MedKoo Biosciences, Inc.
Tel:   +1-919-636-5577    Fax:   +1-919-980-4831    Email:   sales@medkoo.com
Search
Login Register
Search
MedKoo Cat#: 318493 | Name: Pilocarpine Hydrochloride
Featured New

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Pilocarpine hydrochloride is a slowly hydrolyzed muscarinic agonist with no nicotinic effects. Systemic administration of (+)-pilocarpine is typically used as an animal model for temporal lobe epilepsy and can mimic the generation of complex partial seizures by producing changes in hippocampal neuron morphology, membrane properties, and synaptic responses. Pilocarpine is used as a miotic and in the treatment of glaucoma.

Chemical Structure

Pilocarpine Hydrochloride
Pilocarpine Hydrochloride
CAS#54-71-7 (HCl)

Theoretical Analysis

MedKoo Cat#: 318493

Name: Pilocarpine Hydrochloride

CAS#: 54-71-7 (HCl)

Chemical Formula: C11H17ClN2O2

Exact Mass: 0.0000

Molecular Weight: 244.72

Elemental Analysis: C, 53.99; H, 7.00; Cl, 14.49; N, 11.45; O, 13.08

Price and Availability

Size Price Availability Quantity
500mg USD 150.00 Ready to ship
1g USD 250.00 Ready to ship
2g USD 450.00 Ready to ship
5g USD 850.00 2 Weeks
Bulk Inquiry
Buy Now
Add to Cart
Related CAS #
54-71-7 (HCl) 92-13-7 (free base) 148-72-1 (nitrate)
Synonym
Pilocarpine Hydrochloride; Pilocarpal; Pilocar; (+)-Pilocarpine hydrochloride; Pilocar SMP; Salagen; Pilocarpine Mononitrate, (3S-cis)-Isomer; Pilocarpine Nitrate; Pilocarpine, Monohydrochloride, (3S-cis)-Isomer; Ocusert; Pilocarpine HCl;
IUPAC/Chemical Name
(3S,4R)-3-ethyl-4-[(3-methylimidazol-4-yl)methyl]oxolan-2-one;hydrochloride
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
SMILES Code
CCC1C(COC1=O)CC2=CN=CN2C.Cl
Appearance
White to off-white crystalline powder.
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO, not in water
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info
Product Data
Product Data
Certificate of Analysis
View CoA: current batch, Lot# C22M11C28
Safety Data Sheet (SDS)
View Safety Data Sheet (SDS)
Instruction
View handling instruction
Biological target:
Pilocarpine Hydrochloride is a potent M3-type muscarinic acetylcholine receptor (M3 muscarinic receptor) agonist.
In vitro activity:
Pilocarpine at concentrations above 0.625 g/L (1/32 of its clinical therapeutic dosage) has a dose- and time-dependent cytotoxicity to HCS cells by inducing apoptosis in these cells, which is most probably regulated by a death receptor-mediated mitochondrion-dependent signaling pathway. Reference: Int J Ophthalmol. 2016 Apr 18;9(4):505-11. https://pubmed.ncbi.nlm.nih.gov/27162720/
In vivo activity:
Pilocarpine induced a greater amount of saliva in the exercised rats than in the CN. Expression levels of AQP1 mRNA and protein were significantly higher in SMGs of exercised rats than in those of the CN, but the expression of AQP5 was not affected by voluntary exercise. Voluntary exercise increased the expression of vascular endothelial growth factor (VEGF) and cluster of differentiation 31 (CD31), a marker for endothelial cells, in the SMGs. Voluntary exercise promoted pilocarpine-induced saliva secretion, probably via an increase in the expression level of AQP1 due to VEGF-induced CD31-positive angiogenesis in the SMG. Reference: FEBS Open Bio. 2017 Dec 7;8(1):85-93. https://pubmed.ncbi.nlm.nih.gov/29321959/
Solvent mg/mL mM comments
Solubility
DMF 2.0 8.17
DMSO 30.2 123.25
Ethanol 25.5 104.20
PBS (pH 7.2) 10.0 0.41
Water 36.8 150.47
