Pilocarpine

Identification

Summary

Pilocarpine is a muscarinic agonist used to treat dry mouth and various ophthalmic conditions, such as presbyopia, increased intraocular pressure, and angle-closure glaucoma.

Brand Names
Betoptic Pilo, Isoptocarpine, Minims Pilocarpine Nitrate, Salagen, Vuity
Generic Name
Pilocarpine
DrugBank Accession Number
DB01085
Background

A naturally occurring alkaloid derived from the Pilocarpus plants, pilocarpine is a muscarinic acetylcholine agonist.1,2 Pilocarpine is associated with parasympathomimetic effects by selectively working on muscarinic receptors.2 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 1875.3

Type
Small Molecule
Groups
Approved, Investigational
Structure
Weight
Average: 208.2569
Monoisotopic: 208.121177766
Chemical Formula
C11H16N2O2
Synonyms
  • 2(3H)-FURANONE, 3-ETHYLDIHYDRO-4-((1-METHYL-1H-IMIDAZOL-5-YL)METHYL)-, (3S-CIS)-
  • OCUCARPINE
  • Pilocarpina
  • Pilocarpine
  • PILOKARPIN
  • SPERSACARPINE
  • SYNCARPINE

Pharmacology

Indication

Pilocarpine oral tablets are indicated for the treatment of dry mouth caused by Sjogren's Syndrome or radiotherapy for cancer of the head and neck.9

Pilocarpine ophthalmic formulations are used to treat presbyopia in adults,7,10 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.8

Reduce drug development failure rates
Build, train, & validate machine-learning models
with evidence-based and structured datasets.
See how
Build, train, & validate predictive machine-learning models with structured datasets.
See how
Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Management ofAcute angle-closure glaucoma••••••••••••
Symptomatic treatment ofDry mouth••••••••••••••••••
Symptomatic treatment ofDry mouth•••••••••••••••• ••• •••• ••••••••••••
Management ofElevated intraocular pressure••••••••••••
Management ofElevated intraocular pressure••••••••••••
Contraindications & Blackbox Warnings
Prevent Adverse Drug Events Today
Tap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.
Learn more
Avoid life-threatening adverse drug events with our Clinical API
Learn more
Pharmacodynamics

Pilocarpine is a muscarinic agent that mediates diaphoretic, miotic, and central nervous system effects. Pilocarpine stimulates the secretion of various exocrine glands, such as sweat, lacrimal, salivary, and gastrointestinal glands. Following oral administration, pilocarpine increased the mean salivary flow rate by 2- to lO-folds than placebo. Its peak levels were maintained for at least one to two hours.2,7 Pilocarpine increases smooth muscle tone, contracts the pupillary and iris sphincter muscles, and induces miosis.2,7,9,10

Because pilocarpine may affect all five muscarinic receptor subtypes, it is associated with parasympathetic side effects.1,3

Mechanism of action

The muscarinic M3 receptor is expressed in various endocrine and exocrine glands, including the gastric and salivary glands.3 It is also found in smooth muscle cells in pupillary sphincter and ciliary bodies. The M3 receptor is a Gq-protein-coupled receptor that activates phospholipase C and upregulates inositol trisphosphate and intracellular calcium. M3 receptor activation has been implicated in smooth muscle contraction and the stimulation of salivary glands.1 Pilocarpine is an agonist for M1 and M2 receptors,3,4 and is a full and partial agonist at the M3 receptor.1

TargetActionsOrganism
AMuscarinic acetylcholine receptor M3
agonist
Humans
AMuscarinic acetylcholine receptor M1
agonist
Humans
AMuscarinic acetylcholine receptor M2
agonist
Humans
UMuscarinic acetylcholine receptor M4
partial agonist
Humans
UMuscarinic acetylcholine receptor M5
agonist
Humans
Absorption

Following oral administration of pilocarpine 5mg three times daily in healthy male subjects, peak plasma drug concentrations of 15μg/L were reached in 1.25 hours. At the dose of pilocarpine 10mg three times daily, peak plasma drug concentrations of 41μg/L were reached in 0.85 hours. The rate of absorption is increased when taken with food.2

Following ophthalmic administration in healthy subjects, the overall median Tmax was 2.2 hours. The mean (SD) Cmax and AUC0-t were 897.2 (287.2) pg/mL and 2699 (741.4) hr x pg/mL, respectively.7 In patients with presbyopia, the mean Cmax and AUC0-t,ss values were 1.95 ng/mL and 4.14 ng x hr/mL, respectively. The median Tmax was 0.3 hours postdose with a range from 0.2 to 0.5 hours post-dose.10

Volume of distribution

There is no information available.

