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Identification
Name Pilocarpine
Accession Number DB01085 (APRD00382)
Type small molecule
Groups approved
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
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
Adsorbocarpine
Beta-pilocarpine hydrochloride
Pilocarpin
Pilocarpine chloride
Pilocarpine HCl
Pilocarpine hydrochloride
Pilocarpine monohydrochloride
Pilocarpine muriate
Pilokarpin
Pilokarpin monohydrochloride
Spersacarpine
Spersacarpine hydrochloride
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Salts Not Available
Brand names
Name Company
Akarpine
Almocarpine
Ami-Pilo
Amistura P
Epicar
Isopto Carpine
Isoptocarpine
Mi-Pilo
Mi-Pilo Ophth Sol
Minims Pilocarpine
Miocarpine
Mistura P
Ocu-Carpine
Ocusert P 20
Ocusert Pilo
Ocusert Pilo-20
Ocusert Pilo-40
P.V. Carpine Liquifilm
Pilagan
Pilocar
Pilocar SMP
Pilocarpal
Pilocarpol
Pilocel
Pilokarpol
Pilomiotin
Pilopine HS
Piloptic-1
Piloptic-1/2
Piloptic-2
Piloptic-3
Piloptic-4
Piloptic-6
Pilostat
Pilovisc
Salagen
Sno Pilo
Syncarpine
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Brand mixtures
Brand Name Ingredients
E-Pilo 1 Ophthalmic Solution Epinephrine bitartrate + Pilocarpine hydrochloride
E-Pilo 2 Ophthalmic Solution Epinephrine bitartrate + Pilocarpine hydrochloride
E-Pilo 4 Ophthalmic Solution Epinephrine Bitartrate + Pilocarpine Hydrochloride
E-Pilo 6 Ophthalmic Solution Epinephrine Bitartrate + Pilocarpine Hydrochloride
E-Pilo-1 Oph Soln Epinephrine Bitartrate + Pilocarpine Hydrochloride
E-Pilo-2 Oph Soln Epinephrine Bitartrate + Pilocarpine Hydrochloride
E-Pilo-4 Oph Soln Epinephrine Bitartrate + Pilocarpine Hydrochloride
E-Pilo-6 Oph Soln Epinephrine Bitartrate + Pilocarpine Hydrochloride
Timpilo 2 Pilocarpine Hydrochloride + Timolol Maleate
Timpilo 4 Pilocarpine Hydrochloride + Timolol Maleate
Categories
  • Muscarinic Agonists
  • Miotics
  • Cholinergic Agents
CAS number 54-71-7
Weight Average: 208.2569
Monoisotopic: 208.121177766
Chemical Formula C11H16N2O2
InChI Key InChIKey=QCHFTSOMWOSFHM-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
Plain Text
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
Plain Text
Mass Spec Not Available
Taxonomy
Kingdom Organic
Classes
  • Carboxylic Acids and Derivatives
  • Lactones
  • Alkaloids and Alkaloid Derivatives
Substructures
  • Carboxylic Acids and Derivatives
  • Acetates
  • Lactones
  • Ethers
  • Imidazoles
  • Heterocyclic compounds
  • Aromatic compounds
  • Furans
  • Imines
  • Cyanamides
  • Alkaloids and Alkaloid Derivatives
Pharmacology
Indication For the treatment of radiation-induced dry mouth (xerostomia) and symptoms of dry mouth in patients with Sjögrens syndrome.
Pharmacodynamics Pilocarpine 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 action 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.
Absorption 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
Volume of distribution Not Available
Protein binding Not Available
Metabolism Possibly occurs at the neuronal synapses and in the plasma
Route of elimination Not Available
Half life 0.76 hours
Clearance Not Available
Toxicity Not Available
Affected organisms
  • Humans and other mammals
Pathways Not Available
Pharmacoeconomics
Manufacturers
  • Akorn inc
  • Alcon laboratories inc
  • Alcon inc
  • Corepharma llc
  • Impax laboratories inc
  • Lannett holdings inc
  • Roxane laboratories inc
  • Eisai inc
Packagers
Dosage forms
Form Route Strength
Gel Ophthalmic
Liquid Ophthalmic
Liquid Oral
Solution Ophthalmic
Solution / drops Oral
Tablet Oral
Prices
Unit description Cost Unit
Pilopine HS 4% Gel 4 gm Tube 64.08 USD tube
Isopto Carpine 4% Solution 15ml Bottle 37.5 USD bottle
Isopto Carpine 4% Solution 30ml Bottle 36.99 USD bottle
Isopto Carpine 1% Solution 15ml Bottle 36.37 USD bottle
Isopto Carpine 2% Solution 15ml Bottle 36.36 USD bottle
Pilocarpine HCl 2% Solution 15ml Bottle 35.01 USD bottle
Isopto Carpine 2% Solution 30ml Bottle 34.99 USD bottle
Pilocarpine HCl 1% Solution 15ml Bottle 32.24 USD bottle
Pilocar 6% Solution 15ml Bottle 15.99 USD bottle
Pilopine hs 4% eye gel 15.24 USD g
Pilocar 4% Solution 15ml Bottle 14.99 USD bottle
Pilocar 1% Solution 15ml Bottle 13.99 USD bottle
Pilocar 2% Solution 15ml Bottle 13.99 USD bottle
Pilocar 0.5% Solution 15ml Bottle 12.99 USD bottle
Pilocarpine nitrate crystal 9.85 USD g
Pilocarpine hcl crystals 8.19 USD g
Pilocarpine 1% eye drops 2.88 USD ml
Pilocarpine 2% eye drops 2.88 USD ml
Pilocarpine 4% eye drops 2.88 USD ml
Pilopine Hs 4 % Gel 2.81 USD g
Salagen 7.5 mg tablet 2.48 USD tablet
Isopto carpine 4% eye drops 2.37 USD ml
Isopto carpine 2% eye drops 2.26 USD ml
Isopto carpine 1% eye drops 2.21 USD ml
Salagen 5 mg tablet 2.14 USD tablet
Pilocarpine hcl 7.5 mg tablet 1.99 USD tablet
Pilocarpine hcl 5 mg tablet 1.55 USD tablet
Salagen 5 mg Tablet 1.23 USD tablet
Pilocarpine 6% eye drops 0.87 USD ml
Piloptic-6 eye drops 0.87 USD ml
Piloptic-3 eye drops 0.71 USD ml
Pilocarpine 3% eye drops 0.53 USD ml
Pilocarpine 0.5% eye drops 0.43 USD ml
Isopto Carpine 4 % Solution 0.3 USD ml
Isopto Carpine 2 % Solution 0.27 USD ml
Isopto Carpine 1 % Solution 0.23 USD ml
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DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents Not Available
Properties
State solid
Experimental Properties
Property Value Source
melting point 204-205 °C PhysProp
water solubility 1E+006 mg/L (at 25 °C) SEIDELL,A (1941)
logP 1.1 Not Available
pKa 6.78 Not Available
Predicted Properties
Property Value Source
water solubility 2.07e+00 g/l ALOGPS
logP 1.15 ALOGPS
logP 0.95 ChemAxon
logS -2 ALOGPS
pKa (strongest basic) 6.61 ChemAxon
physiological charge 0 ChemAxon
hydrogen acceptor count 2 ChemAxon
hydrogen donor count 0 ChemAxon
polar surface area 44.12 ChemAxon
rotatable bond count 3 ChemAxon
refractivity 56.53 ChemAxon
polarizability 22.34 ChemAxon
References
Synthesis Reference Not Available
General Reference Not Available
External Links
Resource Link
KEGG Drug D00525 Link_out
KEGG Compound C07474 Link_out
PubChem Compound 5910 Link_out
PubChem Substance 46507475 Link_out
ChemSpider 5699 Link_out
ChEBI 39462 Link_out
ChEMBL 39462 Link_out
Therapeutic Targets Database DAP001113 Link_out
PharmGKB PA450962 Link_out
IUPHAR 305 Link_out
Guide to Pharmacology 305 Link_out
Drug Product Database 2229556 Link_out
RxList http://www.rxlist.com/cgi/generic3/salagen.htm Link_out
Drugs.com http://www.drugs.com/cdi/pilocarpine-drops.html Link_out
Wikipedia http://en.wikipedia.org/wiki/Pilocarpine Link_out
ATC Codes
  • N07AX01
  • S01EB01
AHFS Codes
  • 12:04.00
  • 52:20.00
  • 92:02.00*
PDB Entries Not Available
FDA label show (160 KB)
MSDS show (73.3 KB)
Interactions
Drug Interactions
Drug Interaction
Tacrine The acetylcholinesterase inhibitor, Tacrine, may increase the adverse/toxic effects of Pilocarpine, a cholinergic agonist. Monitor for increased cholinergic effects and toxicity.
Food Interactions Not Available
Targets

