Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C11H16N2O2.HNO3 |
Molecular Weight | 271.2698 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 2 / 2 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
O[N+]([O-])=O.CC[C@H]1[C@@H](CC2=CN=CN2C)COC1=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
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.
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: P20309 Gene ID: 1131.0 Gene Symbol: CHRM3 Target Organism: Homo sapiens (Human) |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Secondary | SALAGEN Approved UseSALAGEN 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 Date1994 |
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Palliative | SALAGEN Approved UseSALAGEN 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 Date1994 |
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Primary | ISOPTO CARPINE Approved UseIsopto 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 Date2010 |
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Primary | ISOPTO CARPINE Approved UseIsopto 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 Date2010 |
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Primary | ISOPTO CARPINE Approved UseIsopto 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 Date2010 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
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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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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
Dose | Population | Adverse 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 |
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) Sources: Lacrimation (1 patient) Vomiting (1 patient) Anxiety (1 patient) Tremor (1 patient) |
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
AE | Significance | Dose | Population |
---|---|---|---|
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 |
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 |
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 |
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 |
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 |
unhealthy, 46 years n = 1 Health Status: unhealthy Condition: xerostomia Age Group: 46 years Sex: F Population Size: 1 Sources: |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Page: 3.0 |
moderate | |||
Sources: https://www.fda.gov/media/79033/download#page=3 Page: 3.0 |
yes [Ki 1 uM] | |||
yes [Ki 360 uM] |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Sources: https://www.fda.gov/media/79033/download#page=20 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 Sources: https://www.fda.gov/media/79033/download#page=20 Page: 20.0 |
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Sources: https://www.fda.gov/media/79033/download#page=20 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 Sources: https://www.fda.gov/media/79033/download#page=20 Page: 20.0 |
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Sources: https://www.fda.gov/media/79033/download#page=20 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 Sources: https://www.fda.gov/media/79033/download#page=20 Page: 20.0 |
||
Sources: https://www.fda.gov/media/79033/download#page=20 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 Sources: https://www.fda.gov/media/79033/download#page=20 Page: 20.0 |
||
Sources: https://www.fda.gov/media/79033/download#page=20 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 Sources: https://www.fda.gov/media/79033/download#page=20 Page: 20.0 |
||
Sources: https://www.fda.gov/media/79033/download#page=20 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 Sources: https://www.fda.gov/media/79033/download#page=20 Page: 20.0 |
||
yes | ||||
Sources: https://www.fda.gov/media/79033/download#page=3 Page: 3.0 |
yes | |||
Sources: https://www.fda.gov/media/79033/download#page=3 Page: 3.0 |
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 Sources: https://www.fda.gov/media/79033/download#page=3 Page: 3.0 |
PubMed
Title | Date | PubMed |
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Multiple pilocarpine-induced status epilepticus in developing rats: a long-term behavioral and electrophysiological study. | 2000 |
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Remodeling dendritic spines of dentate granule cells in temporal lobe epilepsy patients and the rat pilocarpine model. | 2000 |
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Nonconvulsive status epilepticus in rats: impaired responsiveness to exteroceptive stimuli. | 2000 Dec 20 |
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Motor and electrographic response of refractory experimental status epilepticus in rats and effect of calcium channel blockers. | 2000 Feb |
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In vivo study of the effect of valpromide and valnoctamide in the pilocarpine rat model of focal epilepsy. | 2000 Nov |
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Rapid alterations in diffusion-weighted images with anatomic correlates in a rodent model of status epilepticus. | 2000 Nov-Dec |
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Flumazenil prevents diazepam-elicited anticonvulsant action and concomitant attenuation of glutamate overflow. | 2000 Oct 27 |
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Lipid peroxidation in hippocampus early and late after status epilepticus induced by pilocarpine or kainic acid in Wistar rats. | 2000 Sep 22 |
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Synchronized feeding as a "conditioned stimulus" for overt seizures in chronically (limbic) epileptic rats: a model for "psychogenic seizures" with complex partial epilepsy. | 2001 |
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A new medication for treatment of dry mouth in Sjögren's syndrome. | 2001 Apr |
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Immediate diode laser peripheral iridoplasty as treatment of acute attack of primary angle closure glaucoma: a preliminary study. | 2001 Apr |
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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 |
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Impaired neurotransmitter release from lacrimal and salivary gland nerves of a murine model of Sjögren's syndrome. | 2001 Apr |
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Stress response to surgical procedures in the submandibular region and its influence on salivary secretion in mice. | 2001 Apr |
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Initiation of network bursts by Ca2+-dependent intrinsic bursting in the rat pilocarpine model of temporal lobe epilepsy. | 2001 Apr 1 |
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Exploring the potential for subtype-selective muscarinic agonists in glaucoma. | 2001 Apr 27 |
