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

Details

Stereochemistry ABSOLUTE
Molecular Formula C11H16N2O2.ClH
Molecular Weight 244.7182
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PILOCARPINE HYDROCHLORIDE

SMILES

CC[C@@]1([H])[C@@]([H])(Cc2cncn2C)COC1=O.Cl

InChI

InChIKey=RNAICSBVACLLGM-GNAZCLTHSA-N
InChI=1S/C11H16N2O2.ClH/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;1H/t8-,10-;/m0./s1

HIDE SMILES / InChI

Molecular Formula ClH
Molecular Weight 36.4609
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C11H16N2O2
Molecular Weight 208.2574
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

7.642944E11
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

7.642944E11
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

1.27716478E12
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

1.27716478E12
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

1.27716478E12
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
Effects of pilocarpine- and kainate-induced seizures on thyrotropin-releasing hormone biosynthesis and receptors in the rat brain.
1999
N-methyl-D-aspartate receptor activation regulates refractoriness of status epilepticus to diazepam.
1999
p75 neurotrophin receptor expression is induced in apoptotic neurons after seizure.
1999 Aug 15
Prevalence of epileptic seizures along the wakefulness-sleep cycle in adult rats submitted to status epilepticus in early life.
1999 Nov
Attenuation of focal adhesion kinase signaling following depletion of agonist-sensitive pools of phosphatidylinositol 4,5-bisphosphate.
1999 Nov
Selective alterations of glycosaminoglycans synthesis and proteoglycan expression in rat cortex and hippocampus in pilocarpine-induced epilepsy.
1999 Nov 1
Patterns of status epilepticus-induced substance P expression during development.
2000
Remodeling dendritic spines of dentate granule cells in temporal lobe epilepsy patients and the rat pilocarpine model.
2000
Seizure-induced neuronal necrosis: implications for programmed cell death mechanisms.
2000
Nonconvulsive status epilepticus in rats: impaired responsiveness to exteroceptive stimuli.
2000 Dec 20
Rapid alterations in diffusion-weighted images with anatomic correlates in a rodent model of status epilepticus.
2000 Nov-Dec
Flumazenil prevents diazepam-elicited anticonvulsant action and concomitant attenuation of glutamate overflow.
2000 Oct 27
[The effect of physiological and extreme irritants on zinc metabolism in pancreatic islets and hippocampus cells].
2001
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
Adenosine A2A receptor knockout mice are partially protected against drug-induced catalepsy.
2001 Apr 17
Neostriatal muscarinic receptor subtypes involved in the generation of tremulous jaw movements in rodents implications for cholinergic involvement in parkinsonism.
2001 Apr 27
Beta-adrenergic blocker therapy and the trabecular meshwork.
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
Regional and subunit-specific downregulation of acid-sensing ion channels in the pilocarpine model of epilepsy.
2001 Feb
Relationship between neuronal loss and interictal glucose metabolism during the chronic phase of the lithium-pilocarpine model of epilepsy in the immature and adult rat.
2001 Feb
The role of sensory signals from the insect coxa-trochanteral joint in controlling motor activity of the femur-tibia joint.
2001 Feb
Uveal effusion after cataract surgery: an echographic study.
2001 Jan
Xerostomia, xerophthalmia, and plasmacytic infiltrates of the salivary glands (Sjögren's-like syndrome) in a cat.
2001 Jan 1
Reliable measurement of mouse intraocular pressure by a servo-null micropipette system.
2001 Jul
Evaluation of spontaneous contamination of ocular medications.
2001 Jul-Aug
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
Calculation of the uncertainty in complication probability for various dose-response models, applied to the parotid gland.
2001 May 1
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 Jun 25 20:57:40 UTC 2021
Edited
by admin
on Fri Jun 25 20:57:40 UTC 2021
Record UNII
0WW6D218XJ
Record Status Validated (UNII)
Record Version
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Name Type Language
PILOCARPINE HYDROCHLORIDE
EP   MART.   MI   ORANGE BOOK   USP   USP-RS   VANDF   WHO-DD   WHO-IP  
Common Name English
2(3H)-FURANONE, 3-ETHYLDIHYDRO-4-((1-METHYL-1H-IMIDAZOL-5-YL)METHYL)-, MONOHYDROCHLORIDE, (3S,4R)-
Common Name English
SALAGEN
Common Name English
PILOCARPINE HCL
VANDF  
Common Name English
PILOCARPINI HYDROCHLORIDUM [WHO-IP LATIN]
Common Name English
PILOCARPINUM MURIATICUM [HPUS]
Common Name English
PILOCARPINE HYDROCHLORIDE [USP-RS]
Common Name English
