Carbenoxolone

Identification

Summary

Carbenoxolone is a drug used to symptomatically treat lip sores and mouth ulcers.

Generic Name

Carbenoxolone

DrugBank Accession Number

DB02329

Background

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

3D

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MOLSDF3D-SDFPDBSMILESInChI

Similar Structures

Structure for Carbenoxolone (DB02329)

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Weight

Average: 570.7566
Monoisotopic: 570.355653954

Chemical Formula

C₃₄H₅₀O₇

Synonyms

• Carbenoxolona
• Carbenoxolone

Pharmacology

Indication

Not Available

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Associated Conditions

• Oral Herpes Simplex

Contraindications & Blackbox Warnings

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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	inhibitor	Humans

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

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Toxicity

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

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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

A02BX71 — Carbenoxolone, combinations with psycholeptics

• 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

A02BX51 — Carbenoxolone, combinations excl. psycholeptics

• 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

• Alimentary Tract and Metabolism
• Anti-Ulcer Agents
• Drugs for Acid Related Disorders
• Drugs for Peptic Ulcer and Gastro-Oesophageal Reflux Disease (Gord)
• Gastrointestinal Agents
• Pentacyclic Triterpenes
• Terpenes
• Triterpenes

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

Affected organisms

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

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. [Article]

External Links

PubChem Compound

636403

PubChem Substance

46508820

ChemSpider

552190

BindingDB

50247012

RxNav

2017

ChEMBL

CHEMBL499915

ZINC

ZINC000003977823

Therapeutic Targets Database

DNC000388

PDBe Ligand

CBO

Wikipedia

Carbenoxolone

PDB Entries

1hdc / 2bel / 6wbi / 6wbl / 7byi

Clinical Trials

Clinical Trials

Phase	Status	Purpose	Conditions	Count

Pharmacoeconomics

Manufacturers

Not Available

Packagers

Not Available

Dosage Forms

Form	Route	Strength
Gel	Topical	2 %w/w

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

ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

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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Details1. 3-alpha-(or 20-beta)-hydroxysteroid dehydrogenase

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. [Article]
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. [Article]

Binding Properties

×

Property	Measurement	pH	Temperature (°C)	References
IC 50 (nM)	330	N/A	N/A	A29892
IC 50 (nM)	500	N/A	N/A	A29893 / A29894 / A18427
IC 50 (nM)	83	N/A	N/A	A29892

Details

Binding Properties2. Corticosteroid 11-beta-dehydrogenase isozyme 1

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

1. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]

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Drug created at June 13, 2005 13:24 / Updated at May 19, 2021 03:45