Compound: pilocarpine
SMILES: O=C1OC[C@@H]([C@@H]1CC)Cc2n(cnc2)C
InChIKey: QCHFTSOMWOSFHM-WPRPVWTQSA-N
Synonyms: pilocarpine, 92-13-7, Pilokarpin, Pilocarpol, Syncarpine, Ocusert pilo, Pilocarpin, Spersacarpine, Ocusert pilo-20, Ocusert Pilo-40, Ocusert P 20, ocucarpine, Pilocarpine muriate, Pilovisc, Pilocarpinum, Spersacarpine hydrochloride, Pilokarpin monohydrochloride, 01MI4Q9DI3, DTXSID1021162, (3S,4R)-3-ethyl-4-[(1-methyl-1H-imidazol-5-yl)methyl]oxolan-2-one, (3S,4R)-3-ethyl-4-[(3-methylimidazol-4-yl)methyl]oxolan-2-one, Imidazole-5-butyric acid, alpha-ethyl-beta-(hydroxymethyl)-1-methyl-, gamma-lactone, CHEBI:8207, DTXCID901162, (3S,4R)-3-ethyldihydro-4-((1-methyl-1H-imidazol-5-yl)methyl)-2(3H)-furanone, Hydrochloride, Pilocarpine, (3S,4R)-3-ethyl-4-((3-methylimidazol-4-yl)methyl)oxolan-2-one, (3S,4R)-3-ethyl-4-((1-methyl-1H-imidazol-5-yl)methyl)oxolan-2-one, Nitrate, Pilocarpine, RefChem:56450, CHEBI:39462, Pilocarpine Mononitrate, (3S-cis)-, Pilocarpine, Monohydrochloride, (3S-cis)-, 202-128-4, (+)-Pilocarpine, Isoptocarpine, Epicar, Pilocarpine chloride, (3S,4R)-3-ethyl-4-[(1-methyl-1H-imidazol-5-yl)methyl]dihydrofuran-2(3H)-one, (3S,4R)-3-Ethyl-4-((1-methyl-1H-imidazol-5-yl)methyl)dihydrofuran-2(3H)-one, Pilokarpol, CHEMBL550, (3S-cis)-3-Ethyldihydro-4-((1-methyl-1H-imidazol-5-yl)methyl)-2(3H)-furanone, (3S-cis)-3-ethyldihydro-4-[(1-methyl-1H-imidazol-5-yl)methyl]-2(3H)-furanone, MFCD00153042, 2(3H)-Furanone, 3-ethyldihydro-4-((1-methyl-1H-imidazol-5-yl)methyl)-, (3S,4R)-, NCGC00023339-09, Pilocarpine 100 microg/mL in Acetonitrile, (3S,4R)-3-ethyl-4-[(3-methylimidazol-4-yl)methyl]tetrahydrofuran-2-one, 2(3H)-Furanone, 3-ethyldihydro-4-[(1-methyl-1H-imidazol-5-yl)methyl]-, (3S,4R)-, Pilocarpine nitrate salt, Pilocarpine (Hydrochloride), CAS-92-13-7, HSDB 3163, Pilocarpine (JAN/USP), EINECS 202-128-4, Ocusert pilo-20 (TN), UNII-01MI4Q9DI3, Pilocaroine, Pilocarpine [USP:BAN:JAN], AI3-50523, (3S,4R)-3-ethyl-4-[(1-methylimidazol-5-yl)methyl]-3,4,5-trihydrofuran-2-one, Ocucarpine; Ocusert P 20; Ocusert Pilo, 92-13-7 (FREE BASE), Spectrum_001107, Tocris-0694, PILOCARPINE [MI], Prestwick0_000449, Prestwick1_000449, Prestwick2_000449, Prestwick3_000449, Spectrum2_001284, Spectrum3_000546, Spectrum4_000478, Spectrum5_001379, PILOCARPINE [JAN], PILOCARPINE [HSDB], PILOCARPINE [VANDF], PILOCARPINUM [HPUS], PILOCARPINE [MART.], Lopac0_000950, Lopac0_000960, SCHEMBL15146, BSPBio_000498, BSPBio_002191, GTPL305, KBioGR_000956, KBioSS_001587, PILOCARPINE [USP-RS], PILOCARPINE [WHO-DD], BIDD:GT0217, DivK1c_000358, SPBio_001287, SPBio_002437, BPBio1_000548, HY-B0726A, KBio1_000358, KBio2_001587, KBio2_004155, KBio2_006723, KBio3_001691, PILOCARPINE [ORANGE BOOK], NINDS_000358, GLXC-20879, HMS2089K17, PILOCARPINE [USP MONOGRAPH], MSK40310, Tox21_110887, BDBM50008072, EBC-26203, SBB012409, AKOS016010311, Tox21_110887_1, CCG-205031, DB01085, FP05587, SDCCGMLS-0003164.P005, SDCCGSBI-0050924.P006, IDI1_000358, NCGC00023339-03, NCGC00023339-06, NCGC00023339-07, NCGC00023339-08, NCGC00023339-10, NCGC00023339-11, NCGC00023339-12, NCGC00023339-13, NCGC00023339-14, NCGC00023339-16, NCGC00023339-27, NCGC00023339-28, BS-18966, DA-76884, NCI60_004403, ST069319, SBI-0050924.P004, CS-0013746, NS00007560, C07474, D00525, E87145, AB00053525-27, AB00053525_28, AB00053525_29, EN300-19632236, Q411461, BRD-K85090592-003-18-6, BRD-K85090592-003-19-4, BRD-K85090592-008-05-2, BRD-K85090592-008-15-1, BRD-K85090592-008-22-7, SR-01000075339-11, 102282-25-7
Theoretical properties:
molecular_formula: C11H16N2O2
molecular_weight: 208.26 g/mol
exact_mass: 208.121177757 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 0
hydrogen_bond_acceptor_count: 3
rotatable_bond_count: 3
heavy_atom_count: 15
topological_polar_surface_area: 44.1 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
physical_state: OIL OR CRYSTALS
color: OIL OR CRYSTALS
boiling_point: 260 °C @ 5 MM HG (PARTIAL CONVERSION TO ISOPILOCARPINE)
melting_point: 195-205
solubility: FREELY SOL IN ETHANOL; INSOL IN DIETHYL ETHER /HCL/
Descriptions:
pubchem: (+)-pilocarpine is the (+)-enantiomer of pilocarpine. It has a role as an antiglaucoma drug. It is an enantiomer of a (-)-pilocarpine.
chebi: The (+)-enantiomer of pilocarpine.
chembl: PILOCARPINE is a small molecule listed in the ChEMBL database and has reached clinical trial phase 4.0.
wikipedia: 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.
Pilocarpine was isolated in 1874 by Hardy and Gerrard and has been used to treat glaucoma for more than 100 years. It is on the World Health Organization's List of Essential Medicines. It was originally made from the South American plant Pilocarpus.