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Showing drug card for Biperiden (DB00810)

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Version 2.5
Creation Date 2005-06-13 13:24:05
Update Date 2009-06-23 18:07:08
Primary Accession Number DB00810
Secondary Accession Number
  • APRD00725
Name Biperiden
Drug Type
  • Approved
  • Small Molecule
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]
Synonyms
  1. Beperiden
  2. Biperiden Hydrochloride
  3. Biperiden [Usan:Ban:Inn:Jan]
  4. Biperidene Hydrochloride
  5. Biperidene [INN-French]
  6. Biperideno [INN-Spanish]
  7. Biperidenum [INN-Latin]
  8. Biperidine
  9. Biperidine Hydrochloride
Brand Names
  1. Akineton
  2. Akinophyl
Brand Mixtures Not Available
Chemical IUPAC Name 1-(6-bicyclo[2.2.1]hept-2-enyl)-1-phenyl-3-piperidin-1-ylpropan-1-ol
Chemical Formula C21H29NO
Chemical Structure Structure
CAS Registry Number 514-65-8
InChI Identifier InChI=1/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
InChI Key YSXKPIUOCJLQIE-UHFFFAOYAP
KEGG Drug D00779 Link Image
KEGG Compound C07941 Link Image
PubChem Compound 2381 Link Image
PubChem Substance 153864 Link Image
ChEBI ID Not Available
PharmGKB ID PA448626 Link Image
HET ID Not Available
GenBank ID Not Available
Drug ID Number [DIN] 00124982 Link Image
RxList Link http://www.rxlist.com/cgi/generic2/biperiden.htm Link Image
PDRhealth Link Not Available
Wikipedia Link http://en.wikipedia.org/wiki/Biperiden Link Image
FDA Label Not Available
Material Safety Data Sheet (MSDS) Not Available
Synthesis Reference Not Available
Average Molecular Weight 311.4611
Monoisotopic Molecular Weight 311.2249
State Solid
Melting Point 114 oC
Experimental Water Solubility 25.1 mg/L Source: PhysProp
Predicted Water Solubility 4.26e-03 mg/mL Calculated using ALOGPS
Experimental LogP/Hydrophobicity 4.1 Source: PhysProp
Predicted LogP 4.28 Calculated using ALOGPS
Experimental LogS Not Available
Predicted LogS -4.86 Calculated using ALOGPS
Experimental Caco2 Permeability Not Available
pKa/Isoelectric Point Not Available
Mass Spectrum Not Available
MOL File Show Link Image | Download Link Image
SDF File Show Link Image | Download Link Image
PDB File Show Link Image | Download Link Image
2D Structure
3D Structure
Experimental PDB ID Not Available
Isomeric SMILES O[C@@](CCN1CCCCC1)([C@@H]1C[C@H]2C[C@@H]1C=C2)C1=CC=CC=C1
Canonical SMILES OC(CCN1CCCCC1)(C1CC2CC1C=C2)C1=CC=CC=C1
Drug Category
  • Antidyskinetics
  • Antiparkinson Agents
  • Muscarinic Antagonists
  • Parasympatholytics
ATC Codes
AHFS Codes
  • 12:08.04
Indication For use as an adjunct in the therapy of all forms of parkinsonism and control of extrapyramidal disorders secondary to neuroleptic drug therapy.
Pharmacology 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
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.
Protein Binding 60%
Biotransformation The metabolism of biperiden is not completely understood, but does involve hydroxylation.
Half Life Not Available
Dosage Forms
Form Route
Tablet Oral
Patient Information Not Available
Contraindications Show Link Image
Interactions Show Link Image
Drug Interactions
Drug Interaction
Donepezil Possible antagonism of action
Galantamine Possible antagonism of action
Haloperidol The anticholinergic increases the risk of psychosis and tardive dyskinesia
Rivastigmine Possible antagonism of action
Food Interactions
  • Avoid alcohol.
  • Take with food.
