Identification

Name
Pilocarpine
Accession Number
DB01085  (APRD00382)
Type
Small Molecule
Groups
Approved, Investigational
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
  • (3S-cis)-3-Ethyldihydro-4-[(1-methyl-1H-imidazol-5-yl)methyl]-2(3H)-furanone
  • (3S,4R)-3-Ethyldihydro-4-((1-methyl-1H-imidazol-5-yl)methyl)-2(3H)-furanone
  • Pilocarpine
Product Ingredients
IngredientUNIICASInChI Key
Pilocarpine hydrochloride0WW6D218XJ54-71-7RNAICSBVACLLGM-GNAZCLTHSA-N
Pilocarpine nitrateM20T465H6J148-72-1PRZXEPJJHQYOGF-GNAZCLTHSA-N
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Isopto CarpineSolution / drops10 mg/mLOphthalmicAlcon, Inc.1974-01-01Not applicableUs
Isopto CarpineLiquid10 mgOphthalmicNovartis1959-12-312017-05-24Canada
Isopto CarpineSolution / drops40 mg/mLOphthalmicAlcon, Inc.1974-01-01Not applicableUs
Isopto CarpineLiquid20 mgOphthalmicNovartis1959-12-31Not applicableCanada
Isopto CarpineSolution / drops20 mg/mLOphthalmicAlcon, Inc.1974-01-01Not applicableUs
Isopto CarpineLiquid40 mgOphthalmicNovartis1959-12-31Not applicableCanada
Isopto Carpine 0.5%Liquid0.5 %OphthalmicAlcon, Inc.1951-12-312002-04-16Canada
Isopto Carpine Liq 6%Liquid60 gOphthalmicAlcon, Inc.1959-12-312001-08-14Canada
Minims Pilocarpine Nitrate 2%Solution / drops2 %OphthalmicValeant Canada Lp Valeant Canada S.E.C.1995-12-31Not applicableCanada
Minims Pilocarpine Nitrate 4%Solution / drops4 %OphthalmicChauvin Pharmaceuticals Limited1995-12-312009-02-04Canada
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Odan-pilocarpineSolution2 %OphthalmicOdan Laboratories Ltd1992-12-31Not applicableCanada
Odan-pilocarpineSolution1 %OphthalmicOdan Laboratories Ltd1991-12-31Not applicableCanada
Odan-pilocarpineSolution4 %OphthalmicOdan Laboratories Ltd1991-12-31Not applicableCanada
Pilocarpine HydrochlorideTablet, film coated5 mg/1OralLannett Company, Inc.2006-01-31Not applicableUs
Pilocarpine HydrochlorideTablet5 mg/1OralRoxane Laboratories2004-12-222016-03-11Us
Pilocarpine HydrochlorideSolution / drops40 mg/mLOphthalmicSandoz1996-02-21Not applicableUs
Pilocarpine HydrochlorideSolution / drops10 mg/mLOphthalmicAkorn2017-09-28Not applicableUs
Pilocarpine hydrochlorideTablet, film coated5 mg/1OralCarilion Materials Management2011-09-13Not applicableUs
Pilocarpine HydrochlorideTablet, film coated5 mg/1OralKaiser Foundations Hospitals2014-05-29Not applicableUs
Pilocarpine HydrochlorideSolution / drops40 mg/mLOphthalmicAkorn2017-09-28Not applicableUs
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Betoptic/piloPilocarpine hydrochloride (1.75 %) + Betaxolol (0.25 %)SuspensionOphthalmicAlcon, Inc.Not applicableNot applicableCanada
E-pilo 1 Ophthalmic SolutionPilocarpine hydrochloride (10 mg) + Epinephrine bitartrate (10 mg)Solution / dropsOphthalmicCiba Vision1996-12-311999-01-27Canada
E-pilo 2 Ophthalmic SolutionPilocarpine hydrochloride (20 mg) + Epinephrine bitartrate (10 mg)Solution / dropsOphthalmicCiba Vision1997-02-111999-05-10Canada
E-pilo 4 Ophthalmic SolutionPilocarpine hydrochloride (40 mg) + Epinephrine bitartrate (10 mg)Solution / dropsOphthalmicCiba Vision1995-12-311999-07-13Canada
E-pilo 6 Ophthalmic SolutionPilocarpine hydrochloride (60 mg) + Epinephrine bitartrate (10 mg)Solution / dropsOphthalmicCiba Vision1997-02-111999-05-10Canada
E-pilo-1 Oph SolnPilocarpine hydrochloride (10 mg) + Epinephrine bitartrate (10 mg)Solution / dropsOphthalmicIolab Pharmaceuticals1988-12-311996-09-09Canada
E-pilo-2 Oph SolnPilocarpine hydrochloride (20 mg) + Epinephrine bitartrate (10 mg)Solution / dropsOphthalmicIolab Pharmaceuticals1988-12-311997-07-23Canada
E-pilo-4 Oph SolnPilocarpine hydrochloride (40 mg) + Epinephrine bitartrate (10 mg)Solution / dropsOphthalmicIolab Pharmaceuticals1988-12-311996-09-09Canada
E-pilo-6 Oph SolnPilocarpine hydrochloride (60 mg) + Epinephrine bitartrate (10 mg)Solution / dropsOphthalmicIolab Pharmaceuticals1988-12-311997-07-23Canada
Timpilo 2Pilocarpine hydrochloride (2 %) + Timolol (0.5 %)SolutionOphthalmicMerck Ltd.1992-12-312005-08-09Canada
International/Other Brands
Diocarpine / Miocarpine / Pilostat / Pilovisc / Timpilo
Categories
UNII
01MI4Q9DI3
