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Record Information
Version2.0
Creation Date2009-07-21 20:28:20 UTC
Update Date2014-12-24 20:25:54 UTC
Accession NumberT3D2979
Identification
Common NamePilocarpine
ClassSmall Molecule
DescriptionPilocarpine is only found in individuals that have used or taken this drug. It is a slowly hydrolyzed muscarinic agonist with no nicotinic effects. Pilocarpine is used as a miotic and in the treatment of glaucoma. [PubChem]Pilocarpine is a cholinergic parasympathomimetic agent. It increase secretion by the exocrine glands, and produces contraction of the iris sphincter muscle and ciliary muscle (when given topically to the eyes) by mainly stimulating muscarinic receptors.
Compound Type
  • Cholinergic Agent
  • Drug
  • Ester
  • Ether
  • Metabolite
  • Miotic
  • Muscarinic Agonist
  • Organic Compound
  • Synthetic Compound
Chemical Structure
Thumb
Synonyms
Synonym
(3S,4R)-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
Adsorbocarpine
beta-Pilocarpine hydrochloride
Diocarpine
Miocarpine
Pilocarpin
Pilocarpine chloride
Pilocarpine HCl
Pilocarpine hydrochloride
Pilocarpine monohydrochloride
Pilocarpine muriate
Pilokarpin
Pilokarpin monohydrochloride
Pilostat
Pilovisc
Salagen
Spersacarpine
Spersacarpine hydrochloride
Timpilo
Chemical FormulaC11H16N2O2
Average Molecular Mass208.257 g/mol
Monoisotopic Mass208.121 g/mol
CAS Registry Number54-71-7
IUPAC Name(3S,4R)-3-ethyl-4-[(1-methyl-1H-imidazol-5-yl)methyl]oxolan-2-one
Traditional Namepilocarpine
SMILES[H][C@]1(CC2=CN=CN2C)COC(=O)[C@@]1([H])CC
InChI IdentifierInChI=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
InChI KeyInChIKey=QCHFTSOMWOSFHM-WPRPVWTQSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as alkaloids and derivatives. These are naturally occurring chemical compounds that contain mostly basic nitrogen atoms. This group also includes some related compounds with neutral and even weakly acidic properties. Also some synthetic compounds of similar structure are attributed to alkaloids. In addition to carbon, hydrogen and nitrogen, alkaloids may also contain oxygen, sulfur and more rarely other elements such as chlorine, bromine, and phosphorus.
KingdomOrganic compounds
Super ClassAlkaloids and derivatives
ClassNot Available
Sub ClassNot Available
Direct ParentAlkaloids and derivatives
Alternative Parents
Substituents
  • Alkaloid or derivatives
  • Gamma butyrolactone
  • N-substituted imidazole
  • Azole
  • Imidazole
  • Heteroaromatic compound
  • Tetrahydrofuran
  • Carboxylic acid ester
  • Lactone
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Carbonyl group
  • Organonitrogen compound
  • Organooxygen compound
  • Organic oxygen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point204-205°C
Boiling PointNot Available
Solubility1E+006 mg/L (at 25°C)
LogP1.1
Predicted Properties
PropertyValueSource
Water Solubility2.07 g/LALOGPS
logP1.15ALOGPS
logP0.95ChemAxon
logS-2ALOGPS
pKa (Strongest Basic)6.61ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area44.12 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity56.53 m³·mol⁻¹ChemAxon
Polarizability22.34 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9500000000-dadfea39cdf9ef51bb38JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableJSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-0a4i-1090000000-2fd25e6044f26134a0aaJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-0002-9400000000-20a06057a274f78a95cdJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0090000000-defeea6e1be7da5df19cJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-0002-9000000000-cb6dd4c8fd9faf642a5bJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - 50V, Positivesplash10-0002-9100000000-a58d77d501ea8e44d237JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-1090000000-90bbfd0f103bf2df2350JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-0a4j-5290000000-d69679a4b81e0442184fJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-0a4i-1190000000-b781ed76499fdad467c3JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-1090000000-a96142a7f969311e7a5bJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-0a4j-7790000000-914d8ed86ae8535d11faJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-0002-9300000000-ad4d9d6aa3e5e27b8fc3JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0090000000-2df89b2b774b30adf514JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0090000000-bb2a8fea255c0847828fJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-0002-9300000000-3efb8b2920ff65a813d0JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-052b-9580000000-49f5b565991796fac6e9JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0090000000-6baeabdd0794d63b5d1dJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - 50V, Positivesplash10-0002-9100000000-2a0733ac2670b486ceadJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-1190000000-7cb82eee0859eb856641JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - 50V, Positivesplash10-0002-9100000000-9d497ccde6e92e5082acJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0690000000-786fb6f080bd545dbc39JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0cka-1920000000-56d387d24bcc6e2e3637JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9300000000-e57c52a1b125f83b1903JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0190000000-fc43dc1afe8440f3e607JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0bt9-1930000000-b7fcb5510042754cd666JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4j-9800000000-0f44a4b4787f9e119567JSpectraViewer
Toxicity Profile
Route of ExposureOral ; eye contact. There was a decrease in the rate of absorption of pilocarpine from SALAGEN Tablets when taken with a high fat meal by 12 healthy male volunteers
Mechanism of ToxicityPilocarpine is a cholinergic parasympathomimetic agent. It increase secretion by the exocrine glands, and produces contraction of the iris sphincter muscle and ciliary muscle (when given topically to the eyes) by mainly stimulating muscarinic receptors.
MetabolismPossibly occurs at the neuronal synapses and in the plasma Half Life: 0.76 hours
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesFor the treatment of radiation-induced dry mouth (xerostomia) and symptoms of dry mouth in patients with Sjögrens syndrome.
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentOverdosage should be treated with atropine titration (0. 5 mg to 1. 0 mg given subcutaneously or intravenously) and supportive measures to maintain respiration and circulation. Epinephrine (0. 3 mg to 1. 0 mg, subcutaneously or intramuscularly) may also be of value in the presence of severe cardiovascular depression or bronchoconstriction. (2)
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDDB01085
HMDB IDHMDB15217
PubChem Compound ID5910
ChEMBL IDCHEMBL611494
ChemSpider ID5699
KEGG IDC07474
UniProt IDNot Available
OMIM ID
ChEBI ID39462
BioCyc IDNot Available
CTD IDNot Available
Stitch IDPilocarpine
PDB ID9PL
ACToR IDNot Available
Wikipedia LinkPilocarpine
References
Synthesis Reference

