Biperiden

Last updated
Biperiden
Biperiden Stereoisomers.png
Biperiden-3D-sticks.png
Clinical data
Trade names Akineton
AHFS/Drugs.com Monograph
MedlinePlus a699058
License data
Pregnancy
category
  • AU:B2
Routes of
administration 		By mouth, intramuscular injection (IM), intravenous therapy (IV)
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability 33 ± 5% (by mouth)
Protein binding 60%
Metabolism Liver hydroxylation
Elimination half-life 18 to 24 hours
Excretion Kidney
Identifiers
  • (1RS,2SR,4RS)-1-(bicyclo[2.2.1]hept-5-en-2-yl)-1-phenyl-3-(piperidin- 1-yl)propan-1-ol
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard 100.007.441 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C21H29NO
Molar mass 311.469 g·mol−1
3D model (JSmol)
  • OC(c1ccccc1)(CCN2CCCCC2)C4C3\C=C/C(C3)C4
  • 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 Yes check.svgY
  • Key:YSXKPIUOCJLQIE-UHFFFAOYSA-N Yes check.svgY
   (verify)

Biperiden, sold under the brand name Akineton among others, is a medication used to treat Parkinson disease, certain drug-induced movement disorders [3] and Tourette Syndrome [ citation needed ]. It is not recommended for tardive dyskinesias. [4] It is taken by mouth, injection into a vein, or muscle. [3] [4]

Contents

Common side effects include blurred vision, dry mouth, sleepiness, constipation, and confusion. [3] It should not be used in people with a bowel obstruction or glaucoma. [3] It is unclear if use in pregnancy or breastfeeding is safe. [5] Biperiden is in the anticholinergic family of medication. [3]

Biperiden was approved for medical use in the United States in 1959. [3] It is on the World Health Organization's List of Essential Medicines. [6] Biperiden is no longer marketed in the United States. [7] [8] [9]

Medical uses

Biperiden is used for the adjunctive treatment of all forms of Parkinson's disease (postencephalitic, idiopathic, and arteriosclerotic Parkinson's) and for reduced sweating in methadone users. It seems to exert better effects in the postencephalitic and idiopathic than in the arteriosclerotic type.

Biperiden is also commonly used to improve acute extrapyramidal side effects related to antipsychotic drug therapy, such as akathisia.

It relieves muscle rigidity, reduces abnormal sweating related with clozapine and methadone use [10] [11] and salivation, improves abnormal gait, and to lesser extent, tremor.

In its role as a synthetic acetylcholine antagonist, biperiden has been analyzed as an alternative anticonvulsant for usage in the treatment of intoxication by organophosphorus nerve agents, such as sarin. [12]

It was also suggested by IV route for neuroleptic malignant syndrome. [13]

Pregnancy and lactation

Children

Children and adolescents aged 1 year and older may be treated. The clinical experience is mainly on the short-term treatment of acute drug induced dystonic reactions. Doses should be reduced according to the weight of the patients.[ citation needed ]

Contraindications

Side effects

Dose-dependent side effects are frequent. Particularly geriatric patients may react with confusional states or develop delirium.

Interactions

Overdose

Biperiden mimics an atropine intoxication with mydriasis, dryness of mucous membranes, red face, atonic states of bowels and bladder, and hyperthermia in high doses. Central consequences are agitation, confusion, and hallucinations. An untreated overdose may be fatal, particularly in children. Premortal signs are respiratory depression and cardiac arrest. A specific antagonist is physostigmine which combines a peripheral and a central action. Carbachol can be used to treat atonic bowels and bladder. The vital functions should be monitored and stabilized. It may be necessary to treat hyperthermia with cooling blankets.

Pharmacology

Pharmacodynamics

Anticholinergic activity

Biperiden is an anticholinergic. [15] It is specifically an antimuscarinic, acting as a non-selective muscarinic acetylcholine receptor antagonist. [15] It antagonizes all five subtypes of the muscarinic acetylcholine receptor. [15] However, it is said to have weaker antagonistic activity at the muscarinic acetylcholine M2 receptor compared to the M1, M3, M4, and M5 receptor. [15] It has an atropine-like blocking effect on all peripheral structures which are parasympathetic-innervated (e.g. cardiovascular and visceral organs). It also has a prominent central blocking effect on M1 receptors.

Other actions

Biperiden also acts as FIASMA (functional inhibitor of acid sphingomyelinase). [16]

Pharmacokinetics

The oral bioavailability is only 33 ± 5% due to extensive first-pass metabolism. In young, healthy volunteers, peak plasma concentrations following a single oral 4 mg immediate-release dose are reached after 1.5 hours. The elimination half-life has been determined as 18.4 hours, and may be prolonged in geriatric patients. After a 4 mg intravenous dose, the elimination half-life is approximately 24 hours.

