Pilocarpine

Pilocarpine
Pilocarpine
Systematic (IUPAC) name
(3S,4R)- 3-ethyl- 4-((1-methyl- 1H-imidazol- 5-yl) methyl)dihydrofuran- 2(3H)-one
Clinical data
Trade names Salagen
AHFS/Drugs.com monograph
MedlinePlus a608039
Pregnancy cat. C
Legal status ℞-only (US)
Routes gtts, p.o.
Pharmacokinetic data
Half-life 0.76 hours (5 mg), 1.35 hours (10 mg)[citation needed]
Excretion urine
Identifiers
CAS number 92-13-7 YesY
54-71-7 (hydrochloride)
ATC code N07AX01 S01EB01
PubChem CID 5910
IUPHAR ligand 305
DrugBank APRD00382
ChemSpider 5699 YesY
UNII 01MI4Q9DI3 YesY
KEGG D00525 YesY
ChEBI CHEBI:8207 N
ChEMBL CHEMBL550 YesY
Chemical data
Formula C11H16N2O2 
Mol. mass 208.257 g/mol
SMILES eMolecules & PubChem
 N(what is this?)  (verify)

Pilocarpine is a parasympathomimetic alkaloid obtained from the leaves of tropical American shrubs from the genus Pilocarpus. It is a non-selective muscarinic receptor agonist[1] in the parasympathetic nervous system, which acts therapeutically at the muscarinic acetylcholine receptor M3 due to its topical application,[2] e.g., in glaucoma and xerostomia.

Contents

Uses

Clinical

Pilocarpine has been used in the treatment of chronic open-angle glaucoma and acute angle-closure glaucoma for over 100 years.[3] It acts on a subtype of muscarinic receptor (M3) found on the iris sphincter muscle, causing the muscle to contract and engage in miosis. Pilocarpine also acts on the ciliary muscle and causes it to contract. When the ciliary muscle contracts, it opens the trabecular meshwork through increased tension on the scleral spur. This action facilitates the rate that aqueous humor leaves the eye to decrease intraocular pressure.

Pilocarpine is often used as an antidote for scopolamine, atropine, and hyoscyamine poisoning.

In ophthalmology pilocarpine is also used to reduce the possibility of glare at night from lights if the patient underwent implantation of phakic intraocular lenses; the use of pilocarpine would reduce the size of the pupils, relieving these symptoms. The most common concentration for this use is pilocarpine 1%, the weakest concentration.

Pilocarpine is also used to treat dry mouth (xerostomia) which can occur, for example, as a side effect of radiation therapy for head and neck cancers. Pilocarpine stimulates the secretion of large amounts of saliva and sweat.[4]

Pilocarpine is used to stimulate sweat glands in a sweat test to measure the concentration of chloride and sodium that is excreted in sweat. It is used to diagnose cystic fibrosis (CF).

Preparation

The drug and powdered leaf of pilocarpin microfelixis are subjected to extracted forotoal alkaloid with ethanol acidified with HCl with solvents removed under reduced pressure and resultant aqueous residue is neutralized with ammonia and kept aside till all the resin is settled down completely. It is filtered and concentrated by sugar solution to a small volume, made alkaloid with ammonia, and finally extracted with chloroform. The solvent is removed under reduced pressure.

Scientific

Pilocarpine is used to induce chronic epilepsy in rodents, commonly rats, as a means to study the disorder's physiology and to examine different treatments. Smaller doses may be used to induce salivation in order to collect samples of saliva, for instance, to obtain information about IgA antibodies.

Veterinary

Pilocarpine is given in moderate doses (about 2 mg) to induce emesis in cats who have ingested foreign plants, foods, or drugs. One feline trial determined it was effective, even though the usual choice of emetic is xylazine.

Trade names

Pilocarpine is available under several trade names such as: Diocarpine (Dioptic), Isopto Carpine (Alcon), Miocarpine (CIBA Vision), Ocusert Pilo-20 and -40 (Alza), Pilopine HS (Alcon), Salagen (MGI Pharma), Scheinpharm Pilocarpine (Schein Pharmaceutical), and Timpilo (Merck Frosst).

Adverse effects

Use of pilocarpine may result in a range of adverse effects, most of them related to its non-selective action as a muscarinic receptor agonist. Pilocarpine has been known to cause excessive sweating, excessive salivation, bronchospasm, increased bronchial mucus secretion, bradycardia, vasodilation, brow ache (when used as eye drops) and diarrhea. It can also result in miosis when used chronically as an eye drop. Systemic injection of pilocarpine can compromise the blood-brain barrier allowing the pilocarpine to gain access to the brain. This can lead to chronic epilepsy.

