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Biperiden

HCID 2381
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Basic information

CAS
514-65-8
Standard SMILES
OC(CCN1CCCCC1)(c1ccccc1)C1CC2C=CC1C2
InChIKey
YSXKPIUOCJLQIE-UHFFFAOYSA-N
Molecular formula
C21H29NO
Average molar mass
311.5 g/mol
Monoisotopic mass
311.22491455

Overview

Biperiden is a member of the class of piperidines that is N-propylpiperidine in which the methyl hydrogens have been replaced by hydroxy, phenyl, and 5-norbornen-2-yl groups. A muscarinic antagonist affecting both the central and peripheral nervous systems, it is used in the treatment of all forms of Parkinson's disease. It has a role as an antidote to sarin poisoning, an antiparkinson drug, a muscarinic antagonist, a parasympatholytic and an antidyskinesia agent. It is a member of piperidines, a tertiary alcohol and a tertiary amino compound.

Names & identifiers

Preferred name
Biperiden
IUPAC
1-(2-bicyclo[2.2.1]hept-5-enyl)-1-phenyl-3-piperidin-1-ylpropan-1-ol
English name
Bipariden
Molecular formula
C21H29NO
Molecular weight
311.46106

Names & synonyms

biperiden514-65-8BiperideneBiperidineBiperidenoBiperidenumKL 373Akineton-alpha-5-Norbornen-2-yl-alpha-phenyl-1-piperidinepropanol0FRP6G56LD1-(bicyclo[2.2.1]hept-5-en-2-yl)-1-phenyl-3-(piperidin-1-yl)propan-1-olNSC-759145
Show more names
kl373AkinetonBeperidenbiparidenAkinophylBibristanBiperidenHcl
alpha-bicyclo[2.2.1]hept-5-en-2-yl-alpha-phenyl-1-piperidinepropanol1-{bicyclo[2.2.1]hept-5-en-2-yl}-1-phenyl-3-(piperidin-1-yl)propan-1-olCHEBI:3112DTXSID60226801-Piperidinepropanol, alpha-bicyclo(2.2.1)hept-5-en-2-yl-alpha-phenyl-alpha-Bicyclo(2.2.1)hept-5-en-2-yl-alpha-phenyl-1-piperidinepropanol1-Bicyclo(2.2.1)hept-5-en-2-yl-1-phenyl-3-piperidin-1-yl-propan-1-ol1-Bicyclo[2.2.1]hept-5-en-2-yl-1-phenyl-3-piperidin-1-yl-propan-1-ol

Database identifiers

CAS
514-65-8
PubChem CID
2381
DTXSID
DTXSID6022680
ChEMBL

Properties

Computed structural properties

XLogP
4.3
Topological polar surface area
23.5 Ų
Hydrogen bond donors
1
Hydrogen bond acceptors
2
Rotatable bonds
5
Heavy atoms
23
Formal charge
0
Complexity
422

Experimental & physicochemical properties

DrugsPharmaceuticals
SpringerMaterials PropertiesFusion temperature
LogP · 3 items

log Kow = 4.25

4.1

4.25

Color/FormCrystals
Solubility · 3 items

Fluffy white powder, mp 238 °C. Solubility in water (mg/100 mL) at 30 °C: 220 (ph 3.8), 280 (pH 5.5), 290 (pH 6.7), 264 (pH 7.9), 244 (pH 9.2-10.1) /Hydrochloride/

Slightly soluble in ethanol; readily soluble in methanol

4.26e-03 g/L

Human Drugs · 3 items

Breast Feeding; Lactation; Milk, Human; Antiparkinson Agents; Parasympatholytics; Muscarinic Antagonists

Pharmaceuticals

Medicines for parkinsonism

Melting Point · 2 items

101 °C

114 °C

Physical DescriptionSolid
Collision Cross Section

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

GHS classification

GHS Classification · 4 items

Warning

H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]

P264, P270, P301+P317, P330, and P501 (click each P-code to see the statement)

The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.

