U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C11H16N2O2
Molecular Weight 208.2569
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of Pilocarpine

SMILES

CC[C@H]1[C@@H](CC2=CN=CN2C)COC1=O

InChI

InChIKey=QCHFTSOMWOSFHM-WPRPVWTQSA-N
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

HIDE SMILES / InChI

Molecular Formula C11H16N2O2
Molecular Weight 208.2569
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

Pilocarpine is an alkaloid extracted from plants of the genus Pilocarpus. The drug stimulates the muscarinic receptors (especially M3, which is expressed in smooth muscles and glands) and thus induces salivation, hypertension and water intake. Pilocarpine was appoved by FDA for the alleviation of symptoms of xerostomia in patients who have undergone radiation therapy to their head and neck cancer and in patients with Sjogren's Syndrome. Ophthalmic solution of the drug is prescribed for the treatment of glaucoma, ocular hypertension, postoperative elevated intraocular pressure, etc.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Secondary
SALAGEN

Approved Use

SALAGEN Tablets are indicated for 1) the treatment of symptoms of dry mouth from salivary gland hypofunction caused by radiotherapy for cancer of the head and neck; and 2) the treatment of symptoms of dry mouth in patients with Sjogren's syndrome.

Launch Date

1994
Palliative
SALAGEN

Approved Use

SALAGEN Tablets are indicated for 1) the treatment of symptoms of dry mouth from salivary gland hypofunction caused by radiotherapy for cancer of the head and neck; and 2) the treatment of symptoms of dry mouth in patients with Sjogren's syndrome.

Launch Date

1994
Primary
ISOPTO CARPINE

Approved Use

Isopto Carpine is a muscarinic cholinergic agonist indicated for (1) the reduction of elevated intraocular pressure (IOP) in patients with open-angle glaucoma or ocular hypertension; (2) the management of acute angle-closure glaucoma; (3) the prevention of postoperative elevated IOP associated with laser surgery; (4) the induction of miosis.

Launch Date

2010
Primary
ISOPTO CARPINE

Approved Use

Isopto Carpine is a muscarinic cholinergic agonist indicated for (1) the reduction of elevated intraocular pressure (IOP) in patients with open-angle glaucoma or ocular hypertension; (2) the management of acute angle-closure glaucoma; (3) the prevention of postoperative elevated IOP associated with laser surgery; (4) the induction of miosis.

Launch Date

2010
Primary
ISOPTO CARPINE

Approved Use

Isopto Carpine is a muscarinic cholinergic agonist indicated for (1) the reduction of elevated intraocular pressure (IOP) in patients with open-angle glaucoma or ocular hypertension; (2) the management of acute angle-closure glaucoma; (3) the prevention of postoperative elevated IOP associated with laser surgery; (4) the induction of miosis.

Launch Date

2010
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
15 ng/mL
5 mg 3 times / day multiple, oral
dose: 5 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
PILOCARPINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
33 ng × h/mL
5 mg 3 times / day multiple, oral
dose: 5 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
PILOCARPINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
0.76 h
5 mg 3 times / day multiple, oral
dose: 5 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
PILOCARPINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
100%
5 mg 3 times / day multiple, oral
dose: 5 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
PILOCARPINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
2 % 4 times / day multiple, ophthalmic
Recommended
Dose: 2 %, 4 times / day
Route: ophthalmic
Route: multiple
Dose: 2 %, 4 times / day
Sources:
unhealthy, 44-75 years
Health Status: unhealthy
Age Group: 44-75 years
Sex: M
Sources:
Disc. AE: Vision blurred...
AEs leading to
discontinuation/dose reduction:
Vision blurred (moderate, 2 patients)
Sources:
20 mg single, oral
Overdose
Dose: 20 mg
Route: oral
Route: single
Dose: 20 mg
Sources:
unhealthy, 46 years
Health Status: unhealthy
Age Group: 46 years
Sex: F
Sources:
Other AEs: Increased salivation, Lacrimation...
Other AEs:
Increased salivation (1 patient)
Lacrimation (1 patient)
Vomiting (1 patient)
Anxiety (1 patient)
Tremor (1 patient)
Sources:
100 mg single, oral
Overdose
Dose: 100 mg
Route: oral
Route: single
Dose: 100 mg
Sources:
unhealthy
1.54 % 3 times / day multiple, topical
Recommended
Dose: 1.54 %, 3 times / day
Route: topical
Route: multiple
Dose: 1.54 %, 3 times / day
Sources:
unhealthy
Health Status: unhealthy
Sources:
AEs