CAS number
92-13-7
Weight
Average: 208.2569
Monoisotopic: 208.121177766
Chemical Formula
C11H16N2O2
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

Pharmacology

Indication

For the treatment of radiation-induced dry mouth (xerostomia) and symptoms of dry mouth in patients with Sjögrens syndrome.

Structured Indications
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.

TargetActionsOrganism
AMuscarinic acetylcholine receptor M3
agonist
Human
AMuscarinic acetylcholine receptor M1
agonist
Human
AMuscarinic acetylcholine receptor M2
agonist
Human
UMuscarinic acetylcholine receptor M4
partial agonist
Human
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
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteractionDrug group
1,10-PhenanthrolineThe risk or severity of adverse effects can be increased when 1,10-Phenanthroline is combined with Pilocarpine.Experimental
AcebutololThe risk or severity of adverse effects can be increased when Acebutolol is combined with Pilocarpine.Approved, Investigational
Acetyl sulfisoxazoleThe metabolism of Pilocarpine can be decreased when combined with Acetyl sulfisoxazole.Approved, Vet Approved
AlprenololThe risk or severity of adverse effects can be increased when Alprenolol is combined with Pilocarpine.Approved, Withdrawn
AmbenoniumThe risk or severity of adverse effects can be increased when Ambenonium is combined with Pilocarpine.Approved
AmiodaroneThe metabolism of Pilocarpine can be decreased when combined with Amiodarone.Approved, Investigational
ApalutamideThe serum concentration of Pilocarpine can be decreased when it is combined with Apalutamide.Approved, Investigational
AprepitantThe serum concentration of Pilocarpine can be increased when it is combined with Aprepitant.Approved, Investigational
ArotinololThe risk or severity of adverse effects can be increased when Arotinolol is combined with Pilocarpine.Investigational
ArtesunateThe serum concentration of the active metabolites of Artesunate can be reduced when Artesunate is used in combination with Pilocarpine resulting in a loss in efficacy.Approved, Investigational
AsunaprevirThe serum concentration of Asunaprevir can be increased when it is combined with Pilocarpine.Approved, Investigational, Withdrawn
AtazanavirThe metabolism of Pilocarpine can be decreased when combined with Atazanavir.Approved, Investigational
AtenololThe risk or severity of adverse effects can be increased when Atenolol is combined with Pilocarpine.Approved
AtomoxetineThe metabolism of Pilocarpine can be decreased when combined with Atomoxetine.Approved
AtorvastatinThe risk or severity of adverse effects can be increased when Pilocarpine is combined with Atorvastatin.Approved
BefunololThe risk or severity of adverse effects can be increased when Befunolol is combined with Pilocarpine.Experimental
BetaxololThe risk or severity of adverse effects can be increased when Betaxolol is combined with Pilocarpine.Approved, Investigational
BevantololThe risk or severity of adverse effects can be increased when Bevantolol is combined with Pilocarpine.Approved
BisoprololThe risk or severity of adverse effects can be increased when Bisoprolol is combined with Pilocarpine.Approved
BoceprevirThe metabolism of Pilocarpine can be decreased when combined with Boceprevir.Approved, Withdrawn
BopindololThe risk or severity of adverse effects can be increased when Bopindolol is combined with Pilocarpine.Approved
BortezomibThe metabolism of Pilocarpine can be decreased when combined with Bortezomib.Approved, Investigational
BosentanThe serum concentration of Pilocarpine can be decreased when it is combined with Bosentan.Approved, Investigational
BosutinibThe serum concentration of Bosutinib can be increased when it is combined with Pilocarpine.Approved
BromocriptineThe risk or severity of adverse effects can be increased when Bromocriptine is combined with Pilocarpine.Approved, Investigational
BucindololThe risk or severity of adverse effects can be increased when Bucindolol is combined with Pilocarpine.Investigational
BufuralolThe risk or severity of adverse effects can be increased when Bufuralol is combined with Pilocarpine.Experimental, Investigational