Protein binding

Pilocarpine does not bind to human or rat plasma proteins over a concentration range of 5 to 25,000 ng/mL. The effect of pilocarpine on plasma protein binding of other drugs has not been evaluated.9

Metabolism

There is limited information available about the metabolism of pilocarpine in humans. Inactivation of pilocarpine can occur at neuronal synapses and probably in plasma.9 Pilocarpine is reported to undergo CYP2A6-mediated 3-hydroxylation to form stereoisomers of 3-hydroxypilocaripine.5 Pilocaripine also undergoes hydrolysis mediated by paraoxonase 1, a calcium-dependent esterase in plasma and the human liver.5 Pilocarpic acid is a possible metabolic product of hydrolysis.6 Pilocarpine metabolites are reported to possess negligible or no pharmacological activity.9

Hover over products below to view reaction partners

Route of elimination

Pilocarpine and its degradation products are eliminated predominantly in the urine.2

Half-life

The elimination half-life was 0.76 and 1.35 hours following administration of a 5mg or lOmg dose 3 times daily, respectively.2

Following ophthalmic administration in healthy subjects, the half-life was 3.96 hours.7

Clearance

There is no information available.

Adverse Effects
Improve decision support & research outcomes
With structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!
See the data
Improve decision support & research outcomes with our structured adverse effects data.
See a data sample
Toxicity

The oral LD50 value in mice for pilocarpine hydrochloride are 200 mg/kg. The intraperitoneal and subcutaneous LD50 values in rats for pilocarpine hydrochloride are 203 mg/kg and 230 mg/kg, respectively.11

Overdosage can produce sweating, salivation, nausea, tremors, slowing of the pulse, and decreased blood pressure.8 Fatal overdosage with pilocarpine has been reported in the scientific literature at doses presumed to be greater than 100 mg. Severe overdosage should be treated with titrated atropine (0.5 mg to 1.0 mg given subcutaneously or intravenously), which is a muscarinic antagonist. Supportive measures should be initiated to maintain respiration and circulation. Epinephrine (0.3 mg to 1.0 mg, subcutaneously or intramuscularly) may also be used in response to severe cardiovascular depression or bronchoconstriction. It is not known if pilocarpine is dialyzable.9 Systemic toxicity following ophthalmic use of pilocarpine is rare, but some patients may experience sweating and gastrointestinal overactivity at therapeutic doses.8

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
AcebutololThe risk or severity of adverse effects can be increased when Acebutolol is combined with Pilocarpine.
AmbenoniumThe risk or severity of adverse effects can be increased when Ambenonium is combined with Pilocarpine.
AmikacinThe therapeutic efficacy of Pilocarpine can be decreased when used in combination with Amikacin.
AprotininThe risk or severity of adverse effects can be increased when Aprotinin is combined with Pilocarpine.
AtenololThe risk or severity of adverse effects can be increased when Atenolol is combined with Pilocarpine.
Food Interactions
  • Take with or without food. A high fat meal decreases Cmax and the time to reach Cmax, but not to a clinically significant extent.