Hazard information

FDA Requirements · 1 item

The Approved Drug Products with Therapeutic Equivalence Evaluations List identifies currently marketed prescription drug products, incl biperiden hydrochloride, approved on the basis of safety and effectiveness by FDA under sections 505 of the Federal Food, Drug, and Cosmetic Act. /Biperiden hydrochloride/

Hazard Classes and CategoriesAcute Tox. 4 (100%)

Safety & protection

Storage ConditionsBiperiden hydrochloride tablets should be stored in tight, light-resistant containers at 15-30 °C.
Disposal Methods · 1 item

SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

Toxicology

Treatment · 1 item

Treatment of acute overdose revolves around symptomatic and supportive therapy. If Biperiden was administered orally, gastric lavage or other measures to limit absorption should be instituted. A small dose of diazepam or a short acting barbiturate may be administered if CNS excitation is observed. Phenothiazines are contraindicated because the toxicity may be intensified due to their antimuscarinic action, causing coma. Respiratory support, artificial respiration or vasopressor agents may be necessary. Hyperpyrexia must be reversed, fluid volume replaced and acid-base balance maintained. Urinary catheterization may be necessary. Routine use of physostigmine for overdose is controversial. Delirium, hallucinations, coma, and supraventricular tachycardia (not ventricular tachycardias or conduction defects) seem to respond. If indicated, 1 mg (half this amount for the children or elderly) may be given intramuscularly or by slow intravenous infusion. If there is no response within 20 minutes, and additional 1 mg dose may be given; this may be repeated until a total of 4 mg has been administered, a reversal of the toxic effects occur or excessive cholinergic signs are seen. Frequent monitoring of clinical signs should be done. Since physostigmine is rapidly destroyed, additional injections may be required every one or two hours to maintain control. The relapse intervals tend to lengthen as the toxic anticholinergic agent is metabolized, so the patient should be carefully observed for 8 to 12 hours following the last relapse. (L1712)

Chemistry & industry

Pharmacology

ATC Code · 4 items

N04AA02

N - Nervous system

QN - Nervous system

N04AA02

Protein Binding60%
Pharmacodynamics · 1 item

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 · 3 items

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.

Akineton is a weak peripheral anticholinergic agent. It has, therefore, some antisecretory, antispasmodic and mydriatic effects. In addition, Akineton possesses nicotinolytic activity. 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 Akineton is considered to relate to competitive antagonism of acetylcholine at cholinergic receptors in the corpus striatum, which then restores the balance.

Like other antimuscarinic agents of the trihexyphenidyl group, biperiden has an atropine-like blocking action on parasympathetic-innervated peripheral structures, including smooth muscle. In addition to antispasmodic, antisecretory, and mydriatic effects, biperiden has an antinicotinic potency about 6 times that of atropine and 5 times that of trihexyphenidyl on a weight basis in experimental animals.

Biological Half-Life · 1 item

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Related reactions

2 records
New reaction record
HRID 1204931 reaction equation
HRID 1204931As productTraining data from https://doi.org/10.1039/C8SC04228D (5/10)
HRID 1796694 reaction equation
HRID 1796694As productuspto-grants-2006_04

Compound notes

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On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
CHEMBL1101
ChEBI
CHEBI:3112
UNII
0FRP6G56LD
EC Number
208-184-6
Nikkaji
J2.059A
· 2 items

175.7 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

175.06 Ų [M+K]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

Physicochemical properties

Melting point
114 °C · 114°C
Boiling point
451.49 °C · 451.49°C (rough estimate)
Density
1.0202 · 1.0202 (rough estimate)
refractive index
1.5614 · 1.5614 (estimate)
storage temp.
2 · 2-8°C
solubility
Chloroform (Slightly), DMSO (Slightly,Sonicated), Methanol (Slightly, Sonicated)
form
Solid
pka
14.05 · 14.05±0.29(Predicted)
color
White to Off-White
Water Solubility
25.1 mg/L · 25.1 mg/L
EWG's Food Scores
1 · 1
FDA UNII
0 FRP6G56LD · 0FRP6G56LD
NIST Chemistry Reference
Biperiden(514-65-8)
ATC code
4 AA02 · N04AA02
Symbol(GHS)
7 · GHS07
Signal word
Warning
Hazard statements
302 · H302
Precautionary statements
280 · P280-P305+P351+P338
Hazardous Substances Data
514 · 514-65-8(Hazardous Substances Data)
Toxicity
50 in · LD50 in mice (mg/kg): 195 s.c., 56 i.v. (Klavehn)
Interactions · 3 items