BupranololThe risk or severity of adverse effects can be increased when Bupranolol is combined with Pilocarpine.Approved
CabergolineThe risk or severity of adverse effects can be increased when Cabergoline is combined with Pilocarpine.Approved
CarbamazepineThe metabolism of Pilocarpine can be increased when combined with Carbamazepine.Approved, Investigational
CarteololThe risk or severity of adverse effects can be increased when Carteolol is combined with Pilocarpine.Approved
CarvedilolThe risk or severity of adverse effects can be increased when Carvedilol is combined with Pilocarpine.Approved, Investigational
CeliprololThe risk or severity of adverse effects can be increased when Celiprolol is combined with Pilocarpine.Approved, Investigational
CeritinibThe serum concentration of Pilocarpine can be increased when it is combined with Ceritinib.Approved
CerivastatinThe serum concentration of Cerivastatin can be increased when it is combined with Pilocarpine.Approved, Withdrawn
CimetropiumPilocarpine may decrease the anticholinergic activities of Cimetropium.Experimental, Investigational
ClarithromycinThe metabolism of Pilocarpine can be decreased when combined with Clarithromycin.Approved
ClemastineThe metabolism of Pilocarpine can be decreased when combined with Clemastine.Approved, Investigational
CloranololThe risk or severity of adverse effects can be increased when Cloranolol is combined with Pilocarpine.Experimental
ClotrimazoleThe metabolism of Pilocarpine can be decreased when combined with Clotrimazole.Approved, Vet Approved
CobicistatThe metabolism of Pilocarpine can be decreased when combined with Cobicistat.Approved
ConivaptanThe serum concentration of Conivaptan can be increased when it is combined with Pilocarpine.Approved, Investigational
CoumaphosThe risk or severity of adverse effects can be increased when Coumaphos is combined with Pilocarpine.Vet Approved
CrizotinibThe metabolism of Pilocarpine can be decreased when combined with Crizotinib.Approved
CyclosporineThe metabolism of Pilocarpine can be decreased when combined with Cyclosporine.Approved, Investigational, Vet Approved
Cyproterone acetateThe serum concentration of Pilocarpine can be decreased when it is combined with Cyproterone acetate.Approved, Investigational
DabrafenibThe serum concentration of Pilocarpine can be decreased when it is combined with Dabrafenib.Approved, Investigational
DarunavirThe metabolism of Pilocarpine can be decreased when combined with Darunavir.Approved
DasatinibThe serum concentration of Pilocarpine can be increased when it is combined with Dasatinib.Approved, Investigational
DecamethoniumThe risk or severity of adverse effects can be increased when Decamethonium is combined with Pilocarpine.Approved
DeferasiroxThe serum concentration of Pilocarpine can be decreased when it is combined with Deferasirox.Approved, Investigational
DelavirdineThe metabolism of Pilocarpine can be decreased when combined with Delavirdine.Approved
DemecariumThe risk or severity of adverse effects can be increased when Demecarium is combined with Pilocarpine.Approved
DichlorvosThe risk or severity of adverse effects can be increased when Dichlorvos is combined with Pilocarpine.Vet Approved
DihydroergocornineThe risk or severity of adverse effects can be increased when Dihydroergocornine is combined with Pilocarpine.Approved
DihydroergocristineThe risk or severity of adverse effects can be increased when Dihydroergocristine is combined with Pilocarpine.Approved, Experimental
DihydroergocryptineThe risk or severity of adverse effects can be increased when Dihydroergocryptine is combined with Pilocarpine.Experimental
DihydroergotamineThe risk or severity of adverse effects can be increased when Dihydroergotamine is combined with Pilocarpine.Approved, Investigational
DiltiazemThe metabolism of Pilocarpine can be decreased when combined with Diltiazem.Approved, Investigational
DistigmineThe risk or severity of adverse effects can be increased when Distigmine is combined with Pilocarpine.Experimental
