Synonym
Mepenzolate Bromide; Cantil; Gastropidil; Cantilaque; Cantilon; mepenzolate iodide; mepenzolic acid;
IUPAC/Chemical Name
(1,1-dimethylpiperidin-1-ium-3-yl) 2-hydroxy-2,2-diphenylacetate;bromide
InChi Key
JRRNZNSGDSFFIR-UHFFFAOYSA-M
InChi Code
InChI=1S/C21H26NO3.BrH/c1-22(2)15-9-14-19(16-22)25-20(23)21(24,17-10-5-3-6-11-17)18-12-7-4-8-13-18;/h3-8,10-13,19,24H,9,14-16H2,1-2H3;1H/q+1;/p-1
SMILES Code
C[N+]1(CCCC(C1)OC(=O)C(C2=CC=CC=C2)(C3=CC=CC=C3)O)C.[Br-]
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
Biological target:
Mepenzolate Bromide is a muscarinic antagonist.
In vitro activity:
In this study’s attempt to isolate the pharmacologically active ingredients in the aqueous extracts of Mareya micrantha, this study has selected the contractions of the longitudinal muscle of the isolated guinea-pig ileum preparation as a pharmacological marker to monitor retention of pharmacological activity during the chromatographic separation. Mepenzolate (10(-8)-10(-5) M), a specific muscarinic receptor antagonist, similarly antagonized contractions elicited by the aqueous extracts suggesting that the cholinergic ingredient(s) in the extract are acting at the muscarinic receptors of the preparation.
Reference: J Ethnopharmacol. 1995 Mar;45(3):215-22. https://pubmed.ncbi.nlm.nih.gov/7623487/
In vivo activity:
The present study aimed at exploring the effect of niacin on experimental colitis in rats as well as throwing some light on the ability of niacin to modulate angiogenesis which plays a crucial role of in the pathogenesis of inflammatory bowel disease. Mepenzolate bromide, a GPR109A receptor blocker, abolished the beneficial effects of niacin on body weight, colon wet weight as well as colonic levels of MPO and VEGF.
Reference: Sci Rep. 2017 Aug 2;7(1):7139. https://pubmed.ncbi.nlm.nih.gov/28769047/
|
Solvent |
mg/mL |
mM |
Solubility |
DMF |
5.0 |
11.89 |
DMSO |
30.0 |
71.37 |
PBS (pH 7.2) |
1.0 |
2.38 |
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
420.35
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. Tsai CS, Guede-Guina F, Smith MO, Vangah-Manda M, Ochillo RF. Isolation of cholinergic active ingredients in aqueous extracts of Mareya micrantha using the longitudinal muscle of isolated guinea-pig ileum as a pharmacological activity marker. J Ethnopharmacol. 1995 Mar;45(3):215-22. doi: 10.1016/0378-8741(94)01219-p. PMID: 7623487.
2. Tsai CS, Ochillo RF. Low temperature and muscarinic receptor activities. Cryobiology. 1989 Oct;26(5):485-95. doi: 10.1016/0011-2240(89)90072-2. PMID: 2791613.
3. Salem HA, Wadie W. Effect of Niacin on Inflammation and Angiogenesis in a Murine Model of Ulcerative Colitis. Sci Rep. 2017 Aug 2;7(1):7139. doi: 10.1038/s41598-017-07280-y. PMID: 28769047; PMCID: PMC5541000.
4. Zheng Y, Wang X, Ji S, Tian S, Wu H, Luo P, Fang H, Wang L, Wu G, Xiao S, Xia Z. Mepenzolate bromide promotes diabetic wound healing by modulating inflammation and oxidative stress. Am J Transl Res. 2016 Jun 15;8(6):2738-47. PMID: 27398156; PMCID: PMC4931167.
In vitro protocol:
1. Tsai CS, Guede-Guina F, Smith MO, Vangah-Manda M, Ochillo RF. Isolation of cholinergic active ingredients in aqueous extracts of Mareya micrantha using the longitudinal muscle of isolated guinea-pig ileum as a pharmacological activity marker. J Ethnopharmacol. 1995 Mar;45(3):215-22. doi: 10.1016/0378-8741(94)01219-p. PMID: 7623487.
2. Tsai CS, Ochillo RF. Low temperature and muscarinic receptor activities. Cryobiology. 1989 Oct;26(5):485-95. doi: 10.1016/0011-2240(89)90072-2. PMID: 2791613.
In vivo protocol:
1. Salem HA, Wadie W. Effect of Niacin on Inflammation and Angiogenesis in a Murine Model of Ulcerative Colitis. Sci Rep. 2017 Aug 2;7(1):7139. doi: 10.1038/s41598-017-07280-y. PMID: 28769047; PMCID: PMC5541000.
2. Zheng Y, Wang X, Ji S, Tian S, Wu H, Luo P, Fang H, Wang L, Wu G, Xiao S, Xia Z. Mepenzolate bromide promotes diabetic wound healing by modulating inflammation and oxidative stress. Am J Transl Res. 2016 Jun 15;8(6):2738-47. PMID: 27398156; PMCID: PMC4931167.
1: Yamashita Y, Tanaka K, Asano T, Yamakawa N, Kobayashi D, Ishihara T, Hanaya K,
Shoji M, Sugai T, Wada M, Mashimo T, Fukunishi Y, Mizushima T. Synthesis and
biological comparison of enantiomers of mepenzolate bromide, a muscarinic
receptor antagonist with bronchodilatory and anti-inflammatory activities. Bioorg
Med Chem. 2014 Jul 1;22(13):3488-97. doi: 10.1016/j.bmc.2014.04.029. Epub 2014
Apr 30. PubMed PMID: 24844758.
2: Kurotsu S, Tanaka K, Niino T, Asano T, Sugizaki T, Azuma A, Suzuki H,
Mizushima T. Ameliorative effect of mepenzolate bromide against pulmonary
fibrosis. J Pharmacol Exp Ther. 2014 Jul;350(1):79-88. doi:
10.1124/jpet.114.213009. Epub 2014 Apr 25. PubMed PMID: 24769542.
3: Tanaka K, Kurotsu S, Asano T, Yamakawa N, Kobayashi D, Yamashita Y, Yamazaki
H, Ishihara T, Watanabe H, Maruyama T, Suzuki H, Mizushima T. Superiority of
pulmonary administration of mepenzolate bromide over other routes as treatment
for chronic obstructive pulmonary disease. Sci Rep. 2014 Mar 28;4:4510. doi:
10.1038/srep04510. PubMed PMID: 24676126; PubMed Central PMCID: PMC3968453.
4: Tanaka K, Ishihara T, Sugizaki T, Kobayashi D, Yamashita Y, Tahara K, Yamakawa
N, Iijima K, Mogushi K, Tanaka H, Sato K, Suzuki H, Mizushima T. Mepenzolate
bromide displays beneficial effects in a mouse model of chronic obstructive
pulmonary disease. Nat Commun. 2013;4:2686. doi: 10.1038/ncomms3686. PubMed PMID:
24189798.
5: Mepenzolate bromide in mucomembranous colitis. A report from the General
Practitioner research group. Practitioner. 1974 Jun;212(1272):890-4. PubMed PMID:
4608714.
6: Friedman HL, Wang RI. Oral absorption of 14 C-labeled mepenzolate bromide in
humans. J Pharm Sci. 1972 Oct;61(10):1663-5. PubMed PMID: 5072426.