Carbenoxolone
Identification
- Name
- Carbenoxolone
- Accession Number
- DB02329
- 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]
- Type
- Small Molecule
- Groups
- Experimental
- Structure
- Weight
- Average: 570.7566
Monoisotopic: 570.355653954 - Chemical Formula
- C34H50O7
- Synonyms
- Carbenoxolona
- Carbenoxolone
Pharmacology
- Accelerate your drug discovery research with the industry’s only fully connected ADMET dataset, ideal for:Accelerate your drug discovery research with our fully connected ADMET dataset
- Indication
- Not Available
- Associated Conditions
- Contraindications & Blackbox Warnings
- Contraindications & Blackbox WarningsWith our commercial data, access important information on dangerous risks, contraindications, and adverse effects.Our Blackbox Warnings cover Risks, Contraindications, and Adverse Effects
- Pharmacodynamics
- Not Available
- Mechanism of action
Target Actions Organism U3-alpha-(or 20-beta)-hydroxysteroid dehydrogenase Not Available Streptomyces exfoliatus UCorticosteroid 11-beta-dehydrogenase isozyme 1 inhibitorHumans - 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
- Adverse Effects
- Reduce medical errorsand improve treatment outcomes with our comprehensive & structured data on drug adverse effects.Reduce medical errors & improve treatment outcomes with our adverse effects data
- Toxicity
- Not Available
- Affected organisms
- Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.Not Available
- Food Interactions
- Not Available
Products
- Comprehensive & structured drug product infoFrom application numbers to product codes, connect different identifiers through our commercial datasets.Easily connect various identifiers back to our datasets
- Product Ingredients
Ingredient UNII CAS InChI Key Carbenoxolone disodium F1MP7242Z5 7421-40-1 BQENDLAVTKRQMS-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
- ATC Codes
- A02BX01 — Carbenoxolone
- A02BX — Other drugs for peptic ulcer and gastro-oesophageal reflux disease (GORD)
- A02B — DRUGS FOR PEPTIC ULCER AND GASTRO-OESOPHAGEAL REFLUX DISEASE (GORD)
- A02 — DRUGS FOR ACID RELATED DISORDERS
- A — ALIMENTARY TRACT AND METABOLISM
- A02BX — Other drugs for peptic ulcer and gastro-oesophageal reflux disease (GORD)
- A02B — DRUGS FOR PEPTIC ULCER AND GASTRO-OESOPHAGEAL REFLUX DISEASE (GORD)
- A02 — DRUGS FOR ACID RELATED DISORDERS
- A — ALIMENTARY TRACT AND METABOLISM
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- 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
- Aliphatic homopolycyclic compound / Carbonyl group / Carboxylic acid / Carboxylic acid derivative / Carboxylic acid ester / Cyclohexenone / Fatty acid ester / Fatty acyl / Hydrocarbon derivative / Ketone
- Molecular Framework
- Aliphatic homopolycyclic compounds
- External Descriptors
- Not Available
Chemical Identifiers
- UNII
- MM6384NG73
- CAS number
- 5697-56-3
- 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
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
- 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
- 2017
- ChEMBL
- CHEMBL499915
- ZINC
- ZINC000003977823
- Therapeutic Targets Database
- DNC000388
- PDBe Ligand
- CBO
- Wikipedia
- Carbenoxolone
- PDB Entries
- 1hdc / 2bel / 6wbi / 6wbl
Clinical Trials
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Gel - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 292.5 °C PhysProp - Predicted Properties
Property Value Source Water Solubility 0.000738 mg/mL ALOGPS logP 5.46 ALOGPS logP 6.3 ChemAxon logS -5.9 ALOGPS pKa (Strongest Acidic) 4.04 ChemAxon pKa (Strongest Basic) -5.1 ChemAxon Physiological Charge -2 ChemAxon Hydrogen Acceptor Count 6 ChemAxon Hydrogen Donor Count 2 ChemAxon Polar Surface Area 117.97 Å2 ChemAxon Rotatable Bond Count 6 ChemAxon Refractivity 154.31 m3·mol-1 ChemAxon Polarizability 64.99 Å3 ChemAxon Number of Rings 5 ChemAxon Bioavailability 0 ChemAxon Rule of Five No ChemAxon Ghose Filter No ChemAxon Veber's Rule No ChemAxon MDDR-like Rule Yes ChemAxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9612 Blood Brain Barrier + 0.809 Caco-2 permeable - 0.5933 P-glycoprotein substrate Substrate 0.83 P-glycoprotein inhibitor I Non-inhibitor 0.7249 P-glycoprotein inhibitor II Inhibitor 0.8388 Renal organic cation transporter Non-inhibitor 0.8358 CYP450 2C9 substrate Non-substrate 0.8343 CYP450 2D6 substrate Non-substrate 0.9271 CYP450 3A4 substrate Substrate 0.7984 CYP450 1A2 substrate Non-inhibitor 0.9145 CYP450 2C9 inhibitor Non-inhibitor 0.8921 CYP450 2D6 inhibitor Non-inhibitor 0.9482 CYP450 2C19 inhibitor Non-inhibitor 0.9274 CYP450 3A4 inhibitor Non-inhibitor 0.6959 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.8713 Ames test Non AMES toxic 0.821 Carcinogenicity Non-carcinogens 0.9485 Biodegradation Not ready biodegradable 0.9745 Rat acute toxicity 2.3981 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9285 hERG inhibition (predictor II) Non-inhibitor 0.7892
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available
Targets

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- 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
- 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]
- 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
- Humans
- 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
- 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 13:24 / Updated on February 21, 2021 18:51