In rats the pharmacokinetic interactions between the anticholinergic drug biperiden and [3(H)]quinuclidinyl benzylate ([3(H)]QNB) or [3(H)]N-methylscopolamine ([3(H)]NMS) is affected by the sequence in which the drugs are administered. Drug concentrations in various tissues were determined after intravenous administration of [3(H)]QNB or [3(H)]NMS (325 ng kg(-1)). Biperiden (6.4 mg kg(-1)) was administered either 5 min before, concomitantly with or 20 min after injection of [3(H)]QNB or [3(H)]NMS. When biperiden was administered concomitantly with or before [3(H)]QNB, distribution of [3(H)]QNB among the regions of the brain and other tissues was reduced; at 4 hr the ratio of the distribution of [3(H)]QNB for experimental animals to that for control animals ranged from 0.15 to 0.9. When biperiden was administered after [3(H)]QNB, the distribution of [3H]QNB in the brain and other tissues was significantly higher than for the other two treatments (P < 0.01). However, for [3(H)]NMS the sequence of administration had no effect on the distribution of the drug in the brain and other tissues except for the kidney. In-vitro, in crude synaptosomal membranes, the amount of [3(H)]QNB at 2 hr relative to the control concentration at equilibrium was 87% when biperiden was added before [3(H)]QNB and 56% when biperiden was added after [3(H)]QNB. In both instances the concentration of [3(H)]NMS reached equilibrium within 30 min. These findings suggest that the difference between the rate constant of association and dissociation at the possible site of action gives rise to the effect of the sequence of administration on the pharmacokinetic interaction.

Concomitant administration of biperiden with other drugs having anticholinergic effects (e.g., opiate agonists, phenothiazines and other antipsychotics, tricyclic antidepressants, quinidine, antihistamines) may increase the risk of adverse anticholinergic effects.

In order to find molecules affected by administration of an antipsychotic drug with an antimuscarinic drug, which is a common prescription used to prevent extrapyramidal adverse effects caused by the antipsychotic drugs, gene expression profiling in the frontal cortex was studied in mice. After 14 days of administration with 2 mg/kg haloperidol, a typical antipsychotic drug, and 2 mg/kg biperiden, a high-affinity antagonist for muscarinic receptors in the brain, approximately 500 mRNAs related to synaptic function were investigated. The levels of the mRNAs related to the ubiquitin-related systems were significantly reduced after the combined administration. However, the separate administration of either haloperidol or biperiden had little effect on the levels of the mRNAs. This result suggests that coadministration of haloperidol and biperiden specifically affects the ubiquitin-related system.

Hepatotoxicity · 1 item

Biperiden has not been reported to cause serum aminotransferase elevations, but it has not been evaluated for effects on serum enzyme levels in a prospective manner. Despite its use for more than 50 years, there have been no reports of biperiden liver injury in the literature and it must be a very rare cause of liver injury, if it occurs at all.

Exposure RoutesOral
Toxicity Summary · 1 item

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.

Signs and Symptoms · 1 item

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.

Human Toxicity Excerpts · 4 items

/SIGNS AND SYMPTOMS/ Overdosage with Akineton produces typical central symptoms of atropine intoxication (the central anticholinergic syndrome). Correct diagnosis depends upon recognition of the peripheral signs of parasympathetic blockade including 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, and urinary retention. Neuropsychiatric signs such as delirium, disorientation, anxiety, hallucinations, illusions, confusion, incoherence, agitation, hyperactivity, ataxia, loss of memory, paranoia, combativeness, and seizures may be present. The condition can progress to stupor, coma, paralysis, and cardiac and respiratory arrest and death.

/CASE REPORTS/ Two cases of self-induced intoxication with the anticholinergic agent biperiden (oral ingestion of at least 200 mg. in case 1, and of 60 mg. in combination with 300-400 mg levomepromazine in case 2) /were reported/. An acute delirious state and other somatic symptoms of a toxic anticholinergic action dominated the clinical picture. Serial measurements of biperiden serum levels revealed values up to 50-fold (case 1) and 15-fold (case 2) of those usually observed under therapeutic doses of biperiden. In both cases, the intoxication was controlled by the application of physostigmine and general therapeutic measures. ... The prognosis of biperiden intoxications, and the clinical symptomatology and therapy of drug-induced anticholinergic syndromes /is discussed/.

