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Compound Detail

CHEMBL632

BETAMETHASONE
💊 Approved Drug
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💊 Approved Drug
C[C@H]1C[C@H]2[C@@H]3CCC4=CC(=O)C=C[C@]4(C)[C@@]3(F)[C@@H](O)C[C@]2(C)[C@@]1(O)C(=O)CO
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL632
Name BETAMETHASONE
Phase Approved
Structure Type MOL
InChI Key UREBDLICKHMUKA-DVTGEIKXSA-N
Therapeutic ✓ Yes

Known Names

Betametasona Betamethasone Betasolan Betnelan Celestone Flubenisolone Lotrisone NSC-39470 Rinderon SCH 4831 SCH-4831 Taclonex +1 more
5
Targets
11
Activities
2
Assay Types
7
PK Parameters
20
Publications
13
Known Names
20
Indications
1
Mechanisms

Molecular Properties

392.5
MW (Da)
1.90
ALogP
5
HBA
3
HBD
94.8
PSA (Ų)
0.67
QED
0
Ro5 Violations
2
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1961
Availability Discontinued
Chirality Single Enantiomer

Routes of Administration

Oral Topical
USAN Year 1962

Extended Properties

Molecular Formula C22H29FO5
MW 392.47
Aromatic Rings 0
Heavy Atoms 28
NP-Likeness 2.21

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Glucocorticoid receptor agonist AGONIST Glucocorticoid receptor ✓ ✓

Indications

Eye Diseases Hemorrhoids Lung Diseases, Obstructive Nasal Obstruction Carpal Tunnel Syndrome Cough Eczema Gout Hypersensitivity Lichen Planus, Oral Orbital Pseudotumor Pharyngitis Pregnancy Premature Birth Psoriasis Psoriasis Respiratory Distress Syndrome Rhinitis, Allergic, Seasonal Bronchiolitis Dermatitis, Atopic

ATC Classification

A07EA04
betamethasone
Level 1: ALIMENTARY TRACT AND METABOLISM
Level 2: ANTIDIARRHEALS, INTESTINAL ANTIINFLAMMATORY/ANTIINFECTIVE AGENTS
C05AA05
betamethasone
Level 1: CARDIOVASCULAR SYSTEM
Level 2: VASOPROTECTIVES
D07AC01
betamethasone
Level 1: DERMATOLOGICALS
Level 2: CORTICOSTEROIDS, DERMATOLOGICAL PREPARATIONS
D07XC01
betamethasone
Level 1: DERMATOLOGICALS
Level 2: CORTICOSTEROIDS, DERMATOLOGICAL PREPARATIONS
H02AB01
betamethasone
Level 1: SYSTEMIC HORMONAL PREPARATIONS, EXCL. SEX HORMONES AND INSULINS
Level 2: CORTICOSTEROIDS FOR SYSTEMIC USE
R01AD06
betamethasone
Level 1: RESPIRATORY SYSTEM
Level 2: NASAL PREPARATIONS
R03BA04
betamethasone
Level 1: RESPIRATORY SYSTEM
Level 2: DRUGS FOR OBSTRUCTIVE AIRWAY DISEASES
S01BA06
betamethasone
Level 1: SENSORY ORGANS
Level 2: OPHTHALMOLOGICALS
S01CB04
betamethasone
Level 1: SENSORY ORGANS
Level 2: OPHTHALMOLOGICALS
S02BA07
betamethasone
Level 1: SENSORY ORGANS
Level 2: OTOLOGICALS

Activity Summary

IC50 10 meas. best 8.11
Ki 1 meas. best 8.45

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Glucocorticoid receptor
CHEMBL2034
 Ki 8.45 8.45 3.5 1
Glucocorticoid receptor
CHEMBL2034
 IC50 8.11 8.11 7.7 1
THP-1
CHEMBL614245
 IC50 7.89 7.775 13.0 2
Keratinocyte
CHEMBL613995
 IC50 6.52 6.52 300.0 1
Whole blood
CHEMBL2367389
 IC50 6.0 6.0 1000.0 1
Plasmodium falciparum
CHEMBL364
 IC50 5.0 4.9 10000.0 5