AEs

AESignificanceDosePopulation
Vision blurred moderate, 2 patients
Disc. AE
2 % 4 times / day multiple, ophthalmic
Recommended
Dose: 2 %, 4 times / day
Route: ophthalmic
Route: multiple
Dose: 2 %, 4 times / day
Sources:
unhealthy, 44-75 years
Health Status: unhealthy
Age Group: 44-75 years
Sex: M
Sources:
Anxiety 1 patient
20 mg single, oral
Overdose
Dose: 20 mg
Route: oral
Route: single
Dose: 20 mg
Sources:
unhealthy, 46 years
Health Status: unhealthy
Age Group: 46 years
Sex: F
Sources:
Increased salivation 1 patient
20 mg single, oral
Overdose
Dose: 20 mg
Route: oral
Route: single
Dose: 20 mg
Sources:
unhealthy, 46 years
Health Status: unhealthy
Age Group: 46 years
Sex: F
Sources:
Lacrimation 1 patient
20 mg single, oral
Overdose
Dose: 20 mg
Route: oral
Route: single
Dose: 20 mg
Sources:
unhealthy, 46 years
Health Status: unhealthy
Age Group: 46 years
Sex: F
Sources:
Tremor 1 patient
20 mg single, oral
Overdose
Dose: 20 mg
Route: oral
Route: single
Dose: 20 mg
Sources:
unhealthy, 46 years
Health Status: unhealthy
Age Group: 46 years
Sex: F
Sources:
Vomiting 1 patient
20 mg single, oral
Overdose
Dose: 20 mg
Route: oral
Route: single
Dose: 20 mg
Sources:
unhealthy, 46 years
Health Status: unhealthy
Age Group: 46 years
Sex: F
Sources:
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG



