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
Structure for Pilocarpine (DB01085)
- 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 ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Associated Conditions
Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Management of Acute angle-closure glaucoma •••••••••••• Symptomatic treatment of Dry mouth •••••••••••• •••••• Symptomatic treatment of Dry mouth •••••••••••• •••• ••• •••• •••••• •••••• Management of Elevated intraocular pressure •••••••••••• Management of Elevated intraocular pressure •••••••••••• - Contraindications & Blackbox Warnings
Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- 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
Target Actions Organism AMuscarinic acetylcholine receptor M3 agonistHumans AMuscarinic acetylcholine receptor M1 agonistHumans AMuscarinic acetylcholine receptor M2 agonistHumans UMuscarinic acetylcholine receptor M4 partial agonistHumans UMuscarinic acetylcholine receptor M5 agonistHumans - 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 outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- 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 Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
- Not Available
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
- 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.
Drug Interaction Integrate drug-drug
interactions in your softwareAcebutolol The risk or severity of adverse effects can be increased when Acebutolol is combined with Pilocarpine. Ambenonium The risk or severity of adverse effects can be increased when Ambenonium is combined with Pilocarpine. Amikacin The therapeutic efficacy of Pilocarpine can be decreased when used in combination with Amikacin. Aprotinin The risk or severity of adverse effects can be increased when Aprotinin is combined with Pilocarpine. Atenolol The 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 regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Product Ingredients
Ingredient UNII CAS InChI Key Pilocarpine hydrochloride 0WW6D218XJ 54-71-7 RNAICSBVACLLGM-GNAZCLTHSA-N Pilocarpine nitrate M20T465H6J 148-72-1 PRZXEPJJHQYOGF-GNAZCLTHSA-N Pilocarpine pamoate 9O3667EIIX 63036-94-2 ZCECPEINCZVBPT-IWXKTIJTSA-N - Product Images
- International/Other Brands
- Diocarpine / Miocarpine / Pilostat / Pilovisc / Timpilo
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Isopto Carpine Solution / drops 10 mg/1mL Ophthalmic ALCON LABORATORIES, INC. 1974-01-01 2023-04-30 US 
Isopto Carpine Liquid 2 % Ophthalmic Novartis 1959-12-31 Not applicable Canada 
Isopto Carpine Solution / drops 40 mg/1mL Ophthalmic ALCON LABORATORIES, INC. 1974-01-01 2022-05-31 US Isopto Carpine Liquid 4 % Ophthalmic Novartis 1959-12-31 2022-07-18 Canada Isopto Carpine Solution / drops 20 mg/1mL Ophthalmic ALCON LABORATORIES, INC. 1974-01-01 2023-03-31 US - Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Jamp Pilocarpine Tablet 5 mg Oral Jamp Pharma Corporation 2021-04-30 Not applicable Canada Odan-pilocarpine Solution 1 % Ophthalmic Odan Laboratories Ltd 1991-12-31 Not applicable Canada Odan-pilocarpine Solution 4 % Ophthalmic Odan Laboratories Ltd 1991-12-31 Not applicable Canada Odan-pilocarpine Solution 2 % Ophthalmic Odan Laboratories Ltd 1992-12-31 Not applicable Canada Pilocarpine Hydrchloride Tablet, film coated 5 mg/1 Oral Padagis US LLC 2020-08-24 Not applicable US - Over the Counter Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image ISOPTO CARPINE STERILE OPHTHALMIC SOLUTION 2% Solution 2 % Ophthalmic NOVARTIS (SINGAPORE) PTE LTD 1990-06-13 Not applicable Singapore 
