Skip to main content
Free research Free research Free compound review with research home and workspace preview
Quick search ChEMBL 36
Compound Detail

CHEMBL2146123

METHACYCLINE HYDROCHLORIDE
💊 Approved Drug
Enter ChEMBL ID:
Free Research Context This compound will appear in recent viewed items on the research home for this browser.
Research home View demo workspace
💊 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.Cl

Basic Information

ChEMBL ID CHEMBL2146123
Name METHACYCLINE HYDROCHLORIDE
Phase Approved
Structure Type MOL
InChI Key VZQARNDJLLWXGL-CCHMMTNSSA-N
Therapeutic ✓ Yes
Parent Compound CHEMBL249837
Active Moiety CHEMBL249837

Known Names

Metacycline hydrochloride Methacycline hcl Methacycline hydrochloride NSC-356465 NSC-757835 Rondomycin
6
Targets
14
Activities
2
Assay Types
0
PK Parameters
9
Publications
6
Known Names
1
Indications
1
Mechanisms

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

Routes of Administration

Oral
USAN Stem -cycline

Extended Properties

Molecular Formula C22H23ClN2O8
MW 478.89
Aromatic Rings 1
Heavy Atoms 32
NP-Likeness 1.56

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Bacterial 70S ribosome inhibitor INHIBITOR Bacterial 70S ribosome

Indications

Osteomyelitis

Activity Summary

IC50 9 meas. best 6.42
EC50 5 meas. best 7.03

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Streptokinase A
CHEMBL1293228
EC50 7.03 7.03 93.0 1
Streptococcus sp. 'group A'
CHEMBL612389
EC50 7.0 7.0 99.0 1
Streptococcus
CHEMBL612313
EC50 6.96 6.96 109.0 1
Unchecked
CHEMBL612545
IC50 6.42 5.9629 376.0 7
DNA repair protein RAD52 homolog
CHEMBL2362978
IC50 5.7 5.56 2000.0 2
Nuclear receptor subfamily 1 group I member 2
CHEMBL3401
EC50 5.5 5.2 3200.0 2

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Streptokinase A EC50 = 93.0 nM 7.03 PUBCHEM_BIOASSAY: Luminescence Microorganism-Based Dose Confirmation HTS to Iden... -
Streptococcus sp. 'group A' EC50 = 99.0 nM 7.0 PUBCHEM_BIOASSAY: Luminescence Microorganism-Based Dose Confirmation HTS to Iden... -
Streptococcus EC50 = 109.0 nM 6.96 PUBCHEM_BIOASSAY: Luminescence Microorganism-Based Dose Response HTS to Identify... -
Unchecked IC50 = 376.0 nM 6.42 PUBCHEM_BIOASSAY: A screen for inhibitors of the PhoP region in Salmonella Typhi... -
Unchecked IC50 = 390.0 nM 6.41 PUBCHEM_BIOASSAY: A screen for inhibitors of the PhoP region in Salmonella Typhi... -
Unchecked IC50 = 560.0 nM 6.25 PUBCHEM_BIOASSAY: A small molecule screen for inhibitors of the PhoP region in S... -
Unchecked IC50 = 670.0 nM 6.17 PUBCHEM_BIOASSAY: A Counter Screen to identiry small molecule screen for inhibit... -
Unchecked IC50 = 1410.0 nM 5.85 PUBCHEM_BIOASSAY: A small molecule screen for inhibitors of the PhoP region in S... -
DNA repair protein RAD52 homolog IC50 = 2000.0 nM 5.7 Inhibition of RAD52 (unknown origin) assessed as reduction in RAD52-ssDNA intera... -
Unchecked IC50 = 2725.0 nM 5.57 PubChem BioAssay. TR-FRET-based biochemical high throughput dose response assay ... -
Nuclear receptor subfamily 1 group I member 2 EC50 = 3200.0 nM 5.5 Competitive binding affinity to human PXR LBD (111 to 434) by TR-FRET assay 20966043
DNA repair protein RAD52 homolog IC50 = 3800.0 nM 5.42 Inhibition of RAD52 (unknown origin) assessed as effect on RAD52-mediated anneal... -
Unchecked IC50 = 8534.0 nM 5.07 PubChem BioAssay. Counterscreen for inhibitors of LEDGF/p75-dependent integratio... -
Nuclear receptor subfamily 1 group I member 2 EC50 = 12600.0 nM 4.9 Activation of human PXR expressed in human HepG2 (DPX-2) cells assessed as induc... 20966043

Literature References

PubMed DOI Target Context # Activities
20966043 10.1124/dmd.110.035105 Nuclear receptor subfamily 1 group I member 2 6
20553011 10.1021/tx1000865 Hepatotoxicity 1
20843939 10.1124/dmd.110.035113 Hepatotoxicity 1
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 1
22257890 10.1016/j.bmcl.2011.12.103 Nucleic Acid 1
22257890 10.1016/j.bmcl.2011.12.103 No relevant target 1
23571415 10.1124/mol.112.084152 Solute carrier organic anion transporter family member 1B3 1
23571415 10.1124/mol.112.084152 Solute carrier organic anion transporter family member 1B1 1
- 10.1101/2020.04.03.023846 SARS-CoV-2 1

Data from ChEMBL 36 via Core Engine