Carbenoxolone: Difference between revisions

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Carbenoxolone
Clinical data
AHFS/Drugs.com	International Drug Names
ATC code	A02BX01 (WHO) ;
Identifiers
	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;
CAS Number	5697-56-3 ;
PubChem CID	636403;
DrugBank	DB02329 ;
ChemSpider	552190 ;
UNII	MM6384NG73;
ChEMBL	ChEMBL499915 ;
E number	{{#property:P628}}
ECHA InfoCard	{{#property:P2566}}Lua error in Module:EditAtWikidata at line 36: attempt to index field 'wikibase' (a nil value).
Chemical and physical data
Formula	C34H50O7
Molar mass	570.765 g/mol
3D model (JSmol)	Interactive image;
	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 ;
(what is this?) (verify)

VisualWikitext

Revision as of 14:50, 10 April 2015

Editor-In-Chief: C. Michael Gibson, M.S., M.D. [1]

Overview

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.

Template:Drugs for peptic ulcer and GORD Template:Nootropics Template:Corticosteroidics

[1] "Tales of a Dirty Drug: Carbenoxolone, Gap Junctions, and Seizures".

[2] "PubChem Compound".

[3] "Sigma-Aldrich" (PDF).

[4] "Tales of a Dirty Drug: Carbenoxolone, Gap Junctions, and Seizures".

[pmid15071189-5] 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.

[1]

[2]

[3]

[4]

[5]