ISOPTO CARPINE STERILE OPHTHALMIC SOLUTION 4% Solution 4 % Ophthalmic NOVARTIS (SINGAPORE) PTE LTD 1990-06-13 Not applicable Singapore - Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Betoptic Pilo Pilocarpine hydrochloride (17.5 mg/1mL) + Betaxolol hydrochloride (2.5 mg/1mL) Kit Ophthalmic ALCON LABORATORIES, INC. 2006-09-26 Not applicable US Betoptic/pilo Pilocarpine hydrochloride (1.75 %) + Betaxolol hydrochloride (0.25 %) Suspension Ophthalmic Alcon, Inc. Not applicable Not applicable Canada E-pilo 1 Ophthalmic Solution Pilocarpine hydrochloride (10 mg / mL) + Epinephrine bitartrate (10 mg / mL) Solution / drops Ophthalmic Ciba Vision 1996-12-31 1999-01-27 Canada E-pilo 2 Ophthalmic Solution Pilocarpine hydrochloride (20 mg / mL) + Epinephrine bitartrate (10 mg / mL) Solution / drops Ophthalmic Ciba Vision 1997-02-11 1999-05-10 Canada E-pilo 4 Ophthalmic Solution Pilocarpine hydrochloride (40 mg / mL) + Epinephrine bitartrate (10 mg / mL) Solution / drops Ophthalmic Ciba Vision 1995-12-31 1999-07-13 Canada - Unapproved/Other Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Pilocarpine Hydrochloride Pilocarpine hydrochloride (40 mg/1mL) Solution / drops Conjunctival Physicians Total Care, Inc. 2011-10-07 2013-01-11 US Pilocarpine Hydrochloride Pilocarpine hydrochloride (20 mg/1mL) Solution / drops Conjunctival Bauch & Lomb Incorporated 2010-09-15 2011-04-15 US Pilocarpine Hydrochloride Pilocarpine hydrochloride (10 mg/1mL) Solution / drops Conjunctival Physicians Total Care, Inc. 2010-09-15 2013-01-11 US Pilocarpine Hydrochloride Pilocarpine hydrochloride (10 mg/1mL) Solution / drops Conjunctival Bauch & Lomb Incorporated 2010-09-15 2011-03-11 US Pilocarpine Hydrochloride Pilocarpine hydrochloride (40 mg/1mL) Solution / drops Conjunctival Bauch & Lomb Incorporated 2010-09-15 2011-04-18 US
Categories
- ATC Codes
- N07AX01 — Pilocarpine
- N07AX — Other parasympathomimetics
- N07A — PARASYMPATHOMIMETICS
- N07 — OTHER NERVOUS SYSTEM DRUGS
- N — NERVOUS SYSTEM
- S01EB — Parasympathomimetics
- S01E — ANTIGLAUCOMA PREPARATIONS AND MIOTICS
- S01 — OPHTHALMOLOGICALS
- S — SENSORY ORGANS
- Drug Categories
- Alkaloids
- Antiglaucoma Preparations and Miotics
- Autonomic Agents
- Cholinergic Agents
- Cholinergic Agonists
- Cholinergic Receptor Agonist
- Cytochrome P-450 CYP2A6 Inhibitors
- Cytochrome P-450 CYP2A6 Inhibitors (strong)
- Cytochrome P-450 CYP2A6 Substrates
- Cytochrome P-450 CYP3A Inhibitors
- Cytochrome P-450 CYP3A4 Inhibitors
- Cytochrome P-450 CYP3A4 Inhibitors (strength unknown)
- Cytochrome P-450 Enzyme Inhibitors
- Cytochrome P-450 Substrates
- Miotics
- Muscarinic Agonists
- Nervous System
- Neurotransmitter Agents
- Ophthalmologicals
- Parasympathomemetic (Cholinergic) Agents
- Parasympathomimetics
- Peripheral Nervous System Agents
- Sensory Organs
- 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
- Panarese V, Moshirfar M: Pilocarpine. . [Article]
- 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]
- 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]
- 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]
- 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]
- 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]
- FDA Approved Drug Products: QLOSI (pilocarpine hydrochloride ophthalmic solution) 0.4%, for topical ophthalmic use (October 2023) [Link]
- FDA Approved Drug Products: Isopto Carpine (pilocarpine hydrochloride) ophthalmic solution 1%, 2% and 4% (June 2010) [Link]
- DailyMed Label: SALAGEN (pilocarpine hydrochloride) Oral Tablets, film coated [Link]
- FDA Approved Drug Products: VUITY (pilocarpine hydrochloride) 1.25% ophthalmic solution (April 2023) [Link]
- Cayman Chemical: (+)-Pilocarpine hydrochloride MSDS [Link]
- External Links
- Human Metabolome Database
- HMDB0015217
- KEGG Drug
- D00525
- KEGG Compound
- C07474
- PubChem Compound
- 5910
- PubChem Substance
- 46507475
- ChemSpider
- 5699
- BindingDB
- 50008072
- 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 Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count 4 Completed Health Services Research Pupils unequal 1 4 Completed Treatment Angle-Closure Glaucoma 1 4 Completed Treatment Dry Mouth / Primary Sjögren's Syndrome (pSS) / Secondary Sjogren 1 4 Completed Treatment Open Angle Glaucoma (OAG) 1 4 Unknown Status Treatment Dry Mouth 1
