Chemical Component Summary

Name(3S,4R)-3-ethyl-4-[(1-methyl-1H-imidazol-5-yl)methyl]dihydrofuran-2(3H)-one
SynonymsPILOCARPINE
Identifiers(3S,4R)-3-ethyl-4-[(3-methylimidazol-4-yl)methyl]oxolan-2-one
FormulaC11 H16 N2 O2
Molecular Weight208.257
TypeNON-POLYMER
Isomeric SMILESCC[C@H]1[C@H](COC1=O)Cc2cncn2C
InChIInChI=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
InChIKeyQCHFTSOMWOSFHM-WPRPVWTQSA-N

Chemical Details

Formal Charge0
Atom Count31
Chiral Atom Count2
Bond Count32
Aromatic Bond Count5

Drug Info: DrugBank

DrugBank IDDB01085 
NamePilocarpine
Groups
  • investigational
  • approved
DescriptionA naturally occurring alkaloid derived from the _Pilocarpus_ plants, pilocarpine is a muscarinic acetylcholine agonist.[A262016, A262036] Pilocarpine is associated with parasympathomimetic effects by selectively working on muscarinic receptors.[A262036] Pilocarpine is used to treat dry mouth and various ophthalmic conditions, including elevated intraocular pressure and glaucoma. The usage of glaucoma by pilocarpine dates back to 1875.[A262041]
Synonyms
  • SYNCARPINE
  • Pilocarpina
  • Pilocarpine pamoate
  • Pilocarpine hydrochloride
  • PILOKARPIN
Brand Names
  • E-pilo 4 Ophthalmic Solution
  • Pilocarpine Hydrochloride 1% - Liq Oph
  • Pilocarpine
  • PMS-pilocarpine 2%
  • E-pilo 2 Ophthalmic Solution
IndicationPilocarpine oral tablets are indicated for the treatment of dry mouth caused by Sjogren's Syndrome or radiotherapy for cancer of the head and neck.[L48566] Pilocarpine ophthalmic formulations are used to treat presbyopia in adults,[L48556, L48631] reduce elevated intraocular pressure (IOP) in patients with open-angle glaucoma or ocular hypertension, manage acute angle-closure glaucoma, prevent postoperative elevated IOP associated with laser surgery, and induce miosis.[L48561]
Categories
  • Alkaloids
  • Antiglaucoma Preparations and Miotics
  • Autonomic Agents
  • Cholinergic Agents
  • Cholinergic Agonists
ATC-Code
  • N07AX01
  • S01EB01
  • S01EB51
CAS number92-13-7

Drug Targets

NameTarget SequencePharmacological ActionActions
Muscarinic acetylcholine receptor M3MTLHNNSTTSPLFPNISSSWIHSPSDAGLPPGTVTHFGSYNVSRAAGNFS...unknownagonist
Muscarinic acetylcholine receptor M1MNTSAPPAVSPNITVLAPGKGPWQVAFIGITTGLLSLATVTGNLLVLISF...unknownagonist
Muscarinic acetylcholine receptor M2MNNSTNSSNNSLALTSPYKTFEVVFIVLVAGSLSLVTIIGNILVMVSIKV...unknownagonist
Muscarinic acetylcholine receptor M4MANFTPVNGSSGNQSVRLVTSSSHNRYETVEMVFIATVTGSLSLVTVVGN...unknownpartial agonist
Muscarinic acetylcholine receptor M5MEGDSYHNATTVNGTPVNHQPLERHRLWEVITIAAVTAVVSLITIVGNVL...unknownagonist
View More
Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682

Related Resource References

Resource NameReference
Pharos CHEMBL550
PubChem 5910
ChEMBL CHEMBL550
ChEBI CHEBI:8207
CCDC/CSD PICGEH