Products

Drug product information from 10+ global regions
Our datasets provide approved product information including:
dosage, form, labeller, route of administration, and marketing period.
Access now
Access drug product information from over 10 global regions.
Access now
Product Ingredients
IngredientUNIICASInChI Key
Pilocarpine hydrochloride0WW6D218XJ54-71-7RNAICSBVACLLGM-GNAZCLTHSA-N
Pilocarpine nitrateM20T465H6J148-72-1PRZXEPJJHQYOGF-GNAZCLTHSA-N
Pilocarpine pamoate9O3667EIIX63036-94-2ZCECPEINCZVBPT-IWXKTIJTSA-N
Product Images
International/Other Brands
Diocarpine / Miocarpine / Pilostat / Pilovisc / Timpilo
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Isopto CarpineSolution / drops20 mg/1mLOphthalmicALCON LABORATORIES, INC.1974-01-012023-03-31US flag
Isopto CarpineLiquid2 %OphthalmicNovartis1959-12-31Not applicableCanada flag
Isopto CarpineSolution / drops10 mg/1mLOphthalmicALCON LABORATORIES, INC.1974-01-012023-04-30US flag
Isopto CarpineSolution / drops40 mg/1mLOphthalmicALCON LABORATORIES, INC.1974-01-012022-05-31US flag
Isopto CarpineLiquid4 %OphthalmicNovartis1959-12-312022-07-18Canada flag
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Jamp PilocarpineTablet5 mgOralJamp Pharma Corporation2021-04-30Not applicableCanada flag
Odan-pilocarpineSolution2 %OphthalmicOdan Laboratories Ltd1992-12-31Not applicableCanada flag
Odan-pilocarpineSolution1 %OphthalmicOdan Laboratories Ltd1991-12-31Not applicableCanada flag
Odan-pilocarpineSolution4 %OphthalmicOdan Laboratories Ltd1991-12-31Not applicableCanada flag
Pilocarpine HydrchlorideTablet, film coated5 mg/1OralPadagis US LLC2020-08-24Not applicableUS flag
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
ISOPTO CARPINE STERILE OPHTHALMIC SOLUTION 2%Solution2 %OphthalmicNOVARTIS (SINGAPORE) PTE LTD1990-06-13Not applicableSingapore flag
ISOPTO CARPINE STERILE OPHTHALMIC SOLUTION 4%Solution4 %OphthalmicNOVARTIS (SINGAPORE) PTE LTD1990-06-13Not applicableSingapore flag
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
Betoptic PiloPilocarpine hydrochloride (17.5 mg/1mL) + Betaxolol hydrochloride (2.5 mg/1mL)KitOphthalmicALCON LABORATORIES, INC.2006-09-26Not applicableUS flag
Betoptic/piloPilocarpine hydrochloride (1.75 %) + Betaxolol hydrochloride (0.25 %)SuspensionOphthalmicAlcon, Inc.Not applicableNot applicableCanada flag
E-pilo 1 Ophthalmic SolutionPilocarpine hydrochloride (10 mg / mL) + Epinephrine bitartrate (10 mg / mL)Solution / dropsOphthalmicCiba Vision1996-12-311999-01-27Canada flag
E-pilo 2 Ophthalmic SolutionPilocarpine hydrochloride (20 mg / mL) + Epinephrine bitartrate (10 mg / mL)Solution / dropsOphthalmicCiba Vision1997-02-111999-05-10Canada flag
E-pilo 4 Ophthalmic SolutionPilocarpine hydrochloride (40 mg / mL) + Epinephrine bitartrate (10 mg / mL)Solution / dropsOphthalmicCiba Vision1995-12-311999-07-13Canada flag
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
Pilocarpine HydrochloridePilocarpine hydrochloride (40 mg/1mL)Solution / dropsConjunctivalPhysicians Total Care, Inc.2011-10-072013-01-11US flag
Pilocarpine HydrochloridePilocarpine hydrochloride (20 mg/1mL)Solution / dropsConjunctivalBauch & Lomb Incorporated2010-09-152011-04-15US flag
Pilocarpine HydrochloridePilocarpine hydrochloride (10 mg/1mL)Solution / dropsConjunctivalPhysicians Total Care, Inc.2010-09-152013-01-11US flag
Pilocarpine HydrochloridePilocarpine hydrochloride (10 mg/1mL)Solution / dropsConjunctivalBauch & Lomb Incorporated2010-09-152011-03-11US flag
Pilocarpine HydrochloridePilocarpine hydrochloride (40 mg/1mL)Solution / dropsConjunctivalBauch & Lomb Incorporated2010-09-152011-04-18US flag

