Identification

Name
Carbenoxolone
Accession Number
DB02329  (EXPT00848)
Type
Small Molecule
Groups
Experimental
Description

An agent derived from licorice root. It is used for the treatment of digestive tract ulcers, especially in the stomach. Antidiuretic side effects are frequent, but otherwise the drug is low in toxicity. [PubChem]

Structure
Thumb
Synonyms
  • Carbenoxolona
Product Ingredients
IngredientUNIICASInChI Key
Carbenoxolone disodiumF1MP7242Z57421-40-1BQENDLAVTKRQMS-SBBGFIFASA-L
International/Other Brands
Carbelone (Royal) / Carbosan (Rowa) / Carboxe (Shiteh Organic) / Copu (Winston) / Herpesan (Rowa) / Rösch & Handel (Rowa) / Rowadermat (Rösch & Handel) / Rowagel (Rowa) / Sanodin (Ern)
Categories
UNII
MM6384NG73
CAS number
5697-56-3
Weight
Average: 570.7566
Monoisotopic: 570.355653954
Chemical Formula
C34H50O7
InChI Key
OBZHEBDUNPOCJG-WBXJDKIVSA-N
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
IUPAC Name
(2S,4aS,6aS,6bR,8aR,10S,12aS,12bR,14bR)-10-[(3-carboxypropanoyl)oxy]-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
SMILES
[H][C@@]1(CC[C@@]2(C)[C@@]([H])(CC[C@]3(C)[C@]2([H])C(=O)C=C2[C@]4([H])C[C@](C)(CC[C@]4(C)CC[C@@]32C)C(O)=O)C1(C)C)OC(=O)CCC(O)=O

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
U3-alpha-(or 20-beta)-hydroxysteroid dehydrogenaseNot AvailableStreptomyces exfoliatus
UCorticosteroid 11-beta-dehydrogenase isozyme 1
inhibitor
Human
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

Synthesis Reference

Gottfried, S. and Baxendale, L.; U.S. Patent 3,070,623; December 25,1962; assigned to Biorex Laboratories Limited, England.

General References
  1. Sandeep TC, Yau JL, MacLullich AM, Noble J, Deary IJ, Walker BR, Seckl JR: 11Beta-hydroxysteroid dehydrogenase inhibition improves cognitive function in healthy elderly men and type 2 diabetics. Proc Natl Acad Sci U S A. 2004 Apr 27;101(17):6734-9. Epub 2004 Apr 7. [PubMed:15071189]
External Links
PubChem Compound
636403
PubChem Substance
46508820
ChemSpider
552190
BindingDB
50247012
ChEMBL
CHEMBL499915
Therapeutic Targets Database
DNC000388
HET
CBO
Wikipedia
Carbenoxolone
ATC Codes
A02BX71 — Carbenoxolone, combinations with psycholepticsA02BX51 — Carbenoxolone, combinations excl. psycholepticsA02BX01 — Carbenoxolone
PDB Entries
1hdc / 2bel

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)292.5 °CPhysProp
Predicted Properties
PropertyValueSource
Water Solubility0.000738 mg/mLALOGPS
logP5.46ALOGPS
logP6.3ChemAxon
logS-5.9ALOGPS
pKa (Strongest Acidic)4.04ChemAxon
pKa (Strongest Basic)-5.1ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area117.97 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity154.31 m3·mol-1ChemAxon
Polarizability64.99 Å3ChemAxon
Number of Rings5ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9612
Blood Brain Barrier+0.809
Caco-2 permeable-0.5933
P-glycoprotein substrateSubstrate0.83
P-glycoprotein inhibitor INon-inhibitor0.7249
P-glycoprotein inhibitor IIInhibitor0.8388
Renal organic cation transporterNon-inhibitor0.8358
CYP450 2C9 substrateNon-substrate0.8343
CYP450 2D6 substrateNon-substrate0.9271
CYP450 3A4 substrateSubstrate0.7984
CYP450 1A2 substrateNon-inhibitor0.9145
CYP450 2C9 inhibitorNon-inhibitor0.8921
CYP450 2D6 inhibitorNon-inhibitor0.9482
CYP450 2C19 inhibitorNon-inhibitor0.9274
CYP450 3A4 inhibitorNon-inhibitor0.6959
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8713
Ames testNon AMES toxic0.821
CarcinogenicityNon-carcinogens0.9485
BiodegradationNot ready biodegradable0.9745
Rat acute toxicity2.3981 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9285
hERG inhibition (predictor II)Non-inhibitor0.7892
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units.
Kingdom
Organic compounds
Super Class
Lipids and lipid-like molecules
Class
Prenol lipids
Sub Class
Triterpenoids
Direct Parent
Triterpenoids
Alternative Parents
Tricarboxylic acids and derivatives / Fatty acid esters / Cyclohexenones / Carboxylic acid esters / Carboxylic acids / Organic oxides / Hydrocarbon derivatives
Substituents
Triterpenoid / Tricarboxylic acid or derivatives / Cyclohexenone / Fatty acid ester / Fatty acyl / Ketone / Carboxylic acid ester / Carboxylic acid / Carboxylic acid derivative / Organic oxygen compound
Molecular Framework
Aliphatic homopolycyclic compounds
External Descriptors
Not Available

Targets

Kind
Protein
Organism
Streptomyces exfoliatus
Pharmacological action
Unknown
General Function
Androstan-3-alpha,17-beta-diol dehydrogenase activity
Specific Function
Not Available
Gene Name
Not Available
Uniprot ID
P19992
Uniprot Name
3-alpha-(or 20-beta)-hydroxysteroid dehydrogenase
Molecular Weight
26483.77 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
11-beta-hydroxysteroid dehydrogenase [nad(p)] activity
Specific Function
Catalyzes reversibly the conversion of cortisol to the inactive metabolite cortisone. Catalyzes reversibly the conversion of 7-ketocholesterol to 7-beta-hydroxycholesterol. In intact cells, the rea...
Gene Name
HSD11B1
Uniprot ID
P28845
Uniprot Name
Corticosteroid 11-beta-dehydrogenase isozyme 1
Molecular Weight
32400.665 Da
References
  1. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]

Drug created on June 13, 2005 07:24 / Updated on November 05, 2018 17:48