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: Page: p. 36
unhealthy, 44-75 years
n = 2
Health Status: unhealthy
Age Group: 44-75 years
Sex: M
Population Size: 2
Sources: Page: p. 36
Disc. AE: Vision blurred...
AEs leading to
discontinuation/dose reduction:
Vision blurred (moderate, 2 patients)
Sources: Page: p. 36
20 mg single, oral
Overdose
Dose: 20 mg
Route: oral
Route: single
Dose: 20 mg
Sources:
unhealthy, 46 years
n = 1
Health Status: unhealthy
Condition: xerostomia
Age Group: 46 years
Sex: F
Population Size: 1
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
n = 2
Health Status: unhealthy
Population Size: 2
Sources:
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
n = 20
Health Status: unhealthy
Condition: xerostomia
Population Size: 20
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: Page: p. 36
unhealthy, 44-75 years
n = 2
Health Status: unhealthy
Age Group: 44-75 years
Sex: M
Population Size: 2
Sources: Page: p. 36
Anxiety 1 patient
20 mg single, oral
Overdose
Dose: 20 mg
Route: oral
Route: single
Dose: 20 mg
Sources:
unhealthy, 46 years
n = 1
Health Status: unhealthy
Condition: xerostomia
Age Group: 46 years
Sex: F
Population Size: 1
Sources:
Increased salivation 1 patient
20 mg single, oral
Overdose
Dose: 20 mg
Route: oral
Route: single
Dose: 20 mg
Sources:
unhealthy, 46 years
n = 1
Health Status: unhealthy
Condition: xerostomia
Age Group: 46 years
Sex: F
Population Size: 1
Sources:
Lacrimation 1 patient
20 mg single, oral
Overdose
Dose: 20 mg
Route: oral
Route: single
Dose: 20 mg
Sources:
unhealthy, 46 years
n = 1
Health Status: unhealthy
Condition: xerostomia
Age Group: 46 years
Sex: F
Population Size: 1
Sources:
Tremor 1 patient
20 mg single, oral
Overdose
Dose: 20 mg
Route: oral
Route: single
Dose: 20 mg
Sources:
unhealthy, 46 years
n = 1
Health Status: unhealthy
Condition: xerostomia
Age Group: 46 years
Sex: F
Population Size: 1
Sources:
Vomiting 1 patient
20 mg single, oral
Overdose
Dose: 20 mg
Route: oral
Route: single
Dose: 20 mg
Sources:
unhealthy, 46 years
n = 1
Health Status: unhealthy
Condition: xerostomia
Age Group: 46 years
Sex: F
Population Size: 1
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
Norepinephrine in treatment of ocular hypertension and glaucoma.
1975 Mar
[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
A new medication for treatment of dry mouth in Sjögren's syndrome.
2001 Apr
Immediate diode laser peripheral iridoplasty as treatment of acute attack of primary angle closure glaucoma: a preliminary study.
2001 Apr
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 Apr
Alkaline phosphatase activity in whitefly salivary glands and saliva.
2001 Apr
Impaired neurotransmitter release from lacrimal and salivary gland nerves of a murine model of Sjögren's syndrome.
2001 Apr
Stress response to surgical procedures in the submandibular region and its influence on salivary secretion in mice.
2001 Apr
Initiation of network bursts by Ca2+-dependent intrinsic bursting in the rat pilocarpine model of temporal lobe epilepsy.
2001 Apr 1
Adenosine A2A receptor knockout mice are partially protected against drug-induced catalepsy.
2001 Apr 17
Exploring the potential for subtype-selective muscarinic agonists in glaucoma.
2001 Apr 27
Neostriatal muscarinic receptor subtypes involved in the generation of tremulous jaw movements in rodents implications for cholinergic involvement in parkinsonism.
2001 Apr 27
Alteration of cardiovascular and neuronal function in M1 knockout mice.
2001 Apr 27
The effect of pilocarpine on salivary constituents in patients with chronic graft-versus-host disease.
2001 Aug
Beta-adrenergic blocker therapy and the trabecular meshwork.
2001 Feb
Randomized double blind, placebo-controlled study of pilocarpine administered during head and neck irradiation to reduce xerostomia.
2001 Feb
Brief successive temporal observational sampling as a possible indicator of daily overt seizure activity in epileptic rats.
2001 Feb
The acute effect of pilocarpine on pulsatile ocular blood flow in ocular hypertension.
2001 Feb
Twenty-four hour intraocular pressure reduction with latanoprost compared with pilocarpine as third-line therapy in exfoliation glaucoma.
2001 Feb
Normalization of spatial learning despite brain damage in rats receiving ketamine after seizure-induction: evidence for the neuromatrix.
2001 Feb
Do recurrent febrile convulsions decrease the threshold for pilocarpine-induced seizures? Effects of nitric oxide.
2001 Feb 28
Protection by selenium of lead-acetate-induced alterations on rat submandibular gland function.
2001 Jan
[Dry mouth].
