Carbenoxolone

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 Y
PubChem CID	636403
IUPHAR/BPS	4151
DrugBank	DB02329 Y
ChemSpider	552190 Y
UNII	MM6384NG73
ChEMBL	ChEMBL499915 Y
CompTox Dashboard (EPA)	DTXSID4022733
ECHA InfoCard	100.024.704
Chemical and physical data
Formula	C34H50O7
Molar mass	570.767 g·mol−1
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 Y Key:OBZHEBDUNPOCJG-WBXJDKIVSA-N Y
NY (what is this?)  (verify)

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 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.^[2][3]

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

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