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Identification
- Summary
Biperiden is a muscarinic receptor antagonist used to treat parkinsonism and control extrapyramidal side effects of neuroleptic drugs.
- Generic Name
- Biperiden
- DrugBank Accession Number
- DB00810
- Background
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.
- Type
- Small Molecule
- Groups
- Approved, Investigational
- Structure
Structure for Biperiden (DB00810)
- Weight
- Average: 311.4611
Monoisotopic: 311.224914555 - Chemical Formula
- C21H29NO
- Synonyms
- 1-Bicyclo[2.2.1]hept-5-en-2-yl-1-phenyl-3-piperidin-1-yl-propan-1-ol
- alpha-5-norbornen-2-yl-alpha-phenyl-1-piperidinepropanol
- alpha-bicyclo[2.2.1]hept-5-en-2-yl-alpha-phenyl-1-piperidinepropanol
- Biperiden
- Biperidene
- Biperideno
- Biperidenum
- External IDs
- KL 373
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.
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Associated Conditions
Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Management of Extrapyramidal symptoms •••••••••••• •••••••••• •••••••• Management of Extrapyramidal disorder caused by neuroleptic drugs without tardive dyskinesia •••••••••••• •••••••••• •••••••• Management of Parkinson's disease (pd) •••••••••••• •••••••••• •••••••• Treatment of Parkinson's disease (pd) •••••••••••• ••••••• ••••••• •••••••• ••••••• Reversal of Poisoning caused by nicotine •••••••••••• •••••••••• •••••••• - Contraindications & Blackbox Warnings
Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- 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.
Target Actions Organism AMuscarinic acetylcholine receptor M1 antagonistHumans - 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
- Adverse Effects
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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.
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your softwareAcebutolol The metabolism of Acebutolol can be decreased when combined with Biperiden. Acetaminophen The metabolism of Acetaminophen can be decreased when combined with Biperiden. Aclidinium The risk or severity of adverse effects can be increased when Biperiden is combined with Aclidinium. Adenosine The risk or severity of Tachycardia can be increased when Adenosine is combined with Biperiden. Albuterol The risk or severity of Tachycardia can be increased when Biperiden is combined with Salbutamol. - Food Interactions
- Avoid alcohol.
- Take with food.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Product Ingredients
Ingredient UNII CAS InChI Key Biperiden hydrochloride K35N76CUHF 1235-82-1 RDNLAULGBSQZMP-UHFFFAOYSA-N Biperiden lactate 09TD6C5147 7085-45-2 GLPUBCPQWZZFNJ-UHFFFAOYSA-N - International/Other Brands
- Bilino (Winston) / Ipsatol (Orion)
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Akineton Tablet 2 mg/1 Oral Physicians Total Care, Inc. 1996-06-10 2006-12-31 US 
Akineton Tablet 2 mg/1 Oral Par Pharmaceutical 2004-12-12 2006-12-12 US Akineton Tab 2mg Tablet 2 mg Oral Abbott 1985-12-31 2007-07-31 Canada 
Categories
- ATC Codes
- N04AA02 — Biperiden
- Drug Categories
- Agents producing tachycardia
- Anti-Dyskinesia Agents
- Anti-Parkinson Drugs
- Anticholinergic Agents
- Autonomic Agents
- Aza Compounds
- Azabicyclo Compounds
- Bridged-Ring Compounds
- Central Nervous System Agents
- Cholinergic Agents
- Cytochrome P-450 CYP2D6 Inhibitors
- Cytochrome P-450 CYP2D6 Inhibitors (strength unknown)
- Cytochrome P-450 Enzyme Inhibitors
- Muscarinic Antagonists
- Nervous System
- Neurotransmitter Agents
- Nicotinic Antagonists
- Parasympatholytics
- Peripheral Nervous System Agents
- Piperidines
- Tertiary Amines
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as aralkylamines. These are alkylamines in which the alkyl group is substituted at one carbon atom by an aromatic hydrocarbyl group.
