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Identification
NamePilocarpine
Accession NumberDB01085  (APRD00382)
TypeSmall Molecule
GroupsApproved
Description

A slowly hydrolyzed muscarinic agonist with no nicotinic effects. Pilocarpine is used as a miotic and in the treatment of glaucoma. [PubChem]

Structure
Thumb
Synonyms
SynonymLanguageCode
(3S-cis)-3-Ethyldihydro-4-[(1-methyl-1H-imidazol-5-yl)methyl]-2(3H)-furanoneNot AvailableNot Available
(3S,4R)-3-Ethyldihydro-4-((1-methyl-1H-imidazol-5-yl)methyl)-2(3H)-furanoneNot AvailableNot Available
PilocarpineNot AvailableNot Available
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Pilocarpine Hydrochloridetablet, film coated5 mgoralActavis Elizabeth LLC2011-09-13Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Pilocarpine Hydrochloridetablet, film coated7.5 mgoralActavis Elizabeth LLC2011-09-13Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Pilocarpine Hydrochloridesolution/ drops10 mg/mLconjunctivalRebel Distributors Corp2010-06-22Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Pilocarpine Hydrochloridesolution40 mgophthalmicREMEDYREPACK INC.2013-04-15Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Pilocarpine Hydrochloridesolution10 mg/mLophthalmicFalcon Pharmaceuticals, Ltd.1996-02-21Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Pilocarpine Hydrochloridesolution20 mg/mLophthalmicFalcon Pharmaceuticals, Ltd.1996-02-21Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Pilocarpine Hydrochloridesolution40 mg/mLophthalmicFalcon Pharmaceuticals, Ltd.1996-02-21Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Salagentablet, film coated5 mgoralEisai Inc.1994-03-22Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Salagentablet, film coated7.5 mgoralEisai Inc.1994-03-22Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Pilocarpine Hydrochloridetablet5 mgoralRoxane Laboratories, Inc2004-12-222016-03-11Us 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Pilocarpine Hydrochloridetablet, film coated7.5 mgoralGlobal Pharmaceuticals, Division of Impax Laboratories, Inc.2007-05-01Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Pilocarpine Hydrochloridetablet, film coated5 mgoralGlobal Pharmaceuticals, Division of Impax Laboratories, Inc.2007-05-01Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Pilocarpine Hydrochloridetablet, film coated5 mgoralKAISER FOUNDATION HOSPITALS2014-05-29Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Pilocarpine Hydrochloridetablet, film coated5 mgoralLannett Company, Inc.2006-01-31Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Pilocarpine Hydrochloridetablet, film coated7.5 mgoralLannett Company, Inc.2009-08-10Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Pilocarpine Hydrochloridetablet5 mgoralRebel Distributors Corp2006-03-31Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Pilocarpine Hydrochloridetablet, film coated5 mgoralPhysicians Total Care, Inc.2011-07-21Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Pilocarpine Hydrochloridetablet, film coated5 mgoralCore Pharma, Llc2004-11-16Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Over the Counter ProductsNot Available
International Brands
NameCompany
DiocarpineNot Available
MiocarpineNot Available
PilostatNot Available
PiloviscNot Available
TimpiloNot Available
Brand mixtures
Brand NameIngredients
E-Pilo 1 Ophthalmic SolutionEpinephrine bitartrate + Pilocarpine hydrochloride
E-Pilo 2 Ophthalmic SolutionEpinephrine bitartrate + Pilocarpine hydrochloride
E-Pilo 4 Ophthalmic SolutionEpinephrine Bitartrate + Pilocarpine Hydrochloride
E-Pilo 6 Ophthalmic SolutionEpinephrine Bitartrate + Pilocarpine Hydrochloride
E-Pilo-1 Oph SolnEpinephrine Bitartrate + Pilocarpine Hydrochloride
E-Pilo-2 Oph SolnEpinephrine Bitartrate + Pilocarpine Hydrochloride
E-Pilo-4 Oph SolnEpinephrine Bitartrate + Pilocarpine Hydrochloride
E-Pilo-6 Oph SolnEpinephrine Bitartrate + Pilocarpine Hydrochloride
Timpilo 2Pilocarpine Hydrochloride + Timolol Maleate
Timpilo 4Pilocarpine Hydrochloride + Timolol Maleate
Salts
Name/CASStructureProperties
Pilocarpine Hydrochloride
Thumb
  • InChI Key: RNAICSBVACLLGM-GNAZCLTHSA-N
  • Monoisotopic Mass: 244.097855505
  • Average Mass: 244.718
DBSALT000307
Categories
CAS number54-71-7
WeightAverage: 208.2569
Monoisotopic: 208.121177766
Chemical FormulaC11H16N2O2
InChI KeyQCHFTSOMWOSFHM-WPRPVWTQSA-N
InChI
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
IUPAC Name
(3S,4R)-3-ethyl-4-[(1-methyl-1H-imidazol-5-yl)methyl]oxolan-2-one
SMILES
CC[C@H]1[C@@H](CC2=CN=CN2C)COC1=O
Taxonomy
DescriptionThis compound 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
  • Pilocarpine
  • Alkaloid or derivatives
  • N-substituted imidazole
  • Gamma butyrolactone
  • Heteroaromatic compound
  • Oxolane
  • Imidazole
  • Azole
  • Lactone
  • Carboxylic acid ester
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Pharmacology
IndicationFor the treatment of radiation-induced dry mouth (xerostomia) and symptoms of dry mouth in patients with Sjögrens syndrome.
PharmacodynamicsPilocarpine is a choline ester miotic and a positively charged quaternary ammonium compound. Pilocarpine, in appropriate dosage, can increase secretion by the exocrine glands. The sweat, salivary, lacrimal, gastric, pancreatic, and intestinal glands and the mucous cells of the respiratory tract may be stimulated. When applied topically to the eye as a single dose it causes miosis, spasm of accommodation, and may cause a transitory rise in intraocular pressure followed by a more persistent fall. Dose-related smooth muscle stimulation of the intestinal tract may cause increased tone, increased motility, spasm, and tenesmus. Bronchial smooth muscle tone may increase. The tone and motility of urinary tract, gallbladder, and biliary duct smooth muscle may be enhanced. Pilocarpine may have paradoxical effects on the cardiovascular system. The expected effect of a muscarinic agonist is vasodepression, but administration of pilocarpine may produce hypertension after a brief episode of hypotension. Bradycardia and tachycardia have both been reported with use of pilocarpine.
Mechanism of actionPilocarpine 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.
AbsorptionThere 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
Volume of distributionNot Available
Protein bindingNot Available
Metabolism

