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Pilocarpine HCl

Alias: NSC 5746 HCl; Pilocarpine Hydrochloride; Pilocarpal; Pilocar; (+)-Pilocarpine hydrochloride; NSC-5746 HCl;NSC5746 HCl;Pilocar SMP; Salagen; Pilocarpine Mononitrate, (3S-cis)-Isomer; Pilocarpine Nitrate; Pilocarpine, Monohydrochloride, (3S-cis)-Isomer; Ocusert; Pilocarpine hydrochloride; 54-71-7; (+)-Pilocarpine hydrochloride; Pilocarpine HCl; Almocarpine; Salagen; Pilocarpal; Pilocar SMP;
Cat No.:V1206 Purity: ≥98%
Pilocarpine HCl (Pilocarpal;NSC-5746; Ocusert; Pilocar;Pilocar SMP; Salagen; NSC5746),the hydrochloride salt of pilocarpine,is a naturally occurring and nonselective muscarinic acetylcholine receptor agonist used to treat dry mouth caused by radiotherapy in patients with head and neck cancer and in patients with Sjogrens syndrome.
Pilocarpine HCl
Pilocarpine HCl Chemical Structure CAS No.: 54-71-7
Product category: AChR Receptor
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
250mg
500mg
1g
2g
5g
Other Sizes

Other Forms of Pilocarpine HCl:

  • Pilocarpine-d5 hydrochloride
  • Pilocarpine-d3 HCl
  • Pilocarpine
  • Pilocarpine nitrate
Official Supplier of:
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Purity & Quality Control Documentation

Purity: ≥98%

Product Description

Pilocarpine HCl (Pilocarpal; NSC-5746; Ocusert; Pilocar;Pilocar SMP; Salagen; NSC5746), the hydrochloride salt of pilocarpine, is a naturally occurring and nonselective muscarinic acetylcholine receptor agonist used to treat dry mouth caused by radiotherapy in patients with head and neck cancer and in patients with Sjogren's syndrome. It is also used to produce an experimental model of epilepsy. Pilocarpine is a parasympathomimetic alkaloid extracted from the leaves of tropical American shrubs from the genus Pilocarpus. Pilocarpine acts on a subtype of muscarinic receptor (M3) found on the iris sphincter muscle, causing the muscle to contract and engage in miosis.