DonepezilThe risk or severity of adverse effects can be increased when Donepezil is combined with Pilocarpine.Approved
DoxycyclineThe metabolism of Pilocarpine can be decreased when combined with Doxycycline.Approved, Investigational, Vet Approved
DronedaroneThe metabolism of Pilocarpine can be decreased when combined with Dronedarone.Approved
EchothiophateThe risk or severity of adverse effects can be increased when Echothiophate is combined with Pilocarpine.Approved
EdrophoniumThe risk or severity of adverse effects can be increased when Edrophonium is combined with Pilocarpine.Approved
EnzalutamideThe serum concentration of Pilocarpine can be decreased when it is combined with Enzalutamide.Approved
EpanololThe risk or severity of adverse effects can be increased when Epanolol is combined with Pilocarpine.Experimental
ErgonovineThe risk or severity of adverse effects can be increased when Ergonovine is combined with Pilocarpine.Approved
ErgotamineThe risk or severity of adverse effects can be increased when Ergotamine is combined with Pilocarpine.Approved
ErythromycinThe metabolism of Pilocarpine can be decreased when combined with Erythromycin.Approved, Investigational, Vet Approved
EsmololThe risk or severity of adverse effects can be increased when Esmolol is combined with Pilocarpine.Approved
FenthionThe risk or severity of adverse effects can be increased when Fenthion is combined with Pilocarpine.Vet Approved
FluconazoleThe metabolism of Pilocarpine can be decreased when combined with Fluconazole.Approved, Investigational
FluvastatinThe serum concentration of Fluvastatin can be increased when it is combined with Pilocarpine.Approved
FluvoxamineThe metabolism of Pilocarpine can be decreased when combined with Fluvoxamine.Approved, Investigational
FosamprenavirThe metabolism of Pilocarpine can be decreased when combined with Fosamprenavir.Approved
FosaprepitantThe serum concentration of Pilocarpine can be increased when it is combined with Fosaprepitant.Approved
FosphenytoinThe metabolism of Pilocarpine can be increased when combined with Fosphenytoin.Approved, Investigational
Fusidic AcidThe serum concentration of Pilocarpine can be increased when it is combined with Fusidic Acid.Approved, Investigational
GalantamineThe risk or severity of adverse effects can be increased when Galantamine is combined with Pilocarpine.Approved
Gallamine TriethiodideThe risk or severity of adverse effects can be increased when Gallamine Triethiodide is combined with Pilocarpine.Approved
Huperzine AThe risk or severity of adverse effects can be increased when Huperzine A is combined with Pilocarpine.Approved, Investigational
IbrutinibThe serum concentration of Ibrutinib can be increased when it is combined with Pilocarpine.Approved
IdelalisibThe metabolism of Pilocarpine can be decreased when combined with Idelalisib.Approved
ImatinibThe metabolism of Pilocarpine can be decreased when combined with Imatinib.Approved
IndenololThe risk or severity of adverse effects can be increased when Indenolol is combined with Pilocarpine.Withdrawn
IndinavirThe metabolism of Pilocarpine can be decreased when combined with Indinavir.Approved
IpidacrineThe risk or severity of adverse effects can be increased when Ipidacrine is combined with Pilocarpine.Experimental
IsavuconazoleThe serum concentration of Pilocarpine can be increased when it is combined with Isavuconazole.Approved, Investigational
IsavuconazoniumThe metabolism of Pilocarpine can be decreased when combined with Isavuconazonium.Approved, Investigational
IsoflurophateThe risk or severity of adverse effects can be increased when Isoflurophate is combined with Pilocarpine.Approved, Investigational, Withdrawn
IsoniazidThe metabolism of Pilocarpine can be decreased when combined with Isoniazid.Approved, Investigational
IsradipineThe metabolism of Pilocarpine can be decreased when combined with Isradipine.Approved, Investigational
ItraconazoleThe metabolism of Pilocarpine can be decreased when combined with Itraconazole.Approved, Investigational
IvacaftorThe serum concentration of Pilocarpine can be increased when it is combined with Ivacaftor.Approved
