Compound Detail
CHEMBL249837
METHACYCLINE 💊 Approved Drug
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💊 Approved Drug
C=C1c2cccc(O)c2C(=O)C2=C(O)[C@]3(O)C(=O)C(C(N)=O)=C(O)[C@@H](N(C)C)[C@@H]3[C@@H](O)[C@H]12
Basic Information
| ChEMBL ID | CHEMBL249837 |
| Name | METHACYCLINE |
| Phase | Approved |
| Structure Type | MOL |
| InChI Key | MHIGBKBJSQVXNH-IWVLMIASSA-N |
| Therapeutic | ✓ Yes |
4
Targets
6
Activities
2
Assay Types
1
PK Parameters
20
Publications
5
Known Names
2
Indications
Molecular Properties
442.4
MW (Da)
-0.44
ALogP
9
HBA
6
HBD
181.6
PSA (Ų)
0.33
QED
1
Ro5 Violations
2
Rot. Bonds
Drug Information
| Molecule Type | Small molecule |
| First Approval | 1982 |
| Availability | Discontinued |
| Chirality | Single Enantiomer |
Indications
Bacterial Infections Osteomyelitis
ATC Classification
J01AA05
metacycline
Level 1: ANTIINFECTIVES FOR SYSTEMIC USE
Level 2: ANTIBACTERIALS FOR SYSTEMIC USE
Activity Summary
IC50 4 meas. best 5.6
Kd 2 meas. best 5.0
Target Activity Profile
| Target | Type | Best pChEMBL | Mean pChEMBL | Best (nM) | # Data |
|---|---|---|---|---|---|
| Multidrug transporter MdfA CHEMBL4785 | IC50 | 5.6 | 5.6 | 2500.0 | 1 |
| NAD-dependent protein deacylase sirtuin-5, mitochondrial CHEMBL2163183 | IC50 | 5.44 | 5.44 | 3600.0 | 1 |
| microRNA 21 CHEMBL1615322 | Kd | 5.0 | 5.0 | 9900.0 | 1 |
| Unchecked CHEMBL612545 | Kd | 4.77 | 4.77 | 17000.0 | 1 |
| microRNA 21 CHEMBL1615322 | IC50 | 4.25 | 4.25 | 56000.0 | 1 |
| Unchecked CHEMBL612545 | IC50 | 4.01 | 4.01 | 97000.0 | 1 |
Pharmacokinetic Data
| Parameter | Value | Units | Species |
|---|---|---|---|
| F | 58.0 | % | Homo sapiens |
Activity Data Samples
Top measurements by pChEMBL value
| Target | Type | Rel. | Value | Units | pChEMBL | Assay | PubMed |
|---|---|---|---|---|---|---|---|
| Multidrug transporter MdfA | IC50 | = | 2500.0 | nM | 5.6 | Inhibition of [3H]tetracycline uptake into everted membrane vesicles, prepared f... | 8426364 |
| NAD-dependent protein deacylase sirtuin-5, mitochondrial | IC50 | = | 3600.0 | nM | 5.44 | Inhibition of SIRT5 (unknown origin) | 32858418 |
| microRNA 21 | Kd | = | 9900.0 | nM | 5.0 | Binding affinity to biotinylated pre-miRNA-21 (unknown origin) by SPR analysis | 31098005 |
| Unchecked | Kd | = | 17000.0 | nM | 4.77 | Binding affinity to biotinylated pre-let-7d microRNA (unknown origin) by SPR ana... | 31098005 |
| microRNA 21 | IC50 | = | 56000.0 | nM | 4.25 | Inhibition of Dicer mediated biotinylated pre-miRNA-21 (unknown origin) maturati... | 31098005 |
| Unchecked | IC50 | = | 97000.0 | nM | 4.01 | Inhibition of biotinylated pre-let-7d microRNA (unknown origin) maturation prein... | 31098005 |
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 |
| 31098005 | 10.1021/acsmedchemlett.9b00091 | microRNA 21 | 7 |
| 31098005 | 10.1021/acsmedchemlett.9b00091 | Unchecked | 3 |
| 37468498 | 10.1038/s41467-023-40064-9 | Muscarinic acetylcholine receptor M2 | 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 |
| - | 10.6019/CHEMBL4495565 | SARS-CoV-2 | 2 |
| - | 10.6019/CHEMBL4651402 | SARS-CoV-2 | 2 |
| 37468498 | 10.1038/s41467-023-40064-9 | 5-hydroxytryptamine receptor 2A | 2 |
| - | 10.6019/CHEMBL4808148 | Histone deacetylase 6 | 2 |
| 37468498 | 10.1038/s41467-023-40064-9 | 5-hydroxytryptamine receptor 1A | 2 |
| 37468498 | 10.1038/s41467-023-40064-9 | Alpha-2A adrenergic receptor | 2 |
| 37468498 | 10.1038/s41467-023-40064-9 | 5-hydroxytryptamine receptor 2B | 2 |
| 32858418 | 10.1016/j.ejmech.2020.112676 | NAD-dependent protein deacylase sirtuin-5, mitochondrial | 1 |
| 37468498 | 10.1038/s41467-023-40064-9 | Sodium-dependent dopamine transporter | 1 |
| 38318365 | 10.1016/j.isci.2024.108907 | Deoxynucleoside triphosphate triphosphohydrolase SAMHD1 | 1 |
| 37468498 | 10.1038/s41467-023-40064-9 | Voltage-dependent L-type calcium channel subunit alpha-1C | 1 |
| 37468498 | 10.1038/s41467-023-40064-9 | Voltage-gated inwardly rectifying potassium channel KCNH2 | 1 |
| 22194678 | 10.1371/journal.pcbi.1002310 | Hepatotoxicity | 1 |
Data from ChEMBL 36 via Core Engine