Structure via PubChem · Public domain (PubChem)
pilocarpine
Sign in to saveAlso known as pilocarpine hydrochloride, pilocarpine nitrate, pilokarpin, Salagen®, (3S-cis)-3-ethyldihydro-4-[(1-methyl-1H-imidazol-5-yl)methyl]-2(3H)-furanone, (3S,4R)-3-ethyldihydro-4-((1-methyl-1H-imidazol-5-yl)methyl)-2(3H)-furanone, (+)-pilocarpine, (3S,4R)-3-Ethyldihydro-4-((1-methyl-1H-imidazol-5-yl)methyl)-2(3H)-furanone
Pilocarpine is a lactone alkaloid originally extracted from plants of the Pilocarpus genus. It is used as a medication to reduce pressure inside the eye and treat dry mouth. As an eye drop it is used to manage angle closure glaucoma until surgery can be performed, ocular hypertension, primary open angle glaucoma, and to constrict the pupil after dilation. However, due to its side effects, it is no longer typically used for long-term management. Onset of effects with the drops is typically within an hour and lasts for up to a day. By mouth it is used for dry mouth as a result of Sjögren's disea
Key facts
- Drug.Watchedfields
- changed
- Drug.verifiedrevid
- 464206617
- Drug.image
- Pilocarpine.svg
- Drug.image_class
- skin-invert-image
- Drug.width
- 180
- Drug.image2
- Pilocarpine ball-and-stick model.png
- Drug.image_class2
- bg-transparent
- Drug.tradename
- Isopto Carpine, Salagen, others
- Drug.MedlinePlus
- a608039
- Drug.DailyMedID
- Pilocarpine
- Drug.pregnancy_AU
- B3
- Drug.routes_of_administration
- Ophthalmic, by mouth
- Drug.ATC_prefix
- N07
- Drug.ATC_suffix
- AX01
- Drug.legal_AU
- S4
- Drug.legal_UK
- POM
- Drug.legal_US
- Rx-only
- Drug.elimination_half life
- 0.76 hours (5 mg), 1.35 hours (10 mg)
via Wikipedia infobox
Chemical data
- Formula
- C11H16N2O2
- Molecular weight
- 208.26 g/mol
- IUPAC name
- (3S,4R)-3-ethyl-4-[(3-methylimidazol-4-yl)methyl]oxolan-2-one
- SMILES
- CC[C@H]1[C@H](COC1=O)CC2=CN=CN2C
- InChIKey
- QCHFTSOMWOSFHM-WPRPVWTQSA-N
- XLogP
- 1.1
- Polar surface area
- 44.1 Ų
- H-bond donors
- 0
- H-bond acceptors
- 3
- Formal charge
- 0
via PubChem
Research
10,651 papers- The pilocarpine paradox.Journal of glaucoma · 1996
- Pilocarpine.Ophthalmology · 1981
- Pilocarpine psychosis.Psychosomatics · 2005
- Oral pilocarpine: a review of its pharmacological properties and clinical potential in xerostomia.Drugs · 1995
- Vuity - pilocarpine ophthalmic solution for presbyopia.The Medical letter on drugs and therapeutics · 2022
via PubMed
Wikidata facts
- Mass
- 208.121
Show 5 more facts
- Commons category
- Pilocarpine
- chemical formula
- C₁₁H₁₆N₂O₂
- isomeric SMILES
- CC[C@H]1[C@H](COC1=O)CC2=CN=CN2C
- canonical SMILES
- CCC1C(COC1=O)CC2=CN=CN2C
- defined daily dose
- 10
via Wikidata · CC0
~7 min read
Article
12 sectionsContents
- Medical uses
- Surgery
- Presbyopia
- Other
- Adverse effects
- Pharmacology
- Society and culture
- Preparation
- Brand names
- Research
- References
- External links
Pilocarpine is a lactone alkaloid originally extracted from plants of the Pilocarpus genus. It is used as a medication to reduce pressure inside the eye and treat dry mouth. As an eye drop it is used to manage angle closure glaucoma until surgery can be performed, ocular hypertension, primary open angle glaucoma, and to constrict the pupil after dilation. However, due to its side effects, it is no longer typically used for long-term management. Onset of effects with the drops is typically within an hour and lasts for up to a day. By mouth it is used for dry mouth as a result of Sjögren's disease or radiation therapy.
Common side effects of the eye drops include irritation of the eye, increased tearing, headache, and blurry vision. Other side effects include allergic reactions and retinal detachment. Use is generally not recommended during pregnancy. Pilocarpine is in the miotics family of medication. It works by activating cholinergic receptors of the muscarinic type which cause the trabecular meshwork to open and the aqueous humor to drain from the eye.