Categories

ATC Codes
N07AX01 — PilocarpineS01EB01 — PilocarpineS01EB51 — Pilocarpine, combinations
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This 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.
Kingdom
Organic compounds
Super Class
Alkaloids and derivatives
Class
Not Available
Sub Class
Not Available
Direct Parent
Alkaloids and derivatives
Alternative Parents
N-substituted imidazoles / Gamma butyrolactones / Tetrahydrofurans / Heteroaromatic compounds / Carboxylic acid esters / Oxacyclic compounds / Monocarboxylic acids and derivatives / Azacyclic compounds / Organopnictogen compounds / Organonitrogen compounds
show 3 more
Substituents
Alkaloid or derivatives / Aromatic heteromonocyclic compound / Azacycle / Azole / Carbonyl group / Carboxylic acid derivative / Carboxylic acid ester / Gamma butyrolactone / Heteroaromatic compound / Hydrocarbon derivative
show 13 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
pilocarpine (CHEBI:8207) / Imidazole alkaloids (C07474)
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
01MI4Q9DI3
CAS number
92-13-7
InChI Key
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
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

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 References
  1. Panarese V, Moshirfar M: Pilocarpine. . [Article]
  2. Wiseman LR, Faulds D: Oral pilocarpine: a review of its pharmacological properties and clinical potential in xerostomia. Drugs. 1995 Jan;49(1):143-55. doi: 10.2165/00003495-199549010-00010. [Article]
  3. Pronin AN, Wang Q, Slepak VZ: Teaching an Old Drug New Tricks: Agonism, Antagonism, and Biased Signaling of Pilocarpine through M3 Muscarinic Acetylcholine Receptor. Mol Pharmacol. 2017 Nov;92(5):601-612. doi: 10.1124/mol.117.109678. Epub 2017 Sep 11. [Article]
  4. Belmonte KE, Jacoby DB, Fryer AD: Increased function of inhibitory neuronal M2 muscarinic receptors in diabetic rat lungs. Br J Pharmacol. 1997 Aug;121(7):1287-94. doi: 10.1038/sj.bjp.0701274. [Article]
  5. Hioki T, Fukami T, Nakajima M, Yokoi T: Human paraoxonase 1 is the enzyme responsible for pilocarpine hydrolysis. Drug Metab Dispos. 2011 Aug;39(8):1345-52. doi: 10.1124/dmd.111.038141. Epub 2011 Apr 26. [Article]
  6. Endo T, Ban M, Hirata K, Yamamoto A, Hara Y, Momose Y: Involvement of CYP2A6 in the formation of a novel metabolite, 3-hydroxypilocarpine, from pilocarpine in human liver microsomes. Drug Metab Dispos. 2007 Mar;35(3):476-83. doi: 10.1124/dmd.106.013425. Epub 2006 Dec 18. [Article]
  7. FDA Approved Drug Products: QLOSI (pilocarpine hydrochloride ophthalmic solution) 0.4%, for topical ophthalmic use (October 2023) [Link]
  8. FDA Approved Drug Products: Isopto Carpine (pilocarpine hydrochloride) ophthalmic solution 1%, 2% and 4% (June 2010) [Link]
  9. DailyMed Label: SALAGEN (pilocarpine hydrochloride) Oral Tablets, film coated [Link]
  10. FDA Approved Drug Products: VUITY (pilocarpine hydrochloride) 1.25% ophthalmic solution (April 2023) [Link]
  11. Cayman Chemical: (+)-Pilocarpine hydrochloride MSDS [Link]
Human Metabolome Database
HMDB0015217
KEGG Drug
D00525
KEGG Compound
C07474
PubChem Compound
5910
PubChem Substance
46507475
ChemSpider
5699
BindingDB
50008072
RxNav
8328
ChEBI
8207
ChEMBL
CHEMBL550
ZINC
ZINC000000075008
Therapeutic Targets Database
DAP001113
PharmGKB
PA450962
Guide to Pharmacology
GtP Drug Page
PDBe Ligand
9PL
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Pilocarpine
PDB Entries
3t3q / 3t3r / 3t3s / 3t3z