Pathways Not Available
General References
  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 Link Image]
  2. Drugs.com Link Image
  3. Wikipedia Link Image
  4. RxList Link Image
Organisms Affected
  • Humans and other mammals
Targets
  1. Muscarinic acetylcholine receptor M1
  2. Neuronal acetylcholine receptor subunit alpha-2
Drug Target 1 [top]
Target 1 ID 103
Target 1 Name Muscarinic acetylcholine receptor M1
Target 1 Synonyms Not Available
Target 1 Gene Name CHRM1
Target 1 Protein Sequence >Muscarinic acetylcholine receptor M1 
MNTSAPPAVSPNITVLAPGKGPWQVAFIGITTGLLSLATVTGNLLVLISFKVNTELKTVN
NYFLLSLACADLIIGTFSMNLYTTYLLMGHWALGTLACDLWLALDYVASNASVMNLLLIS
FDRYFSVTRPLSYRAKRTPRRAALMIGLAWLVSFVLWAPAILFWQYLVGERTVLAGQCYI
QFLSQPIITFGTAMAAFYLPVTVMCTLYWRIYRETENRARELAALQGSETPGKGGGSSSS
SERSQPGAEGSPETPPGRCCRCCRAPRLLQAYSWKEEEEEDEGSMESLTSSEGEEPGSEV
VIKMPMVDPEAQAPTKQPPRSSPNTVKRPTKKGRDRAGKGQKPRGKEQLAKRKTFSLVKE
KKAARTLSAILLAFILTWTPYNIMVLVSTFCKDCVPETLWELGYWLCYVNSTINPMCYAL
CNKAFRDTFRLLLLCRWDKRRWRKIPKRPGSVHRTPSRQC
Target 1 Number of Residues 467
Target 1 Molecular Weight 51421
Target 1 Theoretical pI 9.67
Target 1 GO Classification
Function
amine receptor activity
muscarinic acetylcholine receptor activity
signal transducer activity
receptor activity
transmembrane receptor activity
G-protein coupled receptor activity
rhodopsin-like receptor activity
Process
cellular process
cell communication
signal transduction
cell surface receptor linked signal transduction
G-protein coupled receptor protein signaling pathway
Component
cell
membrane
intrinsic to membrane
integral to membrane
Target 1 General Function Involved in rhodopsin-like receptor activity
Target 1 Specific Function 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
Target 1 Pathways Not Available
Target 1 Reactions Not Available
Target 1 Pfam Domain Function
Target 1 Signals
  • None
Target 1 Transmembrane Regions
  • 25-47
  • 62-82
  • 100-121
  • 142-164
  • 187-209
  • 367-387
  • 402-421
Target 1 Essentiality Non-Essential
Target 1 GenBank ID Protein 34451 Link Image
Target 1 UniProtKB/Swiss-Prot ID P11229 Link Image
Target 1 UniProtKB/Swiss-Prot Entry Name ACM1_HUMAN Link Image
Target 1 PDB ID Not Available
Target 1 Cellular Location
  • Membrane
  • multi-pass membrane protein
Target 1 Gene Sequence >1383 bp 
ATGAACACTTCAGCCCCACCTGCTGTCAGCCCCAACATCACCGTCCTGGCACCAGGAAAG
GGTCCCTGGCAAGTGGCCTTCATTGGGATCACCACGGGCCTCCTGTCGCTAGCCACAGTG
