| Revision as of 20:03, 10 November 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,074 edits Script assisted update of identifiers for the Chem/Drugbox validation project (updated: 'DrugBank', 'CAS_number').← Previous edit |
Latest revision as of 00:22, 1 March 2023 edit undoGraeme Bartlett (talk | contribs)Administrators250,201 edits removed Category:Carboxylic acids; added Category:Dicarboxylic acids using HotCat |
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{{Short description|Chemical compound}} |
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{{Drugbox |
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{{Drugbox |
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| Verifiedfields = changed |
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| Verifiedfields = changed |
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| verifiedrevid = 399705134 |
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| verifiedrevid = 460017787 |
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| IUPAC_name = (3β)-3--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 |
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| IUPAC_name = (3β)-3--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 |
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| image = Carbenoxolone.png |
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| image = Carbenoxolone.png |
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| alt = Skeletal formula of carbenoxolone |
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| width = 270 |
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| image2 = Carbenoxolone 3D ball.png |
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| alt2 = Ball-and-stick model of the carbenoxolone molecule |
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<!--Clinical data--> |
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<!--Clinical data--> |
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| tradename = |
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| tradename = |
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| pregnancy_category = |
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| pregnancy_category = |
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| legal_status = |
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| legal_status = |
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| routes_of_administration = |
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| routes_of_administration = |
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<!--Pharmacokinetic data--> |
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<!--Pharmacokinetic data--> |
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| protein_bound = |
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| protein_bound = |
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| metabolism = |
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| metabolism = |
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| elimination_half-life = |
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| elimination_half-life = |
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<!--Identifiers--> |
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<!--Identifiers--> |
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| CAS_number_Ref = {{cascite|correct|??}} |
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| IUPHAR_ligand = 4151 |
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| CAS_number_Ref = {{cascite|correct|CAS}} |
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| CAS_number = <!-- blanked - oldvalue: 5697-56-3 --> |
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| CAS_number = 5697-56-3 |
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| ATC_prefix = A02 |
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| ATC_prefix = A02 |
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| ATC_suffix = BX01 |
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| ATC_suffix = BX01 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 552190 |
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| ChemSpiderID = 552190 |
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| UNII_Ref = {{fdacite|changed|FDA}} |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = MM6384NG73 |
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| UNII = MM6384NG73 |
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| ChEMBL_Ref = {{ebicite|changed|EBI}} |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| ChEMBL = 499915 |
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| ChEMBL = 499915 |
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<!--Chemical data--> |
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<!--Chemical data--> |
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| C=34 | H=50 | O=7 |
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| C=34 | H=50 | O=7 |
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| molecular_weight = 570.765 g/mol |
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| smiles = O=C(O)CCC(=O)O4CC3(5C(=O)/C=C2/1C(C(=O)O)(C)CC1(C)CC2(5(CC3C4(C)C)C)C)C |
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| smiles = O=C(O)CCC(=O)O4CC3(5C(=O)/C=C2/1C(C(=O)O)(C)CC1(C)CC2(5(CC3C4(C)C)C)C)C |
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| 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 |
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| InChIKey = OBZHEBDUNPOCJG-WBXJDKIVBR |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| 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 |
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| 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 |
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}} |
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'''Carbenoxolone '''('''CBX''') is a ] derivative with a steroid-like structure, similar to substances found in the root of the ]. Carbenoxolone is used for the treatment of peptic, esophageal and oral ]ation and inflammation. Electrolyte imbalance is a serious side effect of carbenoxolone when used systemically.<ref>{{Cite journal|title = Tales of a Dirty Drug: Carbenoxolone, Gap Junctions, and Seizures | pmc=3316363 | pmid=22473546 | doi=10.5698/1535-7511-12.2.66 | volume=12 | issue=2 | year=2012 | journal=Epilepsy Curr | pages=66–8 | vauthors=Connors BW}}</ref> |
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'''Carbenoxolone''', a synthetic derivative of ], is a licensed drug (in the ]) for ] ulceration and inflammation. Other uses include treatment of oral and perioral lesions. |
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Carbenoxolone reversibly inhibits the conversion of inactive ] to ] by blocking ] (11β-HSD). 11β-HSD also reversibly catalyzes the conversion of 7-ketocholesterol to 7-beta-hydroxycholesterol.<ref>{{Cite web|url = https://pubchem.ncbi.nlm.nih.gov/compound/46936354?from=summary#section=DrugBank-Interactions|title = PubChem Compound}}</ref><ref>{{Cite web|url = https://www.sigmaaldrich.com/content/dam/sigma-aldrich/docs/Aldrich/Product_Information_Sheet/c4790pis.pdf|title = Sigma-Aldrich}}</ref> |
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Carbenoxolone (aka Carbenoxolone, CBX) is also used as a blocker of the enzyme ] (11β-HSD), of pannexon membrane channels (comprising 6 subunits of ]) and the related innexon channels (consisting of invertebrate ]), and at higher concentrations, as a blocker of ] channels ("hemichannels" made up of 6 ] subunits each) and of ] (2 connexons joined together). |
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Carbenoxolone is a modestly potent, reasonably effective, water-soluble blocker of ].<ref>{{Cite journal|title = Tales of a Dirty Drug: Carbenoxolone, Gap Junctions, and Seizures | pmc=3316363 | pmid=22473546 | doi=10.5698/1535-7511-12.2.66 | volume=12 | issue=2 | year=2012 | journal=Epilepsy Curr | pages=66–8 | vauthors=Connors BW}}</ref> |
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Carbenoxolone has also been used in topical creams such as Carbosan gel, marketed for treatment of lip sores and mouth ulcers. |
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==Nootropic effects== |
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==Nootropic effects== |
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Carbenoxolone has also been investigated for ] 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> |
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Carbenoxolone has also been investigated for ] effects.<ref name="pmid15071189">{{cite journal |vauthors=Sandeep TC, Yau JL, MacLullich AM |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 |pmc=404114|display-authors=etal|doi-access=free }}</ref> This research started from an observation that long-term exposure to ]s may have negative effects on cognition. Carbenoxolone may decrease the amount of active glucocorticoid in the brain, because the drug inhibits 11β-HSD, an enzyme which regenerates ], an active glucocorticoid, from inactive ]. |
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This research started from an observation that long-term exposure to ]s may have negative effects on cognition. Carbenoxolone may decrease the amount of active glucocortocoid in the brain, because the drug inhibits ], an enzyme which activates ] from ], 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, ] ] was co-administered with carbenoxolone, since carbenoxolone used by itself may cause ] by increasing cortisol in the kidneys. |
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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, ] ] was co-administered with carbenoxolone, since carbenoxolone used by itself may cause ] by increasing cortisol in the kidneys. |
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==See also== |
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* ] |
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==References== |
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==References== |
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{{reflist}} |
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{{Reflist}} |
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{{Drugs for peptic ulcer and GORD}} |
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{{Drugs for peptic ulcer and GORD}} |
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{{Corticosteroids}} |
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{{Psychostimulants, agents used for ADHD and nootropics}} |
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{{Glucocorticoidics}} |
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