Inc., an enterprise genomic information company serving the life science community.