KetoconazoleThe metabolism of Pilocarpine can be decreased when combined with Ketoconazole.Approved, Investigational
LabetalolThe risk or severity of adverse effects can be increased when Labetalol is combined with Pilocarpine.Approved
LandiololThe risk or severity of adverse effects can be increased when Landiolol is combined with Pilocarpine.Investigational
LevobunololThe risk or severity of adverse effects can be increased when Levobunolol is combined with Pilocarpine.Approved
LisurideThe risk or severity of adverse effects can be increased when Lisuride is combined with Pilocarpine.Approved, Investigational
LopinavirThe metabolism of Pilocarpine can be decreased when combined with Lopinavir.Approved
LorpiprazoleThe serum concentration of Pilocarpine can be increased when it is combined with Lorpiprazole.Approved
LovastatinThe serum concentration of Lovastatin can be increased when it is combined with Pilocarpine.Approved, Investigational
LuliconazoleThe serum concentration of Pilocarpine can be increased when it is combined with Luliconazole.Approved
LumacaftorThe metabolism of Pilocarpine can be increased when combined with Lumacaftor.Approved
Lysergic Acid DiethylamideThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Pilocarpine.Illicit, Investigational, Withdrawn
MalathionThe risk or severity of adverse effects can be increased when Malathion is combined with Pilocarpine.Approved, Investigational
MefloquineThe risk or severity of adverse effects can be increased when Mefloquine is combined with Pilocarpine.Approved, Investigational
MemantineThe risk or severity of adverse effects can be increased when Memantine is combined with Pilocarpine.Approved, Investigational
MepindololThe risk or severity of adverse effects can be increased when Mepindolol is combined with Pilocarpine.Experimental
MetergolineThe risk or severity of adverse effects can be increased when Metergoline is combined with Pilocarpine.Experimental
Methanesulfonyl FluorideThe risk or severity of adverse effects can be increased when Methanesulfonyl Fluoride is combined with Pilocarpine.Investigational
MethylergometrineThe risk or severity of adverse effects can be increased when Methylergometrine is combined with Pilocarpine.Approved
MethysergideThe risk or severity of adverse effects can be increased when Methysergide is combined with Pilocarpine.Approved
MetipranololThe risk or severity of adverse effects can be increased when Metipranolol is combined with Pilocarpine.Approved
MetoclopramideThe risk or severity of adverse effects can be increased when Metoclopramide is combined with Pilocarpine.Approved, Investigational
MetoprololThe risk or severity of adverse effects can be increased when Metoprolol is combined with Pilocarpine.Approved, Investigational
MevastatinThe serum concentration of Mevastatin can be increased when it is combined with Pilocarpine.Experimental
MifepristoneThe serum concentration of Pilocarpine can be increased when it is combined with Mifepristone.Approved, Investigational
MinaprineThe risk or severity of adverse effects can be increased when Minaprine is combined with Pilocarpine.Approved
MitotaneThe serum concentration of Pilocarpine can be decreased when it is combined with Mitotane.Approved
NadololThe risk or severity of adverse effects can be increased when Nadolol is combined with Pilocarpine.Approved
NebivololThe risk or severity of adverse effects can be increased when Nebivolol is combined with Pilocarpine.Approved, Investigational
NefazodoneThe metabolism of Pilocarpine can be decreased when combined with Nefazodone.Approved, Withdrawn
NelfinavirThe metabolism of Pilocarpine can be decreased when combined with Nelfinavir.Approved
NeostigmineThe risk or severity of adverse effects can be increased when Neostigmine is combined with Pilocarpine.Approved, Vet Approved
NetupitantThe serum concentration of Pilocarpine can be increased when it is combined with Netupitant.Approved, Investigational
NevirapineThe metabolism of Pilocarpine can be increased when combined with Nevirapine.Approved
NicergolineThe risk or severity of adverse effects can be increased when Nicergoline is combined with Pilocarpine.Approved, Investigational