ACAGGCAACCTGCTGGTACTCATCTCTTTCAAGGTCAACACGGAGCTCAAGACAGTCAAT
AACTACTTCCTGCTGAGCCTGGCCTGTGCTGACCTCATCATCGGTACCTTCTCCATGAAC
CTCTATACCACGTACCTGCTCATGGGCCACTGGGCTCTGGGCACGCTGGCTTGTGACCTC
TGGCTGGCCCTGGACTATGTGGCCAGCAATGCCTCCGTCATGAATCTGCTGCTCATCAGC
TTTGACCGCTACTTCTCCGTGACTCGGCCCCTGAGCTACCGTGCCAAGCGCACACCCCGC
CGGGCAGCTCTGATGATCGGCCTGGCCTGGCTGGTTTCCTTTGTGCTCTGGGCCCCAGCC
ATCCTCTTCTGGCAGTACCTGGTAGGGGAGCGGACAGTGCTAGCTGGGCAGTGCTACATC
CAGTTCCTCTCCCAGCCCATCATCACCTTTGGCACAGCCATGGCTGCCTTCTACCTCCCT
GTCACAGTCATGTGCACGCTCTACTGGCGCATCTACCGGGAGACAGAGAACCGAGCACGG
GAGCTGGCAGCCCTTCAGGGCTCCGAGACGCCAGGCAAAGGGGGTGGCAGCAGCAGCAGC
TCAGAGAGGTCTCAGCCAGGGGCTGAGGGCTCACCAGAGACTCCTCCAGGCCGCTGCTGT
CGCTGCTGCCGGGCCCCCAGGCTGCTGCAGGCCTACAGCTGGAAGGAAGAAGAGGAAGAG
GACGAAGGCTCCATGGAGTCCCTCACATCCTCAGAGGGAGAGGAGCCTGGCTCCGAAGTG
GTGATCAAGATGCCAATGGTGGACCCCGAGGCACAGGCCCCCACCAAGCAGCCCCCACGG
AGCTCCCCAAATACAGTCAAGAGGCCGACTAAGAAAGGGCGTGATCGAGCTGGCAAGGGC
CAGAAGCCCCGTGGAAAGGAGCAGCTGGCCAAGCGGAAGACCTTCTCGCTGGTCAAGGAG
AAGAAGGCGGCTCGGACCCTGAGTGCCATCCTCCTGGCCTTCATCCTCACCTGGACACCG
TACAACATCATGGTGCTGGTGTCCACCTTCTGCAAGGACTGTGTTCCCGAGACCCTGTGG
GAGCTGGGCTACTGGCTGTGCTACGTCAACAGCACCATCAACCCCATGTGCTACGCACTC
TGCAACAAAGCCTTCCGGGACACCTTTCGCCTGCTGCTGCTTTGCCGCTGGGACAAGAGA
CGCTGGCGCAAGATCCCCAAGCGCCCTGGCTCCGTGCACCGCACTCCCTCCCGCCAATGC
TGA
Target 1 GenBank Gene ID
Target 1 GeneCard ID CHRM1 Link Image
Target 1 GenAtlas ID CHRM1 Link Image
Target 1 HGNC ID HGNC:1950 Link Image
Target 1 Chromosome Location 11
Target 1 Locus 11q13
Target 1 SNPs SNPJam Report Link Image
Target 1 General References
  1. Arden JR, Nagata O, Shockley MS, Philip M, Lameh J, Sadee W: Mutational analysis of third cytoplasmic loop domains in G-protein coupling of the HM1 muscarinic receptor. Biochem Biophys Res Commun. 1992 Nov 16;188(3):1111-5. [PubMed Link Image]
  2. Chapman CG, Browne MJ: Isolation of the human ml (Hml) muscarinic acetylcholine receptor gene by PCR amplification. Nucleic Acids Res. 1990 Apr 25;18(8):2191. [PubMed Link Image]
  3. Peralta EG, Ashkenazi A, Winslow JW, Smith DH, Ramachandran J, Capon DJ: Distinct primary structures, ligand-binding properties and tissue-specific expression of four human muscarinic acetylcholine receptors. EMBO J. 1987 Dec 20;6(13):3923-9. [PubMed Link Image]
  4. Allard WJ, Sigal IS, Dixon RA: Sequence of the gene encoding the human M1 muscarinic acetylcholine receptor. Nucleic Acids Res. 1987 Dec 23;15(24):10604. [PubMed Link Image]