Possibly occurs at the neuronal synapses and in the plasma

Route of eliminationNot Available
Half life0.76 hours
ClearanceNot Available
ToxicityNot Available
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9816
Blood Brain Barrier+0.9758
Caco-2 permeable+0.6202
P-glycoprotein substrateNon-substrate0.5806
P-glycoprotein inhibitor INon-inhibitor0.8457
P-glycoprotein inhibitor IINon-inhibitor0.9432
Renal organic cation transporterNon-inhibitor0.6467
CYP450 2C9 substrateNon-substrate0.8408
CYP450 2D6 substrateNon-substrate0.9116
CYP450 3A4 substrateNon-substrate0.6665
CYP450 1A2 substrateNon-inhibitor0.9045
CYP450 2C9 substrateNon-inhibitor0.8732
CYP450 2D6 substrateNon-inhibitor0.9231
CYP450 2C19 substrateNon-inhibitor0.9026
CYP450 3A4 substrateInhibitor0.7961
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8682
Ames testNon AMES toxic0.6957
CarcinogenicityNon-carcinogens0.9166
BiodegradationNot ready biodegradable0.6808
Rat acute toxicity2.6826 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9432
hERG inhibition (predictor II)Non-inhibitor0.9009
Pharmacoeconomics
ManufacturersNot Available
Packagers
Dosage forms
FormRouteStrength
Solutionophthalmic10 mg/mL
Solutionophthalmic20 mg/mL
Solutionophthalmic40 mg
Solutionophthalmic40 mg/mL
Solution/ dropsconjunctival10 mg/mL
Tabletoral5 mg
Tablet, film coatedoral5 mg
Tablet, film coatedoral7.5 mg
Prices
Unit descriptionCostUnit
Pilopine HS 4% Gel 4 gm Tube64.08USD tube
Isopto Carpine 4% Solution 15ml Bottle37.5USD bottle
Isopto Carpine 4% Solution 30ml Bottle36.99USD bottle
Isopto Carpine 1% Solution 15ml Bottle36.37USD bottle
Isopto Carpine 2% Solution 15ml Bottle36.36USD bottle
Pilocarpine HCl 2% Solution 15ml Bottle35.01USD bottle
Isopto Carpine 2% Solution 30ml Bottle34.99USD bottle
Pilocarpine HCl 1% Solution 15ml Bottle32.24USD bottle
Pilocar 6% Solution 15ml Bottle15.99USD bottle
Pilopine hs 4% eye gel15.24USD g
Pilocar 4% Solution 15ml Bottle14.99USD bottle
Pilocar 1% Solution 15ml Bottle13.99USD bottle
Pilocar 2% Solution 15ml Bottle13.99USD bottle
Pilocar 0.5% Solution 15ml Bottle12.99USD bottle
Pilocarpine nitrate crystal9.85USD g
Pilocarpine hcl crystals8.19USD g
Pilocarpine 1% eye drops2.88USD ml
Pilocarpine 2% eye drops2.88USD ml
Pilocarpine 4% eye drops2.88USD ml
Pilopine Hs 4 % Gel2.81USD g
Salagen 7.5 mg tablet2.48USD tablet
Isopto carpine 4% eye drops2.37USD ml
Isopto carpine 2% eye drops2.26USD ml
Isopto carpine 1% eye drops2.21USD ml
Salagen 5 mg tablet2.14USD tablet
Pilocarpine hcl 7.5 mg tablet1.99USD tablet
Pilocarpine hcl 5 mg tablet1.55USD tablet
Salagen 5 mg Tablet1.23USD tablet
Pilocarpine 6% eye drops0.87USD ml
Piloptic-6 eye drops0.87USD ml
Piloptic-3 eye drops0.71USD ml
Pilocarpine 3% eye drops0.53USD ml
Pilocarpine 0.5% eye drops0.43USD ml
Isopto Carpine 4 % Solution0.3USD ml
Isopto Carpine 2 % Solution0.27USD ml
Isopto Carpine 1 % Solution0.23USD ml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point204-205 °CPhysProp
water solubility1E+006 mg/L (at 25 °C)SEIDELL,A (1941)
logP1.1Not Available
pKa6.78Not Available
Predicted Properties
PropertyValueSource
Water Solubility2.07 mg/mLALOGPS
logP1.15ALOGPS
logP0.95ChemAxon
logS-2ALOGPS
pKa (Strongest Basic)6.61ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area44.12 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity56.53 m3·mol-1ChemAxon
Polarizability22.34 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
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.

