Synonym
Alverine; Alverine Citrate; Phenopropamine; Phenpropamine; Profenil; Dipropyline; Spasmaverine; Sestron; Dipropylin; NSC35459; NSC 35459; NSC-35459
IUPAC/Chemical Name
N-ethyl-3-phenyl-N-(3-phenylpropyl)propan-1-amine 2-hydroxypropane-1,2,3-tricarboxylate
InChi Key
RYHCACJBKCOBTJ-UHFFFAOYSA-N
InChi Code
InChI=1S/C20H27N.C6H8O7/c1-2-21(17-9-15-19-11-5-3-6-12-19)18-10-16-20-13-7-4-8-14-20;7-3(8)1-6(13,5(11)12)2-4(9)10/h3-8,11-14H,2,9-10,15-18H2,1H3;13H,1-2H2,(H,7,8)(H,9,10)(H,11,12)
SMILES Code
CCN(CCCC1=CC=CC=C1)CCCC2=CC=CC=C2.C(C(=O)O)C(CC(=O)O)(C(=O)O)O
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:
Alverine citrate is a 5-HT1A receptor antagonist, with an IC50 of 101 nM.
In vitro activity:
To examine the effects of alverine on macrophage-mediated inflammatory responses, NO production was first investigated in alverine-treated, RAW264.7, macrophage-like cells. NO production was induced by LPS and poly(I:C), which are TLR4 and TLR3 ligands, respectively. Alverine dose- and time-dependently blocked NO production in LPS- and poly(I:C)-stimulated RAW264.7 cells up to 61% at 200 μM under the LPS-stimulation condition, or 55% under the poly(I:C)-treated condition (Figure 1B,C).
Reference: Biomolecules. 2020 Apr; 10(4): 611. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7225962/
In vivo activity:
To determine the anti-inflammatory activity of alverine in animals, in vivo gastritis was induced by injecting HCl/EtOH into mice. Alverine ameliorated the ulcerative lesions in a dose-dependent manner (Figure 4A). Similar to the in vitro results, iNOS and TNF-α mRNA levels in the stomach tissue lysates of gastritis mice were also lower in the alverine administration group (Figure 4B). Additionally, this study assessed whether alverine modulated the NF-κB signaling pathway in the stomach tissues of gastritis-induced mice. Alverine clearly suppressed mRNA expression of iNOS and TNF-α under 200 mg/kg-treated conditions (Figure 4C and Supplementary Figure S1A). Finally, it was found that the levels of phosphorylated p65 and IκBα were reduced in stomach tissue lysates prepared from alverine-treated groups (Figure 4D and Supplementary Figure S1B).
Reference: Biomolecules. 2020 Apr; 10(4): 611. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7225962/
|
Solvent |
mg/mL |
mM |
comments |
| Solubility |
| DMSO |
75.0 |
158.39 |
|
| DMF |
30.0 |
63.36 |
|
| PBS (pH 7.2) |
1.0 |
2.11 |
|
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
473.50
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. Lee CY, Kim HG, Park SH, Jang SG, Park KJ, Kim DS, Kim JH, Cho JY. Anti-Inflammatory Functions of Alverine via Targeting Src in the NF-κB Pathway. Biomolecules. 2020 Apr 15;10(4):611. doi: 10.3390/biom10040611. PMID: 32326535; PMCID: PMC7225962.
In vitro protocol:
1. Lee CY, Kim HG, Park SH, Jang SG, Park KJ, Kim DS, Kim JH, Cho JY. Anti-Inflammatory Functions of Alverine via Targeting Src in the NF-κB Pathway. Biomolecules. 2020 Apr 15;10(4):611. doi: 10.3390/biom10040611. PMID: 32326535; PMCID: PMC7225962.
In vivo protocol:
1. Lee CY, Kim HG, Park SH, Jang SG, Park KJ, Kim DS, Kim JH, Cho JY. Anti-Inflammatory Functions of Alverine via Targeting Src in the NF-κB Pathway. Biomolecules. 2020 Apr 15;10(4):611. doi: 10.3390/biom10040611. PMID: 32326535; PMCID: PMC7225962.