OverviewOther

Drug as perpetrator​

Drug as perpetrator​

Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
weak
unlikely (co-administration study)
Comment: Given the low systemic exposure following topical ocular administration of ISOPTO® Carpine, clinically relevant drug-drug interactions based on CYP450 interactions is not expected for ISOPTO Carpine
Page: 20.0
weak
unlikely (co-administration study)
Comment: Given the low systemic exposure following topical ocular administration of ISOPTO® Carpine, clinically relevant drug-drug interactions based on CYP450 interactions is not expected for ISOPTO Carpine
Page: 20.0
weak
unlikely (co-administration study)
Comment: Given the low systemic exposure following topical ocular administration of ISOPTO® Carpine, clinically relevant drug-drug interactions based on CYP450 interactions is not expected for ISOPTO Carpine
Page: 20.0
weak
unlikely (co-administration study)
Comment: Given the low systemic exposure following topical ocular administration of ISOPTO® Carpine, clinically relevant drug-drug interactions based on CYP450 interactions is not expected for ISOPTO Carpine
Page: 20.0
weak
unlikely (co-administration study)
Comment: Given the low systemic exposure following topical ocular administration of ISOPTO® Carpine, clinically relevant drug-drug interactions based on CYP450 interactions is not expected for ISOPTO Carpine
Page: 20.0
weak
unlikely (co-administration study)
Comment: Given the low systemic exposure following topical ocular administration of ISOPTO® Carpine, clinically relevant drug-drug interactions based on CYP450 interactions is not expected for ISOPTO Carpine
Page: 20.0
yes
yes
yes
unlikely (co-administration study)
Comment: Given the low systemic exposure following topical ocular administration of ISOPTO® Carpine, clinically relevant drug-drug interactions based on CYP450 interactions is not expected for ISOPTO Carpine
Page: 3.0
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
The effect of pilocarpine on salivary constituents in patients with chronic graft-versus-host disease.
2001-08
Defective fluid secretion and NaCl absorption in the parotid glands of Na+/H+ exchanger-deficient mice.
2001-07-20
Reliable measurement of mouse intraocular pressure by a servo-null micropipette system.
2001-07
Prophylactic effects of pilocarpine hydrochloride on xerostomia models induced by X-ray irradiation in rats.
2001-07
Poly(2-hydroxyethyl methacrylate) film as a drug delivery system for pilocarpine.
2001-07
Agonistic behavior in groups of limbic epileptic male rats: pattern of brain damage and moderating effects from normal rats.
2001-06-29
Salivary acinar cells from aquaporin 5-deficient mice have decreased membrane water permeability and altered cell volume regulation.
2001-06-29
Evaluation of spontaneous contamination of ocular medications.
2001-06-16
Long-term alteration of calcium homeostatic mechanisms in the pilocarpine model of temporal lobe epilepsy.
2001-06-08
Acupuncture for pilocarpine-resistant xerostomia following radiotherapy for head and neck malignancies.
2001-06-01
Modulators with convergent cellular actions elicit distinct circuit outputs.
2001-06-01
Activity-induced expression of common reference genes in individual cns neurons.
2001-06
Salivary scintigraphy for assessing the protective effect of pilocarpine in head and neck irradiated tumours.
2001-06
Potential mechanism for the additivity of pilocarpine and latanoprost.
2001-06
Behavioral and electroencephalographic analysis of seizures induced by intrahippocampal injection of granulitoxin, a neurotoxic peptide from the sea anemone Bunodosoma granulifera.
2001-06
Loss of vesicular zinc and appearance of perikaryal zinc after seizures induced by pilocarpine.
2001-05-25
Status epilepticus causes necrotic damage in the mediodorsal nucleus of the thalamus in immature rats.
2001-05-15
Calculation of the uncertainty in complication probability for various dose-response models, applied to the parotid gland.
2001-05-01
Amino acid derivatives with anticonvulsant activity.
2001-05
Function of pulmonary neuronal M(2) muscarinic receptors in stable chronic obstructive pulmonary disease.
2001-05
Lack of effect of mossy fiber-released zinc on granule cell GABA(A) receptors in the pilocarpine model of epilepsy.
2001-05
Diurnal variation in pilocarpine-induced generalized tonic-clonic seizure activity.
2001-05
Exploring the potential for subtype-selective muscarinic agonists in glaucoma.
2001-04-27
Neostriatal muscarinic receptor subtypes involved in the generation of tremulous jaw movements in rodents implications for cholinergic involvement in parkinsonism.
2001-04-27
Alteration of cardiovascular and neuronal function in M1 knockout mice.
2001-04-27
Adenosine A2A receptor knockout mice are partially protected against drug-induced catalepsy.
2001-04-17
Initiation of network bursts by Ca2+-dependent intrinsic bursting in the rat pilocarpine model of temporal lobe epilepsy.
2001-04-01
A new medication for treatment of dry mouth in Sjögren's syndrome.
2001-04
Immediate diode laser peripheral iridoplasty as treatment of acute attack of primary angle closure glaucoma: a preliminary study.
2001-04
2-chloro-N(6)-cyclopentyladenosine-elicited attenuation of evoked glutamate release is not sufficient to give complete protection against pilocarpine-induced seizures in rats.
2001-04
Alkaline phosphatase activity in whitefly salivary glands and saliva.
2001-04
Impaired neurotransmitter release from lacrimal and salivary gland nerves of a murine model of Sjögren's syndrome.
2001-04
Stress response to surgical procedures in the submandibular region and its influence on salivary secretion in mice.
2001-04
Lithium does not synergize the peripheral action of cholinomimetics as seen in the central nervous system.
2001-03-23
In vivo evaluation of submicron emulsions with pilocarpine: the effect of pH and chemical form of the drug.
2001-03-20
Normal spatial memory following postseizure treatment with ketamine: selective damage attenuates memory deficits in brain-damaged rodents.
2001-03
Cocaine abuse, generalized myasthenia, complete external ophthalmoplegia, and pseudotonic pupil.
2001-03
Brain-derived neurotrophic factor superinduction parallels anti-epileptic--neuroprotective treatment in the pilocarpine epilepsy model.
2001-03
Do recurrent febrile convulsions decrease the threshold for pilocarpine-induced seizures? Effects of nitric oxide.
2001-02-28
Beta-adrenergic blocker therapy and the trabecular meshwork.
2001-02
Randomized double blind, placebo-controlled study of pilocarpine administered during head and neck irradiation to reduce xerostomia.
2001-02
Brief successive temporal observational sampling as a possible indicator of daily overt seizure activity in epileptic rats.
2001-02
The acute effect of pilocarpine on pulsatile ocular blood flow in ocular hypertension.
2001-02
Twenty-four hour intraocular pressure reduction with latanoprost compared with pilocarpine as third-line therapy in exfoliation glaucoma.
2001-02
Normalization of spatial learning despite brain damage in rats receiving ketamine after seizure-induction: evidence for the neuromatrix.
2001-02
[Dry mouth].
2001-01-31
Protection by selenium of lead-acetate-induced alterations on rat submandibular gland function.
2001-01
[The effect of physiological and extreme irritants on zinc metabolism in pancreatic islets and hippocampus cells].
2001
Synchronized feeding as a "conditioned stimulus" for overt seizures in chronically (limbic) epileptic rats: a model for "psychogenic seizures" with complex partial epilepsy.
2001
Norepinephrine in treatment of ocular hypertension and glaucoma.
1975-03
Patents

