Pilocarpine

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Pilocarpine
Clinical data
Trade namesPilopine HS, others
AHFS/Drugs.comMonograph
MedlinePlusa608039
License data
Pregnancy
category
  • AU: B3
Routes of
administration		Topical eye drops, by mouth
Drug class
ATC code
Legal status
Legal status
Pharmacokinetic data
Elimination half-life0.76 hours (5 mg), 1.35 hours (10 mg)[3]
Excretionurine
Identifiers
  • (3S,4R)-3-Ethyl-4-((1-methyl-1H-imidazol-5-yl)methyl)dihydrofuran-2(3H)-one
JSmol)
SMILES
  • O=C2OC[C@H](Cc1n(cnc1)C)[C@@H]2CC
  • InChI=1S/C11H16N2O2/c1-3-10-8(6-15-11(10)14)4-9-5-12-7-13(9)2/h5,7-8,10H,3-4,6H2,1-2H3/t8-,10-/m0/s1 checkY
  • Key:QCHFTSOMWOSFHM-WPRPVWTQSA-N checkY
  (verify)

Pilocarpine, sold under the brand name Pilopine HS among others, is a

Sjögren syndrome or radiation therapy.[9]

Common side effects of the eye drops include irritation of the eye, increased tearing, headache, and blurry vision.

aqueous humor to drain from the eye.[1]

Pilocarpine was isolated in 1874 by Hardy and Gerrard and has been used to treat glaucoma for more than 100 years.[12][13][14] It is on the World Health Organization's List of Essential Medicines.[15] It was originally made from the South American plant Pilocarpus.[12]

Medical uses

Pilocarpine stimulates the secretion of large amounts of

Sjögren syndrome, but also as a side effect of radiation therapy for head and neck cancer.[17]

It may be used to help differentiate Adie syndrome from other causes of unequal pupil size.[18][19]

It may be used to treat a form of

dry eye called aqueous deficient dry eye (ADDE)[20]

Surgery

Pilocarpine is sometimes used immediately before certain types of corneal grafts and cataract surgery.[21][22] It is also used prior to YAG laser iridotomy. In ophthalmology, pilocarpine is also used to reduce symptomatic glare at night from lights when the patient has undergone implantation of phakic intraocular lenses; the use of pilocarpine would reduce the size of the pupils, partially relieving these symptoms.[dubious – discuss] The most common concentration for this use is pilocarpine 1%.[citation needed] Pilocarpine is shown to be just as effective as apraclonidine in preventing intraocular pressure spikes after laser trabeculoplasty.[23]

Presbyopia

In 2021, the US Food and Drug Administration (FDA) approved pilocarpine hydrochloride as an eye drop treatment for presbyopia, age-related difficulty with near-in vision. It works by causing the pupils to constrict, increasing depth of field, similar to the effect of pinhole glasses.[24][2]

Other

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.[25]

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 salivation, sweating, bronchial mucus secretion, bronchospasm, bradycardia, vasodilation, and diarrhea. Eye drops can result in brow ache and chronic use in miosis. It can also cause temporary blurred vision or darkness of vision, temporary shortsightedness, hyphema
and retinal detachment.

Pharmacology

Pilocarpine is a drug that acts as a muscarinic receptor agonist. It acts on a subtype of muscarinic receptor (

accommodative spasm) it causes the eye's lens to thicken and move forward within the eye. This movement causes the iris (which is located immediately in front of the lens) to also move forward, narrowing the Anterior chamber angle. Narrowing of the anterior chamber angle increases the risk of increased intraocular pressure.[26]

Society and culture

Preparation

Plants in the genus Pilocarpus are the only known sources of pilocarpine, and commercial production is derived entirely from the leaves of Pilocarpus microphyllus (Maranham Jaborandi). This genus grows only in South America, and Pilocarpus microphyllus is native to several states in northern Brazil.[27]

Pilocarpine is extracted from the leaves of Pilocarpus microphyllus in a multi-step process : the sample is moistened with dilute sodium hydroxide to transform the alkaloid into its free-base form then extracted using chloroform or a suitable organic solvant. Pilocarpine can then be further purified by re-extracting the resulting solution with aqueous sulfuric acid then readjusting the pH to basic using ammonia and a final extraction by chloroform.[28][29][30]

It can also be synthesized from 2-ethyl-3-carboxy-2-butyrolactone in a 8 steps process from the acyl chloride (by treatment with thionyl chloride) via a Arndt–Eistert reaction with diazomethane then by treatment with potassium phthalimide and potassium thiocyanate.[4]

Brand names

Pilocarpine is available under several brand 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), Timpilo (Merck Frosst), and Vuity (AbbVie).

Research

Pilocarpine is used to induce chronic

IgA
antibodies.

References

  1. ^ a b c d e f g "Pilocarpine". The American Society of Health-System Pharmacists. Archived from the original on 28 December 2016. Retrieved 8 December 2016.
  2. ^ a b "Vuity- pilocarpine hydrochloride solution/ drops". DailyMed. Retrieved 19 December 2021.
  3. PMID 15243470
    .
  4. ^
    ISBN 978-0-444-52166-8
    .
  5. ISBN 978-1-284-16754-2
    .
  6. ISBN 9789241547659
    .
  7. ^ "Glaucoma and ocular hypertension. NICE guideline 81". National Institute for Health and Care Excellence. November 2017. Retrieved 19 September 2019. Ocular hypertension... alternative options include carbonic anhydrase inhibitors such as brinzolamide or dorzolamide, a topical sympathomimetic such as apraclonidine or brimonidine tartrate, or a topical miotic such as pilocarpine, given either as monotherapy or as combination therapy.
  8. S2CID 73438590
    . Pilocarpine is no longer routinely used for long term IOP control due to a poor side effect profile
  9. ISBN 9781284057560
    .
  10. ^ "Pilocarpine ophthalmic Use During Pregnancy". Drugs.com. Archived from the original on 28 December 2016. Retrieved 28 December 2016.
  11. ISBN 9780857111562
    .
  12. ^
    ISBN 978-0-471-89979-2. Archived
    from the original on 29 December 2016.
  13. PMID 1811739
    .
  14. PMID 397371
    .
  15. hdl:10665/325771
    . WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO.
  16. ^ "Pilocarpine". MedLinePlus. U.S. National Library of Medicine. Archived from the original on 6 March 2010.
  17. PMID 26867879
    .
  18. ISBN 978-0-7020-5574-4
    .
  19. ISBN 978-0-7506-9322-6
    .
  20. OCLC 960165358
    .
  21. hdl:1887/50484
    .
  22. ISBN 978-93-5025-175-1
    .
  23. PMID 28231380
    .
  24. PMID 35268476
    .
  25. ISBN 978-3-7438-2141-5
    .
  26. ISBN 978-0-7020-5193-7
    .
  27. S2CID 26058596
    .
  28. PMID 12711138
    .
  29. PMID 18719522
    .
  30. ISBN 978-1-84076-103-0.{{cite book}}: CS1 maint: DOI inactive as of November 2024 (link
    )
  31. doi:10.14232/phd.9734
    .
  32. S2CID 36849482
    .
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