/CASE REPORTS/ Anticholinergic medication (ACM) is frequently used in psychiatry to treat the side-effects of D2 blocking agents. However, ACM is not without adverse effects and, in the elderly, cognitive and memory impairments have been emphasized. The aim of this study was to evaluate the effects of discontinuation of ACM on cognitive functions in a group of elderly chronic schizophrenia patients. Twenty-seven elderly patients (age 60 years or older), who were diagnosed as suffering from schizophrenia (DSM-IV) and receiving ACM in addition to antipsychotic treatment, were enrolled. Before and after ACM was discontinued, the Alzheimer's Disease Assessment Scale-Cognitive (ADAS-Cog) subscale was administered. Twenty-one patients completed the study. All were receiving Akineton (biperiden), 2-6 mg daily before the study. Significant improvement in the ADAS-Cog total score was demonstrated (P < 0.03), as well as in the ideational praxia and orientation subscales. Improvement was correlated with the previous dose of biperidin. No adverse events or emergent extrapyramidal symptoms were noted. Discontinuation of ACM may be warranted in chronic schizophrenia patients since it may improve cognitive functioning with no adverse effects.

/CASE REPORTS/ A case of contact dermatitis to biperiden, an anti-Parkinson agent, and photocontact dermatitis to phenothiazines in a pharmacist was reported. The patient developed eczematous lesions on exposed area after she had worked at a psychiatric hospital for 6 months. She showed positive patch test reaction to biperiden. In addition, she reacted positively to photopatch testing with ultraviolet A and phenothiazines such as chlorpromazine and perphenazine.

Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).
Drug Induced Liver Injury · 6 items

Benchmark Dataset for the Liver Toxicity Knowledge Base (LTKB)

biperiden

Akineton®

Anticholinergics

Not Applicable

no-DILI-concern

Non-Human Toxicity Excerpts · 4 items

/LABORATORY ANIMALS: Acute Exposure/ In dogs under general anesthesia, respiratory arrest occurred at 33 mg/kg (intravenous) and circulatory standstill at 45 mg/kg (intravenous).

/LABORATORY ANIMALS: Acute Exposure/ Biperiden lactate (10 mg/mL) was not irritating to the tissue of rabbits when injected intramuscularly (1.0 mL) into the sacrospinalis muscles and intradermally (0.25 mL) and subcutaneously (0.5 mL) into the shaved abdominal skin. /Biperiden lactate/

/LABORATORY ANIMALS: Acute Exposure/ Biperiden lactate was administered intravenously in overdose to dogs under general anaesthesia. Biperiden appeared to have a toxic influence on respiration and circulation independently. Respiratory arrest occurred at a dose of 33 +/- 10 mg/kg and has probably a central origin. When artificial ventilation was instituted circulatory standstill occurred at a dose of 45 +/- 5 mg/kg. The toxic influence of biperiden is characterised by a decrease of heart rate and of left ventricular contractility resulting in cardiogenic shock. Biperiden is compared with orphenadrine as far as its potential hazard is concerned for patients trying to commit suicide by ingesting an overdose.

/LABORATORY ANIMALS: Neurotoxicity/ ... The anticholinergic drug, biperiden (40 mg/kg i.p.), /was administered/ to 10 adult male Wistar rats and ... the resulting polygraphic recordings, including electroencephalography (EEG), electrooculography (EOG), and electromyography (EMG), for 60 min following injection /was examined/. EEG data were investigated quantitatively by power spectrum analyses using fast Fourier transformation. Ten male Wistar rats receiving saline (i.p.) were used as the control group. Treated rats demonstrated two types of alternating behavioral change: a hyperactive and hypoactive state. In the hyperactive state, rapid walking, excessive random sniffing, and retropulsion were observed, with EEG desynchronization (significantly increased alpha1 (8.0-10.0 Hz), alpha2 (10.0-13.0 Hz), and beta (13.0-30.0 Hz) power values), as well as EEG slowing (significantly increased delta (0.5-4.0 Hz) and theta1 (4.0-6.0 Hz) power values): significantly marked rapid eye movement, and increased EMG activity. In the hypoactive state, motor arrest and drowsiness were observed, with prominent EEG slowing (significantly increased delta and theta1 power values): significantly decreased rapid eye movement and moderately decreased EMG activity. On the other hand, the control group did not show any behavioral or polygraphic changes.

