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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2015/10/14 23:45:58」(JST)

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Carbenoxolone (CBX) is a glycyrrhetinic acid derivative with a steroid-like structure, similar to substances found in the root of the licorice plant. Carbenoxolone is used for the treatment of peptic, esophageal and oral ulceration and inflammation. Electrolyte imbalance is a serious side effect of carbenoxolone when used systemically.^[1]

Carbenoxolone reversibly inhibits the conversion of cortisol to the inactive metabolite cortisone by blocking 11β-hydroxysteroid dehydrogenase (11β-HSD). 11β-HSD also reversibly catalyzes the conversion of 7-ketocholesterol to 7-beta-hydroxycholesterol. ^[2]^[3]

Carbenoxolone is a modestly potent, reasonably effective, water-soluble blocker of gap junctions.^[4]

Nootropic effects

Carbenoxolone has also been investigated for nootropic effects.^[5] This research started from an observation that long-term exposure to glucocorticoids may have negative effects on cognition. Carbenoxolone may decrease the amount of active glucocortocoid in the brain, because the drug inhibits 11β-HSD, an enzyme which regenerates cortisol, an active glucocorticoid, from inactive cortisone.

In the research trial investigating this use of carbenoloxone, it was shown that the drug improved verbal fluency in elderly healthy men (aged 55–75). In type 2 diabetics aged 52–70, the drug improved verbal memory. However, potassium-sparing diuretic amiloride was co-administered with carbenoxolone, since carbenoxolone used by itself may cause hypertension by increasing cortisol in the kidneys.

References

^ "Tales of a Dirty Drug: Carbenoxolone, Gap Junctions, and Seizures".
^ "PubChem Compound".
^ "Sigma-Aldrich" (PDF).
^ "Tales of a Dirty Drug: Carbenoxolone, Gap Junctions, and Seizures".
^ Sandeep TC, Yau JL, MacLullich AM; et al. (2004). "11Beta-hydroxysteroid dehydrogenase inhibition improves cognitive function in healthy elderly men and type 2 diabetics". Proc. Natl. Acad. Sci. U.S.A. 101 (17): 6734–9. doi:10.1073/pnas.0306996101. PMC 404114. PMID 15071189.

UpToDate Contents

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1. 見かけの鉱質コルチコイド過剰（AME）症候群（長期甘草摂取を含む） apparent mineralocorticoid excess syndromes including chronic licorice ingestion
2. 腎集合管ナトリウムチャンネルの遺伝的障害：リドル症候群および偽性低アルドステロン症1型 genetic disorders of the collecting tubule sodium channel liddles syndrome and pseudohypoaldosteronism type 1
3. 低アルドステロン症（4型RTA）の病因、診断、および治療 etiology diagnosis and treatment of hypoaldosteronism type 4 rta

English Journal

ZO-1 expression shows prognostic value in chronic B cell leukemia.

Nesmiyanov PP1, Tolkachev BE2, Strygin AV3.
Immunobiology.Immunobiology.2016 Jan;221(1):6-11. doi: 10.1016/j.imbio.2015.08.008. Epub 2015 Aug 17.
Connexin-mediated gap junctions are vital for tumor cell function. Intracellular pathways of connexin signaling use Zonula Occludens protein-1 (ZO-1) as an intermediate. This report describes the ZO-1 and connexin 43 (Cx43) expression pattern in lymphocytes from chronic B-cell leukemia (B-CLL) patie
PMID 26306999

EGF-Induced Connexin43 Negatively Regulates Cell Proliferation in Human Ovarian Cancer.

Qiu X1, Cheng JC1, Klausen C1, Chang HM1, Fan Q1, Leung PC1.
Journal of cellular physiology.J Cell Physiol.2016 Jan;231(1):111-9. doi: 10.1002/jcp.25058.
Connexin43 (Cx43) has been shown to regulate cell proliferation and its downregulation is correlated with poor prognosis and survival in several types of human cancer. Cx43 expression levels are frequently downregulated in human ovarian cancer, suggesting a potential role for Cx43 in regulating the
PMID 26031779

Protective effect of Carbenoxolone on ER stress-induced cell death in hypothalamic neurons.

Kim J1, Jung EJ2, Moon SS3, Seo M4.
Biochemical and biophysical research communications.Biochem Biophys Res Commun.2015 Nov 11. pii: S0006-291X(15)30904-9. doi: 10.1016/j.bbrc.2015.11.034. [Epub ahead of print]
Hypothalamic endoplasmic reticulum (ER) stress is known to be increased in obesity. Induction of ER stress on hypothalamic neurons has been reported to cause hypothalamic neuronal apoptosis and malfunction of energy balance, leading to obesity. Carbenoxolone is an 11β-hydroxysteroid dehydrogenase t
PMID 26577412

Japanese Journal

Extracellular ATP Evokes Infiltration of Macrophage in Stretched Atrium

Sasano Tetsuo,Oishi Sakiko,Tamura Noriko,Isobe Mitsuaki,Furukawa Tetsushi
Journal of Arrhythmia 27(Supplement), SY11_3-SY11_3, 2011
… Murine macrophages were co-cultured with mechanically stretched HL-1 dells using modified Boyden chamber, with or without drugs including carbenoxolone (CBX, a gap junction channel blocker), apyrase, and pyridoxalphosphate-6-azophenyl-2′,4′-disulphonic acid (PPADS). …
NAID 130002130386

Inhibition of 11.BETA.-Hydroxysteroid Dehydrogenase Improves Glucose Metabolism in Insulin Resistant Otsuka Long-Evans Tokushima Fatty Rats

Kim Dong-Sun,Park Yoo-Sin,Kim Shin-Hee,Kim Young-Hoon,Jhee Ok-Hwa,Lee Seong-Jin,Kim Tae-Wha,Kang Ju-Seop
JOURNAL OF HEALTH SCIENCE 57(4), 378-383, 2011
… The present study was examined whether inhibition of 11β-HSD-1 by carbenoxolone (CBX), a non-selective 11β-HSD inhibitor, improved carbohydrate metabolism in insulin resistant Otsuka Long-Evans Tokushima Fatty (OLETF) rats or not. …
NAID 130001001084

Related Pictures

★リンクテーブル★

リンク元	「カルベノキソロン」
拡張検索	「carbenoxolone sodium」

「カルベノキソロン」

Carbenoxolone
Systematic (IUPAC) name
	(3β)-3-[(3-carboxypropanoyl)oxy]-11-oxoolean-12-en-30-oic acid; OR; (2S,4aS,6aS,6bR,8aR,10S,12aS,12bR,14bR)-10-(3-carboxypropanoyloxy)-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
Clinical data
AHFS/Drugs.com	International Drug Names
Identifiers
CAS Registry Number	5697-56-3
ATC code	A02BX01
PubChem	CID: 636403
IUPHAR/BPS	4151
DrugBank	DB02329
ChemSpider	552190
UNII	MM6384NG73
ChEMBL	CHEMBL499915
Chemical data
Formula	C34H50O7
Molecular mass	570.765 g/mol
	SMILES O=C(O)CCC(=O)O[C@H]4CC[C@@]3([C@H]5C(=O)/C=C2/[C@@H]1C[C@](C(=O)O)(C)CC[C@]1(C)CC[C@]2([C@@]5(CC[C@H]3C4(C)C)C)C)C ;
	InChI 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 ; Key:OBZHEBDUNPOCJG-WBXJDKIVSA-N ;
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