Gerhard R. Reuther, “Process for the preparation of pilocarpine from in vitro cultures of pilocarpus.” U.S. Patent US5059531, issued June, 1987.

MSDSLink
General References
  1. Drugs.com [Link]
  2. RxList: The Internet Drug Index (2009). [Link]
Gene Regulation
Up-Regulated GenesNot Available
Down-Regulated GenesNot Available

Targets

General Function:
Phosphatidylinositol phospholipase c activity
Specific Function:
The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the action of G proteins. Primary transducing effect is Pi turnover.
Gene Name:
CHRM1
Uniprot ID:
P11229
Molecular Weight:
51420.375 Da
Binding/Activity Constants
TypeValueAssay TypeAssay Source
Inhibitory0.012 uMNot AvailableBindingDB 50008072
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [17016423 ]
  3. Mei L, Lai J, Yamamura HI, Roeske WR: Pharmacologic comparison of selected agonists for the M1 muscarinic receptor in transfected murine fibroblast cells (B82). J Pharmacol Exp Ther. 1991 Feb;256(2):689-94. [1704434 ]
  4. Jakubik J, Bacakova L, El-Fakahany EE, Tucek S: Positive cooperativity of acetylcholine and other agonists with allosteric ligands on muscarinic acetylcholine receptors. Mol Pharmacol. 1997 Jul;52(1):172-9. [9224827 ]
General Function:
Receptor activity
Specific Function:
The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the action of G proteins. Primary transducing effect is Pi turnover.
Gene Name:
CHRM3
Uniprot ID:
P20309
Molecular Weight:
66127.445 Da
References
  1. Sykes DA, Dowling MR, Charlton SJ: Exploring the mechanism of agonist efficacy: a relationship between efficacy and agonist dissociation rate at the muscarinic M3 receptor. Mol Pharmacol. 2009 Sep;76(3):543-51. doi: 10.1124/mol.108.054452. Epub 2009 Jun 4. [19498041 ]
  2. Figueroa KW, Griffin MT, Ehlert FJ: Selectivity of agonists for the active state of M1 to M4 muscarinic receptor subtypes. J Pharmacol Exp Ther. 2009 Jan;328(1):331-42. doi: 10.1124/jpet.108.145219. Epub 2008 Sep 29. [18824613 ]
  3. Jakubik J, Bacakova L, El-Fakahany EE, Tucek S: Positive cooperativity of acetylcholine and other agonists with allosteric ligands on muscarinic acetylcholine receptors. Mol Pharmacol. 1997 Jul;52(1):172-9. [9224827 ]
General Function:
G-protein coupled acetylcholine receptor activity
Specific Function:
The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the action of G proteins. Primary transducing effect is adenylate cyclase inhibition. Signaling promotes phospholipase C activity, leading to the release of inositol trisphosphate (IP3); this then triggers calcium ion release into the cytosol.
Gene Name:
CHRM2
Uniprot ID:
P08172
Molecular Weight:
51714.605 Da
References
  1. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [11752352 ]
  2. Jakubik J, Bacakova L, El-Fakahany EE, Tucek S: Positive cooperativity of acetylcholine and other agonists with allosteric ligands on muscarinic acetylcholine receptors. Mol Pharmacol. 1997 Jul;52(1):172-9. [9224827 ]
General Function:
Guanyl-nucleotide exchange factor activity
Specific Function:
The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the action of G proteins. Primary transducing effect is inhibition of adenylate cyclase.
Gene Name:
CHRM4
Uniprot ID:
P08173
Molecular Weight:
53048.65 Da
References
  1. Jakubik J, Bacakova L, El-Fakahany EE, Tucek S: Positive cooperativity of acetylcholine and other agonists with allosteric ligands on muscarinic acetylcholine receptors. Mol Pharmacol. 1997 Jul;52(1):172-9. [9224827 ]