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Compound Detail

CHEMBL575

METHICILLIN
💊 Approved Drug
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💊 Approved Drug
COc1cccc(OC)c1C(=O)N[C@@H]1C(=O)N2[C@@H]1SC(C)(C)[C@@H]2C(=O)O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL575
Name METHICILLIN
Phase Approved
Structure Type MOL
InChI Key RJQXTJLFIWVMTO-TYNCELHUSA-N
Therapeutic ✓ Yes

Known Names

2,6-dimethoxyphenyl penicillin Methicillin Meticilina Meticillin Meticilline
2
Targets
3
Activities
1
Assay Types
5
PK Parameters
20
Publications
5
Known Names
2
Indications

Molecular Properties

380.4
MW (Da)
0.95
ALogP
6
HBA
2
HBD
105.2
PSA (Ų)
0.73
QED
0
Ro5 Violations
5
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1982
Availability Discontinued
Chirality Single Enantiomer

Routes of Administration

Parenteral

Flags

Natural Product
USAN Stem -cillin
USAN Year 1962

Extended Properties

Molecular Formula C17H20N2O6S
MW 380.42
Aromatic Rings 1
Heavy Atoms 26
NP-Likeness 0.43

Indications

Bacterial Infections Osteomyelitis

ATC Classification

J01CF03
meticillin
Level 1: ANTIINFECTIVES FOR SYSTEMIC USE
Level 2: ANTIBACTERIALS FOR SYSTEMIC USE

Activity Summary

IC50 3 meas. best 7.52

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Staphylococcus aureus
CHEMBL352
 IC50 7.52 7.52 30.0 1
Pseudomonas aeruginosa
CHEMBL348
 IC50 6.52 6.52 300.0 1

Pharmacokinetic Data

Parameter Value Units Species
CL 6.6 mL.min-1.kg-1 Homo sapiens
CL 6.6 mL.min-1.kg-1 Homo sapiens
Fu 0.43 - Homo sapiens
MRT 0.8 hr Homo sapiens
T1/2 0.64 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Staphylococcus aureus IC50 = 30.0 nM 7.52 Antimicrobial activity against methicillin-resistant Staphylococcus aureus ATCC ... 31287681
Pseudomonas aeruginosa IC50 = 300.0 nM 6.52 Antimicrobial activity against Pseudomonas aeruginosa ATCC 27853 assessed as inh... 31287681

Literature References

PubMed DOI Target Context # Activities
30347327 10.1016/j.ejmech.2018.10.039 Staphylococcus aureus 58
30503946 10.1016/j.ejmech.2018.11.052 Staphylococcus aureus 28
31520928 10.1016/j.ejmech.2019.111686 Staphylococcus aureus 24
18070966 10.1128/aac.00395-07 Staphylococcus aureus 23
- 10.1016/S0960-894X(01)80927-6 Staphylococcus aureus 17
38289145 10.1021/acs.jmedchem.3c02064 Staphylococcus aureus 16
26483137 10.1016/j.bmcl.2015.10.022 Staphylococcus aureus 16
37659197 10.1016/j.ejmech.2023.115757 Staphylococcus aureus 13
33190958 10.1016/j.ejmech.2020.112996 Staphylococcus aureus 13
35224498 10.1039/d1md00249j Staphylococcus aureus 12
8336336 10.1021/jm00066a006 Staphylococcus aureus 11
38173250 10.1021/acs.jmedchem.3c01360 Staphylococcus aureus 11
15646539 10.1016/s0399-8320(04)95062-2 Unchecked 11
30108711 10.1039/C7MD00387K Staphylococcus aureus 11
19124662 10.1128/aac.01173-08 Staphylococcus aureus 10
26185006 10.1016/j.ejmech.2015.06.047 Staphylococcus aureus 10
15646539 10.1016/s0399-8320(04)95062-2 NON-PROTEIN TARGET 8
25756620 10.1021/np500911k Staphylococcus aureus 8
38845361 10.1021/acs.jmedchem.4c00320 Staphylococcus aureus 6
25756620 10.1021/np500911k Enterococcus faecalis 6

Data from ChEMBL 36 via Core Engine