Antidote and Emergency Treatment · 5 items

Emergency and supportive measures: Maintain an open airway and assist ventilation if needed. Treat hyperthermia, coma, rhabdomyolysis, and seizures if they occur. /Anticholinergics/

Specific drugs and antidotes: A small dose of physostigmine .... can be given to patients with severe toxicity (e.g., hyperthermia, severe delirium, or tachycardia). Caution: Physostigmine can cause AV block, asystole, and seizures, especially in patients with tricyclic antidepressant overdose. Neostigmine, a peripherally acting cholinesterase inhibitor, may be useful in treating anticholinergic-induced ileus. /Anticholinergics/

Decontamination: Administer activated charcoal orally if conditions are appropriate. Gastric lavage is not necessary after small to moderate ingestions if activated charcoal can be given promptly. Because of slowed gastrointestinal motility, gut decontamination procedures may be helpful even in late-presenting patients. /Anticholinergics/

Enhanced elimination: Hemodialysis, hemoperfusion, peritoneal dialysis, and repeat-dose charcoal are not effective in removing anticholinergic agents. /Anticholinergics/

For more Antidote and Emergency Treatment (Complete) data for BIPERIDEN (8 total), please visit the HSDB record page.

Effects During Pregnancy and Lactation◉ Summary of Use during Lactation

Regulatory information

FDA Requirements · 1 item

The Approved Drug Products with Therapeutic Equivalence Evaluations List identifies currently marketed prescription drug products, incl biperiden hydrochloride, approved on the basis of safety and effectiveness by FDA under sections 505 of the Federal Food, Drug, and Cosmetic Act. /Biperiden hydrochloride/

Safety data

Toxicity
LD50 in mice (mg/kg): 195 s.c., 56 i.v. (Klavehn)
Signal word
Warning
Symbol(GHS)
GHS07
Hazard statements
H302
Precautionary statements
P280-P305+P351+P338
Hazardous Substances Data
514-65-8(Hazardous Substances Data)

A single-blind cross-over design was employed with placebo and biperiden (4 mg as commercially available tablets). After a lag time of 0.5 hr, biperiden was rapidly absorbed with a half-life of 0.3 hr, ... Biperiden showed good tissue penetration (distribution half-life 0.6 hr; ratio of total to central distribution volume 9.6), the terminal half-life time of plasma concentration was 18 hr, ... .

Metabolism/Metabolites · 2 items

The metabolism of biperiden is not completely understood, but does involve hydroxylation.

The metabolism of biperiden is not completely understood, but does involve hydroxylation.

FDA Pharmacological Classification · 5 items

0FRP6G56LD

BIPERIDEN

Established Pharmacologic Class [EPC] - Anticholinergic

Mechanisms of Action [MoA] - Cholinergic Antagonists

Biperiden is an Anticholinergic. The mechanism of action of biperiden is as a Cholinergic Antagonist.

MeSH Pharmacological Classification · 3 items

Agents used in the treatment of Parkinson&apos;s disease. The most commonly used drugs act on the dopaminergic system in the striatum and basal ganglia or are centrally acting muscarinic antagonists.

Agents that inhibit the actions of the parasympathetic nervous system. The major group of drugs used therapeutically for this purpose is the MUSCARINIC ANTAGONISTS.

Drugs that bind to but do not activate MUSCARINIC RECEPTORS, thereby blocking the actions of endogenous ACETYLCHOLINE or exogenous agonists. Muscarinic antagonists have widespread effects including actions on the iris and ciliary muscle of the eye, the heart and blood vessels, secretions of the respiratory tract, GI system, and salivary glands, GI motility, urinary bladder tone, and the central nervous system.

Absorption, Distribution and Excretion · 4 items

87% bioavailability

The serum concentration at 1 to 1.5 hours following a single, 4 mg oral dose was 4-5 ng/mL. Plasma levels (0.1-0.2 ng/mL) could be determined up to 48 hours after dosing. Six hours after an oral dose of 250 mg/kg in rats, 87% of the drug had been absorbed.