Epilepsy induced by pilocarpine has been used to develop animal models in rodents in order to study human epilepsy.

References

  1. ^ Spalding et al. 2002.
  2. ^ Pharmacology, (Rang, Dale, Ritter & Moore, ISBN 0443071454, 5:th ed., Churchill Livingstone 2003) Page 144.
  3. ^ Rosin, A. (1991). "Pilocarpine. A miotic of choice in the treatment of glaucoma has passed 110 years of use". Oftalmologia (Romania) 35 (1): 53–55. PMID 1811739. 
  4. ^ "Pilocarpine". http://www.nlm.nih.gov/medlineplus/druginfo/meds/a608039.html. 

Further reading

  • The Italian Journal of Neurological Sciences Volume 16, Numbers 1-2, 33-37, DOI: 10.1007/BF02229072
  • Pathophysiology of Status Epilepticus Induced by Pilocarpine, central nervous system agents in medical chemistry, 2007, vol. 7, no. 1

External links

v · d · eOphthalmologicals: antiglaucoma preparations and miotics (S01E)
Sympathomimetics
Parasympathomimetics
muscarinic
Aceclidine • Pilocarpine
muscarinic/nicotinic
Carbonic anhydrase inhibitors/
(sulfonamides)
Beta blocking agents
Prostaglandin analogues (F2α)
Bimatoprost • Latanoprost • Tafluprost • Travoprost • Unoprostone
Other agents

M: EYE

anat(g/a/p)/phys/devp/prot

noco/cong/tumr, epon

proc, drug(S1A/1E/1F/1L)

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Look at other dictionaries:

  • PILOCARPINE — De formule brute C11H1622, la pilocarpine est un alcaloïde extrait des feuilles de jaborandi, Pilocarpus microphyllus , de la famille des rutacées. C’est un arbuste grêle, à petites feuilles, qui se trouve à l’état sauvage au Brésil. Il existe de …   Encyclopédie Universelle

  • Pilocarpine — La structure de la pilocarpine, un alcaloïde. Général Nom IUPAC …   Wikipédia en Français

  • Pilocarpine — Pi lo*car pine, n. [From NL. {Pilocarpus pennatifolius} jaborandi; L. pilus hair + Gr. karpo s fruit: cf. F. pilocarpine.] (Chem.) An alkaloid extracted from jaborandi ({Pilocarpus pennatifolius}) as a white amorphous or crystalline substance… …   The Collaborative International Dictionary of English

  • pilocarpine — [pī΄lō kär′pēn΄, pī΄lō kär′pin; pil΄ō kär′pēn΄, pil΄ōkär′pin] n. [< ModL Pilocarpus, genus name (< Gr pilos, felt + karpos, fruit: see PILE2 & CARPO ) + INE3] an alkaloid, C11H16N2O2, extracted from the leaves of the jaborandi plant and… …   English World dictionary

  • pilocarpine — An alkaloid obtained from the leaves of Pilocarpus; Microphyllus or P. jaborandi (family Rutaceae), shrubs of the West Indies and tropical America; a parasympathomimetic agent used as a diaphoretic, sialogogue, and stimulant of intestinal… …   Medical dictionary

  • pilocarpine — (entrée créée par le supplément) (pi lo kar pi n ) s. f. Terme de chimie. Sorte d alcaloïde végétal. •   M. Hardy s est proposé d isoler, s il était possible, le principe actif de la plante [le jaborandi] ; l étude chimique qu il a ainsi… …   Dictionnaire de la Langue Française d'Émile Littré

  • pilocarpine — n. a parasympathomimetic drug administered as eye drops or gel to reduce the pressure inside the eye in glaucoma (see miotic). It is also administered orally to treat dry mouth; side effects may include headache, frequent urination, and sweating …   The new mediacal dictionary

  • pilocarpine — A drug used to increase salivation in people who have dry mouth caused by opioids or radiation therapy. Pilocarpine belongs to the family of drugs called alkaloids …   English dictionary of cancer terms

  • pilocarpine hydrochloride — [USP] the monohydrochloride salt of pilocarpine, applied topically to the eye in the treatment of glaucoma or to counteract the effects of cycloplegics and mydriatics following examination or surgery; also administered orally in the treatment of… …   Medical dictionary

  • pilocarpine nitrate — [USP] the nitrate salt of pilocarpine, having the same actions and ophthalmic uses as the hydrochloride salt …   Medical dictionary

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