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
Form Route Strength Kit Ophthalmic Suspension Ophthalmic Tablet, film coated Oral 5 mg Gel Ophthalmic 19.8 mg Tablet Oral 5.000 mg Liquid Ophthalmic Solution / drops Ophthalmic Solution Ophthalmic 20 mg Solution Ophthalmic 2000000 mg Liquid Ophthalmic 0.5 % Liquid Ophthalmic 60 g / L Solution Ophthalmic 4 % Solution / drops Ophthalmic 2 % w/v Solution / drops Ophthalmic 4 % Solution Ophthalmic 2 % w/v Solution / drops Ophthalmic 1 % Solution / drops Ophthalmic 2 % Solution / drops Ophthalmic 6 % Solution / drops Ophthalmic Implant Intraocular 5 mg / imp Implant Intraocular 11 mg / imp Solution Ophthalmic 40.000 mg Solution Ophthalmic 20.000 mg Solution / drops Ophthalmic 10 mg Solution / drops Ophthalmic 20 mg Solution Conjunctival; Ophthalmic 40 mg Solution Conjunctival; Ophthalmic 4 g Solution Ophthalmic Ointment Ophthalmic 1 % Ointment Ophthalmic 2 % Injection Parenteral 2 g Solution Ophthalmic 1 % Solution Ophthalmic 2 % Solution Ophthalmic 6 % Solution Ophthalmic 40 mg/1 Solution / drops Conjunctival 10 mg/1mL Solution / drops Conjunctival 20 mg/1mL Solution / drops Conjunctival 40 mg/1mL Solution / drops Ophthalmic 10 mg/1mL Solution / drops Ophthalmic 20 mg/1mL Solution / drops Ophthalmic 40 mg/1mL Tablet Oral 5 mg/1 Tablet Oral 7.5 mg/1 Tablet, film coated Oral 5 mg/1 Tablet, film coated Oral 7.5 mg/1 Gel Ophthalmic Solution / drops; suspension / drops Ophthalmic 1 % Solution / drops; suspension / drops Ophthalmic 2 % Gel Ophthalmic 40 mg/1g Gel Ophthalmic 4 % Ointment Ophthalmic Liquid Ophthalmic 5 mg / mL Liquid Ophthalmic 10 mg / mL Liquid Ophthalmic 20 mg / mL Liquid Ophthalmic 40 mg / mL Liquid Ophthalmic 60 mg / mL Liquid Ophthalmic 1 % Liquid Ophthalmic 2 % Liquid Ophthalmic 4 % Tablet Oral 5 mg Tablet, coated Oral 7.5 mg Tablet, coated Oral 500000 mg Solution / drops; suspension / drops Ophthalmic 0.5 % Solution Ophthalmic Solution / drops Ophthalmic 12.5 mg/1mL Tablet, coated Oral 5 mg - Prices
Unit description Cost Unit Pilopine HS 4% Gel 4 gm Tube 64.08USD tube Isopto Carpine 4% Solution 15ml Bottle 37.5USD bottle Isopto Carpine 4% Solution 30ml Bottle 36.99USD bottle Isopto Carpine 1% Solution 15ml Bottle 36.37USD bottle Isopto Carpine 2% Solution 15ml Bottle 36.36USD bottle Pilocarpine HCl 2% Solution 15ml Bottle 35.01USD bottle Isopto Carpine 2% Solution 30ml Bottle 34.99USD bottle Pilocarpine HCl 1% Solution 15ml Bottle 32.24USD bottle Pilocar 6% Solution 15ml Bottle 15.99USD bottle Pilopine hs 4% eye gel 15.24USD g Pilocar 4% Solution 15ml Bottle 14.99USD bottle Pilocar 1% Solution 15ml Bottle 13.99USD bottle Pilocar 2% Solution 15ml Bottle 13.99USD bottle Pilocar 0.5% Solution 15ml Bottle 12.99USD bottle Pilocarpine nitrate crystal 9.85USD g Pilocarpine hcl crystals 8.19USD g Pilocarpine 1% eye drops 2.88USD ml Pilocarpine 2% eye drops 2.88USD ml Pilocarpine 4% eye drops 2.88USD ml Pilopine Hs 4 % Gel 2.81USD g Salagen 7.5 mg tablet 2.48USD tablet Isopto carpine 4% eye drops 2.37USD ml Isopto carpine 2% eye drops 2.26USD ml Isopto carpine 1% eye drops 2.21USD ml Salagen 5 mg tablet 2.14USD tablet Pilocarpine hcl 7.5 mg tablet 1.99USD tablet Pilocarpine hcl 5 mg tablet 1.55USD tablet Salagen 5 mg Tablet 1.23USD tablet Pilocarpine 6% eye drops 0.87USD ml Piloptic-6 eye drops 0.87USD ml Piloptic-3 eye drops 0.71USD ml Pilocarpine 3% eye drops 0.53USD ml Pilocarpine 0.5% eye drops 0.43USD ml Isopto Carpine 4 % Solution 0.3USD ml Isopto Carpine 2 % Solution 0.27USD ml Isopto Carpine 1 % Solution 0.23USD ml DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
Patent Number Pediatric Extension Approved Expires (estimated) Region US10610518 No 2020-04-07 2039-04-24 US US11285134 No 2019-04-24 2039-04-24 US US11129812 No 2017-08-18 2037-08-18 US US10639297 No 2017-08-18 2037-08-18 US US9867810 No 2017-08-18 2037-08-18 US