Sample Use Guides

Ophthalmic solution: Instill one drop in the eye(s) up to four times daily. Oral formulation: the recommended dose is 5 mg taken three times a day (Head and Neck Cancer Patients) or 5 mg taken four times a day (Sjogren's Syndrome Patients).
Route of Administration: Other
Rat submandibular gland cells were treated wth 100 uM pilocarpine. The drug elicited a small and sustained increase in [Ca2+]i, indicating that pilocarpine acts as a partial agonist for mAChR-mediated Ca2+ responses.
Substance Class Chemical
Created
by admin
on Mon Mar 31 17:55:15 GMT 2025
Edited
by admin
on Mon Mar 31 17:55:15 GMT 2025
Record UNII
01MI4Q9DI3
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
Pilocarpine
HSDB   JAN   MART.   MI   ORANGE BOOK   USP   USP-RS   VANDF   WHO-DD  
Common Name English
OCUSERT PILO
Preferred Name English
PILOCARPINUM [HPUS]
Common Name English
PILOCARPOL
Common Name English
2(3H)-FURANONE, 3-ETHYLDIHYDRO-4-((1-METHYL-1H-IMIDAZOL-5-YL)METHYL)-, (3S-CIS)-
Systematic Name English
PILOCARPINE [USP MONOGRAPH]
Common Name English
PILOCARPINE [MI]
Common Name English
Pilocarpine [WHO-DD]
Common Name English
PILOCARPINE [MART.]
Common Name English
SPERSACARPINE
Common Name English
OCUCARPINE
Common Name English
PILOCARPINE [VANDF]
Common Name English
PILOCARPINE [HSDB]
Common Name English
PILOCARPINE [USP-RS]
Common Name English
PILOCARPINE [ORANGE BOOK]
Common Name English
PILOCARPINE [JAN]
Common Name English
SYNCARPINE
Common Name English
PILOKARPIN
Common Name English
Classification Tree Code System Code
WHO-VATC QN07AX01
Created by admin on Mon Mar 31 17:55:15 GMT 2025 , Edited by admin on Mon Mar 31 17:55:15 GMT 2025
WHO-ATC N07AX01
Created by admin on Mon Mar 31 17:55:15 GMT 2025 , Edited by admin on Mon Mar 31 17:55:15 GMT 2025
WHO-VATC QS01EB01
Created by admin on Mon Mar 31 17:55:15 GMT 2025 , Edited by admin on Mon Mar 31 17:55:15 GMT 2025
FDA ORPHAN DRUG 45990
Created by admin on Mon Mar 31 17:55:15 GMT 2025 , Edited by admin on Mon Mar 31 17:55:15 GMT 2025
WHO-ESSENTIAL MEDICINES LIST 21.4
Created by admin on Mon Mar 31 17:55:15 GMT 2025 , Edited by admin on Mon Mar 31 17:55:15 GMT 2025
NDF-RT N0000000104
Created by admin on Mon Mar 31 17:55:15 GMT 2025 , Edited by admin on Mon Mar 31 17:55:15 GMT 2025
NCI_THESAURUS C47796
Created by admin on Mon Mar 31 17:55:15 GMT 2025 , Edited by admin on Mon Mar 31 17:55:15 GMT 2025
NDF-RT N0000175884
Created by admin on Mon Mar 31 17:55:15 GMT 2025 , Edited by admin on Mon Mar 31 17:55:15 GMT 2025
WHO-ATC S01EB01
Created by admin on Mon Mar 31 17:55:15 GMT 2025 , Edited by admin on Mon Mar 31 17:55:15 GMT 2025
WHO-VATC QS01EB51
Created by admin on Mon Mar 31 17:55:15 GMT 2025 , Edited by admin on Mon Mar 31 17:55:15 GMT 2025
WHO-ATC S01EB51
Created by admin on Mon Mar 31 17:55:15 GMT 2025 , Edited by admin on Mon Mar 31 17:55:15 GMT 2025
NDF-RT N0000175369
Created by admin on Mon Mar 31 17:55:15 GMT 2025 , Edited by admin on Mon Mar 31 17:55:15 GMT 2025