Target 1 Drug References
  1. 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 Link Image]
  2. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed Link Image]
Drug Target 2 [top]
Target 2 ID 813
Target 2 Name Neuronal acetylcholine receptor subunit alpha-2
Target 2 Synonyms
  1. Neuronal acetylcholine receptor subunit alpha-2 precursor
Target 2 Gene Name CHRNA2
Target 2 Protein Sequence >Neuronal acetylcholine receptor protein subunit alpha-2 precursor 
MGPSCPVFLSFTKLSLWWLLLTPAGGEEAKRPPPRAPGDPLSSPSPTALPQGGSHTETED
RLFKHLFRGYNRWARPVPNTSDVVIVRFGLSIAQLIDVDEKNQMMTTNVWLKQEWSDYKL
RWNPADFGNITSLRVPSEMIWIPDIVLYNNADGEFAVTHMTKAHLFSTGTVHWVPPAIYK
SSCSIDVTFFPFDQQNCKMKFGSWTYDKAKIDLEQMEQTVDLKDYWESGEWAIVNATGTY
NSKKYDCCAEIYPDVTYAFVIRRLPLFYTINLIIPCLLISCLTVLVFYLPSDCGEKITLC
ISVLLSLTVFLLLITEIIPSTSLVIPLIGEYLLFTMIFVTLSIVITVFVLNVHHRSPSTH
TMPHWVRGALLGCVPRWLLMNRPPPPVELCHPLRLKLSPSYHWLESNVDAEEREVVVEEE
DRWACAGHVAPSVGTLCSHGHLHSGASGPKAEALLQEGELLLSPHMQKALEGVHYIADHL
RSEDADSSVKEDWKYVAMVIDRIFLWLFIIVCFLGTIGLFLPPFLAGMI
Target 2 Number of Residues 537
Target 2 Molecular Weight 59736
Target 2 Theoretical pI 6.02
Target 2 GO Classification
Function
excitatory extracellular ligand-gated ion channel activity
nicotinic acetylcholine-activated cation-selective channel activity
transporter activity
ion transporter activity
ion channel activity
ligand-gated ion channel activity
extracellular ligand-gated ion channel activity
signal transducer activity
receptor activity
neurotransmitter receptor activity
Process
physiological process
cellular physiological process
transport
ion transport
Component
postsynaptic membrane
intrinsic to membrane
integral to membrane
cell
membrane
Target 2 General Function Involved in neurotransmitter receptor activity
Target 2 Specific Function 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
Target 2 Pathways Not Available
Target 2 Reactions Not Available
Target 2 Pfam Domain Function
Target 2 Signals
  • 1-26
Target 2 Transmembrane Regions
  • 265-289
  • 297-315
  • 331-352
  • 503-521
Target 2 Essentiality Non-Essential
Target 2 GenBank ID Protein 1458110 Link Image
Target 2 UniProtKB/Swiss-Prot ID Q15822 Link Image
Target 2 UniProtKB/Swiss-Prot Entry Name ACHA2_HUMAN Link Image
Target 2 PDB ID Not Available
Target 2 Cellular Location
  • Membrane
  • multi-pass membrane protein
Target 2 Gene Sequence >1590 bp 
ATGGGCCCCTCCTGTCCTGTGTTCCTGTCCTTCACAAAGCTCAGCCTGTGGTGGCTCCTT
