Carbenoxolone sodium
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MedKoo CAT#: 540060

CAS#: 7421-40-1

Description: Carbenoxolone sodium is a synthetic derivative of glycyrrhizin and inhibitor connexins and 11β-HSD. It is used to treat ulcers and inflammation but also displays other biological activities. It suppresses gap junction communication, delays onset of EAE in vivo, and decreases infarct volume in models of cerebral ischemia/reperfusion.

Chemical Structure

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Carbenoxolone sodium
CAS# 7421-40-1
Instruction

Theoretical Analysis

MedKoo Cat#: 540060
Name: Carbenoxolone sodium
CAS#: 7421-40-1
Chemical Formula: C34H48Na2O7
Exact Mass: 614.32
Molecular Weight: 614.730
Elemental Analysis: C, 66.43; H, 7.87; Na, 7.48; O, 18.22

Price and Availability

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1g USD 250 2 Weeks
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Synonym: Biogastrone; Bioral; Carbenoxolone sodium; Duogastrone; Pyrogastrone; Sanodin

IUPAC/Chemical Name: sodium (2S,4aS,6aS,6bR,8aR,10S,12aS,12bR,14bR)-10-((3-carboxylatopropanoyl)oxy)-2,4a,6a,6b,9,9,12a-heptamethyl-13-oxo-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-2-carboxylate

InChi Key: BQENDLAVTKRQMS-SBBGFIFASA-L

InChi Code: InChI=1S/C34H50O7.2Na/c1-29(2)23-10-13-34(7)27(32(23,5)12-11-24(29)41-26(38)9-8-25(36)37)22(35)18-20-21-19-31(4,28(39)40)15-14-30(21,3)16-17-33(20,34)6;;/h18,21,23-24,27H,8-17,19H2,1-7H3,(H,36,37)(H,39,40);;/q;2*+1/p-2/t21-,23-,24-,27+,30+,31-,32-,33+,34+;;/m0../s1

SMILES Code: CC(C)([C@](CC[C@@]([C@@]1(CC[C@]2(CC[C@](C([O-])=O)(C[C@]2(C1=C3)[H])C)C)C)4C)5[H])[C@@H](OC(CCC([O-])=O)=O)CC[C@]5(C)[C@@]4([H])C3=O.[Na+].[Na+]

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).

HS Tariff Code: 2934.99.9001

More Info:

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 614.73 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:
In vitro protocol:
In vivo protocol:

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1: Wattanakorn N, Asavapichayont P, Nunthanid J, Limmatvapirat S, Sungthongjeen S, Chantasart D, Sriamornsak P. Pectin-based bioadhesive delivery of carbenoxolone sodium for aphthous ulcers in oral cavity. AAPS PharmSciTech. 2010 Jun;11(2):743-51. doi: 10.1208/s12249-010-9424-x. Epub 2010 May 5. PubMed PMID: 20443091; PubMed Central PMCID: PMC2902330.

2: Zhou JJ, Jiang YX, Jin SJ, Tao LJ, Liu LJ. [Studies on analgesic effects and sites of oxymatrine-carbenoxolone sodium complex]. Zhongguo Zhong Yao Za Zhi. 2008 Apr;33(7):822-4. Chinese. PubMed PMID: 18589792.

3: Zhou J, Yang G, Jin S, Tao L, Yu J, Jiang Y. Oxymatrine-carbenoxolone sodium inclusion compound induces antinociception and increases the expression of GABA(A)alpha1 receptors in mice. Eur J Pharmacol. 2010 Jan 25;626(2-3):244-9. doi: 10.1016/j.ejphar.2009.09.065. Epub 2009 Oct 8. PubMed PMID: 19818751.

4: Tykarska E, Gdaniec M. Solid-state supramolecular architecture of carbenoxolone – comparative studies with glycyrrhetinic and glycyrrhizic acids. Acta Crystallogr B Struct Sci Cryst Eng Mater. 2015 Feb;71(Pt 1):25-33. doi: 10.1107/S2052520614026419. Epub 2015 Jan 20. PubMed PMID: 25643713.

5: Zhang Y. [Determination of furazolidone, carbenoxolone sodium and berberine hydrochloride in wei kang tablets by reversed-phase high performance liquid chromatography(RP-HPLC)]. Se Pu. 2002 Jul;20(4):350-2. Chinese. PubMed PMID: 12541921.

6: Suzuki S, Matsuda Y, Sugawara T, Tabata T, Ishibashi H, Hoshikawa Y, Kubo H, Kondo T. Effects of carbenoxolone on alveolar fluid clearance and lung inflammation in the rat. Crit Care Med. 2004 Sep;32(9):1910-5. PubMed PMID: 15343021.

7: de Groot JR, Veenstra T, Verkerk AO, Wilders R, Smits JP, Wilms-Schopman FJ, Wiegerinck RF, Bourier J, Belterman CN, Coronel R, Verheijck EE. Conduction slowing by the gap junctional uncoupler carbenoxolone. Cardiovasc Res. 2003 Nov 1;60(2):288-97. PubMed PMID: 14613858.

