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Compound Detail

CHEMBL499915

CARBENOXOLONE
🧪 Phase II
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🧪 Phase II
CC1(C)[C@@H](OC(=O)CCC(=O)O)CC[C@]2(C)[C@H]3C(=O)C=C4[C@@H]5C[C@@](C)(C(=O)O)CC[C@]5(C)CC[C@@]4(C)[C@]3(C)CC[C@@H]12
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL499915
Name CARBENOXOLONE
Phase Phase II
Structure Type MOL
InChI Key OBZHEBDUNPOCJG-WBXJDKIVSA-N
Therapeutic ✓ Yes

Known Names

Carbenoxolona Carbenoxolone
8
Targets
25
Activities
3
Assay Types
0
PK Parameters
20
Publications
2
Known Names
2
Indications
1
Mechanisms

Molecular Properties

570.8
MW (Da)
6.83
ALogP
5
HBA
2
HBD
118.0
PSA (Ų)
0.35
QED
2
Ro5 Violations
5
Rot. Bonds

Drug Information

Molecule Type Small molecule
Chirality Single Enantiomer

Flags

Natural Product
USAN Stem -olone
USAN Year 1974

Extended Properties

Molecular Formula C34H50O7
MW 570.77
Aromatic Rings 0
Heavy Atoms 41
NP-Likeness 2.77

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
11-beta-hydroxysteroid dehydrogenase inhibitor INHIBITOR 11-beta-hydroxysteroid dehydrogenase ✓ ✓

Indications

Gastroesophageal Reflux Peptic Ulcer

ATC Classification

A02BX01
carbenoxolone
Level 1: ALIMENTARY TRACT AND METABOLISM
Level 2: DRUGS FOR ACID RELATED DISORDERS
A02BX51
carbenoxolone, combinations excl. psycholeptics
Level 1: ALIMENTARY TRACT AND METABOLISM
Level 2: DRUGS FOR ACID RELATED DISORDERS
A02BX71
carbenoxolone, combinations with psycholeptics
Level 1: ALIMENTARY TRACT AND METABOLISM
Level 2: DRUGS FOR ACID RELATED DISORDERS