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 244.72 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
1. Aquino PEA, Siqueira EA, Paes LCF, Magalhães EP, Barbosa TM, Carvalho MAJ, Azul FVCS, Lustosa IR, Mottin M, Sampaio TL, Martins AMC, Silveira ER, Viana GSB. N-Methyl-(2S, 4R)-trans-4-hydroxy-L-proline, the major bioactive compound from Sideroxylon obtusifolium, attenuates pilocarpine-induced injury in cultured astrocytes. Braz J Med Biol Res. 2022 Nov 4;55:e12381. doi: 10.1590/1414-431X2022e12381. PMID: 36350974; PMCID: PMC9635815. 2. Yuan XL, Wen Q, Zhang MY, Fan TJ. Cytotoxicity of pilocarpine to human corneal stromal cells and its underlying cytotoxic mechanisms. Int J Ophthalmol. 2016 Apr 18;9(4):505-11. doi: 10.18240/ijo.2016.04.05. PMID: 27162720; PMCID: PMC4853343. 3. Matsuzaki K, Sugimoto N, Katakura M, Sumiyoshi E, Hara T, Hashimoto M, Shido O. 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. doi: 10.1002/2211-5463.12353. PMID: 29321959; PMCID: PMC5757178. 4. Tonta MA, Parkington HC, Tare M, Coleman HA. 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. doi: 10.1111/j.1476-5381.1994.tb13105.x. PMID: 8075872; PMCID: PMC1910363.
In vitro protocol:
1. Aquino PEA, Siqueira EA, Paes LCF, Magalhães EP, Barbosa TM, Carvalho MAJ, Azul FVCS, Lustosa IR, Mottin M, Sampaio TL, Martins AMC, Silveira ER, Viana GSB. N-Methyl-(2S, 4R)-trans-4-hydroxy-L-proline, the major bioactive compound from Sideroxylon obtusifolium, attenuates pilocarpine-induced injury in cultured astrocytes. Braz J Med Biol Res. 2022 Nov 4;55:e12381. doi: 10.1590/1414-431X2022e12381. PMID: 36350974; PMCID: PMC9635815. 2. Yuan XL, Wen Q, Zhang MY, Fan TJ. Cytotoxicity of pilocarpine to human corneal stromal cells and its underlying cytotoxic mechanisms. Int J Ophthalmol. 2016 Apr 18;9(4):505-11. doi: 10.18240/ijo.2016.04.05. PMID: 27162720; PMCID: PMC4853343.
In vivo protocol:
1. Matsuzaki K, Sugimoto N, Katakura M, Sumiyoshi E, Hara T, Hashimoto M, Shido O. 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. doi: 10.1002/2211-5463.12353. PMID: 29321959; PMCID: PMC5757178. 2. Tonta MA, Parkington HC, Tare M, Coleman HA. 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. doi: 10.1111/j.1476-5381.1994.tb13105.x. PMID: 8075872; PMCID: PMC1910363.
1: Agban Y, Lian J, Prabakar S, Seyfoddin A, Rupenthal ID. Nanoparticle cross-linked collagen shields for sustained delivery of pilocarpine hydrochloride. Int J Pharm. 2016 Mar 30;501(1-2):96-101. doi: 10.1016/j.ijpharm.2016.01.069. Epub 2016 Jan 29. PubMed PMID: 26828672. 2: Shimura T, Kofunato Y, Yashima R, Hara T, Ito H, Takenoshita S. Pilocarpine Hydrochloride Improves Baseline Image of Magnetic Resonance Cholangiopancreatography. Am J Gastroenterol. 2015 Dec;110(12):1735-6. doi: 10.1038/ajg.2015.330. PubMed PMID: 26673507. 3: Pavicić-Astalos J, Lacmanović-Loncar V, Petric-Vicković I, Sarić D, Mandić Z, Csik T, Susić N. Eye drops preservative as the cause of corneal band keratopathy in long-term pilocarpine hydrochloride treatment. Acta Clin Croat. 2012 Mar;51(1):107-11. PubMed PMID: 22920012. 4: Tomiita M, Takei S, Kuwada N, Nonaka Y, Saito K, Shimojo N, Kohno Y. Efficacy and safety of orally administered pilocarpine hydrochloride for patients with juvenile-onset Sjögren's syndrome. Mod Rheumatol. 2010 Oct;20(5):486-90. doi: 10.1007/s10165-010-0313-7. Epub 2010 Jun 3. PubMed PMID: 20517630. 5: El-Deeb S, Schepers U, Wätzig H. Evaluation of monolithic C18 HPLC columns for the fast analysis of pilocarpine hydrochloride in the presence of its degradation products. Pharmazie. 