NicotineThe metabolism of Pilocarpine can be decreased when combined with Nicotine.Approved
NilotinibThe metabolism of Pilocarpine can be decreased when combined with Nilotinib.Approved, Investigational
OlaparibThe metabolism of Pilocarpine can be decreased when combined with Olaparib.Approved
OsimertinibThe serum concentration of Pilocarpine can be increased when it is combined with Osimertinib.Approved
OxprenololThe risk or severity of adverse effects can be increased when Oxprenolol is combined with Pilocarpine.Approved
PalbociclibThe serum concentration of Pilocarpine can be increased when it is combined with Palbociclib.Approved, Investigational
ParaoxonThe risk or severity of adverse effects can be increased when Paraoxon is combined with Pilocarpine.Experimental
PenbutololThe risk or severity of adverse effects can be increased when Penbutolol is combined with Pilocarpine.Approved, Investigational
PentobarbitalThe metabolism of Pilocarpine can be increased when combined with Pentobarbital.Approved, Investigational, Vet Approved
PergolideThe risk or severity of adverse effects can be increased when Pergolide is combined with Pilocarpine.Approved, Investigational, Vet Approved, Withdrawn
PhenobarbitalThe metabolism of Pilocarpine can be increased when combined with Phenobarbital.Approved, Investigational
PhenytoinThe metabolism of Pilocarpine can be increased when combined with Phenytoin.Approved, Vet Approved
PhysostigmineThe risk or severity of adverse effects can be increased when Physostigmine is combined with Pilocarpine.Approved, Investigational
PindololThe risk or severity of adverse effects can be increased when Pindolol is combined with Pilocarpine.Approved, Investigational
PitavastatinThe serum concentration of Pitavastatin can be increased when it is combined with Pilocarpine.Approved
PitolisantThe serum concentration of Pilocarpine can be decreased when it is combined with Pitolisant.Approved, Investigational
Platelet Activating FactorThe risk or severity of adverse effects can be increased when Platelet Activating Factor is combined with Pilocarpine.Experimental
PosaconazoleThe metabolism of Pilocarpine can be decreased when combined with Posaconazole.Approved, Investigational, Vet Approved
PractololThe risk or severity of adverse effects can be increased when Practolol is combined with Pilocarpine.Approved
PravastatinThe serum concentration of Pravastatin can be increased when it is combined with Pilocarpine.Approved
PrimidoneThe metabolism of Pilocarpine can be increased when combined with Primidone.Approved, Vet Approved
PropranololThe risk or severity of adverse effects can be increased when Propranolol is combined with Pilocarpine.Approved, Investigational
PyridostigmineThe risk or severity of adverse effects can be increased when Pyridostigmine is combined with Pilocarpine.Approved, Investigational
RanolazineThe metabolism of Pilocarpine can be decreased when combined with Ranolazine.Approved, Investigational
RifabutinThe metabolism of Pilocarpine can be increased when combined with Rifabutin.Approved, Investigational
RifampicinThe metabolism of Pilocarpine can be increased when combined with Rifampicin.Approved
RifapentineThe metabolism of Pilocarpine can be increased when combined with Rifapentine.Approved, Investigational
RilpivirineThe serum concentration of Rilpivirine can be increased when it is combined with Pilocarpine.Approved
RivastigmineThe risk or severity of adverse effects can be increased when Rivastigmine is combined with Pilocarpine.Approved, Investigational
RosuvastatinThe serum concentration of Rosuvastatin can be increased when it is combined with Pilocarpine.Approved
RucaparibThe metabolism of Pilocarpine can be decreased when combined with Rucaparib.Approved, Investigational
SaquinavirThe metabolism of Pilocarpine can be decreased when combined with Saquinavir.Approved, Investigational
SarilumabThe therapeutic efficacy of Pilocarpine can be decreased when used in combination with Sarilumab.Approved, Investigational