Biological Activity I Assay Protocols (From Reference)
Targets
mAChR3/muscarinic acetylcholine receptor
ln Vitro
The morphology and viability of human corneal stromal (HCS) cells are assessed using light microscopy and the MTT assay, respectively, in order to assess the cytotoxicity of pilocarpine. HCS cells exposed to Pilocarpine at concentrations between 0.625 and 20 g/L exhibit morphological abnormalities such as cellular shrinkage, cytoplasmic vacuolation, detachment from the culture matrix, and eventually death, as well as dose- and time-dependent proliferation retardation, according to morphological observations. However, there is no discernible difference between the controls and those exposed to Pilocarpine below the concentration of 0.625 g/L. The MTT assay results show that after being exposed to pilocarpine above a concentration of 0.625 g/L, the cell viability of HCS cells decreases with time and concentration (P<0.01 or 0.05), but HCS cells treated with pilocarpine below a concentration of 0.625 g/L do not significantly differ from controls[2]. With an EC50 of 2.4 mM, the partial muscarinic agonist Pilocarpine induces concentration-dependent relaxation in isolated rat tail artery segments that have been constricted with Penylephrine (10 to 200 nM)[3].
ln Vivo
Examined is the saliva secreted by the exercised (EX) and control (CN) rats in response to pilocarpine. Pilocarpine induces a considerably higher amount of saliva in the EX rats than in the CN rats (P<0.01). On the other hand, the EX rats' saliva had a considerably lower Na+ concentration than the CN rats' (P<0.05)[1].
Cell Assay
After HCS cells were treated with pilocarpine at a concentration from 0.15625 g/L to 20.0 g/L, their morphology and viability were detected by light microscopy and MTT assay. The membrane permeability, DNA fragmentation and ultrastructure were examined by acridine orange (AO)/ethidium bromide (EB) double-staining. DNA electrophoresis and transmission electron microscopy (TEM), cell cycle, phosphatidylserine (PS) orientation and mitochondrial transmembrane potential (MTP) were assayed by flow cytometry (FCM). And the activation of caspases was checked by ELISA[3].
Animal Protocol
0.5 mg/kg; i.p.
Rats: Male, 10-week-old Wistar rats are assigned to one of two groups, exercise (EX, n=6) and control (CN, n=6). The EX rats are kept for 40 days in cages with a running wheel (SN-451), allowing them to undertake voluntary exercise, while the CN rats are kept in cages with the running wheel locked. On the 40th day, Pilocarpine-induced saliva is measured as follows. Briefly, the rats are anesthetized, preweighed cotton was placed in their mouths sublingually, and Pilocarpine (0.5 mg/kg) is intraperitoneally injected to induce saliva secretion. Each cotton ball is then changed every 10 min for 1 h. The collected cotton balls are weighed again, and the mass of saliva secreted is calculated by subtracting the initial from the final weight.
ADME/Pharmacokinetics
Absorption, Distribution and Excretion
Following oral administration of pilocarpine 5mg three times daily in healthy male subjects, peak plasma drug concentrations of 15μg/L were reached in 1.25 hours. At the dose of pilocarpine 10mg three times daily, peak plasma drug concentrations of 41μg/L were reached in 0.85 hours. The rate of absorption is increased when taken with food. Following ophthalmic administration in healthy subjects, the overall median Tmax was 2.2 hours. The mean (SD) Cmax and AUC0-t were 897.2 (287.2) pg/mL and 2699 (741.4) hr x pg/mL, respectively. In patients with presbyopia, the mean Cmax and AUC0-t,ss values were 1.95 ng/mL and 4.14 ng x hr/mL, respectively. The median Tmax was 0.3 hours postdose with a range from 0.2 to 0.5 hours post-dose.
Pilocarpine and its degradation products are eliminated predominantly in the urine.
There is no information available.
There is no information available.
LITTLE DEFINITIVE INFORMATION IS AVAIL ON FATE & ELIMINATION OF PILOCARPINE. IT IS PARTLY DESTROYED IN BODY, BUT LARGER FRACTION IS EXCRETED IN URINE IN COMBINED FORM.
PILOCARPINE PENETRATES EYE WELL; AFTER TOPICAL INSTILLATION...
POISONING HAS OCCURRED FROM CUTANEOUS ABSORPTION.
Metabolism / Metabolites
There is limited information available about the metabolism of pilocarpine in humans. Inactivation of pilocarpine can occur at neuronal synapses and probably in plasma. Pilocarpine is reported to undergo CYP2A6-mediated 3-hydroxylation to form stereoisomers of 3-hydroxypilocaripine. Pilocaripine also undergoes hydrolysis mediated by paraoxonase 1, a calcium-dependent esterase in plasma and the human liver. Pilocarpic acid is a possible metabolic product of hydrolysis. Pilocarpine metabolites are reported to possess negligible or no pharmacological activity.
Pilocarpine has known human metabolites that include 3-hydroxypilocarpine.
Possibly occurs at the neuronal synapses and in the plasma
Half Life: 0.76 hours
Biological Half-Life
The elimination half-life was 0.76 and 1.35 hours following administration of a 5mg or lOmg dose 3 times daily, respectively. Following ophthalmic administration in healthy subjects, the half-life was 3.96 hours.
Toxicity/Toxicokinetics
Hepatotoxicity
In clinical trials of pilocarpine, serum enzyme elevations were uncommon and no more frequent than with placebo. Despite, wide scale use, there have been no published reports of acute liver injury attributable to pilocarpine.
Effects During Pregnancy and Lactation
◉ Summary of Use during Lactation
Limited information indicates that maternal use of ophthalmic pilocarpine did not adversely affect the breastfed infant. If ophthalmic pilocarpine is used during breastfeeding, monitor the infant for signs of cholinergic excess (diarrhea, lacrimation, and excessive salivation or urination), especially in younger, exclusively breastfed infants. To substantially diminish the amount of drug that reaches the breastmilk after using eye drops, place pressure over the tear duct by the corner of the eye for 1 minute or more, then remove the excess solution with an absorbent tissue.
Because no information is available on the use of oral pilocarpine during breastfeeding, an alternate drug may be preferred, especially while nursing a newborn or preterm infant.
◉ Effects in Breastfed Infants
A woman with glaucoma used a pilocarpine insert (Ocusert; strength not specified) in one eye while nursing (extent not stated) her newborn infant for 9 weeks. No adverse reactions were noted in the infant.[1]
A mother who was taking pilocarpine eye drops (concentration not stated) twice daily as well as 2 drops of timolol 0.5% eye drops daily and acetazolamide 250 mg orally twice daily and delivered a preterm infant at 36 weeks of gestation. The infant began 5 months of exclusive breastfeeding at 6 hours after birth. On day 2, the infant developed electrolyte abnormalities consisting of hypocalcemia, hypomagnesemia, and metabolic acidosis. The infant was treated with oral calcium gluconate and a single dose of intramuscular magnesium sulfate. Despite continued breastfeeding and maternal drug therapy, the infant's mild metabolic acidosis disappeared on day 4 of life and the infant was gaining weight normally at 1, 3 and 8 months, but had mild hypotonicity. The authors considered the metabolic effects to be caused by transplacental passage of acetazolamide that resolved despite the infant being breastfed. The infant gained weight adequately during breastfeeding, but had some mild, residual hypertonicity of the lower limbs requiring physical therapy.[2]
◉ Effects on Lactation and Breastmilk
Relevant published information in nursing mothers was not found as of the revision date. In animals, cholinergic drugs increase oxytocin release,[3] and have variable effects on serum prolactin.[4] Other centrally acting cholinergic drugs increase serum prolactin in humans.[5][6] The prolactin level in a mother with established lactation may not affect her ability to breastfeed.
Protein Binding
Pilocarpine does not bind to human or rat plasma proteins over a concentration range of 5 to 25,000 ng/mL. The effect of pilocarpine on plasma protein binding of other drugs has not been evaluated.
References

