Carbenoxolone

{{Short description|Chemical compound}}

{{Drugbox

| Verifiedfields = changed

| verifiedrevid = 460017787

| 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

| image = Carbenoxolone.png

| alt = Skeletal formula of carbenoxolone

| width = 270

| image2 = Carbenoxolone 3D ball.png

| alt2 = Ball-and-stick model of the carbenoxolone molecule

| tradename =

| Drugs.com = {{drugs.com|international|carbenoxolone}}

| pregnancy_category =

| legal_status =

| routes_of_administration =

| bioavailability =

| protein_bound =

| metabolism =

| elimination_half-life =

| IUPHAR_ligand = 4151

| CAS_number_Ref = {{cascite|correct|CAS}}

| 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

| C=34 | H=50 | O=7

| 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

| 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 (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.{{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}}

Carbenoxolone reversibly inhibits the conversion of inactive cortisone to cortisol by blocking 11β-hydroxysteroid dehydrogenase (11β-HSD). 11β-HSD also reversibly catalyzes the conversion of 7-ketocholesterol to 7-beta-hydroxycholesterol.{{Cite web|url = https://pubchem.ncbi.nlm.nih.gov/compound/46936354?from=summary#section=DrugBank-Interactions|title = PubChem Compound}}{{Cite web|url = https://www.sigmaaldrich.com/content/dam/sigma-aldrich/docs/Aldrich/Product_Information_Sheet/c4790pis.pdf|title = Sigma-Aldrich}}

Carbenoxolone is a modestly potent, reasonably effective, water-soluble blocker of gap junctions.{{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}}

Carbenoxolone has also been used in topical creams such as Carbosan gel, marketed for treatment of lip sores and mouth ulcers.