Activity Summary

IC50 21 meas. best 7.4
Ki 3 meas. best 7.21
EC50 1 meas. best 7.09

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
11-beta-hydroxysteroid dehydrogenase 1
CHEMBL4235
 IC50 7.4 6.5022 40.0 9
11-beta-hydroxysteroid dehydrogenase 1
CHEMBL4235
 Ki 7.21 7.21 62.0 1
11-beta-hydroxysteroid dehydrogenase type 2
CHEMBL3490
 EC50 7.09 7.09 82.0 1
11-beta-hydroxysteroid dehydrogenase type 2
CHEMBL3490
 IC50 7.09 6.89 82.0 2
11-beta-hydroxysteroid dehydrogenase 1
CHEMBL3910
 IC50 6.97 6.7267 108.0 3
11-beta-hydroxysteroid dehydrogenase type 2
CHEMBL3746
 IC50 6.77 6.77 170.0 1
Unchecked
CHEMBL612545
 IC50 6.44 6.01 361.0 2
Unchecked
CHEMBL612545
 Ki 5.3 5.3 5000.0 1
RAW264.7
CHEMBL612557
 IC50 5.18 5.08 6640.0 3
Tyrosine-protein phosphatase non-receptor type 1
CHEMBL335
 Ki 5.16 5.16 7000.0 1
Pannexin-1
CHEMBL4879520
 IC50 5.0 5.0 10000.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
11-beta-hydroxysteroid dehydrogenase 1 IC50 = 40.0 nM 7.4 Inhibition of human 11beta-HSD1 35537608
11-beta-hydroxysteroid dehydrogenase 1 Ki = 62.0 nM 7.21 Inhibition of N-terminal MKHQHQHQHQHQHQQPL-tagged 11beta-HSD1 C272S mutant (unkn... 31294974
11-beta-hydroxysteroid dehydrogenase type 2 IC50 = 82.0 nM 7.09 Inhibition of mouse microsomal 11beta-HSD2 expressed in HEK293 cells assessed as... 19564108
11-beta-hydroxysteroid dehydrogenase type 2 EC50 = 82.0 nM 7.09 Inhibition of mouse 11beta-HSD2 expressed in HEK293 cells assessed as [3H]cortis... 22440625
11-beta-hydroxysteroid dehydrogenase 1 IC50 = 83.0 nM 7.08 Ability to convert [3H]cortisol to the tritium labeled cortisone in the presence... 12190302
11-beta-hydroxysteroid dehydrogenase 1 IC50 = 108.0 nM 6.97 In vitro inhibitory activity against mouse 11 beta hydroxysteroid dehydrogenase ... 12190302
11-beta-hydroxysteroid dehydrogenase type 2 IC50 = 170.0 nM 6.77 Inhibition of 11beta-HSD2 (unknown origin) expressed in HEK293 cells using corti... 31294974
11-beta-hydroxysteroid dehydrogenase type 2 IC50 = 206.0 nM 6.69 Inhibition of mouse 11beta-HSD2 expressed in HEK293 cells assessed as conversion... 22360639
11-beta-hydroxysteroid dehydrogenase 1 IC50 = 243.0 nM 6.61 Inhibition of mouse 11beta-HSD1 expressed in CHOK1 cells using XL665-labeled cor... 31759849
11-beta-hydroxysteroid dehydrogenase 1 IC50 = 250.0 nM 6.6 Inhibition of mouse 11beta-HSD1 expressed in CHO cells after 3 hrs by HTRF corti... 21093259
11-beta-hydroxysteroid dehydrogenase 1 IC50 = 330.0 nM 6.48 In vitro inhibitory activity against human 11 beta hydroxysteroid dehydrogenase ... 12190302
11-beta-hydroxysteroid dehydrogenase 1 IC50 = 330.0 nM 6.48 Inhibition of human 11beta-HSD1 by HTRF assay 32088493
Unchecked IC50 = 361.0 nM 6.44 Inhibition of transglutaminase in human keratinocytes in presence of 10 uM retin... -
11-beta-hydroxysteroid dehydrogenase 1 IC50 = 410.0 nM 6.39 Inhibition of N-terminal MKHQHQHQHQHQHQQPL-tagged 11beta-HSD1 C272S mutant (unkn... 31294974
11-beta-hydroxysteroid dehydrogenase 1 IC50 = 500.0 nM 6.3 Inhibition of human 11beta-HSD1 expressed in CHO cells after 3 hrs by HTRF corti... 21093259
11-beta-hydroxysteroid dehydrogenase 1 IC50 = 500.0 nM 6.3 Inhibition of human 11beta-HSD1 expressed in CHO-K1 cells using cortisone as sub... 24900439
11-beta-hydroxysteroid dehydrogenase 1 IC50 = 500.0 nM 6.3 Inhibition of 11beta-HSD1 in human microsomes by HTRF cortisol assay 20045318
11-beta-hydroxysteroid dehydrogenase 1 IC50 = 1630.0 nM 5.79 Inhibition of human 11beta-HSD1 expressed in CHOK1 cells using XL665-labeled cor... 31759849
Unchecked IC50 = 2630.0 nM 5.58 Inhibition of chymotrypsin-like activity of human 20S proteasome 18562200
Unchecked Ki = 5000.0 nM 5.3 Metabolic Measurements: Glucose in tail blood was measured using a glucometer (O... -

Literature References

PubMed DOI Target Context # Activities
15646539 10.1016/s0399-8320(04)95062-2 Unchecked 11
15646539 10.1016/s0399-8320(04)95062-2 NON-PROTEIN TARGET 8
34973341 10.1016/j.bmcl.2021.128523 RAW264.7 3
20014752 10.1021/tx900326k Hepatotoxicity 3
12190302 10.1021/jm025530f 11-beta-hydroxysteroid dehydrogenase 1 3
37468498 10.1038/s41467-023-40064-9 Nuclear receptor subfamily 1 group I member 2 3
37468498 10.1038/s41467-023-40064-9 Muscarinic acetylcholine receptor M2 2
21093259 10.1016/j.bmcl.2010.10.123 11-beta-hydroxysteroid dehydrogenase 1 2
21376605 10.1016/j.bmc.2011.02.005 11-beta-hydroxysteroid dehydrogenase 1 2
- 10.6019/CHEMBL4651402 SARS-CoV-2 2
21376605 10.1016/j.bmc.2011.02.005 11-beta-hydroxysteroid dehydrogenase type 2 2
31759849 10.1016/j.bmcl.2019.126787 11-beta-hydroxysteroid dehydrogenase 1 2
37468498 10.1038/s41467-023-40064-9 5-hydroxytryptamine receptor 2A 2
37468498 10.1038/s41467-023-40064-9 Androgen receptor 2
37468498 10.1038/s41467-023-40064-9 Beta-2 adrenergic receptor 2
37468498 10.1038/s41467-023-40064-9 Gamma-aminobutyric acid receptor subunit alpha-1 2
37468498 10.1038/s41467-023-40064-9 Progesterone receptor 2
37468498 10.1038/s41467-023-40064-9 5-hydroxytryptamine receptor 2B 2
31294974 10.1021/acs.jmedchem.9b00187 11-beta-hydroxysteroid dehydrogenase 1 2
37468498 10.1038/s41467-023-40064-9 Beta-1 adrenergic receptor 2

Data from ChEMBL 36 via Core Engine