[1]. Daily voluntary exercise enhances pilocarpine-induced saliva secretion and aquaporin 1 expression in rat submandibular glands. FEBS Open Bio. 2017 Dec 7;8(1):85-93.

[2]. Pilocarpine-induced relaxation of rat tail artery by a non-cholinergic mechanism and in the absence of an intact endothelium. Br J Pharmacol. 1994 Jun;112(2):525-32.

[3]. Cytotoxicity of pilocarpine to human corneal stromal cells and its underlying cytotoxic mechanisms. Int J Ophthalmol. 2016 Apr 18;9(4):505-11.

[4]. Post-treatment with the GLP-1 analogue liraglutide alleviate chronic inflammation and mitochondrial stress induced by Status epilepticus. Epilepsy Res. 2018 Mar 9;142:45-52.

Additional Infomation
Pilocarpine hydrochloride is the hydrochloride salt of (+)-pilocarpine, a medication used to treat increased pressure inside the eye and dry mouth. It contains a (+)-pilocarpine.
Pilocarpine Hydrochloride is the hydrochloride salt of a natural alkaloid extracted from plants of the genus Pilocarpus with cholinergic agonist activity. As a cholinergic parasympathomimetic agent, pilocarpine predominantly binds to muscarinic receptors, thereby inducing exocrine gland secretion and stimulating smooth muscle in the bronchi, urinary tract, biliary tract, and intestinal tract. When applied topically to the eye, this agent stimulates the sphincter pupillae to contract, resulting in miosis; stimulates the ciliary muscle to contract, resulting in spasm of accomodation; and may cause a transitory rise in intraocular pressure followed by a more persistent fall due to opening of the trabecular meshwork and an increase in the outflow of aqueous humor.
A slowly hydrolyzed muscarinic agonist with no nicotinic effects. Pilocarpine is used as a miotic and in the treatment of glaucoma.
See also: Pilocarpine (has active moiety); Betaxolol hydrochloride; pilocarpine hydrochloride (component of).
(+)-pilocarpine is the (+)-enantiomer of pilocarpine. It has a role as an antiglaucoma drug. It is an enantiomer of a (-)-pilocarpine.
A naturally occurring alkaloid derived from the Pilocarpus plants, pilocarpine is a muscarinic acetylcholine agonist. Pilocarpine is associated with parasympathomimetic effects by selectively working on muscarinic receptors. Pilocarpine is used to treat dry mouth and various ophthalmic conditions, including elevated intraocular pressure and glaucoma. The usage of glaucoma by pilocarpine dates back to 1875.
Pilocarpine is a Cholinergic Receptor Agonist. The mechanism of action of pilocarpine is as a Cholinergic Agonist, and Cholinergic Muscarinic Agonist.
Pilocarpine is an orally available cholinergic agonist that is used to treat symptoms of dry mouth in patients with keratoconjunctivitis sicca (Sjögren syndrome) or with xerostomia (dry mouth) due to local irradiation. Pilocarpine has not been linked to serum enzyme elevations during therapy or to instances of clinically apparent liver injury.
Pilocarpine has been reported in Pilocarpus microphyllus, Pilocarpus racemosus, and other organisms with data available.
Pilocarpine is a natural alkaloid extracted from plants of the genus Pilocarpus with cholinergic agonist activity. As a cholinergic parasympathomimetic agent, pilocarpine predominantly binds to muscarinic receptors, thereby inducing exocrine gland secretion and stimulating smooth muscle in the bronchi, urinary tract, biliary tract, and intestinal tract. When applied topically to eyes, this agent stimulates the sphincter pupillae to contract, resulting in miosis; stimulates the ciliary muscle to contract, resulting in spasm of accommodation; and may cause a transitory rise in intraocular pressure followed by a more persistent fall due to opening of the trabecular meshwork and an increase in the outflow of aqueous humor.