US5059531
General ReferenceNot Available
External Links
ATC CodesN07AX01S01EB01
AHFS Codes
  • 12:04.00
  • 52:20.00
  • 92:02.00*
PDB EntriesNot Available
FDA labelDownload (160 KB)
MSDSDownload (73.3 KB)
Interactions
Drug Interactions
Drug
AripiprazoleCYP3A4 Inhibitors (Weak) may increase the serum concentration of ARIPiprazole.
DofetilideCYP3A4 Inhibitors (Weak) may increase the serum concentration of Dofetilide.
HydrocodoneCYP3A4 Inhibitors (Weak) may increase the serum concentration of Hydrocodone.
LomitapideCYP3A4 Inhibitors (Weak) may increase the serum concentration of Lomitapide.
PimozideCYP3A4 Inhibitors (Weak) may increase the serum concentration of Pimozide.
Food InteractionsNot Available

Targets

1. Muscarinic acetylcholine receptor M3

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: agonist

Components

Name UniProt ID Details
Muscarinic acetylcholine receptor M3 P20309 Details

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. Epub 2009 Jun 4. Pubmed
  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. Epub 2008 Sep 29. Pubmed

2. Muscarinic acetylcholine receptor M1

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: agonist

Components

Name UniProt ID Details
Muscarinic acetylcholine receptor M1 P11229 Details

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. Pubmed
  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. Pubmed
  3. 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. Epub 2008 Sep 29. Pubmed

3. Muscarinic acetylcholine receptor M2

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: agonist

Components

Name UniProt ID Details
Muscarinic acetylcholine receptor M2 P08172 Details

References:

  1. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed
  2. Moreno-Vinasco L, Verbout NG, Fryer AD, Jacoby DB: Retinoic acid prevents virus-induced airway hyperreactivity and M2 receptor dysfunction via anti-inflammatory and antiviral effects. Am J Physiol Lung Cell Mol Physiol. 2009 Aug;297(2):L340-6. Epub 2009 May 22. Pubmed
  3. 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. Epub 2008 Sep 29. Pubmed

Enzymes

1. Cytochrome P450 2A6

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate inhibitor

Components

Name UniProt ID Details
Cytochrome P450 2A6 P11509 Details

References:

  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed

2. Cytochrome P450 2E1

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Cytochrome P450 2E1 P05181 Details

References:

  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed

3. Cytochrome P450 3A4

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate inhibitor

Components

Name UniProt ID Details
Cytochrome P450 3A4 P08684 Details

References:

  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed

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Drug created on June 13, 2005 07:24 / Updated on September 16, 2013 17:13