Record Information |
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Version | 2.0 |
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Creation Date | 2009-07-21 20:28:20 UTC |
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Update Date | 2014-12-24 20:25:54 UTC |
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Accession Number | T3D2979 |
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Identification |
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Common Name | Pilocarpine |
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Class | Small Molecule |
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Description | Pilocarpine 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. |
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Compound Type | - Cholinergic Agent
- Drug
- Ester
- Ether
- Metabolite
- Miotic
- Muscarinic Agonist
- Organic Compound
- Synthetic Compound
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Chemical Structure | |
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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 |
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Chemical Formula | C11H16N2O2 |
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Average Molecular Mass | 208.257 g/mol |
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Monoisotopic Mass | 208.121 g/mol |
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CAS Registry Number | 54-71-7 |
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IUPAC Name | (3S,4R)-3-ethyl-4-[(1-methyl-1H-imidazol-5-yl)methyl]oxolan-2-one |
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Traditional Name | pilocarpine |
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SMILES | [H][C@]1(CC2=CN=CN2C)COC(=O)[C@@]1([H])CC |
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InChI Identifier | 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 |
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InChI Key | InChIKey=QCHFTSOMWOSFHM-WPRPVWTQSA-N |
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Chemical Taxonomy |
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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. |
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Kingdom | Organic compounds |
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Super Class | Alkaloids and derivatives |
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Class | Not Available |
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Sub Class | Not Available |
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Direct Parent | Alkaloids and derivatives |
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Alternative Parents | |
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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
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Molecular Framework | Aromatic heteromonocyclic compounds |
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External Descriptors | |
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Biological Properties |
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Status | Detected and Not Quantified |
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Origin | Exogenous |
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Cellular Locations | - Cytoplasm
- Extracellular
- Membrane
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Biofluid Locations | Not Available |
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Tissue Locations | Not Available |
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Pathways | Not Available |
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Applications | Not Available |
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Biological Roles | Not Available |
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Chemical Roles | Not Available |
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Physical Properties |
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State | Solid |
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Appearance | White powder. |
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Experimental Properties | Property | Value |
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Melting Point | 204-205°C | Boiling Point | Not Available | Solubility | 1E+006 mg/L (at 25°C) | LogP | 1.1 |
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Predicted Properties | |
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Spectra |
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Spectra | Spectrum Type | Description | Splash Key | View |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-0006-9500000000-dadfea39cdf9ef51bb38 | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0a4i-0690000000-786fb6f080bd545dbc39 | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0cka-1920000000-56d387d24bcc6e2e3637 | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0006-9300000000-e57c52a1b125f83b1903 | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0a4i-0190000000-fc43dc1afe8440f3e607 | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0bt9-1930000000-b7fcb5510042754cd666 | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0a4j-9800000000-0f44a4b4787f9e119567 | JSpectraViewer |
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Toxicity Profile |
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Route of Exposure | Oral ; 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 |
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Mechanism of Toxicity | 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. |
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Metabolism | Possibly occurs at the neuronal synapses and in the plasma
Half Life: 0.76 hours |
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Toxicity Values | Not Available |
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Lethal Dose | Not Available |
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Carcinogenicity (IARC Classification) | No indication of carcinogenicity to humans (not listed by IARC). |
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Uses/Sources | For the treatment of radiation-induced dry mouth (xerostomia) and symptoms of dry mouth in patients with Sjögrens syndrome. |
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Minimum Risk Level | Not Available |
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Health Effects | Not Available |
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Symptoms | Not Available |
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Treatment | Overdosage 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) |
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Normal Concentrations |
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| Not Available |
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Abnormal Concentrations |
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| Not Available |
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External Links |
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DrugBank ID | DB01085 |
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HMDB ID | HMDB15217 |
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PubChem Compound ID | 5910 |
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ChEMBL ID | CHEMBL611494 |
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ChemSpider ID | 5699 |
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KEGG ID | C07474 |
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UniProt ID | Not Available |
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OMIM ID | |
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ChEBI ID | 39462 |
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BioCyc ID | Not Available |
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CTD ID | Not Available |
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Stitch ID | Pilocarpine |
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PDB ID | 9PL |
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ACToR ID | Not Available |
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Wikipedia Link | Pilocarpine |
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References |
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Synthesis Reference | Gerhard R. Reuther, “Process for the preparation of pilocarpine from in vitro cultures of pilocarpus.” U.S. Patent US5059531, issued June, 1987. |
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MSDS | Link |
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General References | - Drugs.com [Link]
- RxList: The Internet Drug Index (2009). [Link]
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Gene Regulation |
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Up-Regulated Genes | Not Available |
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Down-Regulated Genes | Not Available |
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