The subcellular distribution of biperiden (BP), trihexyphenidyl (TP) and (-)-quinuclidinyl benzylate (QNB) in brain, heart and lung following high dose (3.2 mg/kg) iv administration was investigated in rats. The subcellular distribution of BP or TP used clinically conformed with that of QNB, a typical potent central muscarinic antagonist. The concentration-time courses of the brain subcellular fractions for these drugs were of two types which decreased slowly and in parallel to the plasma concentration. The subcellular distribution in the brain and heart was dependent on the protein amount of each fraction. The percent post-nuclear fraction (P2) of the total concentration in the lung was characteristically about 3-5 times larger than that in the heart. It was elucidated that the distribution in the lung differs from that in the brain and heart, with high affinity which is not dependent on the protein amount in the P2 fraction containing lysosomes. On the other hand, at a low dose (650 ng/kg) of 3H-QNB, each fraction as a percentage of the total concentration in the brain increased in synaptic membrane and synaptic vesicles and decreased in nuclei and cytosol as compared with the high dose. These results show that although the tissue concentration-time courses of anticholinergic drugs appear to decrease simply in parallel to plasma concentration, the subcellular distribution exhibits a variety of patterns among various tissues.

The pharmacokinetics of biperiden were studied and compared with pharmacodynamics (pupil size, accommodation, self-rating mood scale) in 6 healthy volunteers. A single-blind cross-over design was employed with placebo and biperiden (4 mg as commercially available tablets). After a lag time of 0.5 hr, biperiden was rapidly absorbed with a half-life of 0.3 hr, plasma peak levels of 5 ng/mL being reached after 1.5 hr. Biperiden showed good tissue penetration (distribution half-life 0.6 hr; ratio of total to central distribution volume 9.6), the terminal half-life time of plasma concentration was 18 hr, and the oral clearance was 146 L/hr. The pharmacodynamic maximum lagged behind the plasma peak concentration by 1 (self-rating) to 4 hr (accommodation).

Cellular LocationsMembrane

Uses & manufacturing

Uses · 3 items

THERAP CAT: Antiparkinsonian

Use (kg; approx.) in Germany (2009): >100

For use as an adjunct in the therapy of all forms of parkinsonism and control of extrapyramidal disorders secondary to neuroleptic drug therapy.

Impurities · 1 item

(1RS)-1-[(1SR,2SR,4SR)-bicyclo[2.2.1]hept-5-en-2-yl]-1-phenyl-3-(piperidin-1-yl)propan-1-ol (endo form); (1RS)-1-[(1SR,2RS,4SR)-bicyclo[2.2.1]hept-5-en-2-yl]-1-phenyl-3-(piperidin-1-yl)propan-1-ol; (1RS)-1-[(1RS,2RS,4RS)-bicyclo[2.2.1]hept-5-en-2-yl]-1-phenyl-3-(piperidin-1-yl)propan-1-ol; 1-[(1RS,2SR,4RS)-bicyclo[2.2.1]hept-5-en-2-yl]-3-(piperidin-1-yl)propan-1-one; 1-[(1RS,2RS,4RS)-bicyclo[2.2.1]hept-5-en-2-yl]-3-(piperidin-1-yl)propan-1-one; benzene

Formulations/PreparationsOral: Tablets: 2 mg Akineton (scored) (Abbott). /Biperiden hydrochloride/
Use ClassificationPharmaceuticals
Applications · 2 items

Usesamoebicide

General DescriptionBiperiden,α-5-norbornen-2-yl- -phenyl-1-piperidinepropanol (Akineton), introduced in 1959,has a relatively weak visceral anticholinergic, but a strongnicotinolytic, action in terms of its ability to block nicotineinducedconvulsions. Therefore, its neurotropic action israther low on intestinal musculature and blood vessels. It hasa relatively strong musculotropic action, which is aboutequal to that of papaverine, in comparison with most syntheticanticholinergic drugs. Its action on the eye, althoughmydriatic, is much lower than that of atropine. These weakanticholinergic effects add to its usefulness in Parkinson syndromeby minimizing side effects.

Upstream & downstream products

Upstream raw materials

Piperidine hydrochlorideDouble ringCycloheptenePropiophenone1,3-CyclopentadieneMagnesiumHydrochloric acidAcetophenoneFormaldehyde
Additional notes · 1 item

DefinitionChEBI: N-Propylpiperidine in which the methyl hydrogens are substituted by hydroxy, phenyl, and 5-norbornen-2-yl groups. A muscarinic antagonist affecting both the central and peripheral nervous systems, it is used in the treatment of all form of Parkinson's disease.