2001 Jan 31
Reliable measurement of mouse intraocular pressure by a servo-null micropipette system.
2001 Jul
Prophylactic effects of pilocarpine hydrochloride on xerostomia models induced by X-ray irradiation in rats.
2001 Jul
Poly(2-hydroxyethyl methacrylate) film as a drug delivery system for pilocarpine.
2001 Jul
Defective fluid secretion and NaCl absorption in the parotid glands of Na+/H+ exchanger-deficient mice.
2001 Jul 20
Evaluation of spontaneous contamination of ocular medications.
2001 Jul-Aug
Activity-induced expression of common reference genes in individual cns neurons.
2001 Jun
Salivary scintigraphy for assessing the protective effect of pilocarpine in head and neck irradiated tumours.
2001 Jun
Potential mechanism for the additivity of pilocarpine and latanoprost.
2001 Jun
Behavioral and electroencephalographic analysis of seizures induced by intrahippocampal injection of granulitoxin, a neurotoxic peptide from the sea anemone Bunodosoma granulifera.
2001 Jun
Acupuncture for pilocarpine-resistant xerostomia following radiotherapy for head and neck malignancies.
2001 Jun 1
Modulators with convergent cellular actions elicit distinct circuit outputs.
2001 Jun 1
Agonistic behavior in groups of limbic epileptic male rats: pattern of brain damage and moderating effects from normal rats.
2001 Jun 29
Salivary acinar cells from aquaporin 5-deficient mice have decreased membrane water permeability and altered cell volume regulation.
2001 Jun 29
Long-term alteration of calcium homeostatic mechanisms in the pilocarpine model of temporal lobe epilepsy.
2001 Jun 8
Normal spatial memory following postseizure treatment with ketamine: selective damage attenuates memory deficits in brain-damaged rodents.
2001 Mar
Cocaine abuse, generalized myasthenia, complete external ophthalmoplegia, and pseudotonic pupil.
2001 Mar
Brain-derived neurotrophic factor superinduction parallels anti-epileptic--neuroprotective treatment in the pilocarpine epilepsy model.
2001 Mar
Lithium does not synergize the peripheral action of cholinomimetics as seen in the central nervous system.
2001 Mar 23
In vivo evaluation of submicron emulsions with pilocarpine: the effect of pH and chemical form of the drug.
2001 Mar-Apr
Amino acid derivatives with anticonvulsant activity.
2001 May
Function of pulmonary neuronal M(2) muscarinic receptors in stable chronic obstructive pulmonary disease.
2001 May
Lack of effect of mossy fiber-released zinc on granule cell GABA(A) receptors in the pilocarpine model of epilepsy.
2001 May
Diurnal variation in pilocarpine-induced generalized tonic-clonic seizure activity.
2001 May
Calculation of the uncertainty in complication probability for various dose-response models, applied to the parotid gland.
2001 May 1
Status epilepticus causes necrotic damage in the mediodorsal nucleus of the thalamus in immature rats.
2001 May 15
Loss of vesicular zinc and appearance of perikaryal zinc after seizures induced by pilocarpine.
2001 May 25
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 Fri Dec 15 15:21:48 GMT 2023
Edited
by admin
on Fri Dec 15 15:21:48 GMT 2023
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
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
OCUSERT PILO
Brand 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 Fri Dec 15 15:21:48 GMT 2023 , Edited by admin on Fri Dec 15 15:21:48 GMT 2023
WHO-ATC N07AX01
Created by admin on Fri Dec 15 15:21:48 GMT 2023 , Edited by admin on Fri Dec 15 15:21:48 GMT 2023
WHO-VATC QS01EB01
Created by admin on Fri Dec 15 15:21:48 GMT 2023 , Edited by admin on Fri Dec 15 15:21:48 GMT 2023
FDA ORPHAN DRUG 45990
Created by admin on Fri Dec 15 15:21:48 GMT 2023 , Edited by admin on Fri Dec 15 15:21:48 GMT 2023
WHO-ESSENTIAL MEDICINES LIST 21.4
Created by admin on Fri Dec 15 15:21:48 GMT 2023 , Edited by admin on Fri Dec 15 15:21:48 GMT 2023