1. Muscarinic acetylcholine receptor M3

Pharmacological action: yes
Actions: agonist

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

Organism class: human
UniProt ID: P20309 Link_out
Gene: CHRM3 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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

Pharmacological action: yes
Actions: agonist

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

Organism class: human
UniProt ID: P11229 Link_out
Gene: CHRM1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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

Pharmacological action: yes
Actions: agonist

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

Organism class: human
UniProt ID: P08172 Link_out
Gene: CHRM2 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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

Actions: substrate, inhibitor

Exhibits a high coumarin 7-hydroxylase activity. Can act in the hydroxylation of the anti-cancer drugs cyclophosphamide and ifosphamide. Competent in the metabolic activation of aflatoxin B1. Constitutes the major nicotine C-oxidase

UniProt ID: P11509 Link_out
Gene: CYP2A6
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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

Actions: substrate

Metabolizes several precarcinogens, drugs, and solvents to reactive metabolites. Inactivates a number of drugs and xenobiotics and also bioactivates many xenobiotic substrates to their hepatotoxic or carcinogenic forms

UniProt ID: P05181 Link_out
Gene: CYP2E1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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

Actions: substrate, inhibitor

Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4- hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. The enzyme also hydroxylates etoposide

UniProt ID: P08684 Link_out
Gene: CYP3A4
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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
Comments
Drug created on June 13, 2005 07:24 / Updated on February 08, 2013 16:19