8: Al-Bader MD, Jasem SA, Kilarkaje N. Carbenoxolone exposure during late gestation in rats alters placental expressions of p53 and estrogen receptors. Eur J Pharmacol. 2016 Nov 15;791:675-685. doi: 10.1016/j.ejphar.2016.09.035. Epub 2016 Sep 28. PubMed PMID: 27693517.

9: Chaytor AT, Marsh WL, Hutcheson IR, Griffith TM. Comparison of glycyrrhetinic acid isoforms and carbenoxolone as inhibitors of EDHF-type relaxations mediated via gap junctions. Endothelium. 2000;7(4):265-78. PubMed PMID: 11201524.

10: Kim J, Jung EJ, Moon SS, Seo M. Protective effect of carbenoxolone on ER stress-induced cell death in hypothalamic neurons. Biochem Biophys Res Commun. 2015 Dec 25;468(4):793-9. doi: 10.1016/j.bbrc.2015.11.034. Epub 2015 Nov 11. PubMed PMID: 26577412.

11: Sewell KJ, Shirley DG, Michael AE, Thompson A, Norgate DP, Unwin RJ. Inhibition of renal 11beta-hydroxysteroid dehydrogenase in vivo by carbenoxolone in the rat and its relationship to sodium excretion. Clin Sci (Lond). 1998 Oct;95(4):435-43. PubMed PMID: 9748419.

12: Azarashvili T, Baburina Y, Grachev D, Krestinina O, Papadopoulos V, Lemasters JJ, Odinokova I, Reiser G. Carbenoxolone induces permeability transition pore opening in rat mitochondria via the translocator protein TSPO and connexin43. Arch Biochem Biophys. 2014 Sep 15;558:87-94. doi: 10.1016/j.abb.2014.06.027. Epub 2014 Jul 1. PubMed PMID: 24995971; PubMed Central PMCID: PMC4547858.

13: Luo L, Deng J, Wang DX, He J, Deng W. Regulation of epithelial sodium channel expression by oestradiol and progestogen in alveolar epithelial cells. Respir Physiol Neurobiol. 2015 Sep 15;216:52-62. doi: 10.1016/j.resp.2015.06.001. Epub 2015 Jun 4. PubMed PMID: 26051998.

14: Brem AS, Matheson KL, Morris DJ. Effect of carbenoxolone sodium on steroid-induced sodium transport in the toad bladder: further studies. J Steroid Biochem Mol Biol. 1992 Sep;42(8):911-4. PubMed PMID: 1525050.

15: Franco-Pérez J, Ballesteros-Zebadúa P, Manjarrez-Marmolejo J. Unilateral microinjection of carbenoxolone into the pontis caudalis nucleus inhibits the pentylenetetrazole-induced epileptiform activity in rats. Neurosci Lett. 2015 Aug 18;602:38-43. doi: 10.1016/j.neulet.2015.06.037. Epub 2015 Jun 30. PubMed PMID: 26141611.

16: Xu Q, Cheong YK, Yang F, Tiwari V, Li J, Liu J, Raja SN, Li W, Guan Y. Intrathecal carbenoxolone inhibits neuropathic pain and spinal wide-dynamic range neuronal activity in rats after an L5 spinal nerve injury. Neurosci Lett. 2014 Mar 20;563:45-50. doi: 10.1016/j.neulet.2014.01.042. Epub 2014 Jan 31. PubMed PMID: 24486838; PubMed Central PMCID: PMC3962020.

17: Moustafa YM, El-Azab MF, Fouda A. 15-PGDH inhibitors: the antiulcer effects of carbenoxolone, pioglitazone and verapamil in indomethacin induced peptic ulcer rats. Eur Rev Med Pharmacol Sci. 2013;17(15):2000-9. PubMed PMID: 23884819.

18: Yulyana Y, Tovmasyan A, Ho IA, Sia KC, Newman JP, Ng WH, Guo CM, Hui KM, Batinic-Haberle I, Lam PY. Redox-Active Mn Porphyrin-based Potent SOD Mimic, MnTnBuOE-2-PyP(5+), Enhances Carbenoxolone-Mediated TRAIL-Induced Apoptosis in Glioblastoma Multiforme. Stem Cell Rev. 2016 Feb;12(1):140-55. doi: 10.1007/s12015-015-9628-2. PubMed PMID: 26454429; PubMed Central PMCID: PMC4926165.

19: Rhee SD, Kim CH, Park JS, Jung WH, Park SB, Kim HY, Bae GH, Kim TJ, Kim KY. Carbenoxolone prevents the development of fatty liver in C57BL/6-Lep ob/ob mice via the inhibition of sterol regulatory element binding protein-1c activity and apoptosis. Eur J Pharmacol. 2012 Sep 15;691(1-3):9-18. doi: 10.1016/j.ejphar.2012.06.021. Epub 2012 Jun 26. PubMed PMID: 22742899.

20: Ventura-Mejía C, Medina-Ceja L. Decreased fast ripples in the hippocampus of rats with spontaneous recurrent seizures treated with carbenoxolone and quinine. Biomed Res Int. 2014;2014:282490. doi: 10.1155/2014/282490. Epub 2014 Sep 3. PubMed PMID: 25276773; PubMed Central PMCID: PMC4168142.