2006 Sep;61(9):751-6. PubMed PMID: 17020149. 6: Wu CH, Hsieh SC, Lee KL, Li KJ, Lu MC, Yu CL. Pilocarpine hydrochloride for the treatment of xerostomia in patients with Sjögren's syndrome in Taiwan--a double-blind, placebo-controlled trial. J Formos Med Assoc. 2006 Oct;105(10):796-803. PubMed PMID: 17000452. 7: Maruyama K, Koshihara N. [Pharmacological and clinical profile of pilocarpine hydrochloride (SALAGEN) Tab. 5 mg)]. Nihon Yakurigaku Zasshi. 2006 May;127(5):399-407. Review. Japanese. PubMed PMID: 16819247. 8: Mosqueda-Taylor A, Luna-Ortiz K, Irigoyen-Camacho ME, Díaz-Franco MA, Coll-Muñoz AM. Effect of pilocarpine hydrochloride on salivary production in previously irradiated head and neck cancer patients. Med Oral. 2004 May-Jul;9(3):204-11. English, Spanish. PubMed PMID: 15122121. 9: Omori Y, Asari T, Maruyama K, Kusama H, Kojima M, Shibata N. Effects of pilocarpine hydrochloride and cevimeline on submandibular/sublingual salivation in rat xerostomia model produced by X-ray irradiation. Arzneimittelforschung. 2003;53(5):342-50. PubMed PMID: 12854361. 10: Asari T, Komatsu Y, Misawa K, Hara K, Akahane M. Prophylactic effects of pilocarpine hydrochloride on xerostomia models induced by X-ray irradiation in rats. Clin Exp Pharmacol Physiol. 2001 Jul;28(7):545-50. PubMed PMID: 11422222. 11: Nagler RM, Nagler A. Pilocarpine hydrochloride relieves xerostomia in chronic graft-versus-host disease: a sialometrical study. Bone Marrow Transplant. 1999 May;23(10):1007-11. PubMed PMID: 10373066. 12: Takaya M, Ichikawa Y, Yamada C, Hoshina Y, Horiki T, Uchiyama M. [Treatment with pilocarpine hydrochloride for sicca symptoms in Sjögren's syndrome]. Ryumachi. 1997 Jun;37(3):453-7. Japanese. PubMed PMID: 9256028. 13: Singhal S, Mehta J, Rattenbury H, Treleaven J, Powles R. Oral pilocarpine hydrochloride for the treatment of refractory xerostomia associated with chronic graft-versus-host disease. Blood. 1995 Feb 15;85(4):1147-8. PubMed PMID: 7849306. 14: Kecik T, Szlaski J, Portacha L, Lewandowski P, Marchlewska B, Pacak I. [Studies of releasing rate of pilocarpine hydrochloride from hydrogel eye ointments]. Klin Oczna. 1993 Jul;95(7):263-4. Polish. PubMed PMID: 8121144. 15: Johansson PA. Stirring device for direct microtitration of pilocarpine hydrochloride in individual single-dose containers. Anal Chem. 1986 Jun;58(7):1587-9. PubMed PMID: 3729000. 16: Kreienbaum MA, Page DP. Stability of pilocarpine hydrochloride and pilocarpine nitrate ophthalmic solutions submitted by U.S. hospitals. Am J Hosp Pharm. 1986 Jan;43(1):109-17. PubMed PMID: 3953580. 17: Mandahl A. Effects of the substance P antagonist [D-Arg1,D-Pro2,D-Trp7,9,Leu11]SP on miosis caused by echothiophate iodide or pilocarpine hydrochloride. Eur J Pharmacol. 1985 Aug 15;114(2):121-7. PubMed PMID: 2412852. 18: Kennedy JM, McNamara PE. High-performance liquid chromatographic analysis of pilocarpine hydrochloride, isopilocarpine, pilocarpic acid and isopilocarpic acid in eye-drop preparations. J Chromatogr. 1981 Aug 7;212(3):331-8. PubMed PMID: 7263802. 19: Miichi H, Nagataki S. [Effect of pilocarpine hydrochloride on the aqueous humor production in the rabbit (author's transl)]. Nippon Ganka Gakkai Zasshi. 1979 Aug 10;83(8):1354-60. Japanese. PubMed PMID: 525565. 20: Weber JD. Pilocarpine hydrochloride in ophthalmic solutions: modification of a high-pressure liquid chromatographic determination and survey. J Assoc Off Anal Chem. 1976 Nov;59(6):1409-15. PubMed PMID: 993193.