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4CompletedHealth Services ResearchPupils unequal1
4CompletedTreatmentAngle-Closure Glaucoma1
4CompletedTreatmentDry Mouth / Primary Sjögren's Syndrome (pSS) / Secondary Sjogren1
4CompletedTreatmentOpen Angle Glaucoma (OAG)1
4Unknown StatusTreatmentDry Mouth1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
  • Actavis Group
  • Advanced Pharmaceutical Services Inc.
  • Akorn Inc.
  • Alcon Laboratories
  • Bausch & Lomb Inc.
  • Corepharma LLC
  • Dispensing Solutions
  • E. Fougera and Co.
  • Eisai Inc.
  • Falcon Pharmaceuticals Ltd.
  • Global Pharmaceuticals
  • Impax Laboratories Inc.
  • Lannett Co. Inc.
  • Mallinckrodt Inc.
  • MGI Pharma
  • Murfreesboro Pharmaceutical Nursing Supply
  • Novartis AG
  • OMJ Pharmaceuticals
  • Optopics
  • Patheon Inc.
  • Pharmedix
  • Physicians Total Care Inc.
  • Prescript Pharmaceuticals
  • Rebel Distributors Corp.
  • Roxane Labs
  • Sandoz
  • Taylor Pharmaceuticals
  • Wa Butler Co.
Dosage Forms
FormRouteStrength
KitOphthalmic
SuspensionOphthalmic
Tablet, film coatedOral5 mg
GelOphthalmic19.8 mg
TabletOral5.000 mg
LiquidOphthalmic
Solution / dropsOphthalmic
SolutionOphthalmic20 mg
SolutionOphthalmic2000000 mg
LiquidOphthalmic0.5 %
LiquidOphthalmic60 g / L
SolutionOphthalmic4 %
Solution / dropsOphthalmic2 % w/v
Solution / dropsOphthalmic4 %
SolutionOphthalmic2 % w/v
Solution / dropsOphthalmic1 %
Solution / dropsOphthalmic2 %
Solution / dropsOphthalmic6 %
Solution / dropsOphthalmic
ImplantIntraocular5 mg / imp
ImplantIntraocular11 mg / imp
SolutionOphthalmic40.000 mg
SolutionOphthalmic20.000 mg
Solution / dropsOphthalmic10 mg
Solution / dropsOphthalmic20 mg
SolutionConjunctival; Ophthalmic40 mg
SolutionConjunctival; Ophthalmic4 g
SolutionOphthalmic
OintmentOphthalmic1 %
OintmentOphthalmic2 %
InjectionParenteral2 g
SolutionOphthalmic1 %
SolutionOphthalmic2 %
SolutionOphthalmic6 %
SolutionOphthalmic40 mg/1
Solution / dropsConjunctival10 mg/1mL
Solution / dropsConjunctival20 mg/1mL
Solution / dropsConjunctival40 mg/1mL
Solution / dropsOphthalmic10 mg/1mL
Solution / dropsOphthalmic20 mg/1mL
Solution / dropsOphthalmic40 mg/1mL
TabletOral5 mg/1
TabletOral7.5 mg/1
Tablet, film coatedOral5 mg/1
Tablet, film coatedOral7.5 mg/1
GelOphthalmic
Solution / drops; suspension / dropsOphthalmic1 %
Solution / drops; suspension / dropsOphthalmic2 %
GelOphthalmic40 mg/1g
GelOphthalmic4 %
OintmentOphthalmic
LiquidOphthalmic5 mg / mL
LiquidOphthalmic10 mg / mL
LiquidOphthalmic20 mg / mL
LiquidOphthalmic40 mg / mL
LiquidOphthalmic60 mg / mL
LiquidOphthalmic1 %
LiquidOphthalmic2 %
LiquidOphthalmic4 %
TabletOral5 mg
Tablet, coatedOral7.5 mg
Tablet, coatedOral500000 mg
Solution / drops; suspension / dropsOphthalmic0.5 %
SolutionOphthalmic
Solution / dropsOphthalmic12.5 mg/1mL
Tablet, coatedOral5 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.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)Region
US10610518No2020-04-072039-04-24US flag
US11285134No2019-04-242039-04-24US flag
US11129812No2017-08-182037-08-18US flag
US10639297No2017-08-182037-08-18US flag
US9867810No2017-08-182037-08-18US flag