History

Biperiden was synthesized by the German chemist W. Klavehn from Knoll AG, Germany. In March 1953 a patent was applied for in Germany [17] and subsequently in many other countries. A US patent application was filed in March 1954 and granted in April 1957. [18]

One website reported that it was not commercially available in the United States as of 2017. [19]

References

  1. ↑ "Therapeutic Goods (Poisons Standard— June 2025) Instrument 2025" (pdf). Therapeutic Goods Administration (TGA). May 2025. Retrieved 31 August 2025.
  2. ↑ Anvisa (2023-03-31). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-04-04). Archived from the original on 2023-08-03. Retrieved 2023-08-16.
  3. 1 2 3 4 5 6 "Biperiden Hydrochloride". The American Society of Health-System Pharmacists. Archived from the original on 21 December 2016. Retrieved 8 December 2016.
  4. 1 2 World Health Organization (2009). Stuart MC, Kouimtzi M, Hill SR (eds.). WHO Model Formulary 2008. World Health Organization. p. 243. hdl: 10665/44053 . ISBN   9789241547659.
  5. ↑ "Biperiden Use During Pregnancy | Drugs.com". www.drugs.com. Archived from the original on 21 December 2016. Retrieved 15 December 2016.
  6. ↑ World Health Organization (2019). World Health Organization model list of essential medicines: 21st list 2019. Geneva: World Health Organization. hdl: 10665/325771 . WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO.
  7. ↑ "Akineton (biperiden hydrochloride): FDA-Approved Drugs". U.S. Food and Drug Administration. Archived from the original on January 25, 2017. Retrieved 2 July 2020.
  8. ↑ "Akineton (biperiden lactate): FDA-Approved Drugs". U.S. Food and Drug Administration. Archived from the original on January 25, 2017. Retrieved 2 July 2020.
  9. ↑ "Akineton Tablets (biperiden hydrochloride)". DailyMed. Retrieved 2 July 2020.
  10. ↑ Richardson C, Kelly DL, Conley RR (August 2001). "Biperiden for excessive sweating from clozapine". Am J Psychiatry. 158 (8): 1329–30. doi:10.1176/appi.ajp.158.8.1329-a. PMID   11481174. Archived from the original on 2012-09-21. Retrieved 2008-11-12.
  11. ↑ Caflisch C, Figner B, Eich D (February 2003). "Biperiden for excessive sweating from methadone" . Am J Psychiatry. 160 (2): 386–7. doi:10.1176/appi.ajp.160.2.386. PMID   12562595.
  12. ↑ Shih TM, McDonough JH (May 2000). "Efficacy of biperiden and atropine as anticonvulsant treatment for organophosphorus nerve agent intoxication". Archives of Toxicology. 74 (3): 165–172. Bibcode:2000ArTox..74..165S. doi:10.1007/s002040050670. PMID   10877003. S2CID   13749842. Archived from the original on September 23, 2017.
  13. ↑ Margetić B, Aukst-Margetić B (May 2010). "Neuroleptic malignant syndrome and its controversies". Pharmacoepidemiology and Drug Safety. 19 (5): 429–435. doi:10.1002/pds.1937. PMID   20306454. S2CID   2457321.
  14. ↑ Nishiyama K, Mizuno T, Sakuta M, Kurisaki H (1993). "Chronic dementia in Parkinson's disease treated by anticholinergic agents. Neuropsychological and neuroradiological examination". Adv Neurol. 60: 479–83. PMID   8420174.
  15. 1 2 3 4 Lakstygal AM, Kolesnikova TO, Khatsko SL, Zabegalov KN, Volgin AD, Demin KA, Shevyrin VA, Wappler-Guzzetta EA, Kalueff AV (May 2019). "DARK Classics in Chemical Neuroscience: Atropine, Scopolamine, and Other Anticholinergic Deliriant Hallucinogens". ACS Chem Neurosci. 10 (5): 2144–2159. doi:10.1021/acschemneuro.8b00615. PMID   30566832.
  16. ↑ Kornhuber J, Muehlbacher M, Trapp S, Pechmann S, Friedl A, Reichel M, Mühle C, Terfloth L, Groemer T, Spitzer G, Liedl K, Gulbins E, Tripal P (2011). "Identification of novel functional inhibitors of acid sphingomyelinase". PLOS ONE. 6 (8): e23852. Bibcode:2011PLoSO...623852K. doi: 10.1371/journal.pone.0023852 . PMC   3166082 . PMID   21909365.{{cite journal}}: CS1 maint: article number as page number (link)
  17. ↑ DE 1005067,Klavehn W,"Verfahren zur Herstellung von bicyclisch substituierten Aminopropanolen",issued 1957, assigned to Knoll AG.
  18. ↑ US 2789110,Klavehn W,"Amino alcohols substituted by bicycloalkyl residues and a process of making same",issued 1957, assigned to Knoll AG.
  19. ↑ "Biperiden". Davis's Drug Guide. Archived from the original on 10 September 2017. Retrieved 6 July 2017.
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