NDF-RT N0000000104
Created by admin on Mon Mar 31 17:55:15 GMT 2025 , Edited by admin on Mon Mar 31 17:55:15 GMT 2025
NDF-RT N0000000104
Created by admin on Mon Mar 31 17:55:15 GMT 2025 , Edited by admin on Mon Mar 31 17:55:15 GMT 2025
Code System Code Type Description
DRUG BANK
DB01085
Created by admin on Mon Mar 31 17:55:15 GMT 2025 , Edited by admin on Mon Mar 31 17:55:15 GMT 2025
PRIMARY
RXCUI
8328
Created by admin on Mon Mar 31 17:55:15 GMT 2025 , Edited by admin on Mon Mar 31 17:55:15 GMT 2025
PRIMARY RxNorm
EPA CompTox
DTXSID1021162
Created by admin on Mon Mar 31 17:55:15 GMT 2025 , Edited by admin on Mon Mar 31 17:55:15 GMT 2025
PRIMARY
HSDB
3163
Created by admin on Mon Mar 31 17:55:15 GMT 2025 , Edited by admin on Mon Mar 31 17:55:15 GMT 2025
PRIMARY
ECHA (EC/EINECS)
202-128-4
Created by admin on Mon Mar 31 17:55:15 GMT 2025 , Edited by admin on Mon Mar 31 17:55:15 GMT 2025
PRIMARY
LACTMED
Pilocarpine
Created by admin on Mon Mar 31 17:55:15 GMT 2025 , Edited by admin on Mon Mar 31 17:55:15 GMT 2025
PRIMARY
FDA UNII
01MI4Q9DI3
Created by admin on Mon Mar 31 17:55:15 GMT 2025 , Edited by admin on Mon Mar 31 17:55:15 GMT 2025
PRIMARY
ChEMBL
CHEMBL550
Created by admin on Mon Mar 31 17:55:15 GMT 2025 , Edited by admin on Mon Mar 31 17:55:15 GMT 2025
PRIMARY
DAILYMED
01MI4Q9DI3
Created by admin on Mon Mar 31 17:55:15 GMT 2025 , Edited by admin on Mon Mar 31 17:55:15 GMT 2025
PRIMARY
WIKIPEDIA
PILOCARPINE
Created by admin on Mon Mar 31 17:55:15 GMT 2025 , Edited by admin on Mon Mar 31 17:55:15 GMT 2025
PRIMARY
IUPHAR
305
Created by admin on Mon Mar 31 17:55:15 GMT 2025 , Edited by admin on Mon Mar 31 17:55:15 GMT 2025
PRIMARY
CAS
92-13-7
Created by admin on Mon Mar 31 17:55:15 GMT 2025 , Edited by admin on Mon Mar 31 17:55:15 GMT 2025
PRIMARY
MESH
D010862
Created by admin on Mon Mar 31 17:55:15 GMT 2025 , Edited by admin on Mon Mar 31 17:55:15 GMT 2025
PRIMARY
PUBCHEM
5910
Created by admin on Mon Mar 31 17:55:15 GMT 2025 , Edited by admin on Mon Mar 31 17:55:15 GMT 2025
PRIMARY
EVMPD
SUB03818MIG
Created by admin on Mon Mar 31 17:55:15 GMT 2025 , Edited by admin on Mon Mar 31 17:55:15 GMT 2025
PRIMARY
MERCK INDEX
m8806
Created by admin on Mon Mar 31 17:55:15 GMT 2025 , Edited by admin on Mon Mar 31 17:55:15 GMT 2025
PRIMARY Merck Index
CHEBI
8207
Created by admin on Mon Mar 31 17:55:15 GMT 2025 , Edited by admin on Mon Mar 31 17:55:15 GMT 2025
PRIMARY
SMS_ID
100000085284
Created by admin on Mon Mar 31 17:55:15 GMT 2025 , Edited by admin on Mon Mar 31 17:55:15 GMT 2025
PRIMARY
DRUG CENTRAL
2166
Created by admin on Mon Mar 31 17:55:15 GMT 2025 , Edited by admin on Mon Mar 31 17:55:15 GMT 2025
PRIMARY
NCI_THESAURUS
C62068
Created by admin on Mon Mar 31 17:55:15 GMT 2025 , Edited by admin on Mon Mar 31 17:55:15 GMT 2025
PRIMARY
RS_ITEM_NUM
1538505
Created by admin on Mon Mar 31 17:55:15 GMT 2025 , Edited by admin on Mon Mar 31 17:55:15 GMT 2025
PRIMARY
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