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)195-205https://www.medisca.com/NDC_SPECS/MUS/0182/MSDS/0182.pdf
logP-3.03https://www.medisca.com/NDC_SPECS/MUS/0182/MSDS/0182.pdf
Predicted Properties
PropertyValueSource
Water Solubility2.07 mg/mLALOGPS
logP1.15ALOGPS
logP0.95Chemaxon
logS-2ALOGPS
pKa (Strongest Basic)6.37Chemaxon
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 RuleNoChemaxon
MDDR-like RuleNoChemaxon
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 inhibitorNon-inhibitor0.8732
CYP450 2D6 inhibitorNon-inhibitor0.9231
CYP450 2C19 inhibitorNon-inhibitor0.9026
CYP450 3A4 inhibitorInhibitor0.7961
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
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-0006-9500000000-dadfea39cdf9ef51bb38
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a4i-0390000000-13e5a828bfc740994c0a
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4i-0190000000-34ce099765686b88b6ba
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-056s-1910000000-a12e72bf6758da72c06f
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0bta-6940000000-5a3473b68a3047bcc953
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-00fr-4900000000-1207f723b1f8a6d58a60
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-014i-9600000000-1c7e6cd03421f5653221
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-155.3026138
predicted
DarkChem Lite v0.1.0
[M-H]-155.9940138
predicted
DarkChem Lite v0.1.0
[M-H]-155.0633138
predicted
DarkChem Lite v0.1.0
[M-H]-144.30807
predicted
DeepCCS 1.0 (2019)
[M+H]+155.5314138
predicted
DarkChem Lite v0.1.0
[M+H]+156.5107138
predicted
DarkChem Lite v0.1.0
[M+H]+155.4929138
predicted
DarkChem Lite v0.1.0
[M+H]+146.70366
predicted
DeepCCS 1.0 (2019)
[M+Na]+155.1996138
predicted
DarkChem Lite v0.1.0
[M+Na]+156.2025138
predicted
DarkChem Lite v0.1.0
[M+Na]+155.2151138
predicted
DarkChem Lite v0.1.0
[M+Na]+152.6361
predicted
DeepCCS 1.0 (2019)

Targets

Build, predict & validate machine-learning models
Use our structured and evidence-based datasets to unlock new
insights and accelerate drug research.
Learn more
Use our structured and evidence-based datasets to unlock new insights and accelerate drug research.
Learn more
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Agonist
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...
Gene Name
CHRM3
Uniprot ID
P20309
Uniprot Name
Muscarinic acetylcholine receptor M3
Molecular Weight
66127.445 Da
References
  1. Wang H, Shi H, Lu Y, Yang B, Wang Z: Pilocarpine modulates the cellular electrical properties of mammalian hearts by activating a cardiac M3 receptor and a K+ current. Br J Pharmacol. 1999 Apr;126(8):1725-34. doi: 10.1038/sj.bjp.0702486. [Article]
  2. Panarese V, Moshirfar M: Pilocarpine. . [Article]
  3. Pronin AN, Wang Q, Slepak VZ: Teaching an Old Drug New Tricks: Agonism, Antagonism, and Biased Signaling of Pilocarpine through M3 Muscarinic Acetylcholine Receptor. Mol Pharmacol. 2017 Nov;92(5):601-612. doi: 10.1124/mol.117.109678. Epub 2017 Sep 11. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Agonist
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...
Gene Name
CHRM1
Uniprot ID
P11229
Uniprot Name
Muscarinic acetylcholine receptor M1
Molecular Weight
51420.375 Da
References
  1. Panarese V, Moshirfar M: Pilocarpine. . [Article]
  2. Pronin AN, Wang Q, Slepak VZ: Teaching an Old Drug New Tricks: Agonism, Antagonism, and Biased Signaling of Pilocarpine through M3 Muscarinic Acetylcholine Receptor. Mol Pharmacol. 2017 Nov;92(5):601-612. doi: 10.1124/mol.117.109678. Epub 2017 Sep 11. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Agonist
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...
Gene Name
CHRM2
Uniprot ID
P08172
Uniprot Name
Muscarinic acetylcholine receptor M2
Molecular Weight
51714.605 Da
References
  1. Panarese V, Moshirfar M: Pilocarpine. . [Article]
  2. Pronin AN, Wang Q, Slepak VZ: Teaching an Old Drug New Tricks: Agonism, Antagonism, and Biased Signaling of Pilocarpine through M3 Muscarinic Acetylcholine Receptor. Mol Pharmacol. 2017 Nov;92(5):601-612. doi: 10.1124/mol.117.109678. Epub 2017 Sep 11. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Partial agonist
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...
Gene Name
CHRM4
Uniprot ID
P08173
Uniprot Name
Muscarinic acetylcholine receptor M4
Molecular Weight
53048.65 Da
References
  1. Panarese V, Moshirfar M: Pilocarpine. . [Article]
  2. Pronin AN, Wang Q, Slepak VZ: Teaching an Old Drug New Tricks: Agonism, Antagonism, and Biased Signaling of Pilocarpine through M3 Muscarinic Acetylcholine Receptor. Mol Pharmacol. 2017 Nov;92(5):601-612. doi: 10.1124/mol.117.109678. Epub 2017 Sep 11. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Agonist
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...
Gene Name
CHRM5
Uniprot ID
P08912
Uniprot Name
Muscarinic acetylcholine receptor M5
Molecular Weight
60073.205 Da
References
  1. Pronin AN, Wang Q, Slepak VZ: Teaching an Old Drug New Tricks: Agonism, Antagonism, and Biased Signaling of Pilocarpine through M3 Muscarinic Acetylcholine Receptor. Mol Pharmacol. 2017 Nov;92(5):601-612. doi: 10.1124/mol.117.109678. Epub 2017 Sep 11. [Article]