- Kingdom
- Organic compounds
- Super Class
- Organic nitrogen compounds
- Class
- Organonitrogen compounds
- Sub Class
- Amines
- Direct Parent
- Aralkylamines
- Alternative Parents
- Piperidines / Benzene and substituted derivatives / Tertiary alcohols / 1,3-aminoalcohols / Trialkylamines / Azacyclic compounds / Organopnictogen compounds / Hydrocarbon derivatives / Aromatic alcohols
- Substituents
- 1,3-aminoalcohol / Alcohol / Aralkylamine / Aromatic alcohol / Aromatic heteropolycyclic compound / Azacycle / Benzenoid / Hydrocarbon derivative / Monocyclic benzene moiety / Organic oxygen compound
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- piperidines, tertiary alcohol, tertiary amino compound (CHEBI:3112)
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- 0FRP6G56LD
- CAS number
- 514-65-8
- InChI Key
- 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
- 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
References
- Synthesis Reference
Peter Klein, "Method for the production of biperiden II." U.S. Patent US20040152899, issued August 05, 2004.
US20040152899- 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. [Article]
- External Links
- Human Metabolome Database
- HMDB0014948
- KEGG Drug
- D00779
- KEGG Compound
- C07941
- PubChem Compound
- 2381
- PubChem Substance
- 46508325
- ChemSpider
- 2289
- BindingDB
- 50240680
- 1589
- ChEBI
- 3112
- ChEMBL
- CHEMBL1101
- Therapeutic Targets Database
- DAP001125
- PharmGKB
- PA448626
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Biperiden
Clinical Trials
- Clinical Trials
Clinical Trial & Rare Diseases Add-on Data Package
Explore 4,000+ rare diseases, orphan drugs & condition pairs, clinical trial why stopped data, & more. Preview package Phase Status Purpose Conditions Count Start Date Why Stopped 100+ additional columns Unlock 175K+ rows when you subscribe.View sample data4 Active Not Recruiting Treatment Dental Care for Disabled 1 somestatus stop reason just information to hide 4 Unknown Status Treatment Dependence, Cocaine 1 somestatus stop reason just information to hide 3 Completed Treatment Dependence, Cocaine 1 somestatus stop reason just information to hide 3 Recruiting Prevention Moderate Traumatic Brain Injury (TBI) / Seizure Disorder, Post Traumatic / Severe Traumatic Brain Injury 1 somestatus stop reason just information to hide 3 Terminated Treatment Anxiety Disorders / Dementia / Depression / Psychosomatic Disorders / Schizophrenia 1 somestatus stop reason just information to hide
Pharmacoeconomics
- Manufacturers
- Abbott laboratories
- Packagers
- Abbott Laboratories Ltd.
- BASF Corp.
- Physicians Total Care Inc.
- Dosage Forms
Form Route Strength Solution Parenteral 5.00 mg Solution / drops Oral 2.3 MG/ML Tablet Oral 2 mg/1 Tablet, coated 4 MG Tablet Oral Tablet, extended release Oral 4 MG Injection, solution Parenteral Injection, solution Intramuscular; Intravenous Injection, solution Intramuscular 5 mg/ml Injection, solution Intramuscular; Intravenous 5 MG/ML Pill Oral 4 MG Tablet Oral 2 mg Tablet Oral 4 MG Tablet Oral 2.000 mg - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 114 °C PhysProp water solubility 25.1 mg/L Not Available logP 4.25 SANGSTER (1993) - Predicted Properties
Property Value Source Water Solubility 0.00426 mg/mL ALOGPS logP 4.28 ALOGPS logP 3.54 Chemaxon logS -4.9 ALOGPS pKa (Strongest Acidic) 13.82 Chemaxon pKa (Strongest Basic) 9.3 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 2 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 23.47 Å2 Chemaxon Rotatable Bond Count 5 Chemaxon Refractivity 97.02 m3·mol-1 Chemaxon Polarizability 36.88 Å3 Chemaxon Number of Rings 4 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule Yes Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9669 Blood Brain Barrier + 0.9808 Caco-2 permeable + 0.6422 P-glycoprotein substrate Substrate 0.7189 P-glycoprotein inhibitor I Inhibitor 0.6211 P-glycoprotein inhibitor II Non-inhibitor 0.8284 Renal organic cation