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Neostriatal muscarinic receptor subtypes involved in the generation of tremulous jaw movements in rodents implications for cholinergic involvement in parkinsonism. | 2001 Apr 27 |
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Beta-adrenergic blocker therapy and the trabecular meshwork. | 2001 Feb |
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Randomized double blind, placebo-controlled study of pilocarpine administered during head and neck irradiation to reduce xerostomia. | 2001 Feb |
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Brief successive temporal observational sampling as a possible indicator of daily overt seizure activity in epileptic rats. | 2001 Feb |
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The acute effect of pilocarpine on pulsatile ocular blood flow in ocular hypertension. | 2001 Feb |
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Twenty-four hour intraocular pressure reduction with latanoprost compared with pilocarpine as third-line therapy in exfoliation glaucoma. | 2001 Feb |
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An animal model of nonconvulsive status epilepticus: a contribution to clinical controversies. | 2001 Feb |
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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 |
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Regional and subunit-specific downregulation of acid-sensing ion channels in the pilocarpine model of epilepsy. | 2001 Feb |
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The role of sensory signals from the insect coxa-trochanteral joint in controlling motor activity of the femur-tibia joint. | 2001 Feb |
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Do recurrent febrile convulsions decrease the threshold for pilocarpine-induced seizures? Effects of nitric oxide. | 2001 Feb 28 |
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Protection by selenium of lead-acetate-induced alterations on rat submandibular gland function. | 2001 Jan |
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Uveal effusion after cataract surgery: an echographic study. | 2001 Jan |
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Xerostomia, xerophthalmia, and plasmacytic infiltrates of the salivary glands (Sjögren's-like syndrome) in a cat. | 2001 Jan 1 |
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Innervation of sweat glands in the forehead. A study in patients with Horner's syndrome. | 2001 Jan 15 |
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[Dry mouth]. | 2001 Jan 31 |
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Reliable measurement of mouse intraocular pressure by a servo-null micropipette system. | 2001 Jul |
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Prophylactic effects of pilocarpine hydrochloride on xerostomia models induced by X-ray irradiation in rats. | 2001 Jul |
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Poly(2-hydroxyethyl methacrylate) film as a drug delivery system for pilocarpine. | 2001 Jul |
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Evaluation of spontaneous contamination of ocular medications. | 2001 Jul-Aug |
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Activity-induced expression of common reference genes in individual cns neurons. | 2001 Jun |
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Salivary scintigraphy for assessing the protective effect of pilocarpine in head and neck irradiated tumours. | 2001 Jun |
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Behavioral and electroencephalographic analysis of seizures induced by intrahippocampal injection of granulitoxin, a neurotoxic peptide from the sea anemone Bunodosoma granulifera. | 2001 Jun |
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Acupuncture for pilocarpine-resistant xerostomia following radiotherapy for head and neck malignancies. | 2001 Jun 1 |
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Modulators with convergent cellular actions elicit distinct circuit outputs. | 2001 Jun 1 |
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Agonistic behavior in groups of limbic epileptic male rats: pattern of brain damage and moderating effects from normal rats. | 2001 Jun 29 |
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Long-term alteration of calcium homeostatic mechanisms in the pilocarpine model of temporal lobe epilepsy. | 2001 Jun 8 |
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Cocaine abuse, generalized myasthenia, complete external ophthalmoplegia, and pseudotonic pupil. | 2001 Mar |
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Brain-derived neurotrophic factor superinduction parallels anti-epileptic--neuroprotective treatment in the pilocarpine epilepsy model. | 2001 Mar |
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Lithium does not synergize the peripheral action of cholinomimetics as seen in the central nervous system. | 2001 Mar 23 |
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In vivo evaluation of submicron emulsions with pilocarpine: the effect of pH and chemical form of the drug. | 2001 Mar-Apr |
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Amino acid derivatives with anticonvulsant activity. | 2001 May |
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Lack of effect of mossy fiber-released zinc on granule cell GABA(A) receptors in the pilocarpine model of epilepsy. | 2001 May |
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Calculation of the uncertainty in complication probability for various dose-response models, applied to the parotid gland. | 2001 May 1 |
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
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/25886199
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.
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Classification Tree | Code System | Code | ||
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NCI_THESAURUS |
C47796
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m8806
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757282
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M20T465H6J
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1539009
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103244
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SUB03821MIG
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148-72-1
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C91038
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PILOCARPINE NITRATE
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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. | ||
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CHEMBL550
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657349
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100000092625
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DBSALT001181
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ACTIVE MOIETY
SUBSTANCE RECORD