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

Details

Stereochemistry ABSOLUTE
Molecular Formula C11H16N2O2.HNO3
Molecular Weight 271.2702
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PILOCARPINE NITRATE

SMILES

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

InChI

InChIKey=PRZXEPJJHQYOGF-GNAZCLTHSA-N
InChI=1S/C11H16N2O2.HNO3/c1-3-10-8(6-15-11(10)14)4-9-5-12-7-13(9)2;2-1(3)4/h5,7-8,10H,3-4,6H2,1-2H3;(H,2,3,4)/t8-,10-;/m0./s1

HIDE SMILES / InChI

Molecular Formula HNO3
Molecular Weight 63.0129
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
Loss of NADPH diaphorase-positive neurons in the hippocampal formation of chronic pilocarpine-epileptic rats.
1999
Recurrent mossy fiber pathway in rat dentate gyrus: synaptic currents evoked in presence and absence of seizure-induced growth.
1999 Apr
p75 neurotrophin receptor expression is induced in apoptotic neurons after seizure.
1999 Aug 15
Effects of diazepam on extracellular brain neurotransmitters in pilocarpine-induced seizures in rats.
1999 Jun 4
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
Differential regulation of cytokine expression following pilocarpine-induced seizure.
1999 Oct
Zinc inhibition of gamma-aminobutyric acid(A) receptor function is decreased in the cerebral cortex during pilocarpine-induced status epilepticus.
1999 Oct
Cognitive functions after pilocarpine-induced status epilepticus: changes during silent period precede appearance of spontaneous recurrent seizures.
1999 Sep
Infiltration of lymphocytes in the limbic brain following stimulation of subclinical cellular immunity and low dosages of lithium and a cholinergic agent.
1999 Sep 20
Patterns of status epilepticus-induced substance P expression during development.
2000
Similar increases in extracellular lactic acid in the limbic system during epileptic and/or olfactory stimulation.
2000
Differential progression of Dark Neuron and Fluoro-Jade labelling in the rat hippocampus following pilocarpine-induced status epilepticus.
2000
Motor and electrographic response of refractory experimental status epilepticus in rats and effect of calcium channel blockers.
2000 Feb
In vivo study of the effect of valpromide and valnoctamide in the pilocarpine rat model of focal epilepsy.
2000 Nov
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
Synchronized feeding as a "conditioned stimulus" for overt seizures in chronically (limbic) epileptic rats: a model for "psychogenic seizures" with complex partial epilepsy.
2001
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
Impaired neurotransmitter release from lacrimal and salivary gland nerves of a murine model of Sjögren's syndrome.
2001 Apr
Initiation of network bursts by Ca2+-dependent intrinsic bursting in the rat pilocarpine model of temporal lobe epilepsy.
2001 Apr 1
Randomized double blind, placebo-controlled study of pilocarpine administered during head and neck irradiation to reduce xerostomia.
2001 Feb
An animal model of nonconvulsive status epilepticus: a contribution to clinical controversies.
2001 Feb
G(q/11) and G(i/o) activation profiles in CHO cells expressing human muscarinic acetylcholine receptors: dependence on agonist as well as receptor-subtype.
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
[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
Evaluation of spontaneous contamination of ocular medications.
2001 Jul-Aug
Behavioral and electroencephalographic analysis of seizures induced by intrahippocampal injection of granulitoxin, a neurotoxic peptide from the sea anemone Bunodosoma granulifera.
2001 Jun
Agonistic behavior in groups of limbic epileptic male rats: pattern of brain damage and moderating effects from normal rats.
2001 Jun 29
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
Reduced excitatory drive onto interneurons in the dentate gyrus after status epilepticus.
2001 Mar 15
Metabotropic glutamate receptor 8 in the rat hippocampus after pilocarpine induced status epilepticus.
2001 Mar 16
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