CTGACCCCAGCAGGTGGAGAGGAAGCTAAGCGCCCACCTCCCAGGGCTCCTGGAGACCCA
CTCTCCTCTCCCAGTCCCACGGCATTGCCGCAGGGAGGCTCGCATACCGAGACTGAGGAC
CGGCTCTTCAAACACCTCTTCCGGGGCTACAACCGCTGGGCGCGCCCGGTGCCCAACACT
TCAGACGTGGTGATTGTGCGCTTTGGACTGTCCATCGCTCAGCTCATCGATGTGGATGAG
AAGAACCAAATGATGACCACCAACGTCTGGCTAAAACAGGAGTGGAGCGACTACAAACTG
CGCTGGAACCCCGCTGATTTTGGCAACATCACATCTCTCAGGGTCCCTTCTGAGATGATC
TGGATCCCCGACATTGTTCTCTACAACAATGCAGATGGGGAGTTTGCAGTGACCCACATG
ACCAAGGCCCACCTCTTCTCCACGGGCACTGTGCACTGGGTGCCCCCGGCCATCTACAAG
AGCTCCTGCAGCATCGACGTCACCTTCTTCCCCTTCGACCAGCAGAACTGCAAGATGAAG
TTTGGCTCCTGGACTTATGACAAGGCCAAGATCGACCTGGAGCAGATGGAGCAGACTGTG
GACCTGAAGGACTACTGGGAGAGCGGCGAGTGGGCCATCGTCAATGCCACGGGCACCTAC
AACAGCAAGAAGTACGACTGCTGCGCCGAGATCTACCCCGACGTCACCTACGCCTTCGTC
ATCCGGCGGCTGCCGCTCTTCTACACCATCAACCTCATCATCCCCTGCCTGCTCATCTCC
TGCCTCACTGTGCTGGTCTTCTACCTGCCCTCCGACTGCGGCGAGAAGATCACGCTGTGC
ATTTCGGTGCTGCTGTCACTCACCGTCTTCCTGCTGCTCATCACTGAGATCATCCCGTCC
ACCTCGCTGGTCATCCCGCTCATCGGCGAGTACCTGCTGTTCACCATGATCTTCGTCACC
CTGTCCATCGTCATCACCGTCTTCGTGCTCAATGTGCACCACCGCTCCCCCAGCACCCAC
ACCATGCCCCACTGGGTGCGGGGGGCCCTTCTGGGCTGTGTGCCCCGGTGGCTTCTGATG
AACCGGCCCCCACCACCCGTGGAGCTCTGCCACCCCCTACGCCTGAAGCTCAGCCCCTCT
TATCACTGGCTGGAGAGCAACGTGGATGCCGAGGAGAGGGAGGTGGTGGTGGAGGAGGAG
GACAGATGGGCATGTGCAGGTCATGTGGCCCCCTCTGTGGGCACCCTCTGCAGCCACGGC
CACCTGCACTCTGGGGCCTCAGGTCCCAAGGCTGAGGCTCTGCTGCAGGAGGGTGAGCTG
CTGCTATCACCCCACATGCAGAAGGCACTGGAAGGTGTGCACTACATTGCCGACCACCTG
CGGTCTGAGGATGCTGACTCTTCGGTGAAGGAGGACTGGAAGTATGTTGCCATGGTCATC
GACAGGATCTTCCTCTGGCTGTTTATCATCGTCTGCTTCCTGGGGACCATCGGCCTCTTT
CTGCCTCCGTTCCTAGCTGGAATGATCTGA
Target 2 GenBank Gene ID
Target 2 GeneCard ID CHRNA2 Link Image
Target 2 GenAtlas ID CHRNA2 Link Image
Target 2 HGNC ID HGNC:1956 Link Image
Target 2 Chromosome Location 8
Target 2 Locus 8p21
Target 2 SNPs SNPJam Report Link Image
Target 2 General References
  1. Elliott KJ, Ellis SB, Berckhan KJ, Urrutia A, Chavez-Noriega LE, Johnson EC, Velicelebi G, Harpold MM: Comparative structure of human neuronal alpha 2-alpha 7 and beta 2-beta 4 nicotinic acetylcholine receptor subunits and functional expression of the alpha 2, alpha 3, alpha 4, alpha 7, beta 2, and beta 4 subunits. J Mol Neurosci. 1996 Fall;7(3):217-28. [PubMed Link Image]
Target 2 Drug References
  1. 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 Link Image]
  2. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed Link Image]

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.