Pilocarpine is only found in individuals that have used or taken this drug. It is a slowly hydrolyzed muscarinic agonist with no nicotinic effects. Pilocarpine is used as a miotic and in the treatment of glaucoma. [PubChem]Pilocarpine is a cholinergic parasympathomimetic agent. It increase secretion by the exocrine glands, and produces contraction of the iris sphincter muscle and ciliary muscle (when given topically to the eyes) by mainly stimulating muscarinic receptors.
A slowly hydrolyzed muscarinic agonist with no nicotinic effects. Pilocarpine is used as a miotic and in the treatment of glaucoma.
See also: Pilocarpine Hydrochloride (has salt form).
Drug Indication
Pilocarpine oral tablets are indicated for the treatment of dry mouth caused by Sjogren's Syndrome or radiotherapy for cancer of the head and neck. Pilocarpine ophthalmic formulations are used to treat presbyopia in adults, reduce elevated intraocular pressure (IOP) in patients with open-angle glaucoma or ocular hypertension, manage acute angle-closure glaucoma, prevent postoperative elevated IOP associated with laser surgery, and induce miosis.
Mechanism of Action
The muscarinic M3 receptor is expressed in various endocrine and exocrine glands, including the gastric and salivary glands. It is also found in smooth muscle cells in pupillary sphincter and ciliary bodies. The M3 receptor is a Gq-protein-coupled receptor that activates phospholipase C and upregulates inositol trisphosphate and intracellular calcium. M3 receptor activation has been implicated in smooth muscle contraction and the stimulation of salivary glands. Pilocarpine is an agonist for M1 and M2 receptors, and is a full and partial agonist at the M3 receptor.
...ACT PRIMARILY @ MUSCARINIC RECEPTORS OF AUTONOMIC EFFECTOR CELLS, GANGLIONIC EFFECTS CAN ALSO BE OBSERVED. THIS IS PARTICULARLY TRUE OF PILOCARPINE, ALTHOUGH ITS GANGLIONIC ACTION ALSO INVOLVES STIMULATION OF MUSCARINIC RECEPTORS...
...AFTER TOPICAL INSTILLATION, MIOSIS BEGINS IN 15 TO 30 MIN & LASTS 4 TO 8 HR. REDUCTION OF INTRAOCULAR PRESSURE IS MAXIMAL IN 2 TO 4 HR, WHICH CORRELATES WITH MAX DECR IN OUTFLOW RESISTANCE. EFFECT ON INTRAOCULAR PRESSURE OUTLASTS EFFECT ON OUTFLOW FACILITY...PILOCARPINE...MAY DECR AQUEOUS PRODUCTION.
...PILOCARPINE /HAS AS/...PRINCIPAL ACTION STIMULATION OF SAME AUTONOMIC EFFECTOR CELLS AS THOSE ACTED UPON BY CHOLINERGIC POSTGANGLIONIC NERVE IMPULSES.
...PILOCARPINE...PRINCIPAL ACTION STIMULATION OF SAME AUTONOMIC EFFECTOR CELLS AS THOSE ACTED UPON BY CHOLINERGIC POSTGANGLIONIC NERVE IMPULSES. IN THIS RESPECT...RESEMBLE CHOLINE ESTERS...
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C11H16N2O2.HCL
Molecular Weight
244.72
Exact Mass
208.121
Elemental Analysis
C, 53.99; H, 7.00; Cl, 14.49; N, 11.45; O, 13.08
CAS #
54-71-7
Related CAS #
Pilocarpine;92-13-7;Pilocarpine nitrate;148-72-1;Pilocarpine-d3 hydrochloride;1217838-88-4
PubChem CID
5909
Appearance
Typically exists as white to off-white solids at room temperature
Density
1.2±0.1 g/cm3
Boiling Point
431.8±18.0 °C at 760 mmHg
Melting Point
202-205 °C(lit.)
Flash Point
215.0±21.2 °C
Vapour Pressure
0.0±1.0 mmHg at 25°C
Index of Refraction
1.585
LogP
-0.09
Hydrogen Bond Donor Count
1
Hydrogen Bond Acceptor Count
3
Rotatable Bond Count
3
Heavy Atom Count
16
Complexity
245
Defined Atom Stereocenter Count
2
SMILES
Cl[H].O1C([C@@]([H])(C([H])([H])C([H])([H])[H])[C@]([H])(C1([H])[H])C([H])([H])C1=C([H])N=C([H])N1C([H])([H])[H])=O
InChi Key
RNAICSBVACLLGM-GNAZCLTHSA-N
InChi Code
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
Chemical Name
(3S,4R)-3-ethyl-4-[(3-methylimidazol-4-yl)methyl]oxolan-2-one;hydrochloride
Synonyms
NSC 5746 HCl; Pilocarpine Hydrochloride; Pilocarpal; Pilocar; (+)-Pilocarpine hydrochloride; NSC-5746 HCl;NSC5746 HCl;Pilocar SMP; Salagen; Pilocarpine Mononitrate, (3S-cis)-Isomer; Pilocarpine Nitrate; Pilocarpine, Monohydrochloride, (3S-cis)-Isomer; Ocusert; Pilocarpine hydrochloride; 54-71-7; (+)-Pilocarpine hydrochloride; Pilocarpine HCl; Almocarpine; Salagen; Pilocarpal; Pilocar SMP;
HS Tariff Code
2934.99.9001
Storage