@@ Line 1: / Line 1: @@
-{{drugbox
+{{Drugbox
- | IUPAC_name = Carbenoxolone
+| Verifiedfields = changed
-  | image = carb1.png
+| verifiedrevid = 460017787
-  | CAS_number = 5697-56-3
+| IUPAC_name = (3β)-3-[(3-carboxypropanoyl)oxy]-11-oxoolean-12-en-30-oic acid<br>OR<br>(2''S'',4a''S'',6a''S'',6b''R'',8a''R'',10''S'',12a''S'',12b''R'',14b''R'')-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
- | ATC_prefix = A02
+| image =Carbenoxolone.png
- | ATC_suffix = BX01
+| alt = Skeletal formula of carbenoxolone
- | ATC_supplemental =
+| width = 270
- | PubChem = 636403
+| image2 =Carbenoxolone 3D ball.png
- | DrugBank = EXPT00848
+| alt2 = Ball-and-stick model of the carbenoxolone molecule
- | C=34 | H=50 | O=7
+<!--Clinical data-->
- | molecular_weight = 570.765 g/mol
+| tradename =
- | bioavailability =
+| Drugs.com = {{drugs.com|international|carbenoxolone}}
- | protein_bound =
+| pregnancy_category =
- | metabolism =
+| legal_status =
- | elimination_half-life =
+| routes_of_administration =
- | pregnancy_category =
- | legal_status =
+<!--Pharmacokinetic data-->
- | routes_of_administration =
+| bioavailability =
+| protein_bound =
+| metabolism =
+| elimination_half-life =
+<!--Identifiers-->
+| CAS_number_Ref = {{cascite|changed|??}}
+| CAS_number = 5697-56-3
+| ATC_prefix = A02
+| ATC_suffix = BX01
+| ATC_supplemental =
+| PubChem = 636403
+| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
+| DrugBank = DB02329
+| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
+| ChemSpiderID = 552190
+| UNII_Ref = {{fdacite|correct|FDA}}
+| UNII = MM6384NG73
+| ChEMBL_Ref = {{ebicite|correct|EBI}}
+| ChEMBL = 499915
+<!--Chemical data-->
+| C=34 | H=50 | O=7
+| molecular_weight = 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 = 1/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
+| InChIKey = OBZHEBDUNPOCJG-WBXJDKIVBR
+| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
+| StdInChI = 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
+| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
+| StdInChIKey = OBZHEBDUNPOCJG-WBXJDKIVSA-N
 }}
-'''Carbenoxolone''', a synthetic derivative of [[Glycyrrhizin|glycyrrhizinic]] acid, is a licensed drug (in the [[United Kingdom|UK]]) for [[Esophagus|oesophageal]] ulceration and inflammation. Other uses include treatment of oral and perioral lesions.
+__NOtoc__
+{{SI}}
+{{CMG}}
+==Overview==
+'''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 [[Ulcer|ulceration]] and inflammation. Electrolyte imbalance is a serious side effect of carbenoxolone when used systemically.<ref>{{Cite web|url = http://www.ncbi.nlm.nih.gov/pmc/articles/PMC3316363/|title = Tales of a Dirty Drug: Carbenoxolone, Gap Junctions, and Seizures|date = |accessdate = |website = |publisher = |last = |first = }}</ref>
+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. <ref>{{Cite web|url = http://pubchem.ncbi.nlm.nih.gov/compound/46936354?from=summary#section=DrugBank-Interactions|title = PubChem Compound|date = |accessdate = |website = |publisher = |last = |first = }}</ref><ref>{{Cite web|url = https://www.sigmaaldrich.com/content/dam/sigma-aldrich/docs/Aldrich/Product_Information_Sheet/c4790pis.pdf|title = Sigma-Aldrich|date = |accessdate = |website = |publisher = |last = |first = }}</ref>
+Carbenoxolone is a modestly potent, reasonably effective, water-soluble blocker of [[gap junctions]].<ref>{{Cite web|url = http://www.ncbi.nlm.nih.gov/pmc/articles/PMC3316363/|title = Tales of a Dirty Drug: Carbenoxolone, Gap Junctions, and Seizures|date = |accessdate = |website = |publisher = |last = |first = }}</ref>
+==Nootropic effects==
+Carbenoxolone has also been investigated for [[nootropic]] effects.<ref name="pmid15071189">{{cite journal |author=Sandeep TC, Yau JL, MacLullich AM, ''et al.'' |title=11Beta-hydroxysteroid dehydrogenase inhibition improves cognitive function in healthy elderly men and type 2 diabetics |journal=Proc. Natl. Acad. Sci. U.S.A. |volume=101 |issue=17 |pages=6734–9 |year=2004 |pmid=15071189 |doi=10.1073/pnas.0306996101 |url=http://www.pnas.org/cgi/pmidlookup?view=long&pmid=15071189 |pmc=404114}}</ref> This research started from an observation that long-term exposure to [[glucocorticoid]]s 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==
+{{Reflist|2}}
-Carbenoxolone (aka Carbenoxylone, CBX) is also finding increasing use as a [[Connexon]] (a hemichannel made up of 6 connexin subunits) blocker and as a [[Gap Junction]] (2 connexons join together) blocker.
-Carbenoxolone has also been investigated for [[nootropic]] effects (PMID 15071189).  This research started from an observation that long-term exposure to [[glucocorticoid]]s may have negative effects on cognition.  Carbenoxolone may decrease the amount of active glucocortocoid in the brain, because the drug inhibits [[11Beta-hydroxysteroid dehydrogenase type 1]], an enzyme which activates [[cortisol]] into [[cortisone]], a glucocorticoid.  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, it should be noted that [[potassium-sparing diuretic]] [[amiloride]] was co-administered with carbenoxolone, since carbenoxolone used by itself may cause [[hypertension]] by increasing cortisol in the kidneys.
 {{Drugs for peptic ulcer and GORD}}
-[[Category:Gastrointestinal system drugs]]
+{{Nootropics}}
+{{Corticosteroidics}}
+[[Category:Drugs acting on the gastrointestinal system and metabolism]]
 [[Category:Nootropics]]
-[[Category:Terpenes and terpenoids]]
+[[Category:Carboxylate esters]]
+[[Category:Ketones]]
-[[nl:Carbenoxolon]]
+[[Category:Triterpenes]]
-{{WikiDoc Help Menu}}
+[[Category:Drug]]
+[[Category:11β-HSD inhibitors]]

Carbenoxolone: Difference between revisions

Revision as of 14:50, 10 April 2015

Overview

Nootropic effects

References

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