NDF-RT N0000000104
Created by admin on Fri Dec 15 15:21:48 GMT 2023 , Edited by admin on Fri Dec 15 15:21:48 GMT 2023
NCI_THESAURUS C47796
Created by admin on Fri Dec 15 15:21:48 GMT 2023 , Edited by admin on Fri Dec 15 15:21:48 GMT 2023
NDF-RT N0000175884
Created by admin on Fri Dec 15 15:21:48 GMT 2023 , Edited by admin on Fri Dec 15 15:21:48 GMT 2023
WHO-ATC S01EB01
Created by admin on Fri Dec 15 15:21:48 GMT 2023 , Edited by admin on Fri Dec 15 15:21:48 GMT 2023
WHO-VATC QS01EB51
Created by admin on Fri Dec 15 15:21:48 GMT 2023 , Edited by admin on Fri Dec 15 15:21:48 GMT 2023
WHO-ATC S01EB51
Created by admin on Fri Dec 15 15:21:48 GMT 2023 , Edited by admin on Fri Dec 15 15:21:48 GMT 2023
NDF-RT N0000175369
Created by admin on Fri Dec 15 15:21:48 GMT 2023 , Edited by admin on Fri Dec 15 15:21:48 GMT 2023
NDF-RT N0000000104
Created by admin on Fri Dec 15 15:21:48 GMT 2023 , Edited by admin on Fri Dec 15 15:21:48 GMT 2023
NDF-RT N0000000104
Created by admin on Fri Dec 15 15:21:48 GMT 2023 , Edited by admin on Fri Dec 15 15:21:48 GMT 2023
Code System Code Type Description
DRUG BANK
DB01085
Created by admin on Fri Dec 15 15:21:48 GMT 2023 , Edited by admin on Fri Dec 15 15:21:48 GMT 2023
PRIMARY
RXCUI
8328
Created by admin on Fri Dec 15 15:21:48 GMT 2023 , Edited by admin on Fri Dec 15 15:21:48 GMT 2023
PRIMARY RxNorm
EPA CompTox
DTXSID1021162
Created by admin on Fri Dec 15 15:21:48 GMT 2023 , Edited by admin on Fri Dec 15 15:21:48 GMT 2023
PRIMARY
HSDB
3163
Created by admin on Fri Dec 15 15:21:48 GMT 2023 , Edited by admin on Fri Dec 15 15:21:48 GMT 2023
PRIMARY
ECHA (EC/EINECS)
202-128-4
Created by admin on Fri Dec 15 15:21:48 GMT 2023 , Edited by admin on Fri Dec 15 15:21:48 GMT 2023
PRIMARY
LACTMED
Pilocarpine
Created by admin on Fri Dec 15 15:21:48 GMT 2023 , Edited by admin on Fri Dec 15 15:21:48 GMT 2023
PRIMARY
FDA UNII
01MI4Q9DI3
Created by admin on Fri Dec 15 15:21:48 GMT 2023 , Edited by admin on Fri Dec 15 15:21:48 GMT 2023
PRIMARY
ChEMBL
CHEMBL550
Created by admin on Fri Dec 15 15:21:48 GMT 2023 , Edited by admin on Fri Dec 15 15:21:48 GMT 2023
PRIMARY
DAILYMED
01MI4Q9DI3
Created by admin on Fri Dec 15 15:21:48 GMT 2023 , Edited by admin on Fri Dec 15 15:21:48 GMT 2023
PRIMARY
WIKIPEDIA
PILOCARPINE
Created by admin on Fri Dec 15 15:21:48 GMT 2023 , Edited by admin on Fri Dec 15 15:21:48 GMT 2023
PRIMARY
IUPHAR
305
Created by admin on Fri Dec 15 15:21:48 GMT 2023 , Edited by admin on Fri Dec 15 15:21:48 GMT 2023
PRIMARY
CAS
92-13-7
Created by admin on Fri Dec 15 15:21:48 GMT 2023 , Edited by admin on Fri Dec 15 15:21:48 GMT 2023
PRIMARY
MESH
D010862
Created by admin on Fri Dec 15 15:21:48 GMT 2023 , Edited by admin on Fri Dec 15 15:21:48 GMT 2023
PRIMARY
PUBCHEM
5910
Created by admin on Fri Dec 15 15:21:48 GMT 2023 , Edited by admin on Fri Dec 15 15:21:48 GMT 2023
PRIMARY
EVMPD
SUB03818MIG
Created by admin on Fri Dec 15 15:21:48 GMT 2023 , Edited by admin on Fri Dec 15 15:21:48 GMT 2023
PRIMARY
MERCK INDEX
m8806
Created by admin on Fri Dec 15 15:21:48 GMT 2023 , Edited by admin on Fri Dec 15 15:21:48 GMT 2023
PRIMARY Merck Index
CHEBI
8207
Created by admin on Fri Dec 15 15:21:48 GMT 2023 , Edited by admin on Fri Dec 15 15:21:48 GMT 2023
PRIMARY
SMS_ID
100000085284
Created by admin on Fri Dec 15 15:21:48 GMT 2023 , Edited by admin on Fri Dec 15 15:21:48 GMT 2023
PRIMARY
DRUG CENTRAL
2166
Created by admin on Fri Dec 15 15:21:48 GMT 2023 , Edited by admin on Fri Dec 15 15:21:48 GMT 2023
PRIMARY
NCI_THESAURUS
C62068
Created by admin on Fri Dec 15 15:21:48 GMT 2023 , Edited by admin on Fri Dec 15 15:21:48 GMT 2023
PRIMARY
RS_ITEM_NUM
1538505
Created by admin on Fri Dec 15 15:21:48 GMT 2023 , Edited by admin on Fri Dec 15 15:21:48 GMT 2023
PRIMARY
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