Pirenzepine HCl | CAS#29868-97-1 | M1 muscarinic receptor

MedKoo Cat#: 318501 | Name: Pirenzepine HCl

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Description:

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

Pirenzepine is a selective muscarinic receptor antagonist, primarily targeting the M1 subtype of muscarinic acetylcholine receptors. Pirenzepine selectively blocks M1 muscarinic receptors found predominantly in the central nervous system and gastric parietal cells. This inhibition reduces the stimulation of parietal cells by the vagus nerve, leading to decreased secretion of hydrochloric acid in the stomach. Unlike non-selective anticholinergics, Pirenzepine has minimal effects on M2 receptors associated with heart rate and smooth muscle, which contributes to its relatively favorable side effect profile. In cell-based assays using isolated gastric tissue, Pirenzepine inhibited acetylcholine-induced gastric acid secretion with IC50 values in the low nanomolar range (typically 1–20 nM).

Chemical Structure

Pirenzepine HCl

CAS#29868-97-1 (2HCl)

Theoretical Analysis

MedKoo Cat#: 318501

Name: Pirenzepine HCl

CAS#: 29868-97-1 (2HCl)

Chemical Formula: C19H23Cl2N5O2

Exact Mass: 0.0000

Molecular Weight: 424.33

Elemental Analysis: C, 53.78; H, 5.46; Cl, 16.71; N, 16.50; O, 7.54

Price and Availability

Size	Price	Availability
500mg	USD 350.00
1g	USD 550.00	2 Weeks
2g	USD 875.00	2 Weeks
5g	USD 1,600.00	2 Weeks

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Related CAS #

28797-61-7 (free base) 29868-97-1 (2HCl) 84827-28-1 (hydrate) 93173-05-8 (HCl)

Synonym

Pirenzepine Dihydrochloride; Pirenzepine hydrochloride; Pircfar; Bisvanil; Leblon; LS 519; LS-519;

IUPAC/Chemical Name

11-[2-(4-methylpiperazin-1-yl)acetyl]-5H-pyrido[2,3-b][1,4]benzodiazepin-6-one;dihydrochloride

InChi Key

FFNMBRCFFADNAO-UHFFFAOYSA-N

InChi Code

InChI=1S/C19H21N5O2.2ClH/c1-22-9-11-23(12-10-22)13-17(25)24-16-7-3-2-5-14(16)19(26)21-15-6-4-8-20-18(15)24;;/h2-8H,9-13H2,1H3,(H,21,26);2*1H

SMILES Code

CN1CCN(CC1)CC(=O)N2C3=CC=CC=C3C(=O)NC4=C2N=CC=C4.Cl.Cl

Appearance

Solid 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

Instruction

View handling instruction

Biological target:

Pirenzepine (LS 519) dihydrochloride is a selective M1 mAChR (muscarinic acetylcholine receptor) antagonist.

In vitro activity:

To determine an optimal drug concentration for use in this study, experiments on PC-3 cells were conducted with CHRM1-specific antagonist pirenzepine and nonselective muscarinic receptor agonist carbachol. Pirenzepine inhibited the PC-3 cell proliferation at 100-140 μg ml−1 in a concentration-dependent manner (Figure 2f). Carbachol (2 μg ml−1) dramatically stimulated the invasion of PC-3 and LNCaP cell lines, while pirenzepine (110 μg ml−1) markedly inhibited the invasion of all three cell lines (P = 0.006; Figure 3a and 3b). Similarly, carbachol promoted the migration of LNCaP and A549 cell lines, and pirenzepine significantly inhibited the migration of PC-3 and A549 cell lines (P = 0.014; Figure 3c and 3d). Reference: Asian J Androl. 2018 Nov-Dec;20(6):608-614. https://pubmed.ncbi.nlm.nih.gov/30027929/

In vivo activity:

The present study measured indices of peripheral neuropathy in the doxycycline (DOX)-inducible HIV-TAT (iTAT) transgenic mouse and investigated the therapeutic efficacy of a selective muscarinic subtype-1 receptor (M1R) antagonist, pirenzepine (PZ). PZ was selected as this study has previously shown that it prevents and/or reverses indices of peripheral neuropathy in multiple disease models. DOX alone induced weight loss, tactile allodynia and paw thermal hypoalgesia in normal C57Bl/6J mice. Conduction velocity of large motor fibers, density of small sensory nerve fibers in the cornea and expression of mitochondria-associated proteins in sciatic nerve were unaffected by DOX in normal mice, whereas these parameters were disrupted when DOX was given to iTAT mice to induce TAT expression. Daily injection of PZ (10 mg/kg s.c.) prevented all of the disorders associated with TAT expression. Reference: Front Neurol. 2021 Jun 15;12:663373. https://pubmed.ncbi.nlm.nih.gov/34211430/

	Solvent	mg/mL	mM
Solubility
	DMSO	13.5	31.82
	PBS (pH 7.2)	10.0	23.57
	Water	80.0	188.53

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 424.33 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.

