Bencycloquidium Bromide

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

MedKoo CAT#: 326852

CAS#: 860804-18-8

Description: Bencycloquidium Bromide, also known as BCQB, is a muscarinic M3 antagonist potentially for the treatment of allergic rhinitis and chronic obstructive. Bencycloquidium bromide inhibits nasal hypersecretion in a rat model of allergic rhinitis. BCQB showed high affinity toward the M(3) receptor in Chinese hamster ovary (CHO) cells (M(3) pKi=8.21, M(2) pKi=7.21, and M(1) pKi=7.86); pA(2)=8.85, 8.71 and 8.57 in methacholine-induced contraction of trachea, ileum and urinary bladder, 8.19 in methacholine-induced bradycardia of right atrium in vitro, respectively.


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Bencycloquidium Bromide, is not in stock, may be available through custom synthesis. For cost-effective reason, minimum 1 gram order is requested. The product will be characterized by NMR, HPLC and MS analysis. Purity (HPLC) is usually >98%. CoA, QC data, MSDS will be provided when product is successfully made. The estimated lead time is 2-3 months. Please send email to sales@medkoo.com to inquire quote.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 326852
Name: Bencycloquidium Bromide
CAS#: 860804-18-8
Chemical Formula: C21H32BrNO2
Exact Mass:
Molecular Weight: 410.396
Elemental Analysis: C, 61.46; H, 7.86; Br, 19.47; N, 3.41; O, 7.80


Synonym: Bencycloquidium Bromide; BCQB.

IUPAC/Chemical Name: 3-(2-cyclopentyl-2-hydroxy-2-phenylethoxy)-1-methylquinuclidin-1-ium bromide

InChi Key: LMUJEWVKOCYOQL-UHFFFAOYSA-M

InChi Code: InChI=1S/C21H32NO2.BrH/c1-22-13-11-17(12-14-22)20(15-22)24-16-21(23,19-9-5-6-10-19)18-7-3-2-4-8-18;/h2-4,7-8,17,19-20,23H,5-6,9-16H2,1H3;1H/q+1;/p-1

SMILES Code: OC(COC1C2CC[N+](CC2)(C1)C)(C3=CC=CC=C3)C4CCCC4.[Br-]


Technical Data

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

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).

Harmonized System Code:
293490


References

1: Zhang SJ, Jiang JX, Ren QQ, Xie QM, Xiong YK. Effects of the inhalation of the m3 receptor antagonist bencycloquidium bromide in a mouse cigarette smoke-induced airway inflammation model. Drug Dev Res. 2015 May;76(3):123-31. doi: 10.1002/ddr.21248. Epub 2015 May 11. PubMed PMID: 25958838.

2: Long R, Zhou Y, Huang J, Peng L, Meng L, Zhu S, Li J. Bencycloquidium bromide inhibits nasal hypersecretion in a rat model of allergic rhinitis. Inflamm Res. 2015 Apr;64(3-4):213-23. doi: 10.1007/s00011-015-0800-6. Epub 2015 Feb 18. PubMed PMID: 25690567.

3: Agbokponto JE, Luo Z, Liu R, Liu Z, Liang M, Ding L. Study of pharmacokinetic interaction of paroxetine and roxithromycin on bencycloquidium bromide in healthy subjects. Eur J Pharm Sci. 2015 Mar 10;69:37-43. doi: 10.1016/j.ejps.2014.12.019. Epub 2015 Jan 2. PubMed PMID: 25559065.

4: Agbokponto JE, Zhang L, Hu L, Feng H, Ding L. In vitro metabolism of bencycloquidium bromide and its inhibitory effects on human P450 isoenzymes: implication of CYP2D6, CYP2C19 and CYP3A4/5. Eur J Drug Metab Pharmacokinet. 2016 Feb;41(1):69-77. doi: 10.1007/s13318-014-0237-2. Epub 2014 Nov 26. PubMed PMID: 25425116.