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
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 Jun 25 21:12:46 UTC 2021
Edited
by admin
on Fri Jun 25 21:12:46 UTC 2021
Record UNII
M20T465H6J
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
PILOCARPINE NITRATE
EP   MART.   MI   USP   USP-RS   VANDF   WHO-DD   WHO-IP  
Common Name English
PILOCARPINE NITRATE [MART.]
Common Name English
PILOCARPINUM NITRICUM
HPUS  
Common Name English
2(3H)-FURANONE, 3-ETHYLDIHYDRO-4-((1-METHYL-1H-IMIDAZOL-5-YL)METHYL)-, (3S-CIS)-, MONONITRATE
Systematic Name English
PILOCARPINE SUBNITRATE
Common Name English
PILOCARPINE NITRATE [EP MONOGRAPH]
Common Name English
PILOCARPINE NITRATE [VANDF]
Common Name English
PILOCARPINE NITRATE [WHO-IP]
Common Name English
PILOCARPINE NITRATE [EP]
Common Name English
PILOCARPINE NITRATE [WHO-DD]
Common Name English
PILOCARPINE NITRATE [USP-RS]
Common Name English
PILOCARPINE MONONITRATE
Common Name English
PILOCARPINI NITRAS [WHO-IP LATIN]
Common Name English
NSC-757282
Code English
PILOCARPINE NITRATE [MI]
Common Name English
PILAGAN
Brand Name English
PILOCARPINE NITRATE [USP]
Common Name English
PILOCARPINUM NITRICUM [HPUS]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C47796
Created by admin on Fri Jun 25 21:12:46 UTC 2021 , Edited by admin on Fri Jun 25 21:12:46 UTC 2021
Code System Code Type Description
MERCK INDEX
M8806
Created by admin on Fri Jun 25 21:12:46 UTC 2021 , Edited by admin on Fri Jun 25 21:12:46 UTC 2021
PRIMARY Merck Index
FDA UNII
M20T465H6J
Created by admin on Fri Jun 25 21:12:46 UTC 2021 , Edited by admin on Fri Jun 25 21:12:46 UTC 2021
PRIMARY
RXCUI
103244
Created by admin on Fri Jun 25 21:12:46 UTC 2021 , Edited by admin on Fri Jun 25 21:12:46 UTC 2021
PRIMARY RxNorm
EVMPD
SUB03821MIG
Created by admin on Fri Jun 25 21:12:46 UTC 2021 , Edited by admin on Fri Jun 25 21:12:46 UTC 2021
PRIMARY
USP_CATALOG
1539009
Created by admin on Fri Jun 25 21:12:46 UTC 2021 , Edited by admin on Fri Jun 25 21:12:46 UTC 2021
PRIMARY USP-RS
CAS
148-72-1
Created by admin on Fri Jun 25 21:12:46 UTC 2021 , Edited by admin on Fri Jun 25 21:12:46 UTC 2021
PRIMARY
ECHA (EC/EINECS)
205-723-7
Created by admin on Fri Jun 25 21:12:46 UTC 2021 , Edited by admin on Fri Jun 25 21:12:46 UTC 2021
PRIMARY
NCI_THESAURUS
C91038
Created by admin on Fri Jun 25 21:12:46 UTC 2021 , Edited by admin on Fri Jun 25 21:12:46 UTC 2021
PRIMARY
WHO INTERNATIONAL PHARMACOPEIA
PILOCARPINE NITRATE
Created by admin on Fri Jun 25 21:12:46 UTC 2021 , Edited by admin on Fri Jun 25 21:12:46 UTC 2021
PRIMARY Description: Colourless crystals or a white, crystalline powder; odourless. Solubility: Freely soluble in water; sparingly soluble in ethanol (~750 g/l) TS; practically insoluble in ether R. Category: Parasympathomimetic; miotic. Storage: Pilocarpine nitrate should be kept in a tightly closed container, protected from light. Additional information: Pilocarpine nitrate is very poisonous; it is affected by light. Even in the absence of light, Pilocarpine nitrate is gradually degraded on exposure to a humid atmosphere, the decomposition being faster at higher temperatures. Definition: Pilocarpine nitrate contains not less than 98.5% and not more than 101.0% of C11H16N2O2,HNO3, calculated with reference to the dried substance.
ChEMBL
CHEMBL550
Created by admin on Fri Jun 25 21:12:46 UTC 2021 , Edited by admin on Fri Jun 25 21:12:46 UTC 2021
PRIMARY
PUBCHEM
657349
Created by admin on Fri Jun 25 21:12:46 UTC 2021 , Edited by admin on Fri Jun 25 21:12:46 UTC 2021
PRIMARY
DRUG BANK
DBSALT001181
Created by admin on Fri Jun 25 21:12:46 UTC 2021 , Edited by admin on Fri Jun 25 21:12:46 UTC 2021
PRIMARY
Related Record Type Details
BASIS OF STRENGTH->SUBSTANCE
ASSAY (TITRATION)
EP
PARENT -> SALT/SOLVATE
BASIS OF STRENGTH->SUBSTANCE
ASSAY (TITRATION)
USP
Related Record Type Details
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
UNSPECIFIED
EP
IMPURITY -> PARENT
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)
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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ACTIVE MOIETY