Carbenoxolone | CAS#5697-56-3 | glycyrrhetinic acid derivative | 11β-HSD inhibitor

MedKoo Cat#: 540059 | Name: Carbenoxolone

Description:

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

Carbenoxolone is a glycyrrhetinic acid derivative and inhibitor of 11β-HSD inhibitor and gap junction connexin channels. It displays a wide variety of biological properties, including decreasing infarction size in cerebral ischemia models, decreasing production of IL-23 and Th17 cells, inhibiting marcrophage migration into atria, and preventing development of fatty liver disease.

Chemical Structure

Carbenoxolone

CAS#5697-56-3 (free acid)

Theoretical Analysis

MedKoo Cat#: 540059

Name: Carbenoxolone

CAS#: 5697-56-3 (free acid)

Chemical Formula: C34H50O7

Exact Mass: 570.3557

Molecular Weight: 570.77

Elemental Analysis: C, 71.55; H, 8.83; O, 19.62

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.

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Related CAS #

5697-56-3 (free acid) 7421-40-1 (sodium)

Synonym

Biogastrone; Bioral; Carbenoxolona; Carbenoxolone

IUPAC/Chemical Name

(2S,4aS,6aS,6bR,8aR,10S,12aS,12bR,14bR)-10-((3-carboxypropanoyl)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-carboxylic acid

InChi Key

OBZHEBDUNPOCJG-WBXJDKIVSA-N

InChi Code

InChI=1S/C34H50O7/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)/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)(C[C@]2(C1=C3)[H])C(O)=O)C)C)4C)5[H])[C@@H](OC(CCC(O)=O)=O)CC[C@]5(C)[C@@]4([H])C3=O

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

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 570.77 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

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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. 5: 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. 6: 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. 7: 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. 8: 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. 9: 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. 10: 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. 11: Sefil F, Bagirici F, Acar MD, Marangoz C. Influence of carbenoxolone on the anticonvulsant efficacy of phenytoin in pentylenetetrazole kindled rats. Acta Neurobiol Exp (Wars). 2012;72(2):177-84. PubMed PMID: 22810219. 12: Dhanesha N, Joharapurkar A, Shah G, Kshirsagar S, Dhote V, Sharma A, Jain M. Inhibition of 11β-hydroxysteroid dehydrogenase 1 by carbenoxolone affects glucose homeostasis and obesity in db/db mice. Clin Exp Pharmacol Physiol. 2012 Jan;39(1):69-77. doi: 10.1111/j.1440-1681.2011.05640.x. PubMed PMID: 22060140. 13: Miura M, Nagano T, Murai N, Taguchi Y, Handoh T, Satoh M, Miyata S, Miller L, Shindoh C, Stuyvers BD. Effect of Carbenoxolone on Arrhythmogenesis in Rat Ventricular Muscle. Circ J. 2016;80(1):76-84. doi: 10.1253/circj.CJ-15-0401. Epub 2015 Oct 26. PubMed PMID: 26497571. 14: Chávez-Piña AE, Tapia-Álvarez GR, Reyes-Ramínrez A, Navarrete A. Carbenoxolone gastroprotective mechanism: participation of nitric oxide/(c) GMP/K(ATP) pathway in ethanol-induced gastric injury in the rat. Fundam Clin Pharmacol. 2011 Dec;25(6):717-22. doi: 10.1111/j.1472-8206.2010.00897.x. Epub 2010 Nov 24. PubMed PMID: 21105909. 15: Teshima T, Matsumoto H, Okusa T, Nakamura Y, Koyama H. Effects of Carbenoxolone on the Canine Pituitary-Adrenal Axis. PLoS One. 2015 Aug 11;10(8):e0135516. doi: 10.1371/journal.pone.0135516. eCollection 2015. PubMed PMID: 26262685; PubMed Central PMCID: PMC4532459. 16: Diao H, Xiao S, Howerth EW, Zhao F, Li R, Ard MB, Ye X. Broad gap junction blocker carbenoxolone disrupts uterine preparation for embryo implantation in mice. Biol Reprod. 2013 Aug 15;89(2):31. doi: 10.1095/biolreprod.113.110106. Print 2013 Aug. PubMed PMID: 23843229; PubMed Central PMCID: PMC4076363. 17: Wang H, Cao Y, Chiang CY, Dostrovsky JO, Sessle BJ. The gap junction blocker carbenoxolone attenuates nociceptive behavior and medullary dorsal horn central sensitization induced by partial infraorbital nerve transection in rats. Pain. 2014 Feb;155(2):429-35. doi: 10.1016/j.pain.2013.11.004. Epub 2013 Nov 14. PubMed PMID: 24239671; PubMed Central PMCID: PMC3901535. 18: Bramley JR, Wiles EM, Sollars PJ, Pickard GE. Carbenoxolone blocks the light-evoked rise in intracellular calcium in isolated melanopsin ganglion cell photoreceptors. PLoS One. 2011;6(7):e22721. doi: 10.1371/journal.pone.0022721. Epub 2011 Jul 29. PubMed PMID: 21829491; PubMed Central PMCID: PMC3146487. 19: Michalski K, Kawate T. Carbenoxolone inhibits Pannexin1 channels through interactions in the first extracellular loop. J Gen Physiol. 2016 Feb;147(2):165-74. doi: 10.1085/jgp.201511505. Epub 2016 Jan 11. PubMed PMID: 26755773; PubMed Central PMCID: PMC4727946. 20: Thakur P, Nehru B. Inhibition of neuroinflammation and mitochondrial dysfunctions by carbenoxolone in the rotenone model of Parkinson's disease. Mol Neurobiol. 2015 Feb;51(1):209-19. doi: 10.1007/s12035-014-8769-7. Epub 2014 Jun 20. PubMed PMID: 24946750.