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. Yin QQ, Xu LH, Zhang M, Xu C. Muscarinic acetylcholine receptor M1 mediates prostate cancer cell migration and invasion through hedgehog signaling. Asian J Androl. 2018 Nov-Dec;20(6):608-614. doi: 10.4103/aja.aja_55_18. PMID: 30027929; PMCID: PMC6219293. 2. Daeffler L, Schmidlin F, Gies JP, Landry Y. Inverse agonist activity of pirenzepine at M2 muscarinic acetylcholine receptors. Br J Pharmacol. 1999 Mar;126(5):1246-52. doi: 10.1038/sj.bjp.0702407. PMID: 10205015; PMCID: PMC1565883. 3. Han MM, Frizzi KE, Ellis RJ, Calcutt NA, Fields JA. Prevention of HIV-1 TAT Protein-Induced Peripheral Neuropathy and Mitochondrial Disruption by the Antimuscarinic Pirenzepine. Front Neurol. 2021 Jun 15;12:663373. doi: 10.3389/fneur.2021.663373. PMID: 34211430; PMCID: PMC8239242. 4. Truong HT, Cottriall CL, Gentle A, McBrien NA. Pirenzepine affects scleral metabolic changes in myopia through a non-toxic mechanism. Exp Eye Res. 2002 Jan;74(1):103-11. doi: 10.1006/exer.2001.1107. PMID: 11878823.

In vitro protocol:

In vivo protocol:

1. Han MM, Frizzi KE, Ellis RJ, Calcutt NA, Fields JA. Prevention of HIV-1 TAT Protein-Induced Peripheral Neuropathy and Mitochondrial Disruption by the Antimuscarinic Pirenzepine. Front Neurol. 2021 Jun 15;12:663373. doi: 10.3389/fneur.2021.663373. PMID: 34211430; PMCID: PMC8239242. 2. Truong HT, Cottriall CL, Gentle A, McBrien NA. Pirenzepine affects scleral metabolic changes in myopia through a non-toxic mechanism. Exp Eye Res. 2002 Jan;74(1):103-11. doi: 10.1006/exer.2001.1107. PMID: 11878823.

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Influence of muscarinic ligands on the amplitudes of the evoked surface potential's late components in the optic tectum of the urodele Plethodon jordani. Neurosci Lett. 2000 May 5;285(1):17-20. doi: 10.1016/s0304-3940(00)01007-7. PMID: 10788697. 12: Yang B, McCaffrey TV. The roles of muscarinic receptor subtypes in modulation of nasal ciliary action. Rhinology. 1996 Sep;34(3):136-9. PMID: 8938879. 13: Morris A, Brown P, Ali MR, Lane M, Palmer R. Treatment of Campylobacter pylori gastritis: a pilot study using pirenzepine dihydrochloride (Gastrozepin) and three formulations of colloidal bismuth subcitrate (De-Nol). N Z Med J. 1988 Oct 26;101(856 Pt 1):651-4. PMID: 3054641. 14: Nakagawa H, Nishiyama K, Matsumoto S, Hamano K, Fukui Y, Goto S. [Promotion of gastrointestinal absorption of pirenzepine dihydrochloride in the rat. I]. Yakugaku Zasshi. 1988 Jul;108(7):669-73. Japanese. doi: 10.1248/yakushi1947.108.7_669. PMID: 3241303. 15: Madrid JA, Salido GM, Martínez de Victoria E. Effect of the antimuscarinic agent pirenzepine on the in vivo biliary secretion of dogs in response to various stimuli. Physiol Bohemoslov. 1988;37(1):67-77. PMID: 2967510. 16: Rattan S, Shah R. Influence of sacral nerves on the internal anal sphincter of the opossum. Am J Physiol. 1987 Sep;253(3 Pt 1):G345-50. doi: 10.1152/ajpgi.1987.253.3.G345. PMID: 3631270. 17: Ishimori A, Yamagata S. Controlled double-blind study of the therapeutic effect of pirenzepine dihydrochloride in duodenal ulcer. Phase III study. Arzneimittelforschung. 1986 Jun;36(6):980-3. PMID: 3527182. 18: Wahbi AM, Abounassif MA, el-Obeid HA, Gad-Kariem EA. Spectrophotometric determination of pirenzepine dihydrochloride using delta A method. Farmaco Prat. 1985 Oct;40(10):334-8. PMID: 3840745. 19: Madrid JA, Salido GM, Martinez de Victoria E, Mañas M, Mataix FJ. Postprandial pancreatic exocrine secretion in dogs after oral administration of pirenzepine dihydrochloride. Arzneimittelforschung. 1985;35(10):1560-2. 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