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Identification
NameCarbenoxolone
Accession NumberDB02329  (EXPT00848)
TypeSmall Molecule
GroupsExperimental
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
SynonymsNot Available
External Identifiers Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
CarbeloneRoyal
CarbosanRowa
CarboxeShiteh Organic
CopuWinston
HerpesanRowa
Rösch & HandelRowa
RowadermatRösch & Handel
RowagelRowa
SanodinErn
Brand mixturesNot Available
Salts
Name/CASStructureProperties
Carbenoxolone disodium
7421-40-1
Thumb
  • InChI Key: BQENDLAVTKRQMS-SBBGFIFASA-L
  • Monoisotopic Mass: 614.31954245
  • Average Mass: 614.731
DBSALT001875
Categories
UNIIMM6384NG73
CAS number5697-56-3
WeightAverage: 570.7566
Monoisotopic: 570.355653954
Chemical FormulaC34H50O7
InChI KeyOBZHEBDUNPOCJG-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
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as oleanane triterpenoids. These are triterpenoids with a structure based on the oleanane skeleton, an 4,4,6a,8a,11,14b-heptamethyl-hexadecahydropicene derivative.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassTriterpenoids
Direct ParentOleanane triterpenoids
Alternative Parents
Substituents
  • Oleanane triterpenoid
  • Tricarboxylic acid or derivatives
  • Fatty acid ester
  • Fatty acyl
  • Ketone
  • Carboxylic acid ester
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
Pharmacology
IndicationNot Available
PharmacodynamicsNot Available
Mechanism of actionNot Available
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organismsNot Available
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
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 )
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point292.5 °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 FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot 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
ATC CodesA02BX01A02BX51A02BX71
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot 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
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 reaction runs only in one direction, from 7-ketocholesterol to 7-beta-hydroxycholesterol (By similarity).
Gene Name:
HSD11B1
Uniprot ID:
P28845
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 ]
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Drug created on June 13, 2005 07:24 / Updated on May 12, 2016 09:34