SildenafilThe metabolism of Pilocarpine can be decreased when combined with Sildenafil.Approved, Investigational
SiltuximabThe serum concentration of Pilocarpine can be decreased when it is combined with Siltuximab.Approved, Investigational
SimeprevirThe serum concentration of Pilocarpine can be increased when it is combined with Simeprevir.Approved
SimvastatinThe serum concentration of Simvastatin can be increased when it is combined with Pilocarpine.Approved
SotalolThe risk or severity of adverse effects can be increased when Sotalol is combined with Pilocarpine.Approved
St. John's WortThe serum concentration of Pilocarpine can be decreased when it is combined with St. John's Wort.Approved, Investigational, Nutraceutical
StiripentolThe serum concentration of Pilocarpine can be increased when it is combined with Stiripentol.Approved
SulfisoxazoleThe metabolism of Pilocarpine can be decreased when combined with Sulfisoxazole.Approved, Vet Approved
TacrineThe risk or severity of adverse effects can be increased when Tacrine is combined with Pilocarpine.Investigational, Withdrawn
TalinololThe risk or severity of adverse effects can be increased when Talinolol is combined with Pilocarpine.Investigational
TelaprevirThe metabolism of Pilocarpine can be decreased when combined with Telaprevir.Approved, Withdrawn
TelithromycinThe metabolism of Pilocarpine can be decreased when combined with Telithromycin.Approved
TergurideThe risk or severity of adverse effects can be increased when Terguride is combined with Pilocarpine.Experimental
TertatololThe risk or severity of adverse effects can be increased when Tertatolol is combined with Pilocarpine.Experimental
TiclopidineThe metabolism of Pilocarpine can be decreased when combined with Ticlopidine.Approved
TimololThe risk or severity of adverse effects can be increased when Timolol is combined with Pilocarpine.Approved
TocilizumabThe serum concentration of Pilocarpine can be decreased when it is combined with Tocilizumab.Approved
TolvaptanThe serum concentration of Tolvaptan can be increased when it is combined with Pilocarpine.Approved
TrichlorfonThe risk or severity of adverse effects can be increased when Trichlorfon is combined with Pilocarpine.Vet Approved
TubocurarineThe risk or severity of adverse effects can be increased when Tubocurarine is combined with Pilocarpine.Approved
TyrothricinThe risk or severity of adverse effects can be increased when Tyrothricin is combined with Pilocarpine.Approved
VemurafenibThe serum concentration of Pilocarpine can be decreased when it is combined with Vemurafenib.Approved
VenlafaxineThe metabolism of Pilocarpine can be decreased when combined with Venlafaxine.Approved
VerapamilThe metabolism of Pilocarpine can be decreased when combined with Verapamil.Approved
VoriconazoleThe metabolism of Pilocarpine can be decreased when combined with Voriconazole.Approved, Investigational
ZiprasidoneThe metabolism of Pilocarpine can be decreased when combined with Ziprasidone.Approved
Food Interactions
Not 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 References
Not Available
External Links
Human Metabolome Database
HMDB0015217
KEGG Drug
D00525
KEGG Compound
C07474
PubChem Compound
5910
PubChem Substance
46507475
ChemSpider
5699
BindingDB
50008072
ChEBI
8207
ChEMBL
CHEMBL550
Therapeutic Targets Database
DAP001113
PharmGKB
PA450962
IUPHAR
305
Guide to Pharmacology
GtP Drug Page
HET
9PL
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Pilocarpine
ATC Codes
S01EB51 — Pilocarpine, combinationsS01EB01 — PilocarpineN07AX01 — Pilocarpine
AHFS Codes
  • 52:40.20 — Miotics
  • 12:04.00 — Parasympathomemetic (Cholinergic) Agents
PDB Entries
3t3q / 3t3r / 3t3s / 3t3z
FDA label
Download (160 KB)
MSDS
Download (73.3 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1CompletedBasic ScienceHealthy Volunteers2
1CompletedTreatmentIncontinence1
2, 3CompletedSupportive CareHead and Neck Carcinoma / Xerostomia1
3CompletedPreventionCancers / Head and Neck Carcinoma1
3CompletedSupportive CareCancer, Breast / Vaginal Dryness1
3CompletedSupportive CareHead and Neck Carcinoma / Oral Complications1
3TerminatedSupportive CareOral Complications / Quality of Life1