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Vitamin d3 25-hydroxylase activity
Specific Function
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 react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. Kimonen T, Juvonen RO, Alhava E, Pasanen M: The inhibition of CYP enzymes in mouse and human liver by pilocarpine. Br J Pharmacol. 1995 Feb;114(4):832-6. [Article]
  2. Endo T, Ban M, Hirata K, Yamamoto A, Hara Y, Momose Y: Involvement of CYP2A6 in the formation of a novel metabolite, 3-hydroxypilocarpine, from pilocarpine in human liver microsomes. Drug Metab Dispos. 2007 Mar;35(3):476-83. doi: 10.1124/dmd.106.013425. Epub 2006 Dec 18. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
General Function
Steroid hydroxylase activity
Specific Function
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. Const...
Gene Name
CYP2A6
Uniprot ID
P11509
Uniprot Name
Cytochrome P450 2A6
Molecular Weight
56501.005 Da
References
  1. Kimonen T, Juvonen RO, Alhava E, Pasanen M: The inhibition of CYP enzymes in mouse and human liver by pilocarpine. Br J Pharmacol. 1995 Feb;114(4):832-6. [Article]
  2. DeVore NM, Meneely KM, Bart AG, Stephens ES, Battaile KP, Scott EE: Structural comparison of cytochromes P450 2A6, 2A13, and 2E1 with pilocarpine. FEBS J. 2012 May;279(9):1621-31. doi: 10.1111/j.1742-4658.2011.08412.x. Epub 2011 Nov 25. [Article]
  3. Ueng YF, Chen CC, Chung YT, Liu TY, Chang YP, Lo WS, Murayama N, Yamazaki H, Soucek P, Chau GY, Chi CW, Chen RM, Li DT: Mechanism-based inhibition of cytochrome P450 (CYP)2A6 by chalepensin in recombinant systems, in human liver microsomes and in mice in vivo. Br J Pharmacol. 2011 Jul;163(6):1250-62. doi: 10.1111/j.1476-5381.2011.01341.x. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Protein homodimerization activity
Specific Function
Hydrolyzes the toxic metabolites of a variety of organophosphorus insecticides. Capable of hydrolyzing a broad spectrum of organophosphate substrates and lactones, and a number of aromatic carboxyl...
Gene Name
PON1
Uniprot ID
P27169
Uniprot Name
Serum paraoxonase/arylesterase 1
Molecular Weight
39730.99 Da
References
  1. Hioki T, Fukami T, Nakajima M, Yokoi T: Human paraoxonase 1 is the enzyme responsible for pilocarpine hydrolysis. Drug Metab Dispos. 2011 Aug;39(8):1345-52. doi: 10.1124/dmd.111.038141. Epub 2011 Apr 26. [Article]

Drug created at June 13, 2005 13:24 / Updated at February 25, 2024 21:03