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 195-205 https://www.medisca.com/NDC_SPECS/MUS/0182/MSDS/0182.pdf logP -3.03 https://www.medisca.com/NDC_SPECS/MUS/0182/MSDS/0182.pdf - Predicted Properties
Property Value Source Water Solubility 2.07 mg/mL ALOGPS logP 1.15 ALOGPS logP 0.95 Chemaxon logS -2 ALOGPS pKa (Strongest Basic) 6.37 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 2 Chemaxon Hydrogen Donor Count 0 Chemaxon Polar Surface Area 44.12 Å2 Chemaxon Rotatable Bond Count 3 Chemaxon Refractivity 56.53 m3·mol-1 Chemaxon Polarizability 22.34 Å3 Chemaxon Number of Rings 2 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9816 Blood Brain Barrier + 0.9758 Caco-2 permeable + 0.6202 P-glycoprotein substrate Non-substrate 0.5806 P-glycoprotein inhibitor I Non-inhibitor 0.8457 P-glycoprotein inhibitor II Non-inhibitor 0.9432 Renal organic cation transporter Non-inhibitor 0.6467 CYP450 2C9 substrate Non-substrate 0.8408 CYP450 2D6 substrate Non-substrate 0.9116 CYP450 3A4 substrate Non-substrate 0.6665 CYP450 1A2 substrate Non-inhibitor 0.9045 CYP450 2C9 inhibitor Non-inhibitor 0.8732 CYP450 2D6 inhibitor Non-inhibitor 0.9231 CYP450 2C19 inhibitor Non-inhibitor 0.9026 CYP450 3A4 inhibitor Inhibitor 0.7961 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.8682 Ames test Non AMES toxic 0.6957 Carcinogenicity Non-carcinogens 0.9166 Biodegradation Not ready biodegradable 0.6808 Rat acute toxicity 2.6826 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9432 hERG inhibition (predictor II) Non-inhibitor 0.9009
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS splash10-0006-9500000000-dadfea39cdf9ef51bb38 Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-0a4i-0390000000-13e5a828bfc740994c0a Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-0a4i-0190000000-34ce099765686b88b6ba Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-056s-1910000000-a12e72bf6758da72c06f Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-0bta-6940000000-5a3473b68a3047bcc953 Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-00fr-4900000000-1207f723b1f8a6d58a60 Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-014i-9600000000-1c7e6cd03421f5653221 Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 155.3026138 predictedDarkChem Lite v0.1.0 [M-H]- 155.9940138 predictedDarkChem Lite v0.1.0 [M-H]- 155.0633138 predictedDarkChem Lite v0.1.0 [M-H]- 144.30807 predictedDeepCCS 1.0 (2019) [M+H]+ 155.5314138 predictedDarkChem Lite v0.1.0 [M+H]+ 156.5107138 predictedDarkChem Lite v0.1.0 [M+H]+ 155.4929138 predictedDarkChem Lite v0.1.0 [M+H]+ 146.70366 predictedDeepCCS 1.0 (2019) [M+Na]+ 155.1996138 predictedDarkChem Lite v0.1.0 [M+Na]+ 156.2025138 predictedDarkChem Lite v0.1.0 [M+Na]+ 155.2151138 predictedDarkChem Lite v0.1.0 [M+Na]+ 152.6361 predictedDeepCCS 1.0 (2019)
Targets
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- 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
- 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]
- Panarese V, Moshirfar M: Pilocarpine. . [Article]
- 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
- Panarese V, Moshirfar M: Pilocarpine. . [Article]
- 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
- Panarese V, Moshirfar M: Pilocarpine. . [Article]
- 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
- Panarese V, Moshirfar M: Pilocarpine. . [Article]
- 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
- 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
- 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]
- 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
- SubstrateInhibitor
- 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
- 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]
- 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]
- 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
- 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 20, 2024 23:54