4CompletedTreatmentGlaucoma, Angle-Closure1
4CompletedTreatmentPrimary Sjogren / Secondary Sjogren / Xerostomia1
4RecruitingTreatmentXerostomia1
Not AvailableCompletedBasic ScienceCystic Fibrosis (CF)1
Not AvailableCompletedSupportive CareXerostomia1
Not AvailableCompletedTreatmentDry Mouth5
Not AvailableRecruitingBasic ScienceGlaucoma1
Not AvailableRecruitingBasic ScienceStability & Variability of Lipid-derived Molecules in Sweat1
Not AvailableRecruitingDiagnosticDiabetes Mellitus (DM)1
Not AvailableRecruitingTreatmentGlaucoma, Angle-Closure1
Not AvailableRecruitingTreatmentOcular Hypertension / Open-angle Glaucoma (OAG)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
FormRouteStrength
SuspensionOphthalmic
Solution / dropsOphthalmic
LiquidOphthalmic10 mg
LiquidOphthalmic20 mg
LiquidOphthalmic40 mg
LiquidOphthalmic0.5 %
LiquidOphthalmic60 g
Solution / dropsOphthalmic4 %
Solution / dropsOphthalmic1 %
Solution / dropsOphthalmic2 %
Solution / dropsOphthalmic6 %
ImplantIntraocular5 mg
ImplantIntraocular11 mg
SolutionOphthalmic1 %
SolutionOphthalmic2 %
SolutionOphthalmic4 %
SolutionOphthalmic6 %
SolutionOphthalmic40 mg/1
Solution / dropsConjunctival10 mg/mL
Solution / dropsOphthalmic10 mg/mL
Solution / dropsOphthalmic20 mg/mL
Solution / dropsOphthalmic40 mg/mL
TabletOral5 mg/1
Tablet, film coatedOral5 mg/1
Tablet, film coatedOral7.5 mg/1
GelOphthalmic4 %
LiquidOphthalmic5 mg
LiquidOphthalmic60 mg
LiquidOphthalmic1 %
LiquidOphthalmic2 %
LiquidOphthalmic4 %
TabletOral5 mg
SolutionOphthalmic
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
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)204-205 °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 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-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

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 / Gamma butyrolactone / N-substituted imidazole / Azole / Imidazole / Heteroaromatic compound / Tetrahydrofuran / Carboxylic acid ester / Lactone / Carboxylic acid derivative
show 13 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
pilocarpine (CHEBI:8207) / Imidazole alkaloids (C07474)

Targets

Kind
Protein
Organism
Human
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. 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. doi: 10.1124/mol.108.054452. Epub 2009 Jun 4. [PubMed:19498041]
  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. doi: 10.1124/jpet.108.145219. Epub 2008 Sep 29. [PubMed:18824613]
Kind
Protein
Organism
Human
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. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  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:17016423]
  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. doi: 10.1124/jpet.108.145219. Epub 2008 Sep 29. [PubMed:18824613]
Kind
Protein
Organism
Human
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. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
  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. doi: 10.1152/ajplung.90267.2008. Epub 2009 May 22. [PubMed:19465517]
  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. doi: 10.1124/jpet.108.145219. Epub 2008 Sep 29. [PubMed:18824613]
Kind
Protein
Organism
Human
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. 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. doi: 10.1124/jpet.108.145219. Epub 2008 Sep 29. [PubMed:18824613]

Enzymes

Kind
Protein
Organism
Human
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. 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. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Steroid hydroxylase activity
Specific Function
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 ...
Gene Name
CYP2E1
Uniprot ID
P05181
Uniprot Name
Cytochrome P450 2E1
Molecular Weight
56848.42 Da
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. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
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. 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. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]

Drug created on June 13, 2005 07:24 / Updated on May 22, 2018 23:49