Pilocarpine

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Structural formula
Structural formula of pilocarpine
General
Surname Pilocarpine
other names
  • (3 S , 4 R ) -3-Ethyl-4 - [(1-methylimidazol-5-yl) methyl] -4,5-dihydrofuran-2 (3 H ) -one
  • (3 S , 4 R ) -3-ethyl-4,5-dihydro-4 - [(1-methylimidazol-5-yl) methyl] furan-2 (3 H ) -one
  • Pilocarpine
Molecular formula C 11 H 16 N 2 O 2
Brief description

oily liquid or crystals

External identifiers / databases
CAS number
PubChem 5910
DrugBank DB01085
Wikidata Q411461
Drug information
ATC code
Drug class

Parasympathomimetics

properties
Molar mass 208.26 g · mol -1
Melting point
  • 34 ° C
  • 193–205 ° C (as hydrochloride)
  • 174 ° C (as nitrate)
boiling point

260 ° C (670 Pa )

pK s value

6.78

solubility

soluble in water, ethanol and chloroform

safety instructions
Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed
GHS hazard labeling from  Regulation (EC) No. 1272/2008 (CLP) , expanded if necessary

(Hydrochloride)

06 - Toxic or very toxic

danger

H and P phrases H: 330-300
P: 260-264-284-301 + 310 + 330-304 + 340 + 310-403 + 233
Toxicological data

402 mg kg −1 ( LD 50 ,  rat ,  oral )

As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Pilocarpine is a drug from the group of direct parasympathomimetics and is used as a miotic (pupil-constricting agent) in ophthalmology. It is an imidazole alkaloid which occurs naturally in Jaborandi leaves ( Ruta herb , Pilocarpus sp., For example Pilocarpus jaborandi or Pilocarpus pennatifolius , a South American shrub).

Effects

As a parasympathomimetic, pilocarpine increases the secretion of exocrine glands ( sweat , salivary , lacrimal , stomach , pancreatic and intestinal glands ) and the production of mucus by the goblet cells in the airways . It also increases the tone of the smooth muscles and the constricted pupil ( sphincter pupillae muscle ).

use

Pilocarpine was discovered or isolated almost simultaneously in 1875 by E. Hardy in France and AW Gerrard in London. It is mainly used in ophthalmology for increased intraocular pressure ( "green star" ). On the one hand, it has a direct exciting effect on the sphincter pupillae muscle and thus triggers a reduction in size ( miosis ) of the pupil . On the other hand, the drainage of the aqueous humor is facilitated by widening the drainage channels, which lowers the intraocular pressure. Pilocarpine is applied directly to the eye, which means that its effect is limited locally to it.

Another area of ​​application is radiation-induced dry mouth (xerostomia). A gel with 0.1% pilocarpine content or tablets to be dissolved in water (trade name Salagen ) are used. Similarly, it can be used against dry mouth in Sjogren's syndrome .

Pilocarpine oil kills pubic lice by blocking their breathing. It is therefore used when the eyelashes are infected with phthiriasis palpebrarum .

In veterinary medicine, pilocarpine is used to diagnose feline dysautonomy . In healthy animals, the pupil constriction only occurs after 45 minutes, in cats with feline dysautonomia within 15 minutes.

In research, pilocarpine is used to induce epileptic seizures.

The pilocarpine iontophoresis sweat test is also used to diagnose cystic fibrosis .

Detection reaction

Pilocarpine or pilocarpine salts can be detected qualitatively by the Helch reaction .

literature

  • Ernst Mutschler et al .: Mutschler - drug effects textbook of pharmacology and toxicology . 9th edition. Scientific Verlagsgesellschaft, Stuttgart 2008, ISBN 978-3-8047-1952-1 .
  • Doris Schwarzmann-Schafhauser: Pilocarpin. In: Werner E. Gerabek , Bernhard D. Haage, Gundolf Keil , Wolfgang Wegner (eds.): Enzyklopädie Medizingeschichte. De Gruyter, Berlin / New York 2005, ISBN 3-11-015714-4 , p. 1163.

Trade names

Monopreparations

Salagen (D, A, CH), Spersacarpine (D, CH), various generics (D, A),

Combination preparations

Arteopilo (CH), Betacarpine (A), Fotil (D, A), Glauko Biciron (D), Normoglaucon (D), TP-Ophtal (D)

Individual evidence

  1. ↑ a b c d e Entry on pilocarpine. In: Römpp Online . Georg Thieme Verlag, accessed on May 30, 2014.
  2. ↑ a b c Entry on pilocarpine in the ChemIDplus database of the United States National Library of Medicine (NLM) .
  3. ↑ Entry on pilocarpine in the GESTIS substance database of the IFA , accessed on February 22, 2017(JavaScript required) .
  4. ↑ a b Entry on pilocarpine hydrochloride in the GESTIS substance database of the IFA , accessed on September 18, 2018(JavaScript required) .
  5. ↑ Entry on Pilocarpine in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on February 1, 2016. Manufacturers or distributors can expand the harmonized classification and labeling .
  6. ↑ Data sheet Pilocarpine hydrochloride from Sigma-Aldrich , accessed on September 18, 2018 ( PDF ).
  7. ^ ME Hardy: Sur le jaborandi (Pilocarpus pinnatus). In: Bulletin Societe Chimi. No. 24, 1875, pp. 497-501.
  8. ^ AW Gerrard: The alkaloid and active principle of Jaborandi. In: Pharm. J. No. 5, 1875, p. 865.
  9. ↑ Renate Langenbach, Ilse Delagardelle: Affects der Mundschlimheit . In: Eberhard Aulbert, Friedemann Nauck, Lukas Radbruch (eds.): Textbook of palliative medicine. Schattauer, Stuttgart (1997) 3rd, updated edition 2012, ISBN 978-3-7945-2666-6 , pp. 265-270, here: pp. 265 f.
  10. ↑ Recommendations for supportive therapy of Sjogren's syndrome. In: www.dgrh.de. German Society for Rheumatology, accessed on August 11, 2019 .
  11. ↑ Anja Gerlatzek et al .: Feline dysautonomy (Key-Gaskell syndrome) in a hangover. In: Small Animal Practice. 56, 2011, pp. 473-481.
  12. ↑ K. Morimoto, M. Fahnestock, RJ Racine: Kindling and status epilepticus models of epilepsy: rewiring the brain . In: Progress in neurobiology . tape 73 , no. 1 , 2004, p. 1-60 , doi : 10.1016 / j.pneurobio.2004.03.009 , PMID 15193778 .