PILOCARPINE HYDROCHLORIDE [EP]
Common Name English
PILOCARPINE HYDROCHLORIDE [USP]
Common Name English
PILOCARPINE HYDROCHLORIDE COMPONENT OF BETOPTIC PILO
Common Name English
PILOCARPINE HYDROCHLORIDE [JAN]
Common Name English
PILOCARPINE HYDROCHLORIDE [MART.]
Common Name English
PILOPINE HS
Brand Name English
PILOCARPINE HYDROCHLORIDE [MI]
Common Name English
PILOPINE
Brand Name English
(3S,4R)-3-ETHYL-4-((1-METHYL-1H-IMIDAZOL-5-YL)METHYL)DIHYDROFURAN-2(3H)-ONE HYDROCHLORIDE
Systematic Name English
PILOCARPINE HYDROCHLORIDE [ORANGE BOOK]
Common Name English
PILOCARPINE MONOHYDROCHLORIDE
WHO-IP  
Common Name English
PILOCARPINE HYDROCHLORIDE [USP MONOGRAPH]
Common Name English
PILOCARPINE HCL [VANDF]
Common Name English
PILOCARPINE HYDROCHLORIDE [VANDF]
Common Name English
PILOCARPINE HYDROCHLORIDE [EP MONOGRAPH]
Common Name English
PILOCARPINUM MURIATICUM
HPUS  
Common Name English
ALMOCARPINE
Common Name English
BETOPTIC PILO COMPONENT PILOCARPINE HYDROCHLORIDE
Common Name English
2(3H)-FURANONE, 3-ETHYLDIHYDRO-4-((1-METHYL-1H-IMIDAZOL-5-YL)METHYL)-, MONOHYDROCHLORIDE, (3S-CIS)-
Common Name English
PILOCARPINE HYDROCHLORIDE [WHO-IP]
Common Name English
VISTACARPIN N
Common Name English
PILOCARPINE HYDROCHLORIDE [WHO-DD]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C47796
Created by admin on Fri Jun 25 20:57:40 UTC 2021 , Edited by admin on Fri Jun 25 20:57:40 UTC 2021
FDA ORPHAN DRUG 62091
Created by admin on Fri Jun 25 20:57:40 UTC 2021 , Edited by admin on Fri Jun 25 20:57:40 UTC 2021
Code System Code Type Description
MERCK INDEX
M8806
Created by admin on Fri Jun 25 20:57:40 UTC 2021 , Edited by admin on Fri Jun 25 20:57:40 UTC 2021
PRIMARY Merck Index
PUBCHEM
5909
Created by admin on Fri Jun 25 20:57:40 UTC 2021 , Edited by admin on Fri Jun 25 20:57:40 UTC 2021
PRIMARY
NCI_THESAURUS
C748
Created by admin on Fri Jun 25 20:57:40 UTC 2021 , Edited by admin on Fri Jun 25 20:57:40 UTC 2021
PRIMARY
ECHA (EC/EINECS)
200-212-5
Created by admin on Fri Jun 25 20:57:40 UTC 2021 , Edited by admin on Fri Jun 25 20:57:40 UTC 2021
PRIMARY
EVMPD
SUB14870MIG
Created by admin on Fri Jun 25 20:57:40 UTC 2021 , Edited by admin on Fri Jun 25 20:57:40 UTC 2021
PRIMARY
DRUG BANK
DBSALT000307
Created by admin on Fri Jun 25 20:57:40 UTC 2021 , Edited by admin on Fri Jun 25 20:57:40 UTC 2021
PRIMARY
ChEMBL
CHEMBL550
Created by admin on Fri Jun 25 20:57:40 UTC 2021 , Edited by admin on Fri Jun 25 20:57:40 UTC 2021
PRIMARY
USP_CATALOG
1538902
Created by admin on Fri Jun 25 20:57:40 UTC 2021 , Edited by admin on Fri Jun 25 20:57:40 UTC 2021
PRIMARY USP-RS
RXCUI
235426
Created by admin on Fri Jun 25 20:57:40 UTC 2021 , Edited by admin on Fri Jun 25 20:57:40 UTC 2021
PRIMARY RxNorm
EPA CompTox
54-71-7
Created by admin on Fri Jun 25 20:57:40 UTC 2021 , Edited by admin on Fri Jun 25 20:57:40 UTC 2021
PRIMARY
WHO INTERNATIONAL PHARMACOPEIA
PILOCARPINE HYDROCHLORIDE
Created by admin on Fri Jun 25 20:57:40 UTC 2021 , Edited by admin on Fri Jun 25 20:57:40 UTC 2021
PRIMARY Description: Colourless crystals or a white, crystalline powder; odourless or almost odourless. Solubility: Very soluble in water; freely soluble in ethanol (~750 g/l) TS; insoluble in ether R. Category: Parasympathomimetic; miotic. Storage: Pilocarpine hydrochloride should be kept in a tightly closed container, protected from light. Additional information: Pilocarpine hydrochloride is very poisonous; it is hygroscopic and is affected by light. Even in the absenceof light, Pilocarpine hydrochloride is gradually degraded on exposure to a humid atmosphere, the decomposition being faster athigher temperatures. Definition: Pilocarpine hydrochloride contains not less than 98.5% and not more than 101.0% of C11H16N2O2,HCl, calculated withreference to the dried substance.
FDA UNII
0WW6D218XJ
Created by admin on Fri Jun 25 20:57:40 UTC 2021 , Edited by admin on Fri Jun 25 20:57:40 UTC 2021
PRIMARY
CAS
54-71-7
Created by admin on Fri Jun 25 20:57:40 UTC 2021 , Edited by admin on Fri Jun 25 20:57:40 UTC 2021
PRIMARY
Related Record Type Details
BASIS OF STRENGTH->SUBSTANCE
ASSAY (HPLC)
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PARENT -> SALT/SOLVATE
BASIS OF STRENGTH->SUBSTANCE
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IMPURITY -> PARENT
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sum of impurities A and B: not more than 3 times the area of the principal peak in the chromatogram obtained with reference solution (a) (1.5 per cent)
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IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
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IMPURITY -> PARENT
UNSPECIFIED
EP
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