1: Lee KJ. Pharmacologic Agents for Chronic Diarrhea. Intest Res. 2015 Oct;13(4):306-312. Epub 2015 Oct 15. Review. PubMed PMID: 26576135; PubMed Central PMCID: PMC4641856.
2: Gupta D, Radhakrishnan M, Kurhe Y. Anxiolytic-like effects of alverine citrate in experimental mouse models of anxiety. Eur J Pharmacol. 2014 Nov 5;742:94-101. doi: 10.1016/j.ejphar.2014.08.033. Epub 2014 Sep 6. PubMed PMID: 25199966.
3: Annaházi A, Róka R, Rosztóczy A, Wittmann T. Role of antispasmodics in the treatment of irritable bowel syndrome. World J Gastroenterol. 2014 May 28;20(20):6031-43. doi: 10.3748/wjg.v20.i20.6031. Review. PubMed PMID: 24876726; PubMed Central PMCID: PMC4033443.
4: Ducrotte P, Grimaud JC, Dapoigny M, Personnic S, O'Mahony V, Andro-Delestrain MC. On-demand treatment with alverine citrate/simeticone compared with standard treatments for irritable bowel syndrome: results of a randomised pragmatic study. Int J Clin Pract. 2014 Feb;68(2):245-54. doi: 10.1111/ijcp.12333. Epub 2013 Oct 21. PubMed PMID: 24147869; PubMed Central PMCID: PMC4282257.
5: Lee SH, Athavankar S, Cohen T, Piran R, Kiselyuk A, Levine F. Identification of alverine and benfluorex as HNF4α activators. ACS Chem Biol. 2013 Aug 16;8(8):1730-6. doi: 10.1021/cb4000986. Epub 2013 May 29. PubMed PMID: 23675775; PubMed Central PMCID: PMC3922238.
6: Bueno L, Beaufrand C, Theodorou V, Andro-Delestrain MC. Influence of simethicone and alverine on stress-induced alterations of colonic permeability and sensitivity in rats: beneficial effect of their association. J Pharm Pharmacol. 2013 Apr;65(4):567-73. doi: 10.1111/jphp.12021. Epub 2013 Jan 17. PubMed PMID: 23488786.
7: Martínez-Vázquez MA, Vázquez-Elizondo G, González-González JA, Gutiérrez-Udave R, Maldonado-Garza HJ, Bosques-Padilla FJ. Effect of antispasmodic agents, alone or in combination, in the treatment of Irritable Bowel Syndrome: systematic review and meta-analysis. Rev Gastroenterol Mex. 2012 Apr-Jun;77(2):82-90. doi: 10.1016/j.rgmx.2012.04.002. Epub 2012 Jun 5. Review. PubMed PMID: 22672854.
8: Beyazit Y, Koklu S, Ozturk ZA, Yüksel O, Ibis M, Arhan M, Gultuna S, Sezer S, Yuksel I, Babali A. Inclusion of a spasmolytic in bowel cleansing: a prospective randomized study. Gastroenterol Nurs. 2011 Sep-Oct;34(5):352-5. doi: 10.1097/SGA.0b013e318229bc90. PubMed PMID: 21979395.
9: Jackson E, Kapp N. Pain control in first-trimester and second-trimester medical termination of pregnancy: a systematic review. Contraception. 2011 Feb;83(2):116-26. doi: 10.1016/j.contraception.2010.07.014. Epub 2010 Aug 30. Review. PubMed PMID: 21237336.
10: Ghosh C, Jha V, Ahir R, Shah S, Shinde CP, Chakraborty BS. A rapid and most sensitive liquid chromatography/tandem mass spectrometry method for simultaneous determination of alverine and its major metabolite, para hydroxy alverine, in human plasma: application to a pharmacokinetic and bioequivalence study. Drug Test Anal. 2010 Jun;2(6):284-91. doi: 10.1002/dta.130. PubMed PMID: 20564607.
