| 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 |
|
| Name |
Biperiden |
| Drug Type |
|
| 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 |
- Beperiden
- Biperiden Hydrochloride
- Biperiden [Usan:Ban:Inn:Jan]
- Biperidene Hydrochloride
- Biperidene [INN-French]
- Biperideno [INN-Spanish]
- Biperidenum [INN-Latin]
- Biperidine
- Biperidine Hydrochloride
|
| Brand Names |
- Akineton
- 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 |
 |
| 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  |
| KEGG Compound |
C07941  |
| PubChem Compound |
2381  |
| PubChem Substance |
153864  |
| ChEBI ID |
Not Available |
| PharmGKB ID |
PA448626  |
| HET ID |
Not Available |
| GenBank ID |
Not Available |
| Drug ID Number [DIN] |
00124982  |
| RxList Link |
http://www.rxlist.com/cgi/generic2/biperiden.htm  |
| PDRhealth Link |
Not Available |
| Wikipedia Link |
http://en.wikipedia.org/wiki/Biperiden  |
| 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 | Download  |
| SDF File |
Show | Download  |
| PDB File |
Show | Download  |
| 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 |
|
| 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 |
|
| Patient Information |
Not Available |
| Contraindications |
Show  |
| Interactions |
Show  |
| 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 |
- 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
]
- Drugs.com

- Wikipedia

- RxList

|
| Organisms Affected |
|
| Targets |
- Muscarinic acetylcholine receptor M1
- 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 |
|
| 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  |
| Target 1 UniProtKB/Swiss-Prot ID |
P11229  |
| Target 1 UniProtKB/Swiss-Prot Entry Name |
ACM1_HUMAN  |
| 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  |
| Target 1 GenAtlas ID |
CHRM1  |
| Target 1 HGNC ID |
HGNC:1950  |
| Target 1 Chromosome Location |
11 |
| Target 1 Locus |
11q13 |
| Target 1 SNPs |
SNPJam Report  |
| Target 1 General References |
- 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
]
- 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
]
- 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
]
- 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
]
|
| Target 1 Drug References |
- 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
]
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed
]
|
|
Drug Target 2
[top]
|
| Target 2 ID |
813 |
| Target 2 Name |
Neuronal acetylcholine receptor subunit alpha-2 |
| Target 2 Synonyms |
- 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 |
|
| Target 2 Transmembrane Regions |
- 265-289
- 297-315
- 331-352
- 503-521
|
| Target 2 Essentiality |
Non-Essential |
| Target 2 GenBank ID Protein |
1458110  |
| Target 2 UniProtKB/Swiss-Prot ID |
Q15822  |
| Target 2 UniProtKB/Swiss-Prot Entry Name |
ACHA2_HUMAN  |
| 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  |
| Target 2 GenAtlas ID |
CHRNA2  |
| Target 2 HGNC ID |
HGNC:1956  |
| Target 2 Chromosome Location |
8 |
| Target 2 Locus |
8p21 |
| Target 2 SNPs |
SNPJam Report  |
| Target 2 General References |
- 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
]
|
| Target 2 Drug References |
- 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
]
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed
]
|