transporter Inhibitor 0.7592 CYP450 2C9 substrate Non-substrate 0.8119 CYP450 2D6 substrate Non-substrate 0.9116 CYP450 3A4 substrate Non-substrate 0.5193 CYP450 1A2 substrate Non-inhibitor 0.9046 CYP450 2C9 inhibitor Non-inhibitor 0.9084 CYP450 2D6 inhibitor Inhibitor 0.8931 CYP450 2C19 inhibitor Non-inhibitor 0.9056 CYP450 3A4 inhibitor Non-inhibitor 0.9041 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9558 Ames test Non AMES toxic 0.8194 Carcinogenicity Non-carcinogens 0.9309 Biodegradation Not ready biodegradable 0.8756 Rat acute toxicity 2.6495 LD50, mol/kg Not applicable hERG inhibition (predictor I) Strong inhibitor 0.6982 hERG inhibition (predictor II) Non-inhibitor 0.6332
Spectra
- Mass Spec (NIST)
- Download (7.72 KB)
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 183.0679287 predictedDarkChem Lite v0.1.0 [M-H]- 172.63222 predictedDeepCCS 1.0 (2019) [M+H]+ 184.0367287 predictedDarkChem Lite v0.1.0 [M+H]+ 174.99022 predictedDeepCCS 1.0 (2019) [M+Na]+ 183.2347287 predictedDarkChem Lite v0.1.0 [M+Na]+ 181.08337 predictedDeepCCS 1.0 (2019)
Targets
Build, predict & validate machine-learning models
Use our structured and evidence-based datasets to unlock newinsights and accelerate drug research.
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Antagonist
- General 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
- Specific Function
- G protein-coupled acetylcholine receptor activity
- Gene Name
- CHRM1
- Uniprot ID
- P11229
- Uniprot Name
- Muscarinic acetylcholine receptor M1
- Molecular Weight
- 51420.375 Da
References
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
- 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. [Article]
- 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 (Vienna). 1999;106(7-8):583-92. [Article]
- 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. [Article]
- Eltze M: Multiple mechanisms of action: the pharmacological profile of budipine. J Neural Transm Suppl. 1999;56:83-105. [Article]
- 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. [Article]
- Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
- Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- A cytochrome P450 monooxygenase involved in the metabolism of fatty acids, steroids and retinoids (PubMed:18698000, PubMed:19965576, PubMed:20972997, PubMed:21289075, PubMed:21576599). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase) (PubMed:18698000, PubMed:19965576, PubMed:20972997, PubMed:21289075, PubMed:21576599). Catalyzes the epoxidation of double bonds of polyunsaturated fatty acids (PUFA) (PubMed:19965576, PubMed:20972997). Metabolizes endocannabinoid arachidonoylethanolamide (anandamide) to 20-hydroxyeicosatetraenoic acid ethanolamide (20-HETE-EA) and 8,9-, 11,12-, and 14,15-epoxyeicosatrienoic acid ethanolamides (EpETrE-EAs), potentially modulating endocannabinoid system signaling (PubMed:18698000, PubMed:21289075). Catalyzes the hydroxylation of carbon-hydrogen bonds. Metabolizes cholesterol toward 25-hydroxycholesterol, a physiological regulator of cellular cholesterol homeostasis (PubMed:21576599). Catalyzes the oxidative transformations of all-trans retinol to all-trans retinal, a precursor for the active form all-trans-retinoic acid (PubMed:10681376). Also involved in the oxidative metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic antidepressants
- Specific Function
- anandamide 11,12 epoxidase activity
- Gene Name
- CYP2D6
- Uniprot ID
- P10635
- Uniprot Name
- Cytochrome P450 2D6
- Molecular Weight
- 55768.94 Da
References
- Kudo S, Uchida M, Odomi M: Metabolism of carteolol by cDNA-expressed human cytochrome P450. Eur J Clin Pharmacol. 1997;52(6):479-85. [Article]
- Ieiri I, Yamada S, Seto K, Morita T, Kaneda T, Mamiya K, Tashiro N, Higuchi S, Otsubo K: A CYP2D6 phenotype-genotype mismatch in Japanese psychiatric patients. Pharmacopsychiatry. 2003 Sep;36(5):192-6. doi: 10.1055/s-2003-43049. [Article]
Drug created at June 13, 2005 13:24 / Updated at October 07, 2024 17:51