Pharmacokinetic Data

Parameter Value Units Species
CL 2.8 mL.min-1.kg-1 Homo sapiens
CL 2.8 mL.min-1.kg-1 Homo sapiens
F 79.0 % Homo sapiens
Fu 0.36 - Homo sapiens
Fu 0.36 - Homo sapiens
MRT 7.9 hr Homo sapiens
T1/2 5.6 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Glucocorticoid receptor Ki = 3.516 nM 8.45 DRUGMATRIX: Glucocorticoid radioligand binding (ligand: [3H] Dexamethasone) -
Glucocorticoid receptor IC50 = 7.735 nM 8.11 DRUGMATRIX: Glucocorticoid radioligand binding (ligand: [3H] Dexamethasone) -
THP-1 IC50 = 13.0 nM 7.89 Inhibition of LPS-induced TNFalpha production in human THP1 cells after 24 hrs 25111439
THP-1 IC50 = 22.0 nM 7.66 Inhibition of LPS-induced IL6 production in human THP1 cells after 24 hrs 25111439
Keratinocyte IC50 = 300.0 nM 6.52 Cytotoxicity against primary human endothelial keratinocytes assessed as inhibit... 28558967
Whole blood IC50 = 1000.0 nM 6.0 Anti-inflammatory activity in Homo sapiens (human) whole blood assessed inhibiti... -
Plasmodium falciparum IC50 = 10000.0 nM 5.0 Antiplasmodial activity against Plasmodium falciparum 3D7 after 72 hrs by SYBR g... 19734910
Plasmodium falciparum IC50 = 12589.25 nM 4.9 Antiplasmodial activity against Plasmodium falciparum 7G8 after 72 hrs by SYBR g... 19734910
Plasmodium falciparum IC50 = 12589.25 nM 4.9 Antiplasmodial activity against Plasmodium falciparum GB4 after 72 hrs by SYBR g... 19734910
Plasmodium falciparum IC50 = 12589.25 nM 4.9 Antiplasmodial activity against Plasmodium falciparum W2 after 72 hrs by SYBR gr... 19734910
Plasmodium falciparum IC50 = 15848.93 nM 4.8 Antiplasmodial activity against Plasmodium falciparum HB3 after 72 hrs by SYBR g... 19734910

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL3885881 Rattus norvegicus 409
- 10.1101/2024.03.28.586928 ADMET 100
- 10.5281/zenodo.13943903 ADMET 19
16472241 10.2174/1570163043334794 Hepatotoxicity 18
15646539 10.1016/s0399-8320(04)95062-2 Unchecked 11
25111439 10.1021/jm500901e Mus musculus 8
15646539 10.1016/s0399-8320(04)95062-2 NON-PROTEIN TARGET 8
2897467 10.1021/jm00401a015 Glucocorticoid receptor 7
19734910 10.1038/nchembio.215 Plasmodium falciparum 5
18426954 10.1124/dmd.108.020479 ADMET 4
- 10.6019/CHEMBL4495565 SARS-CoV-2 4
- 10.1007/s00044-011-9746-6 Whole blood 3
20014752 10.1021/tx900326k Hepatotoxicity 3
34825192 10.1039/D1MD00210D Unchecked 3
28558967 10.1016/j.bmcl.2017.05.021 Keratinocyte 2
19445515 10.1021/jm900403j Homo sapiens 2
10891117 10.1021/jm0000564 ADMET 2
- 10.6019/CHEMBL4495564 Replicase polyprotein 1ab 2
14971904 10.1021/jm030408h ADMET 2
- 10.6019/CHEMBL4808148 Histone deacetylase 6 2

Data from ChEMBL 36 via Core Engine