5: Sun L, Ding L, Wang Y, Zhou W, Yan Z, Sun W, Zhang H, Ou N, Chen X. Pharmacokinetics, safety and tolerability of Bencycloquidium bromide, a novel selective muscarinic M1/M3 receptor antagonist, after single and multiple intranasal doses in healthy chinese subjects: an open-label, single-center, first-in-human study. Drugs R D. 2012 Mar 1;12(1):17-28. doi: 10.2165/11599330-000000000-00000. PubMed PMID: 22339483; PubMed Central PMCID: PMC3585954.

6: Cao R, Dong XW, Jiang JX, Yan XF, He JS, Deng YM, Li FF, Bao MJ, Xie YC, Chen XP, Xie QM. M(3) muscarinic receptor antagonist bencycloquidium bromide attenuates allergic airway inflammation, hyperresponsiveness and remodeling in mice. Eur J Pharmacol. 2011 Mar 25;655(1-3):83-90. doi: 10.1016/j.ejphar.2011.01.024. Epub 2011 Jan 28. PubMed PMID: 21277298.

7: Jiang JX, Cao R, Deng WD, Jin F, Dong XW, Zhu Y, Chen XP, Xie YC, Bao MJ, Li FF, Xie QM. Characterization of bencycloquidium bromide, a novel muscarinic M(3) receptor antagonist in guinea pig airways. Eur J Pharmacol. 2011 Mar 25;655(1-3):74-82. doi: 10.1016/j.ejphar.2011.01.017. Epub 2011 Jan 24. PubMed PMID: 21272572.

8: Li J, He H, Zhou Y, Yuan P, Chen X. Subchronic toxicity and toxicokinetics of long-term intranasal administration of bencycloquidium bromide: a 91-day study in dogs. Regul Toxicol Pharmacol. 2011 Mar;59(2):343-52. doi: 10.1016/j.yrtph.2010.11.006. Epub 2010 Dec 2. PubMed PMID: 21130130.

9: Jiang B, Ruan Z, Lou H, Dong X, Xie Q. Determination of bencycloquidium bromide in dog plasma by liquid chromatography with electrospray ionization tandem mass spectrometry. Biomed Chromatogr. 2010 May;24(5):490-6. doi: 10.1002/bmc.1316. PubMed PMID: 19688815.

10: Zhou W, Ding L, Xu G, Wang Y, Sun L, He J, Huang Y, Hu L, Chen X. Determination of bencycloquidium bromide in human urine using weak cation-exchange solid-phase extraction and LC-ESI-MS: Method validation and application to kinetic study of urinary excretion. J Pharm Biomed Anal. 2009 Aug 15;50(1):35-40. doi: 10.1016/j.jpba.2009.03.012. Epub 2009 Mar 24. PubMed PMID: 19395213.

11: Zhou W, Ding L, Wang Y, Sun L, Huang Y, Hu L, Chen X. Solid phase extraction and liquid chromatography-electrospray ionization-mass spectrometry for the determination of bencycloquidium bromide in human plasma. J Chromatogr B Analyt Technol Biomed Life Sci. 2009 Apr 1;877(10):897-901. doi: 10.1016/j.jchromb.2009.02.027. Epub 2009 Feb 14. PubMed PMID: 19251489.

12: Xu Q, Ding L, Liu WY, Li RS, Song QX, Chen XP. Determination of bencycloquidium bromide, a novel anticholinergic compound, in rat tissues by liquid chromatography-electrospray ionization mass spectrometry. Eur J Mass Spectrom (Chichester, Eng). 2008;14(5):319-27. doi: 10.1255/ejms.937. PubMed PMID: 19023149.

13: Xu Q, Ding L, Liu WY, Chen XP, Liu BM. Study of the metabolites of bencycloquidium bromide racemate, a novel anticholinergic compound, in rat bile by liquid chromatography-tandem mass spectrometry. Eur J Mass Spectrom (Chichester, Eng). 2008;14(2):99-105. doi: 10.1255/ejms.909. PubMed PMID: 18493099.

14: Xu Q, Ding L, Liu W, Bian X, Tang W. Determination of bencycloquidium bromide in rat plasma by liquid chromatography-electrospray ionization-mass spectrometry. J Chromatogr B Analyt Technol Biomed Life Sci. 2007 Feb 1;846(1-2):209-14. Epub 2006 Oct 19. PubMed PMID: 17055347.