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Note: (1). This product is not stable in solution, please use freshly prepared working solution for optimal results.  (2). Please store this product in a sealed and protected environment, avoid exposure to moisture.
Shipping Condition
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
Solubility Data
Solubility (In Vitro)
DMSO:49 mg/mL (200.2 mM)
Water:49 mg/mL (200.2 mM)
Ethanol: N/A
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.08 mg/mL (8.50 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL.
Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution.

Solubility in Formulation 2: ≥ 2.08 mg/mL (8.50 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly.
Preparation of 20% SBE-β-CD in Saline (4°C,1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.

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Solubility in Formulation 3: ≥ 2.08 mg/mL (8.50 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.


Solubility in Formulation 4: 130 mg/mL (531.22 mM) in PBS (add these co-solvents sequentially from left to right, and one by one), clear solution; with ultrasonication.

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 4.0863 mL 20.4315 mL 40.8630 mL
5 mM 0.8173 mL 4.0863 mL 8.1726 mL
10 mM 0.4086 mL 2.0432 mL 4.0863 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.

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Method for preparing DMSO stock solution mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.

Method for preparing in vivo formulation:Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O,mix and clarify.

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Clinical Trial Information
A Study to Assess Safety and Efficacy in Participants Age 40 to 55 With Presbyopia (Old Eye) Who Receive AGN-190584 in Both Eyes Twice Daily
CTID: NCT04983589
Phase: Phase 3
Status: Completed
Date: 2023-03-21
Comparison of a Compound With Pilocarpine and Brimonidine to Improve Near Vision in Healthy Presbyopic Patients
CTID: NCT05001243
Phase: Phase 1
Status: Unknown status
Date: 2021-08-19
Oral Pilocarpine in the Treatment of the Dry Eye of Patients With Sjogrens Syndrome
CTID: NCT04470479
Phase: Phase 3
Status: Completed
Date: 2020-07-14
Pilocarpine in Treating Patients With Dry Mouth Caused by Opioids
CTID: NCT00003686
Phase: Phase 3
Status: Terminated
Date: 2020-04-03
Pilocarpine in Treating Vaginal Dryness in Patients With Breast Cancer
CTID: NCT00343382
Phase: Phase 3
Status: Completed
Date: 2016-08-12
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